I have grand plans for tomorrow, hopefully starting with the remediation crew coming in the morning, telling us that my office and mother-in-law’s room are both dry enough to remove the blowers and dehumidifiers. I assume they will move on to ripping up my dining room and running all the equipment in there.

By then, I hope a roofing company will have picked up the phones and scheduled time to come repair the cause of the leaks ASAP so I can have a reconstruction crew come and fix things.

Meanwhile, Elsa will have gotten Brandy an coveted, expensive, appointment with the dog groomers.

Because we completed all this in the morning and everyone is out the door, we can head out and buy a new range hood.

Lastly, I’ll pack for our two-night away Philly-cation.

Oh, and maybe I’ll finish the last book for my reading goal.

I used to be a great teacher. I tutored all throughout high school and college. It was my primay source of income ($25 an hour, cash, don’t tell the government). Early in my career, I was great at this as well. Sometime over the last five years or so, I’ve felt my ability to communicate complex ideas to non-experts dwindling. I spend so much time time in the weeds and so much time talking to other experts and so much time thinking about hard problems that I’ve totally lost site of the scaffolding.

The last couple of years, I find myself often saying that I don’t know how to teach somethig. I am constantly saying something like, “I’m not really sure how I learned this; I lack the meta-cognition to know how to teach this.”

I am really unhappy with this state of affairs. Being an effective communicator across technical and non-technical audiences is a key skill in my line of work. And while I’m not yet bad at my job because of this, spending ten years at the same company and working in the same domain has had a narrowing effect.

I want to recover my ability to build up information from first principles. I want to be able to teach foundational knowledge that I find valuable.

I don’t know that writing will help, and I hate making end-of-year pronouncements about future writing, but to hell with it. This year, I hope to write at least a few blog posts that are informative about complex topics. I want to exercise that muscle of not just demonstrating expertise but transmitting it. I need to break through the combination of perfectionism and an expert’s eye to be helpful again to others. I need to break down what I know in a way that is accessible to a non-expert.

Hello Jason,

I’m near the top of Mount Rigi as I reply. I’m now on my Christmas holidays and managed to carve out some time to go on a solo mountain holiday (thanks to my wife for allowing that). Unfortunately, the weather is not good. And I was the only person making it to the top (I’ve attached two images from the top - you may publish them with the letter). But I’m not on the mountain to sit outside anyway :-). I hoped to relax, reflect on the year, and write a bit – sometimes, it works better outside of home. But so far, I have not yet written much. Now I sit in the small restaurant beside the railway station on the mountain.

The US being a lot more in the south compared to Europe is also something I forget. But geography is not really a strong suit of mine :-D. I just wondered what the most northerly destination I visited so far. And it must have been Cologne (in Germany). I’ve only been to the US once (for a WWDC), so I’ve seen mostly the conference center and only a little of the country. I’ve enjoyed SF and want to get back at some point. However, there are so many places to go, and I’m unsure when I will manage it. We also have Japan on our list of destinations. We planned to go in the Spring before the pandemic. That did not happen for obvious reasons.

I have the feeling that many companies have downsized their offices now. There is just no need for offices anymore – at least in the computer sciences jobs. And I’m also with you that the company needs to live a remote-first culture for it to work. Luckily, we are small at the moment, and I hope that I can influence the culture in such a way as we grow.

How was moving 375 miles? If I tried that, I would land in a different country, so it would be a significant change (and depending on the direction I move, I would need to learn a new language as well ;-)).

I’m quite the opposite regarding habits; I tend to have compulsive behavior when I’m not careful. Luckily, I now know and understand some of the signs that trigger this so that I can work against it.

It is interesting with the swimming, and I was exhausted at the beginning with the 500m than I’m now with the 1000m. It is a question of the pacing, and I have now found the sweet spot where I can swim it at a usable tempo but also not go quite to my limit. And having done it now for most of the year also helps :-). I’ve lost track of how many books I have read this year. Only a few, I think (compared to other years). I planned on reading three books per month, but I was below that. It was more like two books per month. One of the reasons was that I switched to reading more nonfiction, which takes more time. And then taking notes and thinking about what you learn makes for a slower read. On the upside, it makes the reading more conscious and intentional. It feels less like fast food.

Another big goal was changing my workplace and starting the swimming habit. I don’t know what I want to do next year. One big topic is to be more open about others and be less in my bubble.

I wrote the text above yesterday. The weather is much better today, and I’m back at the top of the mountain. I am sitting in the same restaurant and enjoying my time.

cheers Chris

Hi Chris,

Things have been pretty hectic so it took me a few days to get back to you. While I’m not yet off from work for the holiday, I do already have a rotating cast of family staying with us. Unfortunately, I also had the return of some leaking in the house from severe wind and rain. I’m currently without an office, and soon our dining room will get torn apart as well. Things seem to be moving faster with both mitigation and repair than last time, but it’s a big unexpected expense and a big unexpected mess during a time where it’d be nice for things to slow down and go smoothly.

I want to say that the solo mountain holiday is exactly what this calls for, but seeing those pictures just makes me feel cold.

Moving was interesting. This is the third place I’ve spent a substantial amount of time living. My parents still live in the house they bought before I was born, but I went about 200 miles away for college and stuck around for some time afterwards before this move. It definitely broke a lot of my social groups and connections. I felt, for some time, less connected to where I lived than I ever had before. In some ways that was nice– you can burn out on places like you can with jobs, at least as far as I can tell. I loved where I was living, but I was “burned out” on it, in some ways. I think it’s taken the full seven or so years I’ve been here for it to start to feel like home. I’d be lying if I didn’t say I have a little bit of wanderlust again, but I doubt I’ll be going somewhere else soon.

I think there is something to think about in “finding your pace” in a sense. You found yourself at a pace that you can swim, and a pace that you can read. A lot of the times we set goals rather than set a pace.

I hope that these letters are a small start to getting out of your bubble! I also don’t quite know what’s the goal for next year, but I’m glad that this year I’m feeling introspective and thinking about it. Last year, I really struggled to think about what I wanted and I think that led to a year that was a bit less grounded and focused than I would have liked.

Being “evicted” from my damaged office is leaving me unmoored this week. But hopefully I’ll have something to grab onto in January.

Jason

Hi Jason,

I just realized you were in Europe on holiday :-) How was Paris? It has been quite some while since I last was there. It would be nice to go there again (and it is pretty near – only four hours by train, I think). But then I would need to speak French, and I’m not good at it at all :-D Did you get around well with English?

Wow, that is a long time at the same place. I can not quite compete on that point; I was in my ninth year at the old workplace. There was also a lot of change, but I had more personal change and development in the end. So, I needed something new. And I also wanted to switch to product development compared to agency/consulting work.

Volleyball is fun, but it would not work for me to do regularly – too much social responsibility – which is one reason I like swimming. I can do it alone. But I also like being in the water. It is easy to do, and you can think about stuff while swimming. I don’t need to look outside so much compared to running. And I don’t only use my legs, which is also good, as I have a lot of tension in my arms and shoulders from being at the computer all the time. I started with around 500m at the beginning of the year, and now I’m up to 1000m, which was my unofficial goal for this year. Right now, I need around 30 minutes for it.

It is interesting how sometimes you don’t want to be alone with your brain – I also have this. But it got less so over the past few years (as my mental health got up again). But I’m used to being in my world inside of my brain. And it helps me when my body is doing something physical simultaneously. I struggle with classical meditation, where I must sit still and not think. There is so much going on in my brain at all times :-) Luckily, there is more positive stuff now again.

It is interesting how you can use them as a journal. I was initially using my blog as a journal as well. But when I started to write morning pages, I managed to move some of the stuff to a private place. I can use my blog again more for intentional writing – right now, I’m still trying my hand at fiction writing. But it did not go well this quarter. I was too distracted by the new job and the migraine battle.

Although the workshop was fun, I was much more nervous than I should have been, and I’m still trying to figure out why. I need to work on my pacing; I should have rehearsed it at least once. But at least everybody is not up to date on “Cybersecurity.” They think a bit more about strange emails they receive and ask me whether I made another test with them.

And speaking about work. I’ve seen that you work in a fully remote company. Was this an intentional decision for you to not work in an office? I assume that you were doing this already before the pandemic. I’ve only switched to remote work with the pandemic now. And I would not want to do it any other way. Unfortunately, I have already started to feel the pull of the office as most of my coworkers are in the office regularly. But I don’t want to. Having 100% remote work in my contract is one of the perks of the new position!

Cheers Chris

Hi Chris,

We were fine with mostly English, though we stayed largely in central parts of the city and my partner Elsa does speak French (and Spanish) fluently. I am unsure how I would have felt without her and zero French to fall back on, but I think overall the city was more welcoming to me as a very obvious American than I expected. It was my first time in Paris, and the furthest north I’ve been in Europe (probably pretty close to as far north as I’ve ever been, now that I think about it – most Americans, myself included, don’t remember just how far south we are compared to Europe).

I work with quite a few people who grew tired of agency work and wanted to build a product. I don’t think I’ve ever had someone leave to go back to agency work who had that experience, but I haven’t had a conversation in some time about the advantages or disadvantages with any of my employees. Most of them tired of not getting to influence what they built, of feeling like they did a less good job because clients only wanted to pay to make something work, not make it last and all of that. But I also suspect that swimming in the problems of your own past decisions doesn’t always feel good– I know I’m constantly in a state of frustration with my past self.

Allovue has always been at least partially remote. When I started, I lived in Providence, Rhode Island about 375 miles from where I live now and where our “home office” was. We had a few team members in the Baltimore area, but we always had a few remote. Some of us travel quite a bit for work, and even the folks from Baltimore often worked from home at least a few days per week. Over time as we grew, the team was almost never majority Baltimore based. So as a result, we were always a “remote first” workforce. We had an office, and use ebbed and flowed. Some teams were a bit more locally-based, others more likely to be remote. In the end, with less than a third of the company in Baltimore, we had way more office than we needed. 2020 was year four of a five year lease and we were already contemplating downsizing the office or radically reconfiguring it. We actually subleased most of our space. But COVID was the clear end of in office work for us– we actually got out of our lease early because another tenant wanted our space, and we never seriously considered having space again. We now have a small room in a co-working space that we mostly use as climate controlled storage. It also gives us access to a conference room for times when that makes sense to use.

I was probably one of the folks who used the office most, even though I travel a lot. I moved to Baltimore about 7 years ago for various reasons (I needed to move, and work and my best friend being here made Baltimore the right choice). My first year here I didn’t have any office space at home, so it was pretty important for me to go in. But once I bought a house in the city and space for a home office, it became less important.

I think remote work has to be a priority to actually work. I don’t think you can be a part of a small percentage of people doing it.

I’ve never done morning pages– I’m not a morning person and can’t even really generate a morning routine, unless you count staying in bed too long, then staying in the hot shower too long, then begrudgingly starting my day. But for some time I was writing in a journal at night. I would write the things I got done, then reflect a bit on work and my personal life. I’d write how I was feeling in just a few sentences, then rank the day. It helped me when I needed it, but for some reason didn’t last long.

While I am a person that likes certain comforts and consistency, I don’t know that I have a lot of habits. I think I view a lot of habits as things that are almost compulsions. They don’t stick. But there are times where I can use a … short term habit (which, this feels like totally not a thing) to break out of a certain thought pattern or rut.

Letters-as-journal for me really just means that writing a letter like this at the pace I write them creates time for a kind of introspection and retrospection that I don’t normally have. I don’t let out thoughts that are diary level private, but it’s also not quite a log. That’s why I settled on journal.

Constraints change outcomes. I didn’t want to get too deep into my own head, so I wanted to write in public. I wanted to write letters to slow down the pace of today’s “common” internet interactions. I thought it would build a different kind of communication, and it has. And I wanted to mostly talk to strangers so that the topics would keep me on my toes. That’s worked too.

Congrats on hitting your 1000M goal! Thirty minutes sounds both short enough to be manageable and utterly exhausting. I’m about to start book 29 for the year. I have a very modest goal of 30 books this year– the least I’ve read since 2018– and I hope I’ll hit it. What other goals did you have for this year? As we fast approach 2024, what are your goals for next year?

Jason

This month I’ll be chatting with Chris

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 Chris,

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?

Jason

Anyway, hi. I went to Paris for 4 nights because we got a great deal on tickets and I’ve never been. I will return.

Via @jarrod, originally from Kev Quirk:

🔗 When Was the Last Time Tech Blew Your Mind? // Kev Quirk

The first time I sent an email was really cool. The performance and battery life of my M1 Mac was (is) very impressive; far better than any laptop I’ve ever had before. But I’m not talking about impressive. I’m talking about the kind of impression that makes you say, “holy shit, that’s fucking incredible!”

For me, it was the Vision Pro introduction. The interaction model, the visuals, and the use cases were utterly compelling, and the raw technology necessary left me astonished. Can’t wait.

Kev’s bar is pretty dang high– the first time he saw text messaging? I have had my mind absolutely blown multiple times since then. Off the top of my head:

1. The iPod Nano (more than the original iPod– I had a Archo Jukebox and knew what carrying a harddrive was like)
2. The iMac G4
3. The first time I saw the Compiz rotating cube when switching desktops on Linux
4. Opening a bash terminal on Mac OS X
5. Retina displays, but especially when they came to Mac
6. HDTV, and then again with OLED and 4K.
7. The iPhone– literally everything about the iPhone through the iPhone 5, and then again around the time of the iPhone Xish when the cameras got truly great. I remember watching cyberpunk anime in the 90s that invisaged things like the iPhone and an always connected internet and thinking that the beige computer in my household den with a dial up modem would never fit in my pocket– not in my lifetime.
8. TouchID and FaceID
9. Distributed version control systems

I could go on and on.

A ton has happened in my life time that absolutely blew my mind. Most of the time, I suspect Kev might look at the above and say “something like this could have been imagined before it existed.” That’s true! I did imagine some of this! But also, most of these things executed something I had a fictional version of in my mind that I thought was impossible– and then the real world out did that.

Jarrod, on the other hand, seems to have a bar that’s a bit low for me. I might be blown away by the Vision Pro. I kind of hope I am. But I find it hard to get excited about things I haven’t touched. Maybe that’s because I read far too much Popular Science as a kid and a lot of what I have expected to see in the world never shipped.

But what’s my actual answer?

I had to think for a bit. Funny enough, I think both of the experiences that come to mind are Apple Watch related, even though I think it’s my least important device.

The first was using Apple Pay from my Apple Watch. Double tap, no phone in sight, fastest payment experience I’ve ever had at a store. The second is using my Apple Watch with a Home Key lock. Just raise my wrist, no other input necessary, and my door opens, fast. Small, delightful, fast interactions with the physical world seem to be the technology innovations today that feel the most impressive.

The Marvels misfire is about the rusting of a platinum brand that’s in need of some serious –not polishing, rather, resurfacing.

I think this is spot on, though I disagree with much of what’s written in Deadline about The Marvels’ disappointing box office.

Disney flooded the zone with crap to get Disney+ up and running. Both Star Wars and Marvel have been deeply, creatively mismanaged. Ms. Marvel was a treasure, and absolutely among the best shows on Disney+. But like Andor, being surrounded by mediocrity is not a recipe for audience success.

And so The Marvels comes out with characters that lack the audience they should have, amidst a series of movies and TV shows that were just not worth watching, to an audience that has been taught it’s ok to wait, without any actor support due to the strike.

Unfortunately, the most likely outcome is Disney learns the wrong lessons here.

Now that Mint is shutting down, there are tons of articles being written about budgeting and wealth tracking apps and services. None of them work well for how my partner and I manage our split expenditures.

For example, you can only have one active Chase account connection– but what if I have a personal Chase card and we have join Chase cards with a different account? (we do).

There is no concept of “income” coming from contributions she makes to our joint accounts– they look like bank account transfers from accounts I don’t have access to, because they are.

There is no setting up as some expenses as shared versus individual, which is an important distinction in my own budgeting– this is what we agree to spend together on restaurants and groceries is not the same as some additional food-related expenses I have in my own budget to track.

Often, there is no great way to setup things like “this is a reimbursable work expense and that’s the reimbursement for that expense”.

I don’t think that my setup is all that unique.

Elsa and I have our income go into our personal accounts. We transfer a set amount of money to a join checking account each month. We use joint credit cards for joint expenses (and sometimes direct payments from our joint checking account). We have a modest joint savings and brokerage account. Separately, we each manage our own personal credit cards and finances made up of “whatever is left”. And because I travel for work and sometimes use my own cards, I have some expenses that are for work and reimbursed later (directly into my savings account).

A full picture of my wealth and expenses needs to understand this blending. I need to be able to construct a joint budget and a personal budget each month. I need to understand our joint assets and liabilities as shared, and my personal assets and liabilities as 100% on me.

Everything out there assumes fully integrated or fully segregated financials. This seems bonkers to me.

I’d build it myself, but honestly, we are pretty responsible with our money and the marginal value of budget or wealth tracking software is pretty modest in our lives. Still, it’s frustrating that so few applications seem to have a concept of family finances that seems obvious to me.

I’ve been watching this go around a bunch and though, “My Uses page covers this,” but Matt Birchler’s emoji use and a rainy holiday means I’m in.

So here are my “defaults” in 2023– of course, it’s Top Four rules, meaning there can be more than one support.

• ✉️ Mail service: Fastmail (personal), Gmail (work)
• 📬 Mail client(s): Mimestream on Mac (work), Apple Mail everywhere else
• ✅ Tasks: Things 3 (barely, mostly paper based)
• 📰 RSS service: Feedbin
• 🗞️ RSS client: Reeder
• ⌨️ Launcher: Alfred
• ☁️ Cloud storage: iCloud (barely… I really don’t do this)
• 🌅 Photo library: iCloud
• 🤳🏻 Photo editing: Apple Photos
• 🌐 Web browser: Safari
• 📆 Calendar: Fantastical
• 📖 Reading: Reeder/Kindle/Apple News
• 🌤️ Weather: Carrot Weather
• 🎙️ Podcasts: Overcast
• 🎶 Music: Apple Music
• 🔐 Passwords: 1Password
• 🐘 Mastodon: Ivory
• 💁🏻 Other Social: Micro.blog, Instagram (too much), and Threads (a little)
• 🖼️ Screenshots: CleanShot X
• 📝 Notes: iA Writer (to the extent I do this… I’m not a notes person, and write a fair bit analog)
• 🧮 Code Editor: neovim (but also Nova… which is creeping up and RStudio… which is creeping down)
• 👨🏻‍💻 Terminal: iTerm2
• ✈️ Flight tracking: Flighty
• 📦 Package tracking: Parcel
• 📓 Journaling: Day One
• 🔃 Backup: Backblaze (☁️), Carbon Copy Cloner (🏠)
• 👨🏻 💻 Blogging: MarsEdit

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

Jason,

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.

-Katie

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.

Jason

I admit to being confused about the cries for a 27" iMac. Count me as one of the many people who was mad Apple didn’t make a great stand alone display anymore and needed a solid pro desktop that doesn’t cost $5000. The 27" iMacs were a bad compromise– an expensive display with an end of life connected to a computer that slowly creeped upwards in power due to the lack of any other options.

The world we live in now, with a Mac mini and Mac Studio that cover significantly more range, affordably, as great computers and the very solid (if pricy) Studio Display is far better for the typical professional user. And the 24" iMac is a great consumer computer.

Everything about the current Mac desktop lineup (and displays) is more coherent and better than it’s been in at least a decade, if not more.

For all the methodologies, crappy business books, and numerous project management/product management/brain storming/planning software out there, most of it fails at deep thinking on how a product should work.

My number one tool remains a notepad and a pen. When we had an office, it was a white board and as many markers I could find that still work.

This isn’t in praise of the blank slate of analog tools. This isn’t a comment on the tactile nature of physical things. What I actually want to do is highlight a process I go through.

The most important “tool” in product management is writing things down over and over and over again until they feel right. Write down a flow chart, vocabulary words, diagrams, paragraphs, or whatever it takes to describe a problem and one possible solution and then stop. Think about how it feels. A few days later, don’t review what you wrote– do it again.

Do it again.

Do it again.

Every time I write it down, I either become more convinced that the rough edges are not so rough or I find my way to a slightly different perspective on a problem that leads me closer to the answer. The end result may look exactly like the first thing I wrote down. Maybe the language is a bit different and there are fewer squiggles as I got to my end state more assuredly. But the thought process that took me from my “guess” to my “solution” is a powerful one.

Through repeating my thought process, I become powerful at objection handling. I see the false paths I have already traveled. I become confident in the trade offs I am making along the way. I don’t know the answer to every question about what we’re about to build, but I come to believe that there are answers and that the problems which remain are relatively small. I have avoided the essential pitfalls that lead to us being stuck with no way out but to scrap all our work.

At this point, I have something damn near a “rule of three”– if I haven’t tried to work a problem from a blank page three times, I haven’t thought about it enough.

This weekend I’m going to a baby shower. One request was to bring my favorite childhood book to help build the baby’s library. I knew immediately I’d choose, Go, Dog. Go! , the first book I ever “read”.

I say “read” because I’m pretty sure I just memorized it.

Just seeing the cover and thinking about a young child reading this book the way I remember reading it sitting at my grandmother’s house caused me to tear up a bit.

There’s just something about the way that a timeless object can also be a binding across time and families.

I was surprised Bix’s take that POSSE has It Backwards, especially because this part:

Ultimately, the future would be better served through feeds and microformats making anyone’s website subscribable through any site or service. It’s something I thought about when conceiving my asocial networking site Currently: let anyone “subscribe via URL” if the owner of a now-like page didn’t themselves also have a Currently account.

Writers should only have to worry about the writing, and reader software or whatever sort or kind should allow people to subscribe to whatever they want

To me, this is precisely how POSSE operates. I post to my blog. From there, there are multiple ways readers can read:

1. RSS Feed
2. JSON Feed
3. Micro.blog feed
4. Bluesky feed
5. Mastodon Feed
6. ActivityPub Subscription.

Each of these are just feeds that folks can subscribe to that I make available. The goal for me is “let people read my stuff from wherever they read things, while from my perspective, there’s one post and one source of truth”.

Some folks will never do an RSS subscription— that’s ok, my website makes feeds available where people want to read. It’s all coming from one feed though.

I want to make it easy for me to write— so I write in one place. I want to make it easy for people to read— so I let my feed syndicate as widely as is feasible.

I’ve seen lots of folks with takes I just don’t get when it comes to syndicating posts. Mostly around some idea of implied reciprocity or presence, as though the idea of “bots” or “websites” versus “people” accounts haven’t been around for a long time. I don’t really get it myself.

Denmark appears to get one idea right (segregation can be bad!) and solves it the wrong, Western way (reinventing 1960s US Urban Renewal– instead of building more affordable housing where rich people live, knock down the homes that house poor people!).

And no, segregation is not the same as ethnic enclaves and other immigrant heavy communities.

It’s pretty disappointing to see the social democracies the US left looks at with lust fall into the same forms of social conservatism we have in the US once “diversity” enters the picture.

Humans. We really can’t do cross-cultural empathy.

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:

1+1=[[(9x3)/3]/3]-1

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?

Anna

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.

Jason

Jason,

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?

Anna

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?

Jason

A local file will require uploading if the size of the local file is different than the size of the s3 object, the last modified time of the local file is newer than the last modified time of the s3 object, or the local file does not exist under the specified bucket and prefix.

— from the official docs

I cannot believe that aws s3 sync is based on file size and last modified dates and not something like an md5 hash.

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,

Anna

Anna,

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?

Jason

I still watch just about anything Star Wars live action. But just like I never clicked with Clone Wars, I really didn’t care for Ahsoka. Removing the fandom context, I have no idea why I should care about Ahsoka, Ezra, Sabine, or Thrawn. Ahsoka (the character) was more effective when used in The Mandalorian as the sudden appearance of a Jedi than in her own show.

I am interested in what’s going on with Baylan Skoll and whatever he is seeking– a new galaxy connected only in the distant past to the one we know is a great idea! – but Ahsoka the show seems to think it’ll have 50 episodes to unveil that story at this pace. I have no idea who the Nighsisters are or what magick is in relation to The Force (presumably it’s the same?), but that seems like it could be interesting. Ahsoka (the show) doesn’t seem to think so.

The folks making Star Wars don’t always seem to be interested in the same things that I am.

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,

Anna

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.

Except…

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?

Jason

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!

Jason

For reasons unknown to myself, I decided to write a long Day One journal entry about how hurt I was when I didn’t get any play time my senior year in high school on the volleyball team.

I had what felt like a years long, close personal relationship with my coach that shattered. Neither of us were ever direct and honest about the situation. She never told me I wasn’t going to get play time or gave me feedback on how to improve. She never seemed to even consider that my senior year, even our last game, I might want to take the court. We lost every game that season and not even when a match was clearly forfeit did she put me in.

Not once.

Its one of the few things that I look back on even nearly 20 years later that still feels raw. Writing about it in detail helped a little, but as I write this follow on public post I can still feel how raw it is.

I stopped playing volleyball for 17 years after that. I did not even allow myself the thought of playing in the most social of recreational leagues. Volleyball and rejection became synonymous. I’m glad I have spent more time playing volleyball the last couple of years while I still physically can. I love it just like I did before my senior year. But I still carry some pain, dulled though it is, about the whole thing.

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?

Jacob

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.

Jason