Jason Becker
December 3, 2023

This month I’ll be chatting with Christiaan

Hi Jason,

I was looking forward to December – not only for the start of my turn in the letter wiring – but also as it marked a year of change for me. So today, when I’m writing this letter to you, I’m a pretty different person than earlier in the year when I signed up. And that is for the good :-)

One of the biggest changes I made this year was switching my job. It took so much courage to take the step and go from something known - and not all bad - to something new and unknown. On the other hand, I’ve started to do sports regularly, and that would not be a sentence you heard from me last year. Chris is a computer nerd, and they do not do sports ;-). So I started swimming this year, and I quite enjoy it.

It is early morning right now when I write these words (6:00), and I soon need to start work. I’m conducting a “Cybersecurity” Workshop for my co-workers today. I hope all goes well. It is quite the change now that I’m in a company where I’m currently the only “computer guy.” It is funny how you can’t rely on a common body of terms everybody knows or a “common culture.” I don’t know how to describe that, but we all had the same background and knew the same stuff at the old place.

It is good for me to stretch again and navigate some uncharted waters. Having the same background is not necessarily all good – it makes for an easy life – but not for the best solutions. This also fits perfectly into the theme of change I have for this year: be more open to the world.

So, how was your year? Did the regular writing with strangers change something?

Looking forward to your reply, Chris

Hi Christiaan,

Switching jobs is a big change! One I haven’t made in almost a decade. It’s crazy to think that April 2014 was the last time I had a different employer. And while what I do and everything around me has changed a lot, I still have worked for Allovue for as long as I went to college, high school, and middle school combined. Wow.

A couple of years back I started playing volleyball again, and it has been a huge boost to my mental health. I’m glad you’re enjoying the swimming! What is it that you feel attracts you to swimming, specifically? I haven’t really done it in a long time, but I know how exhausting laps can be. And quiet. I’m not sure I could sit in my head for that long… or swim for that long, for that matter. How much swimming do you do when you go? Something tells me that even in my best shape, 15 to 20 mins would be all I could do.

Writing with strangers has been a highlight of the year. For one, it’s caused me to stop and think about what I’m doing and where I am a lot more than I usually do. Reintroducing myself, digging into different parts of my state of mind and what’s happening has been a form of forced reflection that is sometimes absent. In many ways, these letters are a better journal than any journal I’ve ever kept.

Let me know how your workshop went! Did you feel you were able to communicate effectively? Make it fun?

And now that we’re at the end of the year… what are your plans for next year?


November 10, 2023

Meta note: this month I’m corresponding with Katie Dexter


First, I’d like to apologize in advance that I haven’t written in some time and I’m quite rusty. That said, I’m excited to be writing you a letter as you’ve always been in my periphery during my time in Baltimore. Our circles are similar, yet never seem to quite overlap. Hopefully this exercise can close that gap and allow us to learn more about each other. Hopefully you’re settling into the cooler months, and maybe you have some travels planned to go somewhere warmer sometime this winter, would love to hear if you do!

I’m not sure if you know but my partner and I had a baby in April and it’s been the most fantastic and wildly unexpected thing I’ve ever experienced. I’ve been off work for the past 8 weeks, and I am returning on Monday. My time off has given me much to think about in terms of labor, capitalism, and how I want to spend my time going forward. I won’t lie, I did miss working. There’s something magical about solving problems using code, and I think you will understand how a break from that magic could leave me missing work. What I do not miss is the stress of always being available and online and ready to help and jump into things. This time away has given me a lot of perspective in what work life balance actually means. I hope that when I return it’s not overwhelming and I will be able to uphold some boundaries around my labor. Of course things have gone off the rails during my time off, which is why this letter is delayed. My company was acquired and I’m navigating the stress and uncertainty of returning to something completely different that I left.

I’m curious to know more about your own relationship with work. How do you balance that and doing all of the other things that are important to you? I know there’s a delicate balance and I’m trying to understand how to incorporate taking care of myself, my 6 month old, and still performing at work. It seems….wildly impossible.

Something I’ve been doing the past few months is taking a few hours each night when my baby is asleep to do something enriching for myself. I draw a tarot card, I make meaning of what I interpret from the cards. I read - lately heavily into understanding theories of psychoanalysis and the human psyche. I’ve been catching up on music, and got into listening to some difficult jazz. I wondered if this is me grasping at maintaining my own identity while also being a parent. It’s hard to know, but I do know that it seems easy to just get blended up in just being a parent and that’s not really ideal. Identity is such a big signifier and so is our perception of other people’s identities. I think it could be interesting if we shared our perceptions of each other, since we don’t really know much outside of a social media following. It could be a fun exercise.

Let me know what you’ve been up to, what’s got your attention these days. I look forward to hearing from you, and chatting with you over the next month.


Hi Katie,

I spent a few months in Mexico City last year essentially escaping winter— we were gone from the Friday after Thanksgiving until mid February. This year, no such grand plans. One of our dogs is getting older, and there’s no way we could take extended time away. We did land some stupidly inexpensive flights to Paris, so I’m going for the first time for a few days after Thanksgiving. I think that will be the only non-work trip this winter. That said, I’m writing this from Phoenix, so I do get my share of warmer locales, even if most of my time is at hotel conference areas or in school district buildings.

Congratulations on the baby! I can only imagine the big shift that has created, alongside an acquisition at work and … you somewhat recently moved houses too right? Seems like a lot.

That said, “grasping at maintaining identity” is definitely something I relate to, and it’s a big part of my relationship to work. I’m getting close to my 10 year anniversary at Allovue. And while I’d like to think that I’m a person who is more than his job, it’s often quite hard for me to separate my self-perception and identity from what I do and where I do it. It’s deeply unhealthy, but so much of my time, energy, passion, sweat, pride, fear, stress, frustration, and failure are all wrapped up in what I do.

The last couple of years I’ve started playing Volo Volleyball pretty regularly when I’m at home. Faster pace, team sports are great at turning off my brain. I literally can’t think about work about 97% of the time while playing volleyball. And while I haven’t made some deep, life long friendships, I now have a bit of a sense of community with folks who are regular players that make me feel connected to something that isn’t work— at least a little. Going to the gym to lift weights, which I also do with small group training, doesn’t help in the same way. There’s too much time to be in my own head and thinking. The pace and collaboration of a sport seems key. And it really does help— I come home exhausted, and still sometimes return to work and some of the stresses. But after volleyball, I’m rarely able to be quite worked up to the levels I let myself get whipped into throughout the day.

I love solving problems with code. I love thinking through a process and how to make it more efficient or effective, how to store the data needed for each step along the way, and how to present information more clearly to folks. I even like mentorship and management, when I feel that I’m up to the task. But there’s a lot more that comes with leadership of a small company that isn’t pleasant. And I often wonder, would I be much better at this if I were doing only 3 of the 15 things I am responsible for? And even if I would be better, would I actually be bored? I joke about a simpler job and a simpler life, but the people closest to me don’t think I could last 15 minutes without be overstimulated and pulled in 100 directions. They might be right, but that’s probably something I need to unlearn, someday.

What’s got my attention…

About halfway through this year, I realized the theme I wanted was “lighten” or “light”. In various ways, my life has felt very heavy pretty much since COVID. I have absolutely failed to make any progress on this idea, but I’ve been returning to it a lot lately. I need to find ways to be a little less serious, a little more fun, to feel a little less burdened (mostly self-imposed). So I’ve been trying to pay attention to my media diet and my habits and identify the things that seem to help. I’ve been reading less and watching fewer movies. And I’ve been walking less. And I very much feel as you do – work is a thing I love, but being always available, and letting so many things feel urgent and allow them to spike my anxiety… that’s not so great.

So, as per usual when the days get short, I’m turning inward and trying to get my health back on track. Maybe it’ll work better this year than last year.


October 28, 2023

Hi Jason,

My husband and son want me to pick telekinesis as my superpower. (“You know what, I think I like the couch and the loveseat better where we had them originally. You guys ready, or do you need a break?”)

But if proprioception were an actual superpower, you might be able to predict the future!! Somewhere in the jumble sale I laughingly call my memory, I recall hearing that we move our bodies a split-second before we consciously decide we are going to move our bodies. My hand is already reaching for the coffee cup a split second before I decide to reach for the coffee cup. So my body actually decided before my mind thought it decided. William James speculated about this, and I think science eventually proved it, and it comes up occasionally in discussions related to free will / determinism. So to my mind, proprioception becomes a superpower if you can predict next moves.

I’m getting over a cold. I was just thinking, “What if I had telekinesis, and whenever I sneezed, the cupboards blew open and my dishes fell out?” What would happen with superpowers if you get sick, or have nightmares, or a fever-induced delirium or something? (Another Marvel movie, probably, but what else?)

I love the fall, too! I grew up in New England, compared to which Virginia is but a pale imitation, but there’s an arboretum in the area with a gingko grove with about 300 gingko trees. The leaves turn a gorgeous, saturated golden yellow color which looks amazing against a deep blue sky. So my husband and I will definitely make time for that. I also want to put aside time to visit a family member who is ill. This is difficult, as they live about 300 miles away, and I have to plan for time off and call coverage for work. So I’m trying to figure which days I can take off in the next month or so, in between holiday travel and visitors. Perhaps another great superpower would be bilocation, like a Catholic saint!

You have the ability to hear a lot of details and sift through them and organize them in your mind in such a way that you see what is necessary, and what is superfluous. What a wonderful superpower to have! You are well-placed in your line of work. You called this “meta-structural awareness,” I’m thinking of it as “essentialism,” the ability to see what is essential.

I think the ability to subtract the superfluous is wonderful, and hard to come by. To remind myself to simplify, I printed and posted this equation at my desk, which comes from yet another source I don’t remember off the top of my head:


Agreed that when it comes to collaborative data and tracking lots of data, digital is best. I still keep a digital calendar for that reason, although most of my personal systems are paper-based these days. Back in the day, though, I had a Palm Pilot!

Have you been able to get outside during this beautiful fall weather? What are your favorite places to go to enjoy autumn?


Hi Anna,

I’ve spent just a little bit of time outside so far. It’s something I really should remedy– I know how important it is, but like eating well and moving often, it sometimes just doesn’t happen (and then I feel bad and wonder why). I don’t have a lot of places locally that I associated with “awesome for autumn”, which is sad because it is my favorite time of year and I do have those places for spring. There are a few spots within a 25 minute or so drive that have 2-4 mile hikes or walking paths that are all worth doing when I make the time. Most of them are wooded, and so perfectly pleasant this time of year. But none of them have the kind of “must be there each autumn” feel that a gingko grove would have.

Just around the corner from my house there’s a small field at the entrance of a park with a Zen Garden that I love in spring. There’s something about sitting there just as all the leaves are starting to come in when there’s a nice breeze that I really love. But for some reason, I don’t get the same feeling when I head there this time of year.

Right now, I’m wishing my super power was checking things off of my to do list. I feel like an old convertible with “Just Married” painted on the back and a trail of cans tied to my bumper. I have so many small things that are not individually difficult, and I find myself totally unmotivated to do them, yet the cumulative weight is clearly taking a toll. This is part of the cost of complexity– being responsible for many things, with lots of context switching is just plain hard. It feels like the kind of modern “we weren’t built for this” problem. I know the tools that help people in general, and I know the tools that have helped me in the past, but I just can’t… DO IT. There’s definitely a touch of burn out– I thought I was doing better on vacations and such this year, but it turns out I accumulated a fair amount of vacation time I didn’t take.

With November fast approaching, and two work trips and one “fun” trip coming up in that month, I’m going to try and maximize the cozy I can get for the remainder of fall. For me, this means heading to a pub/tavern type spot or a dark cocktail bar on Friday or Saturday. Sometimes with a friend, sometimes with a book. The key is getting out of my house and spending time somewhere dark, warm, and with a moderate background din. I have always needed third spaces, but never more than post-COVID, fully working from home, when the sun is down long before I stop typing away.


October 22, 2023


I love languages and have studied many. In seminary I got to study Hebrew. It’s the closest language to pure poetry that I’ve encountered. (Greek, on the other hand, is an excellent language if you want to be a lawyer; very precise.) I love organizing things and see organization as a spiritual practice; separating, defining, distinguishing things. I would agree that there is something holy about separation, making something distinct, having its own being. In spiritual matters there is always that tension between connection and separation. God in the first creation story in Genesis makes various aspects of beingness separate and distinct. Above our washer and dryer I used to have a cartoon that showed God whistling while separating the laundry, light from dark.

And speaking of holy separation: a separate home office with a door you can close is a wonderful thing! My office doesn’t have a door, but it’s at a far end of the house; not a lot of traffic except for my two office cats. However, it is around the corner from the kitchen, so I’ll hear important stuff like if a cellophane bag is crinkling and anyone’s making a yummy sound. Then I have to get up and see if somebody is snacking on something really good, that they ought to share with me. (The chocolate stash is often getting raided at these moments.)

I’ve shut off almost all notifications on my devices as well. And, it is bliss to be able to turn off my work phone at the end of the day.

Paper systems! I love those, too. Some years ago I got annoyed at keeping up with apps (and all their dependent devices, and environs, etc etc) and started moving more of my personal organizational processes to paper. It has helped immensely, not least because electronic devices have so many distractions at hand. Since it is my personal system, I have the liberty to be quirky about it. I can see where paper systems would be difficult with a large shared project like managing school finances. I used to be the network administrator for a medical records system with a practice that was transitioning from paper to electronic. If nothing else, paper sure takes up a ton of space, and is hard to back up. Did you see any advantages to the paper system, or anything it could do that was difficult to translate to an online process?

Super powers…. it is embarrassing to admit that the super power I’ve always wanted is to be physically coordinated. I don’t have an intuitive sense of where my body is in space, in relation to other things, which is why all of my sports are solo ones (yoga, hiking). I have to think daily puzzles through, like: “Anna is standing next to the car door with a tote bag, a backpack, a purse, and a coffee thermos that she may, or may not, have remembered to seal shut. It rained, so the ground is muddy. After she unlocks the car door, in what order should she place the bags inside, and place the coffee in the drink slot, without spilling something, dropping something in the mud, or injuring herself with hot coffee or an untimely door slam?” Yeah. It’s that bad.

The super power I have? I never lost the childlike ability to get absorbed in watching or looking at something. Bees entering and exiting a ground nest. Sunrise. Light patterns on the wall. Shadows on water. One of those tiny red mites traversing a board. Dust motes floating in sunlight. Patterns in flooring. Leaves blowing around in a breeze. People’s faces. Dogs, birds, plants, mushrooms. I can find something that I think is interesting or beautiful, anywhere I go. Sometimes it makes me late for things, though. I discovered it by getting in trouble for being “too slow,” or late. However: being a witness to the beauty in this world is my super power, and I will not renounce it. It is a wonderful way to go through life.

And, how about you? What is the super power you wish you had? And what is the one you do have, and how did you discover it?


Hi Anna,

It’s been a bit of a crazy month so I’m a little late to this one.

I think paper works great when you don’t have a system yet. Trying to solve new problems, or try things out, organizing something fresh. The phrase “blank canvas” sticks with us, though few of us are painters, for a reason. But paper really does fall down when collaborating with others or trying to learn from information. Paper can organize you, but paper is woefully inadequate as data. I think a core problem that folks have using software to do their work is that they mistake the needs of lots of organizations to generate data with their need to organize themselves. Quite often, digital systems are actually pretty poor at helping us organize ourselves, but they’re great at generating data that’s easy to share and summarize and learn from in larger groups.

Proprioception is such an interesting superpower choice. I can see how its lack impacts you day to day, but I wonder what a super version of proprioception would mean. Perhaps something like the Bene Gesserit and their precise control over their bodies leading to being great fighters but also things like controlling fertility and fighting against poisons or disease…

Being a keen observer and being able to watch — wow what a great power, and it makes sense given your current profession. As someone who has to consciously remind myself to watch and be in the moment, much like you have to think through the sequence of unburdening yourself as you enter the car, that seems like a great super power. A friend of mine has been making it her personal project to notice great service and then contact companies and managers to make sure they know that the people who helped them did a great job. It’s a simple thing I’m certain is leaving great feelings everywhere in her wake, but it all starts with even spending the time to notice a kindness. Noticing nature and the world around us is critical, but witnessing people may be all the more so. I find both challenging at times. Cis het white guy with a healthy dose of anxiety and main character syndrome over here.

I’ve always wanted telekinesis— the full kind that includes lifting oneself to fly, but importantly, the ability to physically control and manipulate the environment around me. It just seems to cover the full gambit of utility and fun. It’s an incredibly flexible power.

But my real power is the fast accumulation of moderate expertise. I am the type of person that can be placed in most rooms and listen to experts discuss a problem and quickly organize what’s happening, restate the problem more clearly for the folks in the room, and often even see steps to solutions. I can build up a knowledge of jargon quite fast. People often think I have significantly more experience and expertise with whatever it is I’m encountering, because I seem to be able to burrow to understanding fast. I think it’s a combination of systems and strategy thinking— I pretty quickly figure out what information is unimportant, and I often start to see the whys of things. Once you can see the structure and design of something, it’s fairly easy to follow to its conclusions. That’s the best I can describe it— maybe I’d call it something like “meta-structural awareness”. I can see what the human designers of any system were thinking, fast.

I’ve been traveling a lot this month, so I’ve missed a bit of my favorite time of year— the transition into fall. I’m looking forward to two weeks at home as we start to put on coats and sweaters and the air gets a little crisp. I need to create some space over the next couple of weeks to spend time outside. It’s been too chaotic lately, and I don’t want to miss one of the few falls I get to experience in my life. What’s something you should be putting aside time for right now?


October 9, 2023

Dear Jason,

I was in my thirties when the year 2000 came along, so I spent much of my childhood and young adulthood writing letters (phone calls being very expensive, and the proto-internet being unavailable to ordinary mortals). With phone calls, texts, and interactions on social media, communication is a constant back-and-forth. A letter is more like an essay. Yes, you are writing to someone else, but you can more fully unwind your thoughts without interruption. So I think the answer to whether one is having conversations with others or with oneself, when it comes to letters, is “yes.”

Letters are the one form of communication that allows you to finish your sentences. To communicate in paragraphs. And to ponder, over days or weeks, or longer even, what was said and what it sparks in you to say. I don’t think there really is a communications substitute for letters.

I love your comparison with pinning down a job description as being similar to describing the ocean as “blue.” I like the phrase “areas of responsibility,” as well. Perhaps as I get used to my new line of work, I will think of it in terms of areas of responsibility.

And this leads me to your questions about how to manage working with people who are going through serious challenges, while preserving my own soul; as well as shifting to being nondenominational, and what that has done to my tool kit.

The nondenominational aspect is actually more comfortable for me, just because my own personal and familial spiritual and religious background is pretty mixed. I think wisdom traditions like religions tend to hit on the same set of practices because we are all still human beings. I think the relationship of religion to the spiritual aspect of reality, is like the relationship of language to the physical aspect of reality. Religions are human-made modes for articulating and interacting with spiritual realities. So I’m “fluent” in some religious languages, and have a few little travel phrases with others. For patients who are connected with a faith community, my job is to support that, not undermine it. For patients who no longer feel connected to those traditions, or who want nothing to do with those traditions, we can often still do something like meditate together. At heart, I’m a pluralist. One of my favorite quotes from Frederick Buechner (?I think?) is that when it comes to the divine, we are like oysters at a ballet: we might dimly sense light and vibrations and movement, but we really don’t understand what’s going on.

Now, to soul preservation in emotionally intense environments… The rabbi, therapist, and organizational leadership theorist Edwin Friedman wrote brilliant and difficult books about leadership in congregations, based on family systems theory. I honestly think anyone who is in leadership anywhere, ought to read Friedman’s A Failure of Nerve: Leadership in the Age of the Quick Fix. It’s strange, provocative, filled with insights I haven’t seen elsewhere (so many pop culture leadership books are shallow or insular or both). I highlighted my first copy so much I had to buy another one.

It is nothing like any other leadership book I’ve read (and I have endured many). If you decide to read it, abandon your expectations and just experience it, like you would experience meeting a neighbor who was a true eccentric.

One of Friedman’s themes is the importance of self-differentiation for leaders, and how that affects the flow of anxiety through the group (whether it be family, congregation, company, whatever).

The core to healthy leadership in groups like congregations, which have high expectations of “meshing” emotionally with their leaders, and which also have high anxieties – is practicing self-differentiation, and practicing what Friedman called “non-anxious presence” (and what I, and many others call, less anxious presence). A leader who self-differentiates, who is non-anxious when others are anxious, can effect profound change in group dynamics over time. (I did it in my parish; it took several years.)

What does that mean in plain English? To my mind, it means that you know who you are, you know what you are about, you know what is yours to do, and you know what is not yours to do.

Can I be emotionally present with people who are anxious, grieving, in distress, without absorbing their pain and taking it with me to my next visit, or into my own soul? Friedman says, if we’re really intentional and practice a lot, we can self-differentiate and be a non-anxious presence maaaaybe 70% of the time.

I use what I call spiritual disciplines to train myself to self-differentiate, and to be a non-anxious (or less anxious) presence in emotionally difficult situations. Most of these practices might be called self-care practices in the secular world.

I keep a rule of life (what I call on one of my blogs a “personal framework,” because it doesn’t have to be religious), which I try to reread once a week to remind myself of what I am about, in this world. I journal, pray, and do what we jokingly call “speed yoga” each morning, I shut off my phone when the work day is over, I attend church (relaxing not to have to lead the service any more!), I get out for walks, I keep in touch with friends and family. I consider my home to be my sanctuary, and I make it a pleasant and relaxing place to be. I am getting serious again about practicing a real personal Sabbath, a day of rest from Friday night through Saturday. (And not what Eugene Peterson called a “bastardized Sabbath,” where I’m running around doing errands all day, which is what I fell back into.) I also use rituals.

It seems a number of people in hospice work use rituals. A nun I met who was also a chaplain would, when she was washing her hands between visits, envision all the sadness from the previous visit washing down the drain, so she didn’t take it to the next visit, or take it home with her. I know a social worker who discreetly wipes her feet on the mat before she goes in to a home (she is wiping away all of her assumptions and agenda, to be open to what will happen), and who wipes her feet (again, discreetly) as she leaves the house, so that that household’s problems stay there and don’t travel with her to other visits, or to her own home.

I ritually wipe my feet before I get in my car, and on a low stone in the alleyway before I walk into my house. I also ring a meditation bell three times at the end of each work day, which signals to me that my work is done for the day, and I need not think about it any more.

Rituals are fantastic. They communicate to the body as well as the mind, so you truly can let something go, and relax.

…And nobody likes to watch Young Frankenstein with my husband and me, because we quote along with the whole movie 😂

“Put… the candle…. BACK!”

A work trip to Jamaica? Wow, that sounds intriguing! Is this a conference? Have you been to Jamaica before? (I’ve never been, but would like to go.)

What do you do to balance your work life and your home life? How do you leave space and responsibility for YOUR soul (as you put it so well), with a job that can be done – as I am assuming – remotely?

Best regards,



There is a practice in Judaism when returning from a funeral. Before entering your home, you perform a ritualistic washing of the hands. What is the purpose of this? Much of early Judaism was obsessed with purity. The mikveh was a central part of life. It could be seen as a public health measure to wash after being in the presence of remains. But I think it is not merely about physical or spiritual cleanliness. I think the washing is much like the rituals you encounter in hospice workers– we are meant to take a moment and ensure a separation. The funeral was then, our home will be now. The Hebrew word for “holy” means “separate”– that which is holy is separate and distinct; it is holy by being apart. The Sabbath is holy through separation from the rest of the week.

I think learning to be self-differentiated, to be separate, while not being distant is a challenge of leadership. We need to practice deep empathy without being overrun and controlled by it. Empathy doesn’t require that we absorb the anxieties of those we are leading. But the way most of us know how to practice empathy naturally leads to some… leakage. We need moments to flush and seal.

It could be worse, it could be raining.

This was my first time in Jamaica. We’re doing some work to help modernize their school financial management. Quite a lot is still run on paper. It’s a small project for now that might grow significantly. I got to spend some time in a a rural high school reviewing their systems and working with several government agencies. It was a wonderful learning experience and a real stretch for me to apply the skills and knowledge I’ve built up for over a decade in a completely different context.

I do work fully remotely. In this same job, which was always remote-friendly, I started remote, then moved to Baltimore and went into the office for a few years, and during/post-COVID we went fully remote. Remote work was much harder when I lived in Providence. First, we had a one bedroom apartment so my office was the bedroom. Second, I was flying to Baltimore 2-3 times a month in addition to my regular work travel. Things are much better now that we have a large enough house that I have my own office with a door to close.

But separation is still hard, because I work across all of the North American timezones and I’m a bit of a workaholic. So there’s a few things I have to do. For starters, I schedule all of my time at the gym (small group training, with 1 trainer to up to 6 people max) and volleyball each week. I find that if it’s on my calendar, I go. And physical activity is especially helpful for me to achieve separation. It’s hard to think about and be consumed by work while playing a team sport especially.

I struggle sometimes because my work is at a computer, and many of my hobbies are also at a computer. So I only read on my Kindle or with physical books– my iPad would lead me right back to work. I also struggle because I work with my best friend, which is mostly a blessing but occasionally can make it hard to disconnect from work stress and anxiety. Especially when something is big enough to impact us both, it’s a major support that neither of us can lean on because it’ll just lead to a bit of spiraling.

I aggressively use Apple’s new Focus Modes. I broadly let very few things notify me, but I let even less post 6pm or on weekends when I turn on “Down Time” – it hides all my apps for a few useful widgets and reduces who can reach me to just a handful of people. Otherwise, 6pm or weekends means I have to go seek something out for it to get my attention. I’ve found this quite helpful, even if I still impulsively open Slack a few times a day.

This weekend I went to a bar and magic show. One of the tricks involved guessing the super power that people wished they had. What super power have you always wanted? And more importantly, what is your actual super power? How did you discover it?


October 4, 2023

This month I’m corresponding with Anna Havron

Dear Jason,

I’m wondering about your thoughts on this Letters project, now that it has been several months. Do you think of this project as a form of community, or does it feel more like a series of separate conversations? What, if anything, has surprised you about doing this?

Probably the biggest thing going on in my life right now is my career shift in moving from being a parish pastor to being a hospice chaplain. And since it’s both a new job and a career shift, I’m trying to figure out what it is, exactly, that chaplains do.

Even an academic who studies them said that nobody seemed to have an agreed-upon definition. Spirituality is, after all, difficult to define; and so defining spiritual care work is even harder.

Years ago, I did some training for chaplaincy work at a hospital. My supervisor said, “Chaplains are the only people wearing a hospital badge that the patient can refuse to see. Everyone else, the patient has to put up with. Don’t underestimate the healing power for someone being able to kick you out of the room.” That voluntary part is important. The medical people, they have to see. Chaplains are optional. I like to think that I’ve empowered a few people that way.

In reading up again about chaplaincy work, I’ve come across hand-wavy phrases like “spiritual clinician” (a healthcare chaplain educator wrote that), and “secular priest.” Healthcare chaplains are supposed to be able to work with people of any faith, or no faith. But Wendy Cadge, the social scientist, said that no one even agreed on how to define “spirituality,” which is kind of a problem, when chaplains are considered to be responsible for providing spiritual care. Side note: In her book Paging God, a study of hospital chaplains, Cadge outlined the difficulties of designing chapels that are supposed to be welcoming to all.

The lead chaplain where I work now, however, said something that resonated for me.

He said that the thing with medical care is it’s necessarily focused on the mechanics of the physical body. But at interdisciplinary team meetings, he saw himself as the advocate for the whole person. “I am the voice at the table for the soul,” he said.

Or, if you don’t like the word “soul,” I think “inner life,” or “the person” (as opposed to “the patient”) might be good words.

See? So hard to define.

The other thing that clicked for me was hearing a nurse say, “I did not think that existential crises could affect people’s physical health, until I came here.” Some of what I do, is to explore existential crises with people.

That part of the work, driving around to people’s homes, or going to see them at assisted living facilities, visiting with people and learning some of the topography of their inner lives, is work I have done for many years. I did it in the parish when I was a pastor.

What you do, is you look, and especially you listen. What is important to this person? What are the pictures on the wall? What objects are they keeping closest to them? What keeps coming up in conversation? Where does it hurt? What are they proud of? What is unhealed? What are they fighting? What have they made their peace with? What do they wish had been different? What has meaning for them? What seems hollow now?

Some good questions someone asked of me recently: What have you lost? What remains? What are the possibilities before you, right now?

So I listen for those things, if the person can communicate verbally.

If they can’t communicate verbally, if they are so cloaked in dementia or withdrawing as they are dying, I’m still listening. But I listen in a different way. I think of it, as attuning myself with them. You have to be receptive to their presence.

The lead chaplain, who has been doing this for many years, said it is wise to assume that people who appear non-responsive can hear and understand everything. He has known more than one person who awakened from a coma and was able to repeat overheard conversations. I have known people with dementia who were able, briefly, to communicate with sharpness and clarity. But that’s rare. When I talk to people who are non-responsive I speak with the assumption that on a deep level, they can hear me. When I am with someone, if it seems right, I might offer prayer or silent meditation. I’m surprised by how many people have reached out their hand toward mine. Many people get very little human touch.

So that is partly what I do on weekdays now.

But a lot of what I do on weekdays is to get out a laptop and document things into our healthcare application, so that Medicare and the administrative people at the hospice know what it is that I have been doing.

Whatever it is, exactly, that I do, do.1

The driving around, the documentation, and the meetings take more time than the visits.

So I’m still working on understanding what my job is. I would go on to say that nobody understands what anybody else’s job is, in general.

Ask most people outside the field what they think a teacher does all day, or a software engineer, or a forest ranger, or a CEO, and quite often their ideas are wildly different from the lived reality of what it is, to do that work.

What is it that people think you do at your job, and what is it, that you actually do?

Best regards,


Hi Anna,

Thanks for joining me on the Letters journey. And thank you for putting a wonderful Young Frankenstein reference — it’s one of those special movies I share with my father.

This project has been harder than I expected. It’s harder to keep up with, for me and my correspondents. Certainly harder than I expected. Some of that is life— I’m currently writing this from Jamaica on a work trip there— and some of that is wanting to have time to think about what people wrote. In that sense, Letters has been a success. Sometimes I respond right away, sometimes I wait a few days. But I almost always think about each letter for the full week or two between correspondence. I think about the ideas that are brought up, the language, and my own responses. I often wish I was actually having a direct, immediate conversation because of how much feels left unsaid. I’m often glad that I’m not having that immediate conversation that I can draw out until there’s nothing left, and instead get to savor a new conversation when time has passed and we have to move on to new and interesting ideas.

But I don’t feel the letters themselves have created a community or are speaking to each other. I think sometimes folks respond to how other have written and the months they liked the most. But they’re still separate conversations.


I’m not sure if I’m having separate conversations. From my view point, writing these letters feels very similar from week to week. I often wonder if my own responses could be read in isolation and if they would work as a stand alone text. Am I actually having conversations or am I just writing to myself? I’m not always sure.

I can commiserate with how hard it is to define your work, especially as you change roles. My job is hard to explain, and I don’t really have one job. I alternate from executive responsibilities to manager responsibilities to individual contributor responsibilities regularly. I am at once doing “product management”, which is hard to explain, and managing development teams, and focusing on data integration and analysis. Sometimes I’m a researcher, sometimes I’m a software developer. Sometimes I’m a coach or a mentor or a manager. Sometimes I’m trying to run a company. Sometimes I’m trying to be entrepreneurial in discovering future avenues for growth. Sometimes I support our customers directly. That can be detailed instructions on “how to use our product” or problem solving or process engineering or consulting.

I think jobs are hard to describe because they are so often so many things at once. Our areas of responsibility describe what we do about as well as “blue” describes the ocean. It’s not wrong, but it’s far from enough.

How do you handle working with people who are experiencing some of the most difficult times in their life? How do you preserve yourself knowing that if you’re present, it means that things are not going well. How do you leave space and responsibility for your own soul?

I’m also curious about the challenges of being non-denominational. Do you feel that this limits the tools you have to comfort those in need?


  1. Which reminds me, October; time to re-watch Young Frankenstein. “FrankenSHTEEN!” ↩︎

October 1, 2023

Hi Jason,

I totally agree with you on the “more money helps, but don’t expect much” messaging being both a) true and b) not a great story to tell! And I also appreciate your point about the sheer number of school boards not only contributing to the problem of just having too many elected positions, but that there is not enough talent to go around. I suspect that Americans react to poor governance by adding even more oversight (further diluting the talent pool!) rather than cutting the number of elected positions, leading to even worse governance and on and on in a negative feedback loop.

Since I may only have time for one more of your responses, I did want to get your thoughts on mass transit given your interest there. You may know this, but for outside readers: I’ve commuted via MARC train to DC for nearly 10 years. When I started working in DC, that was 4 days a week in the DC office (1 WFH), gradually moving to 3 days a week (2 WFH), then the pandemic (full WFH), and over the past 18 months, roughly 1 day a week in office. Just this week, I received the announcement that our DC office would close and I will be full-time WFH beginning in December. Remote work is its own interesting issue, though I’ll briefly say that I worked remotely for Brown University while working in Iowa for nearly 5 years in 2009-14, and it was really tough. However, the changes in technology, company acceptance, and the sheer percentage of remote co-workers has really made a tremendous positive difference in my work life.

OK, so back to mass transit. I see, on the one hand, mass transit enthusiasts (with whom I sympathize) discuss all the benefits of robust options, and being clear about the need for increased transit frequency to encourage more riders. I read recently about the potential revival of the Red Line in Baltimore, which would finally connect the western and eastern regions of the metro area, which have been significantly underserved for decades. On the other hand, I look at MARC ridership numbers since 2016, and I have significant concerns about the continued viability of commuter rail in the region absent massive infusions of cash. Going from an average of roughly 800k riders per month pre-pandemic to a post-pandemic high of 338k in May 2023 is alarming. I’ll admit that the last time I rode MARC this month had higher ridership than typical, but let’s be really optimistic and say ridership rebounds to 500k per month. A drop of 40% doesn’t seem sustainable to me, but I see a disconnect between transit advocates and the numbers (and my personal experience). MARC trains aren’t infrequent, and I’m not sure there’s capacity on that line, which serves Amtrak as well, to add more trains. MARC has also, for some reason, stopped running their electrified trains and is all-diesel, which is bad both environmentally and travel time-wise. What’s going to happen when Maryland runs out of pandemic aid and has a budget crunch?

I don’t want to overinterpret my experience, though. Perhaps commuter rail’s ridership issues are exacerbated by having ridership that is more likely to shift to remote work. It also appears the federal workforce, compared to other sectors, has disproportionately allowed WFH, and federal workers make up a significant percentage of MARC ridership. Is the future about more investment in intra-city (as opposed to commuter or long-distance) mass transit? Would love your thoughts on this (but please don’t use the word Maglev or I will cry).

Best, Jacob

Hi Jacob

It’s interesting how important feedback loops are in building systems. We see the strains of unexpected pathways all across our current government structure.

I suspect that Americans react to poor governance by adding even more oversight (further diluting the talent pool!) rather than cutting the number of elected positions, leading to even worse governance and on and on in a negative feedback loop.

This is definitely a part of what’s going on. Our inability to build infrastructure is, of course, about a reaction to horrible abuses by government and industry, followed by tons of rules and procedures to avoid those problems, generating new problems.

Proceduralism and legalism are the poor tools we’re strangled by as they act as restraints on abuse.

So let’s talk rail.

Here’s my overall take– moving people with cars first and primarily is a mistake. Moving people with trains works under certain circumstances, which the US largely fails to create. Moving away from electrification with MARC rolling stock is a great example. Instead of electrifying the few, infrequent spots that needed diesel, MARC invested in worse trains that lead to worse speeds and worse service. We standardized on the wrong thing.

I think commuter rail in Baltimore is largely doomed. The distance is too short, and the trains are far too infrequent and too slow. MARC has never had sufficient evening or weekday service. It’s never had service not focused on the heavy commute at 9 and 5. It’s got too many stops on rolling stock that’s far too slow. Baltimore to DC is possible with conventional rail in 25 minutes. It should be the case that trains have been running for decades by now, departing at :00 and :30 on the clock face and getting to DC in 25 minutes. But it hasn’t and it has broken transit. It’s helped to fuel suburban sprawl around DC. It’s just a mess. And of course, Baltimore City itself doesn’t help by having very poor access by public transit to Baltimore Penn. I don’t think we’ll see it “work” in our lifetimes the way that it should. But I do think we should invest anyway, because I think it just takes decades of investment to undo decades of supporting car culture.

Baltimore itself should be focused almost entirely on building better transit within Baltimore and the parts of Baltimore County that should be Baltimore City, except racism. I don’t think that relying on the DC connection and commute is a strong strategy for Baltimore. That’s not how I feel about Providence and Boston, meanwhile– Providence needs the strongest possible connection to Boston to thrive– but Baltimore both stands better on its own with a stronger metro area and has secondary connections to Philadelphia and New York. We should let Amtrak get its shit together on high speed rail along the current alignments in the Northeast Corridor and benefit from that. MARC just needs EMUs and regular service. Baltimore needs to be far less reliant on cars and focus on quality of life.

I once did some back of the envelope math that determined that simply by using bad rolling stock and having 3-4 stops that are largely empty in completely empty places south of the city, the Baltimore Light Rail takes 20-25 extra minutes to get from BWI to the Convention Center. The Nursery Road Light Rail stop makes the Boston suburbs look like transit-oriented development.

I’m pretty concerned about all the Red Line proposals right now. All of the routes have some significant curves that will impact speed which impacts frequency. The vision for tunneling seems to make some tough choices. I’m not convinced Maryland knows how to manage a project like this and do that kind of tunneling inexpensively. Bus rapid transit seems like a terrible idea, but I don’t see the red line as proposed connecting the Light Rail and Subway in such a way that makes for a coherent transit system. It’s clearly a necessary step, and I’m still mad we’re at least a decade behind now, but I also think it’s still too small with no plan for follow through to have the impact we need. I find myself agreeing with some of the advocacy saying that light rail is not enough – we should instead use heavy rail like the subway and MARC, especially with two explicit station connections to the MARC, and save on rolling stock orders and maintenance.

I’d like to see a bigger plan. Could Baltimore push for a better North-South corridor (studies are ongoing, probably should be along Greenmount to York up to Towson, in my opinion) at the same time? Could we explicitly staff up our transit agencies with experts on cut-and-cover tunnels and become the only place on the East Coast that knows how to build with Spanish costs? Could we then export this expertise as part of our investment?

It’s all going to be too expensive and take too long because it’s too small. More is more with transit, but we’re not willing to do that kind of thinking.

That said, if we don’t force denser zoning and construction out at CMS, Security Square, SSA, and the I-70 Park and Ride I’ll be furious. No more trains to parking lots in the County that just lead to people complaining that people from the city can access them.

Thanks for your letters this September!


September 21, 2023

Hi Jason,

I agree that the awards in speculative fiction are great - they’ve been helpful to me in exploring genres that I don’t have a lot of experience with. The Hugo Awards, for example, led me to N.K. Jemisin, Arkady Martine, and Cixin Liu, all of whom I’ve enjoyed. Interestingly, I’ve found that the big literary fiction awards - Pulitzer, National Book Award, Booker Prize - have been misaligned to my taste in fiction. I’m not entirely sure why that’s happened (it’s probably just me getting old). I’m also a reader who will endure through a book I’m not enjoying, particularly if it’s a “classic.” I do need to wean myself from the notion of a canon (the perils of majoring in English!), though there have been books where the struggle has been productive for me and I’m glad I persisted to the end. If only I knew which challenging books would result in that feeling! I’m also with you on a significant chunk of non-fiction books being more well-suited to a long-form article, particularly books that take on current events. It’s unfortunate that there’s not a strong market for non-fiction books too long for a magazine but too short for a full-length book, a sort of non-fiction novella category.

You really had to poke the bear by mentioning school boards. That said, I’ll start with the positives. I truly believe that the vast majority of school board members have good intentions. This is almost exclusively an unpaid, volunteer position. Don’t get me wrong, volunteers are essential. So many of our institutions rely on enthusiastic amateur volunteers to keep them running. This is certainly true in the institutions to which I belong, whether I’m in an active role like co-chairing a social justice committee at my synagogue or leading my neighborhood HOA, or primarily a passive member, like my kids’ schools’ PTAs or community sports leagues. There’s an assumption with these roles that a) everyone is acting with good intentions and b) the complexity of the role/institution is low enough that an amateur can do it without payment. School districts are…not that. I don’t have to tell you about the system complexity and financial complexity of school districts. These are not systems that should be overseen by well-meaning amateurs. However, we have this historical legacy of elected school boards, so what to do? I think the best option would be to, when possible, assign oversight of school districts to elected executives like mayors and county executives. Here in Baltimore County there is clear frustration from the county executive that he has little control over the largest budget item. This also ties into the concern that there are too many elected positions in the United States, which creates policy choke points and low-information/low turnout decisions by the public. This Atlantic piece bluntly states it: Americans Vote Too Much. Alas, a key hurdle here is that a lot of people believe that additional elected positions lead to better, more considered policy decisions, rather than (in my view) confusion about accountability and multiple choke points that stifle good decision-making. Recent attempts to streamline decision-making, like mayoral-led school districts, seem to have fallen out of favor, perhaps due to the unpopular decisions that many mayor-led systems had to make (e.g., school closures).

How do you feel about school boards? Other problems I failed to identify or different ways of looking at them?

Sticking with school governance, I’ve been wondering for the past two years about the roughly $190 billion in federal COVID relief funding to schools, which according to this Chalkbeat article works out to about $4,000 per student. While I know there were certain required set-asides to address learning loss and a few prohibitions, it seemed to me pretty much a blank check. I’ve struggled to find good information on how the funds are being spent or any impact on student outcomes, which is concerning! So I’ll end with a question for you: What do you think will be the long-term impact of the biggest one time infusion of funding into K-12 American education?


Hi Jacob,

I find all of the non-speculative fiction awards similarly frustrating. They’re just not the kind of strong indicator I might like a book that I get from the Hugos or Nebulas. I used to believe in finishing any book I have started, but lately, I’ve been more willing to put something down. Sometimes it’s just not the right time, sometimes it’s just not the right book. I can always go for other attempts, but if a book just stops me in my tracks, it’s time to move on. I’d rather be reading than not reading because of some sense that I should always finish my book.

I think that assumption of complexity– and that an amateur can contribute effectively– permeates huge portions of our American system. A lot of “small d” democracy and volunteerism is built on visions of a society of small towns centered around just a few institutions everyone took part in. That’s why we vote too much (I also loved that article), but it’s also why we have some bad assumptions. I think by ceding control to volunteer amateurs, elected or not (and they’re barely elected), we signal that it is possible for amateurs to do a good job!

I think a core problem with the municipal control piece is that most municipalities, organizationally, are less complex than schools. The web of local, state, and federal funds, statutory requirements, and complexity of service delivery means that most school operations are simply harder than running county or municipal governments. So while I like moving the elected accountability in some sense, from an organizational perspective, the municipal functions would probably be more easily absorbed by the school systems than the other way around. There’s this huge frustration among mayors and county executives and city councils that the schools are a “black hole”– but in truth, the schools are more transparent, have more sophisticated practices, and have more difficult jobs to do– at least in my experience.

I think my core issue with school governance, and boards in general, is less that they exist and more that there are far too many. I think it’s probably about reasonable for Maryland to have county level boards and districts. I think it’s a disaster that Nassau County, New York is over 50 districts or that Rhode Island has 39. I’d like to see consolidation of districts, at least from a governance stand point, and I’d like to see more of their governance move up to the states. There’s no current state capacity, but it’s absolutely not to our advantage that we have so much variation in our school system. The only thing having lots of school districts truly guarantees is inequitable funding of schools, and that’s not the kind of variance worth chasing. But there’s also just not enough talent out there for 15,000 school boards and 15,000 superintendents and central offices. Regional service providers covering some core operations don’t go far enough.

I do think that ESSER was pretty much a blank check by design, and yet, I also think it will have virtually no impact. The data how dollars were spent will, I think, become clear in about 12 months. We’re just about to the end, which means the expenditures should all have been recorded and can be analyzed. We do an “ok” job of this on the Relief Funds tab for districts on the Arizona School Finance Portal – we decided to show the spending on relief funds by “function” code in Arizona. For the most part, it’s a pretty good indicator on the school district activities. We do have the data by object (the “what”) as well.

Ultimately, districts with lots of money largely couldn’t help themselves and hired staff, from what I could see. Some of those staff are just going to go away, some they struggled to hire in the first place, and some may stick around in states like Maryland where additional state funding is sufficiently backfilling ESSER investments. Those that received less funding were more likely, it seems to me, to use it for backlogged capital expenses where possible. Neither of these were necessarily bad uses of funds, but I don’t think that we will really see much impact from any funding that isn’t permanent. Districts just can’t plan to restructure what they do and how without reliable, recurring revenue. And I don’t think there’s a whole lot we can do that is one time, on the margin, with persisting impacts.

This is all conjecture just based on conversations I’ve been having. It’s strange to be on the side of “more money helps” while also saying “like this, don’t expect much”. It’s a horrific position to defend.

I guess this is my pessimistic prediction: the capital projects backlog will continue to be long, but things will be less bad than they would have been. The current interest rate environment is going to make it even harder to chip away at things like build quality, and the ESSER funding may delay that being a total disaster long enough for interest rates to decline a bit.

Sorry for the late response! We had our all-company, in-person meeting last week at the Belvedere followed by our Education Finance Summit at the Maryland Center for History and Culture. I flew up to NY directly from the conference for Rosh Hashanah at my parents and… things got away from me.

Looking forward to your next letter.


September 7, 2023

This month I’m corresponding with Jacob Mishook


I hope you had a great Labor Day weekend. When we originally decided on corresponding in September, you mentioned it would be timely given the start of the school year and that we’ve both worked in education policy. So in keeping with that theme, I’ll start with the biggest education policy story of the last year, the “science of reading,” popularized by the “Sold a Story” podcast. I’m not an early literacy expert so I can’t comment on the merits of the argument of the pendulum swing back towards phonics - though my layperson reaction was that it is compelling - but I do have a few observations:

  • In the twenty-plus years I’ve been in the education policy field, I don’t think I’ve ever seen a reaction to a single piece of research-influenced journalism larger than “Sold a Story” on early literacy policy. I’ve seen various numbers out there, but at the low-end at least 18 states have considered “science of reading” bills in the last year. In a field as frankly slow-moving as education policy, this is truly exceptional, and makes me wonder how it happened. A compelling and lay-friendly story, sure, but that can’t totally explain it (there’s a lot of good journalism out there). I could spin up a “just-so” story about parents seeing their kids struggle during the pandemic, but that seems incomplete as well. Any ideas here?
  • At the same time, the act of reading seems both larger and smaller in American culture now. Larger, of course, due to recent laws restricting what young people can read in their schools and libraries. But also smaller - the National Endowment for the Arts regularly puts out fascinating studies of Americans’ reading habits. The most recent one, from 2020 (using 2017 survey data) focused on the ways in which people read books (e.g., print, electronic, audio). And that’s certainly interesting (as an aside, I’m a dedicated print reader, and do not have the type of concentration needed to listen to audiobooks). But the broader reading trend seems disheartening:

Line chart showing the steady decline in readying for those under 64 and a small increase for those over 65.

I assume reading is falling victim to the crowded landscape of leisure activities, but maybe a real policy focus on reading over time will reverse the trend?

  • Which brings me to a (happier) last point - you and I are enthusiastic readers, though perusing our respective Goodreads activities, we don’t have a lot of overlap. At the risk of some overgeneralization, you appear to have a clear preference for speculative fiction, while I’m maybe more of a magpie but with a tilt towards (hate this but for lack of a better term) “literary” fiction. If my favorite pastime is reading, my second favorite might be reading book reviews, which leads me in a lot of different directions and also a huge pile of unread library books. How do you decide what to read? When and how do you find time to read? Are there books or genres you’d want to read more in depth if you had more time?


Hi Jacob,

I had a great Labor Day Weekend. Although it was too hot here to be outside (which has been my general feeling about Baltimore since about June 1), I took a little time off from work for a “staycation” of sorts. That meant doing a little bit of clean up/clean out at home and heading to Oppenheimer on Tuesday for a solid 3 hours in air conditioning when no one at work could reach me even if they tried on my day off.

It is remarkable how fast “Sold a Story” had an impact– especially since this was one of the least well-kept secrets in education policy… since I started this work in 2009/2010? I remember reading Daniel Willingham on learning styles and reading all the way back then and thinking it was wild how far practice had strayed from evidence. I think like many odd things in the world today, the answer is probably something like “It’s COVID, stupid,” just as you suspect. I’m not sure I would actually attach it to parents seeing their kids struggle. Instead, I think it probably has more to do with the broader breakdown in trust. Education has long been plagued by everyone loving their teachers, but thinking teachers in general are not great. Their school is great, but schools in general, not so much. I think pure enthusiasm from an adult that parents and families trusted and liked translated into belief in their expertise and capability. With so many districts failing to meet parent expectations, whether that meant opening or closing, I think that trust was just broken. We were ripe for a story that politicians of all ideologies could get behind that said, “Schools are doing something wrong that we all agree is wrong.” In so many ways, bad reading instruction was just super popular reading instruction. It was instruction teachers enjoyed, and we just reached the point where that was far from enough for families.

I’m not sure what to make of reading trends. On the one hand, looks bad! On the other hand, there’s this additional culture zeitgeist around things like “booktok” and the seeming staying power of independent booksellers. There’s also this whole world of self-publishing on Amazon and what that has meant or not. Books feel like they’re in a weird place, from a production and business model sense, and I wonder if we have to be careful about “books” versus “reading”. I really like long form, non-serialized storytelling. I like movies over most television most of the time. And I like books. I don’t think the novel is dead, but I wonder if what we’re seeing is a business that is struggling to pivot and deliver what its customers want in a world where culture is changing so fast.

I have a firm rule in my own reading– I try and stay away from most non-fiction. I can enjoy non-fiction, but there are a couple of hang ups I have. First, I find that almost every non-fiction book contains 90% of its value in 10% of its page count. I find myself constantly wishing that books were just longer form articles or monographs or sometimes even blog posts. The other reason is because I read non-fiction all day long every day. I read news magazine articles, blog posts, newspaper articles, and listen to many non-fiction podcasts. I’m awash in non-fiction in all my other media consumption. So there’s a balancing act there as well. I find books to be the wrong form for most non-fiction, and I find myself lacking in fiction every where else I consume new media.

Deciding what to read then is a bit more tough. I do heavily stick to science fiction and fantasy. I’m fan of the term “speculative fiction” because that’s where most of my interest lies. I find that it’s helpful to have unrealistic elements in a story as an animating mechanism. It’s not so much about having an exciting story– I read plenty of philosophical, non-exciting stuff– but instead, it’s that I find it easier to understand the message or ideas of a book when they’re a bit more plain. The point of most good speculative fiction is to manipulate the world and have characters that respond in realistic ways to a world with those rules. Playing with the rules makes the ideas more concrete and obvious to me. Reading literary fiction, which I do enjoy, I often find myself unsure of what an author is saying with their work. Literary fiction for me is all plot. I can’t penetrate the message. I don’t suffer that same deficiency with speculative fiction.

One thing that’s great in science fiction and fantasy is I can track some of the key awards– the Hugos, Nebulas, Locus, etc– and pick up the nominees I have not already read. I also then follow down the path of certain authors as well. I’m not that big into book reviews, but I imagine I could be. I just haven’t really found a spoiler free source that resonates with my own taste. Perhaps the closest thing is a nerdy pop-culture podcast called The Incomparable, which has book club episodes. Sometimes I just look at the “what are we reading?” notes at the end of episodes that have nothing to do with the book discussed and choose things at random.

If I had more time, I probably would read slightly more non-fiction, but quite judiciously. I would have to work harder to find the books that earn their page count. And I also wish I read more short story collections.

I didn’t answer everything, because we would be going on for quite some time, but I’m glad we’ve got September up and running and are discussing reading.

I’ll throw you something that haunts me that you can choose to respond to or not in your next letter– what can be done about school boards? The situation right now is, not good, to say the least.


September 1, 2023

Hi Jason,

At this point Claire and I have sworn a blood oath that we’ll never move again. I struggle to think of other events that so thoroughly expose you to the ways in which your society is seemingly held together with little more than string and wishes…

I think that’s why, as well as attempting to integrate physical note-taking into my life, I have spent a lot of energy thinking about it; I’m attempting to improve my existing invisible armour [sic] for surviving the actions of other people, whilst building whole new defensive mechanisms. My theory: To improve the infrastructure that is my thinking and feeling will inevitably negate at least some of the negative influences of “the crowd”.

Everything you say about the effect of physical working, as if it is tied closely to your ability to take action, is how I feel. When my environment is mostly ok, if not good, then sure enough the digital workspace is reliable; however, when enough “life happens” events occur the physical systems are both a safety net and reminder that I should rely on them in more than just emergency situations. The Analog system has definitely been influential in this way for me as well, though I have yet to begin using the Sidekick.

I like to use outline software — Jess Grosjean’s Bike, specifically — for planning or just dumping my thoughts quickly and have come to use it just for work. Beyond that I can only recall mind mapping being useful when working with other people and haven’t had the experience of trying to do that with software; it’s safe to say I’m doubtful that the experience would be anywhere near good enough to justify the effort involved.

When we moved last it was from the coast to a land-locked region and dealing with the change in air type has been difficult. Coastal air is ridiculously good wherever I’ve been across these isles and the current move will get us back there; it’s the only item on the short list of conditions for moving so soon that was likely to be met… and then of course the unlikely ones fell into place all at once. Life happens, as it were.

Sorry for the late response, again. It’s annoying how much I’ve enjoyed this, though, given the whole life thing happening. I’d happily do this again, once we’re better settled and stuff.


Hi Simon,

I’ve been thinking a lot about “air” myself lately. It somewhat came up in the last letter, but I find myself reflecting more and more on my physical environment and the weather I’m experiencing.

We spent last winter in Mexico City. It was a weird time in my life– work was still quite busy for both of us and I was recovering from surgery. I didn’t really feel physically up for much for some time, and I got severe food poisoning twice. It’s unclear to me how much of that was being in a new country with new foods or just my whole gut being a mess 8 weeks after an appendectomy and some pretty heavy anti-biotics.

We were spending our time somewhere built for indoor-outdoor living during its worst weather– occasionally in the 50s (low 10s C) at night!– and I was not fully myself. But we spent every day at least a little bit outside, walking around, and being in our environment. We explored more than we explore at home, because there was more to explore. Walkability where I am now is great for about a half mile in all directions. Walkability in Mexico City stretches as far as your legs can take you in every direction.

The air is different there– land locked and at altitude without it ever really freezing. Here at home in Baltimore, we are below freezing at night in the winter and have long stretches where the days are never below the 90s (32+C) and the humidity is set to maximum (outside of South Asia, perhaps).

I thought being in Mexico in winter meant avoiding the worst of the weather, but this summer has me wondering if perhaps the heat and humidity is more oppressive to me than the cold.

Unfortunately, in large parts, I think I’ve got the same pact you have with Claire with Elsa. Elsa is quite happy where we are, and any moves we’d make would have to be big. And I have to admit, given our current life needs, we are in the right house that would be terribly difficult to find somewhere else. A move would have to be driven by a need for a different lifestyle leading to a need for a different space, but that doesn’t feel all that likely. I don’t quite feel stuck, but I do feel that the expense, energy, time, and challenges of moving are making it hard and harder to quench my considerable wanderlust. You’d think traveling as much as I do for work and fun would help, but … it’s not quite the same.

When I travel, I really like to do what I call “urban hiking”. Choose a restaurant that’s a solid hour walk away for lunch and spend my morning ambling my way there, stopping wherever and whenever I want. Repeat for dinner. See as many of the neighborhoods as possible, moving through and spending your time like someone who lives in each space, but covering more ground. Sometimes I take a car or public transit 30 minutes away to give myself a new start point and work back toward “home base”. I’m not as engaged by a museum as I am knowing 10 coffee shops, 3 independent bookstores, 4 places the punks hang out, 6 pizza slice shops, and fancy dinner or two.

It doesn’t seem likely I’m going to get to live a different version of myself in these different places, but I want to achieve some poor approximation of that other version of myself while I’m there.

Maybe that’s part of the appeal of a blank page. Somehow, it’s more easily malleable for understanding a different version of myself. My digital tools feel more fixed.


August 16, 2023

Meta: This month I’m corresponding with Simon Woods

Hi Jason,

Sorry for the late start — my reward for scheduling something for August is an unplanned move. I think there’s a line about the quickest way to make god laugh.

I hope all is well for you? Given the wonderfully dystopian nature of our summers now and my inability to consistently keep up to date with, well, much of anything I’m unsure exactly how most people are keeping at the moment.

You hit the nail on the head recently regarding subject matter. Journaling, notebooks, and all associated ephemera have become a sudden, significant part of my life. Not only have I been journaling but I have more than one journal available, as well as two planners, and a host of notebooks of different types. I started building my collection at the very end of last year, beginning from maybe a handful of books.

It definitely caught me off guard and I realised that by separating certain aspects of my thinking from the computers in my life I had found the level of compartmentalisation that matched my long-term ambitions. It helped me to find a source of inspiration for what I mentioned in that original blog post: intention. In many ways, the physical books allow me to talk to myself within the constraints of writing in which I am comfortable and motivated, whilst the computer remains the best tool for talking to other people.

This was all news to me, having struggled to wrangle these thoughts for the past few years, and given that I am curious to know if physical notebooks play any such role for you?

Speak to you soon, Simon

Hi Simon,

I used to joke that the sure sign of when my life is getting chaotic is when I struggle to get a hair cut. I go through entire periods of time where planning something 4-5 weeks out, or even finding a slot that lines up with when I’m free can start to feel nearly impossible. Plans are comfortable fictions we cling to at our own risk. The dystopian nature of summer is making me rethink a lot of things about my life though— I am becoming less tolerant to the heat and humidity as I get older and yet have never lived somewhere with hotter and more humid summers than my home for the last 7 years in Baltimore. Escaping the heat (and cold, to a lesser extent) to be somewhere I actually want to be outside will need to become a permanent feature rather than a partial release.

Physical notebooks have a way of flashing in and out of my life. At times when I am really struggling emotionally, I’ve found that writing some quick and easy reflections at the end of the day can be helpful. Writing on the computer doesn’t always work for writing about how I’m feeling, especially the kind of writing that is never meant to be read. I don’t find that this kind of journaling is meant to be precious or returned to. This is the kind of writing I’m doing to help myself think and reflect.

Sitting at a keyboard and staring at a blank screen feels harder than a blank page. I know that there are people who feel like a beautiful notebook being sullied by first-ink is a meaningful barrier. But for me, staring at a blank screen feels constricting. It’s too easy to pause over a word or a sentence. It’s too easy, with the legibility of text on screens, to keep whole paragraphs in sight and think about the whole. Stream of consciousness on paper feels good. I can’t type fast enough to keep up with my thinking, but I can almost fool myself, which leads to bad writing. Writing by hand has no hope of catching up to my thoughts, so there’s a rhythm and speed to it that feels good when I’m trying to find words.

On the other hand, notebooks for work can play a different role. When I’m particularly scattered, I find a written down task list helpful. I need something physical and outside of my screen that catches my eye and attention throwing me back toward what I should be getting done. Doesn’t always work. So I like using something like the Ugmonk Analog system or Sidekick Notepad. I like using dot grid notebooks because what I write in these books are almost always bulleted lists, task lists, or drawings.

I still can’t get down with “mind mapping” or even diagramming software. When something is amorphous, writing or drawing is far more likely going to help me organize and resolve my thoughts. Sometimes I find myself writing about the same thing over and over again over weeks, each time tweaking it slightly. Going through this process often reveals some strokes that I keep drawing, and they become deeper and more solid. And eventually, I’m writing nearly the same thing and I know that I’ve figured something out.

There’s no ambition in my use of physical notebooks. They come and they go. But there are times in my life and types of thinking that just work better with a nice pen and paper.


July 25, 2023

Hi Jason,

Your mention of Philip K. Dick got me thinking about my reading list. Most people have a “nightstand” stack of books they intend to read. I do also. Stacked up in no order are Amusing Ourselves to Death, How to be Normal, Algorithms of Oppression, Doorways to Transformation, Caste, Reality +, An Autobiography of Skin, To Fall in Love, Drink This, and Exhalation, by Ted Chaing. I’m reading that collection of stories now. Brilliant. I have his earlier collection on hold at the library, and just picked up The White Album by Joan Didion from the library, which I will get to. Spare is on my Kindle, on loan from the library. I’m reading Digital Body Language on Kindle for work. On my Kobo to-read I have How to Blow Up a Pipeline, Ubik (a great Philip K. Dick novel I’ve read before), Murakami’s The Novelist as Vocation, and The Moon is a Harsh Mistress.

Perhaps I’m overly ambitious about this reading list? But I don’t think there’s such as thing as a to-read list that’s too long. My books-to-buy list is longer.

If a book is mine, I pencil notes in the margin or start an index of my favorite parts. I copy Kindle and Kobo highlights using Readwise.io. Every Friday I load all the digital notes into DEVONThink. I get a lot of pleasure out of reading and I like to remember it all. I’m pretty agnostic about digital or paper. Digital is good for work and note-taking. Paper is best for pleasure reading.

Do you have a to-read list, and if so, what’s on it?


Hi Lee,

Just as I received this letter I started getting walloped with a case of food poisoning. My third time in about 8 months. Not fun. It slowed me down responding to this letter and also making progress on Living in Data by Jer Thorp, a rare non-fiction book to make it from my “to read” pile to my “reading” pile. Tread of Angels by Rebecca Roanhorse is right next to it, ready to go.

I don’t keep a “to read” list per se, but I do have stacks of physical books, and an entire section of our bookshelves that are “to be shelved” which means “to be read”. When I buy a physical book, it goes there, and when I actually read it, it’s stored away, alphabetical by author, with fiction in one section and non-fiction by topic in other shelves.

I’m not near my desk at the moment which has a stack of books on design, managing programmers, and running development teams stacked up on it to read. I’ve also got quite a few sequels on that “to be shelved” shelf.

About 70-80% of my book reading is on my Kindle, because I travel a lot for work and it’s simply too convenient versus carrying books and risking reaching the end of one without another ready to go. I like to, when possible, use Libby to take out books from the library first on my Kindle, then buy them from my local bookshop if I really liked it. Of course, I simply preorder the stuff I know I’m going to read and love.

I’ve never been a good highlighter. I try with my Kindle, but instead, I actually find it interesting to see other people’s highlights. I’m not often drawn to the same lines as others, but sometimes I feel like I may have missed just how interesting a particular line or passage really is without the queue that 500 other people highlighted it. When I do remember to highlight, I quite enjoy looking back. I often still love what I found worth noting, though I also feel like when I get to the end of a book, reviewing my highlights doesn’t really capture how I felt about it. I guess part of reading a book is my total immersion in it, and even the best moments pulled out don’t make me feel what the book made me feel.

My best friend loves Joan Didion. I’ve never read any of her pieces. I hope my friend is not reading this blog post, because I’m quite positive I’ve never actually told her this.

I think it’s important to have stacks of books as a reader. Losing momentum with reading is something I’ve found can happen shockingly easily if you don’t have a couple of choices lined up to feel out. I never finish a book and go to bed— I always try to find the next book and read just a little bit of it so that I keep my groove.

Well maybe not never— those nights when you make the mistake of picking up your book with 3 hours of reading left to go at 11pm and realize at midnight there’s no way you’re not finishing it— I let myself crash after those “mistakes”.


July 20, 2023

As a reminder, this month I’m also writing Jarrod letters.

Hi Jarrod,

Thanks for the kind words.

At home, my world is ruled by my dogs. Gracie is a 13 year old Pomeranian-Beagle mix. We got her when she was about 8 months old, right as Elsa and I were going to start living together. In fact, the weekend I closed on my first condo was the weekend Elsa picked up Gracie. A month or so later, Gracie mostly moved in with me and Elsa was shortly behind. She was my first dog since my childhood dog passed away while I was in college. She’s intelligent, loyal, and loving. This summer is almost certainly her last, and we’re doing our best through a lot of money and care to give her as much quality time left as possible. A few weeks ago we thought that would be long gone by now, but I’m happy she’s rebounded pretty well at the moment, so we’re just trying to enjoy our remaining time.

Brandy is a terrier mix of some kind. She moved in with us when Elsa’s mom, also Elsa, moved in with us 7 or so years ago. At the time, she was about 2 years old. She is mostly deaf, very low energy, and incredibly caring. She will take constant rubs, and will kiss you endlessly if you let her. She’s a true lap dog.

Martina was my dog growing up, who we got when I was 4 or 5 and had for a little over 14 years. She was much larger (70-80 lbs, versus Gracie’s 20-21 and Brandy’s 16) and a yellow lab/golden retriever mix. She was a classic American family dog of her breed. My parents never got another dog after her, to my father’s disappointment. As a result, they love Gracie about as much as we do.

So what about the work world? What is “education-finance-technology”? Well, as it turns out, most finance and accounting software is built for finance and accounting people. And it’s mostly built for large businesses or “public sector” in a broad way. But it turns out, schools have lots of specialized needs and there are tons of people in school districts— principals, central office department heads, school board members, and even teachers— that need to be involved in decisions about how we spend public dollars to impact kids. So we sit on top of all that software that’s specialized for GASB accounting and treasury functions and do analytics, budget planning, and resource allocation modeling that makes sense to everyone who didn’t get a degree in financial management. Most of what we build is behind log ins and not super shareable, but this year we built a transparency portal for the state of Arizona that’s pretty cool if you want to poke around.

Being a part of something from the beginning is pretty special. I feel fortunate, not just because I was there early, but because I feel like we built this company deliberately (and sometimes far too slowly) such that I have experienced running a company at three or four distinct phases. I know what it’s like when everyone is an individual contributor doing everything. I know what it’s like when you first start to put a team together and figuring out basic people-management and collaboration. I’ve experience building a company to more than one team that has to collaborate across functions. And lately, I’ve been working on scaling my own function to many smaller teams working independently and collaboratively. So many of the folks I know who have worked for start ups get in when things are pretty good and spend a huge portion of their time hiring as they just keep growing. I feel like I actually learned how to run things. I think if I started at a company with 100 people that scaled to 1000 two years later, I would have learned significantly less about leading teams and managing people and how to build and execute on strategy. In fact, I’m pretty confident I could lead a team that had hundreds of people in total because of what I’ve learned here.

I don’t talk a ton about my work. I don’t think I feel like I’ve found my voice as a product leader outside of my job. In many ways, I can do what I do because of subject matter expertise. But I’m starting to get myself comfortable with the idea that I’ve built up skills specific to product management and even CTO-type skills, since I’ve been managing the engineers for 5 years (maybe more?) now.

I do think a way of bringing passions together is the key to success. Being a mountain guide is something you can bring to your site that no one else could. Maybe “bringing together” just means putting them side by side, two paths running in parallel, never meeting. Maybe there’s a way to braid the two lines together at times. For example, what does it mean to build community among mountain guides and enthusiasts? Where are those folks? How does being outdoors or at the gear shop influence your time with technology, or ability to be without it?

I wonder, as a mountain guide, do you build expertise on particular trails or a particular place? For you, what’s the balance between experiencing somewhere new and exciting versus a deep relationship to a single place? Maybe there are some parallels to my experience getting the time to experience different phases and sizes of my company versus simple scaling the experience of being a guide in a particular place versus further exploration. Maybe not.

I look forward to finding out.


Hey Jason,

It sounds like you enjoy a pet-heavy home. In my opinion, the best kind of home. Animals — particularly the ones that you can tell actually care about you — bring a sense of welcoming and belonging to a place. Judged by the sheer amount of time spent there, my pets are the true owners of our house. And they’re always visibly happy when my wife or I come through the door. They welcome us, and everyone else, in with attention and affection. We, humans, could learn a few lessons from our pets.

Gracie and Brandy sound like such sweethearts. That Brandy is “a true lap dog” rings true here. Our Golden Retriever, Phin (Phineas), loves nothing more than to be snuggled up with us. He’s about four years old now, but seems to think he still has the body of a much younger, smaller dog. He’s goofy, rambunctious and protective, but also a scaredy-cat, lazy and pampered. He contains multitudes. My wife and I got him as a puppy about a year into our marriage.

Ollie (Ollivander) is our Maine Coon cat that we’ve had together since back in 2015 when we were dating, but he also seems to think that he’s a dog. He chatters back and forth with us, will (sometimes) walk on a leash, and used to play fetch before doing so would get him pounced by the real dog. He’s the sweetest, most loving and affectionate cat I’ve ever come across. If he can see you, he’s purring. If he’s close enough, we’ll rub his face on yours. And although he’s coming up on his ninth birthday, he looks and acts as young as he ever did. I’m convinced he’ll live forever.

Our final pet is Remus the turtle. I picked him up (literally, off the ground while on a hike) when I was doing an internship down in Alabama in 2014. I was desperately lonely in a new state, living all by myself in a house that would usually have housed nearly a dozen interns. I needed someone — well, some thing — to talk to, and happened to spot a baby turtle. I’d wanted a turtle since I was a young boy, so he came home with me.

Remus, like my other pets, has lived through an identity crisis. You see, I thought he was an aquatic turtle when I first picked him up. So for the first few weeks of his life with me, he lived in my bathtub with a little rock to lay on until I could get him a proper tank. And then when I got a tank, I likewise mostly filled it with water. He seemed to thrive! He would even sleep underwater. But, as you can probably guess, Remus is not an aquatic turtle. He’s an Eastern Box Turtle, which, despite the name, is a land tortoise. When I finally realized that and switched out his living environment, he did seem happier. But I think he sometimes misses his swimming pool. He was a personable young turtle, very curious and cuddly. Not words I ever know to be associated with turtles, but he was! These days he’s going through what I think is his teen years and is being, in a word, an asshole. I hope he’ll grow out of his grumpiness, and will perhaps be happier again when we can move him into a bigger habitat when we move to our new home soon.

Wow, I didn’t expect this letter to turn into pet central, but here we are!

Your work sounds really important. Many professions and industries seem inaccessible to outsiders because their language and processes are so specific. For example, the medical field, law, software development, and, as you say, finance, are all black boxes. We put things in, we get things out, but your everyday person probably doesn’t have any sort of understanding about how it actually works. Building tools that are more accessible to the public must help them out, but — I imagine — also make the work of finance professionals more pleasant. Kudos to you!

Do you have aspirations to lead a bigger team of your own, perhaps at a different company as a new challenge? The way you talk, it sounds like you feel competent to do so. Does that confidence get you wondering if you should try?

Thank you for your insightful recommendations about blending my interests to showcase on my site. I think you’re right, I don’t see a lot of outdoor and tech enthusiasts out there. Perhaps this isn’t quite what you were suggesting, but maybe the key idea is just to write more about what I’m doing, things I’m trying out, and what’s working. I think, perhaps, I’ve been putting too much pressure on needing an angle for my writing. (Related, I feel conflicted about having two places to write, in general.) Maybe my writing would flourish if I aim for it to be less about what’s “right” and more just about me.

Since I’ve been guiding here in the Adirondacks for only as long as we’ve lived here (about a year and a half), it seems like I often get to experience new and exciting places right alongside my clients. Everywhere is new! That novelty will wear off. In fact, it’s starting to as I begin to take clients on the same key hikes or climbs here — the ones that have a particularly friendly approach or offer a wide range of opportunities for folks at various skill levels. But what’s never the same are the people. They each bring their own unique blend of history, interests, ambitions, challenges, and talents. I love sharing my passion for the outdoors with others, and try to inspire some in them.

But to keep things fresh, I do personal trips with friends and other locals. I never want to guide something that’s at the edge of my ability level, so I always feel like I’m holding back to a degree with clients. That’s a good thing because it means I have some margin to get us out of sticky situations should they arise. It also means that if I want to challenge myself, I can try crossing the same terrain faster, link hikes together to push the mileage, or try for climbs that get me a little scared. And I feel like there’s so much opportunity, even just here in the ADK, that I’ll never run out of things to try.

Thanks for coaxing these thoughts out of me.

Following that train of thought, I’d love to hear — if you’re willing to share — about some things that scare you and how you deal (or don’t deal) with them.

Until next time,


July 14, 2023

Hi Jason,

When it works, Slack is great. I use it for clients and projects. Sometimes it gets a little noisy for me, and I have to remind myself that I don’t have to respond in real time to everything Slack offers.

Your writing about walking in the real world and using paper for thoughts reminded me of a book by a researcher/writer I know. It’s called The Hand and it’s by Frank Wilson. Frank makes a pretty compelling case about how we learn with the hands. Holding things and interacting with them with the hands, he says, helps babies connect words to objects. He interviews jugglers and all kinds of people who work (and entertain) with their hands, to show how rich their lives, their intellect, and their use of language has become because they interact with the world in a tactile way. Great book, if you’re looking for something thoughtful. There are other arguments, too, in books like Zen and the Art of Motorcycle Maintenance and Shop Class as Soulcraft that make the case for a deeper connection with things when we make them with our hands.

This brings me to AR/VR, goggles and all the rest. There are some smart people, like artist Chris Milk, who gave a TED talk about VR media as an empathy machine, who believe that we’re all going to be running around with goggles pretty soon. I hope not. Companies like Meta and Apple have a business model that depends on us using their products and remaining in their world as often and as long as possible. If they can manage to get us all wearing goggles, disconnected from the actual world around us in favor of a digital one, well, that is their dream. But it’s our nightmare.

Even though you can rapidly spin up empathy by being in a world with someone else, and especially if you feel that you are sharing that world with them, I don’t think it’s smart to do this at the expense of spending time in our real world. The real world is in trouble because of the climate crisis, and we need people to pay more attention to it, and appreciate it, so they will be motivated to protect it and protest, and stop the fossil fuel companies from further destroying it.

For me, no amount of the cool factor of AR/VR is a solution there. Exceptions might include museum exhibits, education applications, and helping people with sensory limitations connect with the world around them. So I’m not proposing a blanket ban on goggles, but am raising my hand to note that we can’t let the cool factor and newness take over.


Hi Lee

There’s pretty strong evidence that we remember things better when we write them out by hand than when we type them. I think there’s quite a bit to the idea that some kind of embodied physicality is important to learning and processing information. It’s kind of what we’ve been made for.

I find it hard to muster a strong take on AR/VR like others. There are tons of folks out there with hopes— that it will be huge or that it’ll go away. Riccardo Mori was repulsed, and apparently received lots of low quality, negative feedback. I think a lot of people want to see some philosophy in this. I’m struggling to get there.

Maybe it’ll be cool. Maybe it will stink. Maybe it’ll be so cool that we retreat from other things that seem healthier to me personally. Maybe it’ll be so cool that it replaces things that are even more anti-social and unhealthy today and not encroach on “better” activities. I don’t know what I’d use it for, but I know enough from past experience that I have to use the word “yet” at the end of that sentence. There has been a lot of technology I didn’t think would exist, or I didn’t think would appeal to me, or I didn’t think would represent a meaningful jump from where things are today that turned out to be all of those things. There’s also been a lot I was excited about that just, fizzled.

There’s been a great body of “history” found on the internet, mostly on Twitter threads I care not to find, where someone will take a series of concerns about technology from letters written to newspapers over two centuries and find the exact same concerns and predictions over and over again applied to new technology, none of which quite come to pass.

I guess that’s all to say that I’ve learned that trying to be a “futurist” is somewhat of a fool’s gamble.

I do think there’s a benefit to experiencing the world through another’s eye. Mercerism may have been a lie, but the idea of an empathy box is quite powerful 1. I’m just not sure any of our technology comes even close to generating that kind of closeness and fellowship.

At the same time, here I am, writing these letters each week. They’re often quite personal and revealing. I suspect someone reading along might develop quite a sense of who I am and how I think. Their ability to empathize or care for me is almost certainly increased. So who am I to say what will happen if we increase the ability to be present with strangers?


  1. In Do Androids Dream of Electric Sheep by Philip K. Dick, there’s a pseudo-religion called Mercerism, based on experiencing a horrendous, physically and emotionally challenging struggle by one man via an “empathy box”. I do not think VR is an empathy box. Mercer is revealed to be fictional, but that does not change the power of the ability to have a common experience. www.sparknotes.com/lit/do-an… ↩︎

July 11, 2023

This month I’m writing letters with @leeS.

Hi Jason,

The irony here, to begin with irony, is that your email to me reminding me to start writing my side of this correspondence got lost in my email. We all have a firehose of info coming at us; nothing new there. For me, the dividing line between finishing work at a reasonable hour and staying at it all night has become dictated by the efficiency of my filters.

I’ve thought long and hard, sometimes literally falling asleep to, various mental exercises devoted to creating efficient filters for my emails, workflows, and projects. I could regale you about the efficiencies of Apple Mail vs. Spark vs. Superhuman vs. Hey vs. Fastmail, and on the project side, of Todoist vs. Things vs. ClickUp vs. Sunsama vs. DevonTHINK; and on the short-form writing side, of Bear vs. Ulysses vs. Drafts vs. IA Writer vs. Evernote (Evernote!), and on the long-form writing side, of Ulysses vs. Scrivener. I’ve tried them all, and while fun to work with, and even more fun to port all your data from one to the other in a semi-useless exercise, they all lack something.

They all process my thoughts but none can do my thinking for me.

Let me branch off to another idea before coming back to that. When Threads launched, I was flung into another this vs. that thought cyclone. It went something like this: Should I crosspost on micro.blog and Twitter, vs. crossposting on micro.blog and Mastodon? And if I did that, which Mastodon instance should I favor in my crossposts (I’m in two instances), vs. posting to LinkedIn, vs. Instagram, vs. posting on Threads? And should I post the stuff I used to post on Twitter on Threads, or create some new magical identity that will gain me followers faster than Paris Hilton? And, if I could drink some magic elixir that would turn me into Paris Hilton, with all of her popularity on Threads, would I want to do that anyway?

In the middle of these various thought cyclones, I tested positive for Covid, which has left my mind in a state of crystal clarity. ( Not really.)

What I need, and what everyone needs, is a digital machete to slash our way through the info-forest. But then, I wonder about that. A blunt-force instrument, even if elegantly constructed of software, would cut away stuff we would need. Example: I was recently promoted to assistant professor at USC. My new contract went into spam. Doh. [Head slap evoking Homer Simpson.]

I think the solution is in stepping away from the mechanics that have brought us so much efficiency, and taking a moment, pausing, creating some space by breathing, walking, staying in the shower too long, or by staring into any distant mountains you may happen to have nearby. There is a superb filter already installed in the mind, always auto-updating to its latest version. I find I can turn it on by asking “Does this matter to me?” And being ruthless about the answer.

Looking forward to hearing from you.


Hi Lee,

A funny thing happened in my life about nine years ago. I started working for a startup that was using Slack, way back in the early days of Slack. And starting at that moment, email got quiet for me.

Sure, I have a lot of junk that comes in that I have to clean up from time to time, but I don’t live or die by email. Email that matters to me is rare, and the process of “doing email” is largely unimportant.

Slack didn’t eliminate email for a lot of folks, but for me, it sure quieted it enough to separate signal and noise pretty effectively. Well, that, plus aggressive unsubscribing from various advertising emails and a few well designed filters on emails from popular political campaign donation software.

Personally, I’m back largely on pencil and paper for the true “management” of my time. My tasks are written on Ugmonk Analog cards or in a Cortex Sidekick, depending on my mood. Sometimes it’s not written down at all. My work and life is sufficiently chaotic that there’s often little mystery where my attention needs to be at any given moment. Taking the time to write down a list, and then paying attention to that list, can feel like a luxury.

Walking is my solution. I’m a big fan of taking multiple mid day walks. When I worked in an office, I would often head out to Walgreens or 7-11 a block or two away for a Diet Coke. Yes, I wanted the caffeine, but doing that a couple of times a day and taking the “long way” back around the block cleared my head. My partner, Elsa, doesn’t leave her office in our home the entire working day. I don’t understand how she does it. I routinely have 5,000-7,000 steps already at the end of the work day even though I have a desk job. I need to get outside, I need to think a bit. I even like to take my meetings as regular phone calls (how not-millennial of me) so that I can walk through the park across from our house while talking through a problem.

We get lost in the tools and the mechanics all the time. But the work I do is knowledge work, and brains need rest just like physical muscle. And brains don’t active best sitting and staring at a machine that flashes lights in my eyes.

Perhaps you’ve heard of forest bathing? Or A Need to Walk? I believe in these things so much, it’s one of the only links on my vanity site. To me, a great vacation is 25,000 steps every day without even trying. Seeing a new city is walking its neighborhoods.

For all that time I spend on the computer and on the internet, for all my posts about the social web, I’d trade all of it without a seconds hesitation to take walk on a pleasant day with a friend.

Congratulations on the promotion, and I hope you have a swift recovery from COVID.


And now for something not entirely completely different…

I’m writing a letter to someone else this month. So without any further ado, a double dosing of Letters for July.

Hi Jarrod,

It’s a bit strange to be starting one of these. For those that don’t know me who are reading along, and as a reminder to Jarrod, I started writing Letters on my own blog this year. I wanted to have a different kind of online social interaction, and I wanted to do it with people I may not really know. I thought it’d be a nice way to build up a dialog, be a part of building an Internet more like the one I wanted, strengthen some para-social relationships, and make sure the “long form” content on my blog kept flowing.

Jarrod reached out early, but not early enough for me to have booked up my year. But I’m glad that he decided to do his own project on his blog. I agreed to be a part of that project, so here I am, following my own rules, and writing the first letter for the month of January to Jarrod.

By way of further introduction, I’m the Chief Product Officer at an education-finance technology company, leading engineering, design, and product management. I love what I do, because I get to bridge problem solving and consultative work in my area of expertise (education policy), my skills as a data practitioner, my danger as a software developer, my taste (which exceeds my talent), and my never-strong-enough management skills to solve real problems for K12 schools. It’s wild to be a part of a startup for the last nine years from pre-product, pre-revenue, pre-Series A to now being a “real” company with over 50 employees.

I moved to Baltimore, MD about 7 years ago where I live with my fiancée (which I still have to look up how many “e”s each time), her mother, and our two aging dogs. Prior to that, we lived in Providence, RI for 10 years, and I grew up on Long Island, NY.

These days, besides work, I’m focused quite a bit on volleyball. I played (poorly) in high school, and I play now (slightly less poorly) in adult recreational leagues. This was one of my “I’m vaccinated, let’s go!” activities I reintroduced into my life after 17 years away from the sport. It’s been a ton of fun (and exhausting) and at this point it feels essential to my mental health. I also read quite a bit of fiction (or at least I think), typically hitting between 30-40 books a year. I love to travel, and travel quite a bit for work. Recently, I spent a week split between Portland, OR and Seattle, WA and had a great time getting out of my own routine for a bit and wandering. My style of travel is what I call “urban hiking”— I choose a spot for each of my meals in different parts of a city and wander between them all day long and see what I stumble into. I love getting a feel for somewhere different, and I love to walk.

I’ve been lightly following Hey Dingus, largely impressed with your consistency and keeping an eye on the “Projects” page especially, which is the type of thing I’d like to expand on my own site (see /books, /letters, etc). How do you feel like it’s going? Is it the outlet you hoped for? What’s success for you?

Looking forward to our month.


Hey Jason,

Oh boy, I’m going to have to step up my game this month. That letter had me in awe of your skill as a writer. It flowed, man.

Thank you for that fun introduction. Given the room to stretch out their descriptions, I’ve found that everyone I’ve corresponded with so far has highlighted such interesting parts of their lives. You are no exception.

For a brief introduction of my own, I’ll say that I like to exist at two ends of the spectrum of “extremely online” and “completely disconnected”. Often flip-flopping between them with little warning.

Perhaps a little more explanation is necessary. My day job is as a mountain guide and gear shop specialist, I’ve spent most of my summers as a camp counselor, and I spend much of my free time outside. I’ve spent months (years?) of my life in a tent, gleefully leaving the internet-connected world behind during those times. But I’ve also been a certifiable nerd and Apple enthusiast for as long as I can remember. In fact, in the time between being a full-time camp director and my current job, I spent a few months working as a Technical Specialist in an Apple Store. Technology engages the part of my lizard brain that loves shiny things in a big way. So anytime that I’m not working and I’m not playing in the woods, I’m probably devouring the latest tech news, spelunking the web, or – as of the last few years – sharing that passion through writing my blog.

Lately, I’ve been considering more about how I can build a better bridge between those two interests. Sure, I get into all the topographical navigation apps, track my rock climbing fitness and routes, try the latest camping gadgets, and am generally known as the “tech guy” in my outdoor circles. But I can feel that there’s more to share. I’d like to write more about my experience in the outdoors – to share how and why they make me feel so alive – but it’s proven difficult to break into that genre.

Honestly, that’s one of the reasons I was so eager to follow in your footsteps for this project. I saw it as a way to try out a different kind of writing.

But enough about me, you offered so many jumping-off points about yourself that I want to explore!

What does it mean to work at an “education-finance technology company”? Do you create finance software for K-12 schools? I was corresponding with Chris Verbree last month about how special it is to be part of something – a company, organization, community – from the very beginning. We agreed that having the opportunity to influence the movers and shakers (and sometimes being one yourself) is compelling. What have been your takeaways seeing that company, and your role within it, grow from its infancy?

Your “urban hiking” approach to traveling sounds like the perfect way to explore a new city. I get intimidated by big cities and tend to stick close to my hotel or AirBnB. Case in point, I recently visited your old neck-of-the-woods, Long Island, for the first time but didn’t get out to see hardly any of it. We used DoorDash for a couple of meals and wandered only once. But with a plan and destinations in mind, I could see enjoying the exploration much more.

Your excitement for volleyball is palpable, and I’m so happy you’ve found your way back to it. I strongly believe that having a hobby to stretch your body is as good for you as having one to stretch your mind. Like you, all kinds of foot-powered travel appeal to me. I went for a 10-mile run just this morning that I only intended to be a 5-miler. I just felt so good to be out and moving that I couldn’t stop. A mental health tonic, indeed!

Thank you for your readership of HeyDingus. “Consistency” is my theme for the year, so I’m quite tickled to hear that it has been noticed. After several years of stasis, my appetite for new side projects there has grown considerably. I’m not holding myself to them all going on forever, but they sure are fun to toy around with. My /lists page has been a creative outlet in particular.

Oh, and I’d love to hear more about your pets and what you love about them. I saw your post at the end of June that Gracie’s health hasn’t been the best. Allow me to offer my condolences. It’s so hard to see a family member in decline. My wife and I have a cat, a dog, and a turtle that we call (and treat like) our “fur babies”. They bring us such joy and it’s hard to imagine our family without them.

Finally, I’d like to offer my gratitude for kicking off this Letters project movement (can we call it that?). You nailed the allure of it when you said it was to build up an Internet like the one you want to see. Thanks for putting it out into the world.

Talk to you again soon,


July 2, 2023

Hi Jason,

I will likely get back into D&D soon. Once a few things settle down at work I’ll have a bit more energy to play.

Hobbies come and go. I’ve known that for a long time. I’ll have interest in one, then move to another, and another, eventually coming back to the original. Often I max out on one as it has my interest, then I move one.

I’m a couple of days late on this one. Will just make it within the month of June. Time since the Covid lockdowns has been weird. I had a keen sense of time beforehand and that has gone now. Getting older brings with it the sense of time going quicker. What I’ve lost is my sense of distance with time. An event that’s 2 weeks away feels like it’s later than something 3 months away. Makes me a little sad. Makes it hard to look forward to something.

Today has been a long time in the car. 5 hours as I headed NW to visit a couple of clients and return home. Good audiobook time. I’m listening to “Three Body Problem” off the back of the Netflix trailer. I read the book just 18 month ago and couldn’t have told you what it was about (yeah, ok maybe there is a pattern here) but the memory is returning as I listen to it. Years ago I would have dismissed audiobooks. Now I enjoy them, blending with my Kindle reading and my podcast listening. There is something different about a story being told to you. The slower pacing, even for a book I’ve read, means I often pick up nuances I missed first time around.

I will write up some thoughts on our letter writing in a separate blog post and send you a link when done.

Thanks for the conversation, David

Hi David,

It’s funny, I have been talking a lot about the Three-Body Problem lately. Must be due to the trailer. The idea of the dark forest haunts me.

I have never been able to get fiction audiobooks to click. I listen to tons of podcasts, and I can listen to some non-fiction audiobooks (sped up), but my mind drifts while listening to fiction. For some reason, it doesn’t stick, even though I much prefer to read fiction. I think it’s that slower pace causing me not to focus on details I missed, but instead, drift into the my own thoughts.

One hobby I’ve been dong a bit more of lately is cooking. Of course, I am always at least cooking sometimes. What I’m doing now is taking care when I cook. I’m not slapping cold cuts on cold bread. I’m spending that extra time making a small sauce, toasting my bread, chopping veggies to go inside of it. I’m just being a little less lazy about my food. It feels good. Sometimes I forget that it takes less than 10 extra minutes to make something that’s twice as good.

Sorry I’m late on this response.

Last weekend, this time, I was pretty certain our older dog Gracie had just days to live. She’s home now, comfortable, after 3 nights in the ER followed by a couple of days spending 8am to 6pm at the vet. She’s reached the point where she’s not going to get any better, but she’s mostly stable and seems to still have some time with reasonable quality of life. Thankfully once she was home for a couple of days and out of the anxiety of the overnight pet ER and vet, she seems to be about 80% her normal self. We have to give her fluids at home and she’s on a host of medication. But she’s eating, she still likes going for walks, and she loves us.

All that to say, I’m a bit late at least in part because other than work, the gym, and volleyball, I have done little else lately. My thoughts are, well, preoccupied.

Thanks for chatting with me in June.


David shared some thoughts on our month of letters. I find the format similarly constraining, but part of what I enjoy has been how the conversation has to be different as a result.

Each letter is shorter than addressing everything could be. And we often have to let a thought from the other person drive by or fizzle out, lest the letters end up endless bullet points hopelessly attempting to recreate synchronous conversations.

As bandwidth increased, the internet moved us from asynchronous by default to synchronous by default. We went from websites, journals, blogs, and forums to feeds and streams.

I kind of like the idea of finding a different resting place than the heights of Facebook and Twitter for my own communication. That’s part of why I blog. Letters, in many ways, has been a project to have a different kind of communication, facilitated by blogging, that I don’t always get as a result of writing here. I’m lucky if a post gets one reply. Long posts almost never get any kind of response. That’s fine– but part of what I want out of blogging is for other people to write about things that I’m writing about and vice versa. A broad, loose “conversation” that isn’t a direct exchange, but a diffuse space with lots of folks contributing thoughts and ideas about similar things that I’m interested in.

Letters is not quite that, but it’s helping me to exercise that possibility.

June 21, 2023

Hi Jason,

My gaming took the opposite track to you in the early days. Funnily enough, games then were 2 player at best and unlike the Internet multi-player games we have now - which I tend not to play. In the days of the Commodore 64 we’d sit around and take turns. There was also a large social aspect in “swapping games”.

We were lucky to have the C64. Dad won it at work as a prize for sales I think. That wasn’t his job, but I expect in early 80’s few knew what the prize was. And it was a doozy. A Commodore 64, TV, printer and 5.25" drive.

Fair to say the opportunity was my gateway drug into my career.

I got back into tabletop role playing a year or so before Covid. I’d wanted to play again for a long time. With nobody to play with I headed into my local gaming store and asked if there was a game going. I enjoyed it very much. As an adult there was so much more I could bring to my characters. Covid and anxiety had me pull out. I was playing and DM’ing. It became too much. As a DM playing on Sunday afternoons, not thinking about the game all week until the next Sunday morning and then politely swearing to oneself is a sign of too much. I’m reluctant to get back into it because I’m concerned I’ll end up leaving again at short notice and that’s not fair on others.

I like your guitar story. Justified embellishments aside, were you that self aware of the decision at the time? I’m not sure that I would have been. Hobbies are wonderful things. We each get deep into what calls us and that’s often to the bewilderment of others. They can bring us together in weird and wonderful ways.

Two of my workplaces have had a “What was good last week?” check-in and depending on the cohort in the meeting I’m met with crazed looks or murmurs of appreciation.

Changing habits. Let’s not mention that.



Hi David,

I think my awareness on guitar went as far as this: I am enjoying playing music with friends in all forms, whether with my nascent band at the time or in jazz band and wind ensemble at school, while the video games feel less and less present to me. It just wasn’t a thing I was reaching for with my friends or a thing I much felt like talking about or engaging with anymore. My love of computers didn’t change, and this was an era of all kinds of horrible skinning you could do on Windows and futzing with Linux desktop and the like. But games just fell away, maybe because of shifts in friends or just shifts in priorities. I don’t think the awareness extended to “this is a thing I can do with my friends now” but it definitely was an awareness of “this is a thing that I love doing that energizes me, that is not”.

My early computers was not from the Commodore 64 days– I was at the very early Windows 3.11 Gateway 2000 club. The new hotness was the CD-ROM drive where I had Dinosaurs and Encarta and I spent tons of time browsing through both.

Things come and go. Sometimes I like cooking, sometimes it feels like a chore. Sometimes I like playing guitar, other times I haven’t picked it up in a few months. I’ve stopped feeling guilty about it, but I do try and remind myself that these things bring me joy, and sometimes I don’t feel like doing something because I haven’t done it in a while. Sometimes, I’ve forgotten what things mean to me, and I have to force myself out of a bit of a slump. The activation energy is hard, because remembering the joy can be really tricky.

I think you should head back to the TTRPG world. Just take it easy. I have found that it was way too easy to leave things behind due to COVID that I actually don’t want to leave behind. It has taken real effort to re-introduce those habits and hobbies, but also a great reminder of why they’re important. You need to fill that bucket up. Maybe being a DM is just not a thing that you can keep doing at this stage, or maybe joining an existing campaign will make you realize how much you miss it and give you the motivation to not feel like DMing is Sunday anxiety and drudgery. Or maybe you should try something like a trading card game or board games to see if that can generate a similar joy and social connection without the pressure of DMing each week. I think part of why I have moved away from, and stayed away from, video games is because most of the games I liked were huge commitments. I just didn’t have the energy to play like that anymore, and that’s why it became a chore.


June 14, 2023

Hi Jason,

Funny that you should say “You can’t dance with someone who walks on the floor with the purpose of making you look bad”. I think of conversation as a dance where both people have to be willing to move back and forth, even if there is a stumble from time to time. It’s also similar to something I’ve often said about trying out new things at work. “You can play by new rules if everyone insists on playing the old game.”

Speaking of games, I’ve finished playing The Last of Us Part I this week (4th time through) and have started on Diablo IV. Gaming has become much more acceptable than it was when I was a teenager in the 80’s. Still get weird stares from a lot of people, but not as many now. Like anything else it’s a hobby and I would guess closest to reading - though more interactive. During the Covid lockdowns it was gaming that allowed me to travel to far-flung places and other worlds to escape.

This week I’d like to focus on changing some of my habits. Some work for me and others don’t. My task is to identify the cues that cause a bad habit to kick in and leverage that into a new habit. There are some where it feels like the cue is just the day. “Oh, it’s Monday night so off to the supermarket for a bag of chips.”. I’ll need to be a bit more precise if I’m going to shift things in the right direction.

Tomorrow (if not Wednesday) is going to be a hard day. As a family we made the decision yesterday that it’s time to let our 15 year-old dog Sam pass on. His health has deteriorated over the last 12 months and is accelerating. Most of the time he looks miserable and pleading. Sam came to us at 4 years-old as a second time rescue dog. We believe his first owner abused him and his second was a single male who, because of the way Sam had been treated, wasn’t able to connect to him. I can understand that. For years, Sam would not even come near me. Originally an outside dog, I found out the girls had been letting him inside during the afternoon, and then swooshing him out before I came home from work. Now, he’s as indoor as they get. I’m glad we’ve been able to give him a better life than he started with. If only everyone’s life could work out that way - getting better all the time.



Hi David,

It’s funny– I fit all the trappings of a gamer as a mid-30s white guy in tech who was an absolute nerd my entire life. But, I actually stopped playing games around high school. I remember selling all of my video games to buy a guitar. It didn’t feel like a statement moving away from gaming. In the past, I’ve taken creative license in this re-telling to claim that I was making some kind of move to make myself more attractive or fit in better or something in a self-deprecating way. But honestly, I was just less and less interested in games, even as an avid Nintendo Power reader and someone who woke up to play RPGs for an hour before school, and more and more interested in music. I think it was less about rejecting being a nerd– I couldn’t shed that identity with all the money, dedication, and time in the world. I think it was more about being lonely, and gravitating toward thing that were more social. Playing guitar was something I could do with my band (I started just singing and learned guitar to add that to the mix). Playing video games, at that time, was not something easily done with friends. I wonder if I would have made different choices if I grew up when online gaming and voice chat and all of that were around.

Habit changes are so hard. I have been on a mission to be more healthy since the start of COVID, really jump-started in part from my dad’s heart attack that happened in the first year of the pandemic. I’ve found it’s easier to build new affirmative habits–“start doing this”– then to discard bad habits– “stop doing that”. It’s especially true when the new pattern I want to establish takes something from being an easy default to something that requires attention, intention, and energy. Adding “start going to volleyball” is a lot easier than “stop eating a full pizza every time something bad happens as a coping mechanism”. I hope you find some success in changing your habits. I’ve made it at least part of the way, but I’m currently in a back slide. What I’m thinking about now is how I may need to do more to do less. If it’s easier for me to start something new, maybe I need to fill my time and energy with new things to crowd out what I want to stop. If there’s no time for bad habits, I won’t do them.

Letting go of a loved one is hard. I grew up with a golden retriever/yellow lab mix Martina, from the time I was about 5 until I was about 19. She had a really tough last couple of years, but I think overall had more good than bad in that time. It was very hard to let her go. When I was 24, my partner and I got a dog together, Gracie. She’s now starting to show some real signs of aging, and it’s been really hard on us. The vet visits increase, the vet bills increase, and although she’s absolutely still having a happy life, it’s also clear that there’s less quality. She’s able to do less and is motivated to do less with the passage of time.

Sam knows he is loved, and Sam had a life that was better because you and your family were a part of it. I don’t think that’s enough, but it’s something.


June 2, 2023

Hi Jason,

Friday night, the TV’s on in the background, and I’m wondering where to start.

I first came across your “Letters Project” via previous participant Robb Knight. At the time I was craving conversation and if letters back-and-forth are not conversation, what are they? That seems as good a place to start as any.

As a 50+ year old (mid-early-50’s lol), I’ve been exposed to many concepts. Some resonate strongly and immediately feel right because of their ability to explain my world experiences. The importance of conversations in our life is one of those.

Just now my attention has been taken by the Ben Robert-Smith story on TV. He’s Australia’s most decorated living war-veteran who has lost a defamation case against three newspapers for claims they made that he is a war criminal. The stories are all “He’s guilty! Strip him of his medals! Take him to criminal court!”. The last I agree with as it is the only way to get beyond allegations to evidence.

The media leaves no place for conversation - no place to explore - no place to learn - no place for grey nuance.

I assume the case was thrown out of court because the newspapers had sufficient justification to make the claims they did and so, it’s not defamation. That does not equate to criminal proof. I can’t be sure of that, because it’s not being reported anywhere. Just the result for everybody to lay judgement on.

I see the same in the workplace, in families, on-line. We are not taking the time to sit in conversation. In my training as an ontological coach, we were told conversation is a dance. How much conversation is not a dance but a toe-to-toe fist-fight? The closest it gets to a dance is the gang fight in West Side Story.

I’m confident in saying we’ve forgotten how to listen, but I also think there is a big time factor in there. We don’t leave ourselves time to ask questions, to sit quietly and think, to consider what we’ve heard, or to consider our reaction to it and what that may teach us about ourselves.

That’s the conversation I crave. That’s what I hope you and I can engage with over the coming weeks.

I’ve written enough. Time for me to listen.

Best regards, David

Hi David,

I am also craving conversations, having come to the same set of conclusions as a mid-late-30s year old.

There’s little room for nuance, and so often cries for nuance are made in bad faith. One of the most difficult things about online conversation and media narratives is that they’re so often, fundamentally dishonest. The questions being asked are about framing the debate, not curiosity. Introducing complexity is genuinely seized upon by bad actors to support ideas that are not at all a part of the goal of the initial speaker.

You can’t dance with someone who walks on the floor with the purpose of making you look bad. There has to be some agreement on the basics, and so often these days our dance partners aren’t even listening to the same music we are.

I don’t think individuals have forgotten how to listen. I think this is why in person conversation and face to face interactions are so different from online interactions, especially synchronous or near synchronous, short form, broadcasted “conversations”. 1 One of the reasons I like podcasts so much is that the human voice can generate a level of empathy and compassion for each other that is missing during online sniping. Folks I feel are abhorrent with views that cause my blood to boil become possible to hear from when they are speaking in their own voice in the room with people who disagree. There’s something about having to face other people impacted by your own argument that softens, expands, and explains to a different degree than the online world or even the written word that’s not built in conversation.

Op/Eds are not conversations, they’re screeds.

I enjoy the long form, asynchronous conversations that Letters has provided. It’s a different type of communication that feels like it was common and now, not so much.

Thanks for jumping in this month.


  1. How often do we forget that a conversation in public has audiences besides the interlocutor? ↩︎

May 28, 2023

Hi Jason,

Maybe our therapists are comparing notes!

This right here: “I miss out on entire emotions, because I’ve already rationalized.” Yep. That’s a whole way of being. And the truth is that it has a purpose and, in some cases, it’s a strategy that serves us well. A tough part of growth is realizing when it’s time to let go of strategies that worked in the past but don’t help us move into the future we want.

I’ll take full responsibility for diving into the conversational deep end without pausing for preliminaries. It’s kind of fun to do things backwards though, and I like that our last week of this letter writing month is coming to a close with introductions and light stuff.

So here’s my own paragraph of introduction:

I’m 41 and pretty excited to turn 42 next month and know (or be?) the answer to life, the universe, and everything. I’m a single mom of four kids: three teenagers (13, 15, and 16) and one 12-year-old going on 27. So that’s where a lot of my time and attention goes, and it’s wonderful and difficult and all the things, all at once. We have two enormously spoiled fat cats and live in a cozy apartment in a St. Louis suburb. We moved back to St. Louis in the middle of 2020, after being in Puerto Rico for 5 years. It was an unplanned relocation in the midst of an unexpected divorce, and since then I’ve been rebuilding my life from zero. I really miss beach life (and speaking Spanish… I’m getting rusty) and my PR community, but it’s wonderful to be near family and lifelong friends and have their support and help. I’m a freelance writer and most of what I do is take tech-speak from the dev team and translate it into readable, hopefully interesting material for the people who want to use whatever the dev team is making. I’m innately curious about pretty much everything and being a writer is a free pass on asking questions and doing research. I love reading and usually have 3-4 books going, a mix of nonfiction and sci-fi/fantasy. I also love a good memoir. I spend a lot of time thinking about the why underneath things. I grew up in a religious home and was very involved with the church until my early 30s, when I left the faith. I didn’t want to, but that whole curiosity/asking questions/looking for the why underneath things… Well, sometimes it takes you places you don’t necessarily want to go. I’m happy to be where I am now, though. Life has 100% not turned out as I expected, but I feel so grateful for what I’ve gotten to experience and who I’m getting to become as a result of those experiences. I love food and adventures and dancing and a good whiskey and trees and solitude, not necessarily in that order.

It’s been an absolute pleasure exchanging letters with you over the last few weeks. I’m going to sign off with two book recommendations (and would love to have a couple from you as well). First: Finite and Infinite Games by James P. Carse. This book is one I reread about every year. It colors the way I look at everything. Second: Systemantics (or The Systems Bible) by John Gall. As a structures/systems person, you might particularly like that one. Easy read, entertaining, pithy.

Here’s to good things ahead,


Hi Annie,

Yes, we’re moving backwards, but I reject that book recommendations are “light stuff”. I had to think about that one a bit, since I know that you’ve already tackled Tomorrow, and Tomorrow, and Tomorrow, which will be my default recommendation for quite some time.

I decided to go with books that are not huge commitments and that I don’t feel had any recognition in my own circles. I think all four of these recommendations (well, it’s really three) are best read knowing very little:

Now that the serious business is attended to…

I fell into “product management” largely from a similar skillset– I was able to talk to the dev team about what everyone else wanted built and they were able to build the right thing, whereas in the past that was a struggle. In many ways, my job goes in reverse of what your role does.

I think something I didn’t quite understand when I was younger was just how much work we all have to keep putting into ourselves and how many new things we find when we keep looking for whys and let go of old strategies and pick up some new ones. It feels like the kind of thing you never really understand as a kid. Maybe it’s the time I grew up in, but so much of what society coded as a midlife crisis or a failure to launch or whatever reads so different as an adult. I don’t know where the norma came from that we are meant to be consistent rather than constantly adjusting and discovering and changing along the way. Rebuilding from zero with kids that rely on you sounds… daunting, even without the major relocation. But letting go of strategies and identities that no longer serve us to head out on our next adventure with food, dancing, good whiskey, trees, and a bit of solitude– that sounds like exactly where I’d like to go.

Well, except for the dancing.


May 23, 2023

Dear Jason,

Yesterday I attended an event for youth who are overcoming addiction. For eight weeks, they take lessons in classical guitar and djembe drums, make art, journal, and connect with adults who share their stories of overcoming addiction. Then they put on a concert and share what they’ve learned.

As part of the event, spoken word artist Tracy T-Spirit Stanton shared her story and two of her poems. Her entire performance was stellar, but one line is ringing in my head: “If you lead the body, the mind will follow.”

I put a lot of trust in my mind. I wasn’t the pretty one or the athletic one, but I was the smart one. And I held onto that identity as safety. Not too long ago my therapist said, “It’s really tough for you to be wrong about things, isn’t it?”

Um, yeah. I hate that.

One of the things that was hardest to accept about getting divorced was realizing that my own mind had been unreliable. I’d overlooked, dismissed, rationalized, and denied so many things. Clear signals. But I wasn’t ready to deal with what those signals meant, so my mind invented stories. As long as I didn’t ask too many questions, I could keep ignoring things.

But my body knew. Oh, did my body know. I had migraines regularly. I couldn’t sleep. And I developed an ovarian cyst that required major surgery. It was as if my body was taking all the emotions I wouldn’t let myself feel and truths I wouldn’t let myself face and putting them into this mass that became cancerous and could have killed me.

I had this very vivid dream a few days after surgery. I was still on pain meds, so I’m sure those were in play. In the dream, I was lost, running through the woods. It was like a maze, there was danger, and I was trying to find my way out to safety. This voice came from nowhere, right in my ear, saying: “Wake up. Wake up! WAKE UP!” I woke up startled, heart pounding, disoriented, but with this sense that something important had happened.

I still didn’t want to listen, though. So I went back to ’normal life’ and kept myself busy ignoring as much as I could. Then came quarantine. There was so much time and so little distraction. I couldn’t keep the storylines connected. One early early morning in September I was standing outside. Couldn’t sleep, as usual. Staring at the sky. Thinking, thinking, thinking. So much thinking, but so little sense. And I had this physical sensation like my brain was falling apart. I remember reaching my hands up as if I could slip them inside my skull and hold the pieces together.

That was it, finally. I’m still amazed that my body created a physical sensation to match what I was experiencing mentally and emotionally, and did so in such a powerful way that I couldn’t ignore it. I’m really grateful. And I pay a lot more attention to my body now. I also don’t get migraines anymore, so that’s cool.

I didn’t start this letter with the intention of going through my recent personal history, but it colors everything for me these days. My mind is still trying to sort things out all the time, analyze, categorize, find congruence. That’s part of who I am, and it’s not bad, but finding a balance is the work I’m doing now. Respecting and using my mind, yes. And equally respecting and trusting my body to tell me things more viscerally and immediately, and to listen when she does. The body says no, the body says yes, the body says wait, the body says be careful. Sometimes the body says run the fuck away! And sometimes the body says, “Hang out right here, because this is delightful.”


Hi Annie,

Are we going to the same therapist? I, too, find it tough to be wrong about things. I rationalize. My identity my whole life has been defined by my power to process fast and rationalize. I miss out on entire emotions, because I’ve already rationalized. I blow past signals and warning signs like the train in Back to the Future 3 heading for 88 mph or the gorge, which ever comes first.

This is why going back to playing volleyball has been so important for me. I need to spend literally hours each week playing a game that takes so much of my body and concentration that there is no “mind”. There is no thinking. There are no stories to tell, except maybe about how shitty it feels to be shanking a pass. I have to have time that I shut it down. That’s also why I have to read fiction. I need to fill my mind with a different mind.

Those are forms of rest. They quite the mind. But what I’m less good at is where you seem to have made it – listening to something else entirely. I haven’t figured out how to, in the quiet, let some other signals creep in and teach me things I need to understand about myself.

I have only started to slowly get better at this. Unfortunately, it was also due to excruciating gut pain– my appendix. After being sent home from what could only be described as completely negligent urgent care, I went into the ER a few hours later because I listened. Of course, my body was screaming, but even my doctor was a little surprised (in the best way) that I actually brought myself to the ER because things got worse. And I did so, in many ways, just in time.

The effect has been troubling. I’m far more nervous about aches and pains and changes to my body than I’ve ever been. My body has failed me in the past, but perhaps more importantly, I’ve learned not to trust my own sense of what is serious and what can be ignored. I have recalibrated, and I’m not quite sure yet if my new normal means “listening to my body” or “living with irrational anxieties in yet another area of my life”.

It sounds like you’re getting great feedback. Your body is telling you that the hard things you’ve had to do are the right ones.

We’re coming toward the end of our month, and I realized, partly my fault, we got heavy fast and never did some introductions and light stuff. So I thought I’d take this moment to pull us back a bit, reintroduce some folks to me, who may have already forgotten what I have going since the start of this project 5 months ago, and end us in a place that I hope feels like hanging onto because it’s delightful.

So here’s my run on paragraph about myself.

I’m in my mid 30s, no kids, living with my fiancée (who I’ve been with since 2010 and have been living with since 2011) and her mother. We have two dogs that are getting up there in age. I work for a tech company doing tech things for US K12 school districts after getting a master’s degree in urban education policy and working for school districts and state departments. We’ve been in Baltimore for 6.5 years now and lived in Providence for 10 years before that. I grew up on Long Island in New York. I read 30-40 science fiction/fantasy books a year (I prefer speculative fiction to SFF), play volleyball a few times a week and try to lift weights 3 times a week. I continue to struggle with being meaningfully overweight like I have been my whole life. We love to cook and eat. I am broadly interested in tax policy, urban development, and transit policy. I like to think about the world we’ve built around us how it changes our behavior and how we can build a better world, physically and politically. I’m a structures person, and I think a lot about them, whether when doing policy work or programming and data work. I tend to think of systems and structures as the geography and human behavior as water running over that terrain. I listen to a lot of podcasts. I watch a lot of cooking and educational YouTube videos. I like a great coffee and just about any Diet Coke (no, Pepsi is not ok, but I’ll suffer through it). We love to travel, having recently spent a few months in Mexico City. Elsa, my partner, was born in Mexico and is half-Mexican, half-Haitian, and trilingual. I travel a lot for work and I travel a lot for fun and I’m absolutely terrible about taking vacation.

The last few years, at least partially triggered or accelerated by the pandemic, have led to a lot of changes in my life and what I’m doing and who I feel like I am. But I have to admit, I feel like there’s a lot more coming, any moment now.

Thinking, and thinking, and thinking, and thinking,


May 17, 2023

Hi again Jason,

I love that Ira Glass quote. It brought to mind another, much less eloquent quote which I repeat to myself and my kids often: “Sucking at something is the first step at being sorta good at it.” Pretty sure that’s Jake from Adventure Time bringing the wisdom as usual. Along those same lines, and echoing your thoughts on quitting, is the idea that maybe sucking at something isn’t a sign you need to get better at it. Maybe you just suck at this thing, whatever it is, and that’s okay. Some things, for example, I’d like to quit but can’t: receiving what seems like 100 school emails a week, handling car maintenance, doing taxes. That sort of thing. A while back I decided there are some things in life that don’t deserve or need my level best, and I could be okay with being mediocre at those things.

It’s been freeing. It forced me to make a distinction between what I care enough about to try to master, and what I’m dabbling in without any need for mastery, and what is a necessity to be completed.

In terms of parenting, I realized that I spend a lot of effort working on keeping things clean and organized, making sure we have necessities, cooking meals, etc. I also realized that, while all that’s wonderful, it’s not as important to me as laughing with my kids, or being around when they want to talk, or having the energy to help them sort through drama or difficulties. Sometimes, having the energy and good grace to listen to middle school drama or get outside and throw a baseball means I’m not doing laundry or cooking dinner. Of course, it’s always been okay to make those kind of trade-offs, but for me it took some effort to get clear on why that is okay. It’s okay because everything could matter, but not everything does matter. It’s okay because what steals time, and energy, and opportunity most of the time isn’t an emergency. It’s just the stuff in that mediocre middle. The scope creep of life is something I have to actively manage.

Turns out managing it is mostly about managing my own curiosity and being realistic about my actual capacity.

The next line of that Wordsworth poem is “getting and spending / we lay waste our powers” and it’s a line that rings in my head so often. The frictionless life, as you mentioned, is maybe not the best life. We need friction to give us pause, to force us to take a breath, to make a choice. This or that. What gets my attention? There will always be more options than time, and which option is right for me, right now, is deeply personal. One way I make those choices is by thinking about how I can optimize for delight. What delights me? Delight is a clear-cut emotion for me, which is helpful. If I’m delighted, I know it. “Should” has no place in delight. There’s no halfway with delighted. It’s on or off. So that’s easy to identify, and I don’t need to analyze the Why of delight, only the How: How do I make more time, space, and energy for This Delightful Thing?


Hi Annie,

Jake is a wise friend.

…everything could matter, but not everything does matter.

This captures it all, doesn’t it. It’s funny how much we live with other people’s expectations about things that matter. Because everything could matter, other people, our parents, our friends, society, whatever, all get to yell at us about the things that matter to them. It’s not just that everything could matter, it’s that everything does matter to someone, and those people are telling us all the time. Realizing that not all of those things also need to matter to me has been a huge project of my adult life. That’s probably not what people see, but it is a guilt I carried, and still carry.

Optimizing for delight is a great heuristic. I spent time in 2022 trying to have fun, in many ways in search of the same thing. One of the surprising things about fun is how much it is about getting completely out of my head and fully invested into a moment. There’s no “mind” in my fun. Even when I’m reading a book that’s causing me to laugh or cry, it’s not my mind analyzing an experience or thinking about it. It is my body being taken completely into another world and experience its heartbreaks and joys.

I have to admit, so far, 2023 hasn’t been that much fun. I’ve let a lot of things stress me that should, and a lot of things stress me that probably shouldn’t. I’m doing less well at maintaining routine and a lot less well at making time and space for the things that provide delight. I’ve spent a lot of time this year “giving myself a pass”, but I’ve got to find the motivation soon to stop that– it’s become and excuse to not do the things that I know make me happy and are good for me.

This was a good reminder for me. I have some work travel coming up, then a short period of time before some fun travel. I’m going to work on reclaiming some time for delight in my routine.


May 16, 2023

Meta note: This one came in a bit late– I’m publishing in the order that I receive.

Hi Jason,

Forgive my tardiness and since it’s the second time in a month that I have had to say this, I have realized this is something I have to work on. That is, If I commit myself to a voluntary task, it shouldn’t be considered secondary to my other live obligations especially if it involves someone else. Talking about space, one of my favorite aspects of architecture is in fact, the spaces between the built environment and the world around it. In Indian mythology, a king received a boon that he couldn’t be killed indoors or outdoors and as we can expect, the king soon become a tyrant and one of the gods had to reincarnate himself to kill him on the threshold of the house.

Morbidity aside, I found that loophole interesting since it begs the question at what point does indoors become outdoors. Most architecture makes it quite distinct so the space that blurs the boundaries always fascinates me. Air-conditioning in America often makes such a design impossible but in South India especially in traditional homes, a central courtyard around which a house is built is very common and it works much better than air conditioning in a much warmer climate. Here is an example (there are plenty of examples in the “more like this” under the image). I bet this is very similar to homes in Mexico which is one of the reasons I am hoping to do an extended trip down there like you did. A close second is a public square. It can range from the grand St. Marks’ in Venice to a small plaza outside a movie theater adjoining a Starbucks and an Atlanta Bread Company in Dunwoody, GA where my friends and I hung out all the time.

Moving on to the other topic you raised about our ability to solve problems, my experience of spending nearly half of my life in India actually makes me more hopeful about America. A few months ago, my brother and I were talking about life in India in context of my dad living there after my mom passed away. He’s not exactly a fan of the West and would like to move back whereas me on the other hand, can never think of that possibility but both of us could agree that a civic sense is something that India lacked. I can elaborate that it’s largely a lack of trust in public institutions. The oppressed classes feel it more strongly and that has led to a sense of quiet resentment among the general Indian people which at times erupts in horrific inter-religion or inter-caste riots (literally). Living in America makes me feel more hopeful and even though latest events against democracy, it’s still a country rooted in strong institutional trust, a high sense of civic sense, and participatory democracy. People, in fact, give a shit.

But of course, as you say, in the sense of tragedy of commons, it hasn’t quite worked off late to tackle the large problems that society faces like climate change, healthcare, or even gun control. But I find the root causes are in the amplification of a small minority of “shitposters” even the good-meaning ones who often trivialize talking about solutions. I sometimes come across as argumentative and am expected to “take a chill pill” but that’s mostly because people don’t want to feel uncomfortable and be questioned. And if their beliefs are questioned, they often retreat into a shell of not airing their opinions instead of being open to change. I would say, forget change but even if the historically dominant classes could muster up empathy and recognizing why others are angry, we can make progress.

Anyway, I think between the two of us, we are preaching to the choir but thanks to your experiment of making these letters public, hopefully others can read and ponder without assuming that they are being called on. Thanks once again for doing this and save for my tardiness, I hope this exchange has been meaningful to you. I certainly have learned a lot.

Pratik Mhatré

Hi Pratik,

Elsa and I often joke about how much we love a courtyard. It’s a shame that America spread out with single family homes, but made them all boxes designed like a fortress to the outdoors. All of our knowledge of passive heating and cooling (and siting) left completely by the way side for efficiency. I love the city, and I think most of our homes should be in cities, and the American suburban form seems like all of the efficiency in building with none of the efficiency of living in a city. Cities manage to be beautiful and efficient, but our single family home seem to have chosen, at best, efficiency without beauty— neither form, nor function.

I do love the old courtyards when you can find them in Mexico, whether in older homes now subdivide or incorporated into multi-family apartment structures. The airflow and light alone seem worth it, but so is the blending of indoor and outdoor. A lot of Mexico City is clearly designed for year round comfortable weather, and quite often the indoor-outdoor distinction is more of a veil than a wall.

I find your take on our ability to solve problems at least somewhat comforting. I think it’s hard for Americans to forget about some of the “easy” stuff, that even when it doesn’t work great, is universally expected to work here. I’m thinking the postal service, water and sewage treatment, waste management, and electricity. Even places like schools and libraries, for all that we’re experiencing what feels like an unprecedented erosion in support, are still understood to be present and function well. I do think we give a shit, and most of us expect all of these things to function. We just can’t seem to agree about the why.

There’s a fine balance I think we all have to play when it comes to pushing folks on their beliefs. On the one hand, silently letting small things go by create the underlying conditions for changing what are acceptable beliefs. When someone posts about how they needed to vote via provisional ballot (that was accepted and counted) because of some small issue at a polling place and how that causes erosion of trust in the voting system, how do I respond? On the one hand, in a rational space where we have shared understandings and beliefs, I can have an intellectual conversation about how small inconveniences and errors can cause people to question the efficacy of a bureaucracy. On the other hand, that’s not what this person is saying. And even if that’s what someone is literally saying, that’s not what our current conditions cause others to hear. How important is it to be the voice to say, “Hold on a second, this is very normal, there’s a process, you did vote, your vote was counted, this is everything working in the careful, cautious, correct way that we want. This isn’t a moment to lose trust, this is a moment to understand how these systems function exactly the way you’d want to build trust?” No one likes having to be that person every time. And yet. And yet. And yet.

Where I grew up, casual racism is rampant, and despite having long had large populations of immigrants, mostly from groups that were shit on just like the current wave of immigrants until 70ish years ago (primarily Irish, Italian, and Jewish), anti-immigrant sentiment is rampant. The current, disgusting incarnation of the GOP is rampant. When I go home to my parents, or when I see comments from people I grew up with, I am assaulted with casual opinions that are all just opening a small door to the truly terrible thoughts. The casual prejudice, which we spent so much time in school discussing as one of societies great ills, is everywhere. I can’t help but to challenge it often.

But there is a point at which I can no longer be heard if that is all that I am. There is only so much labor and work I can put into that fight without burning myself out and burning out what tenuous relational currency I had to be heard in the first place. It’s tough to draw the line. I know that for folks like that to truly change their minds, for them to change, they’ll need to be questioned, over and over again by people they trust for decades so that they start to think, “Maybe something is not quite right here.” You have to chip away at beliefs, making the fissures and cracks for self-doubt to creep in.

Keep chipping away.