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

In some ways I am very online, yet there will be no trace of the most important things about me and my life when I’m gone. The best parts of me… the relationships I have…everything good about me will never be recorded. I just have to hope and accept that it exists in those I love.

The responses to Matt Mullenweg’s recent post on how Tumblr was early to a lot of core social features of the web are intense. Lots of complaints about some horrific redesign that has supposedly happened. So I opened up Tumblr, as I do about once a month, and it looks the same?

If anything, Automattic hasn’t done enough. Tumblr is still impenetrable to folks who are not deep power users, and the power users are still convinced that all change is bad. Meanwhile, the platform has one of the worst targeted advertising systems I’ve ever seen (or simply the worst quality ads filling their slots I’ve ever seen) while at it’s core being an absolutely incredibly good social blogging system¹.

I cannot tell what has changed there, and that’s bad. I have spent years wanting to use Tumblr without ever getting it to work. I’m their best shot at conversion, and since the Automattic purchase, nothing has happened that actually helps me become a regular.

Tumblr is all wasted potential. It should have been Instagram. It should have been Twitter. It should have been Mastodon. It has always had everything it needs technically, but has failed to put it together to win from a product perspective. Tumblr should be a case study for anyone in B2C product management. The only problem is, I’m not sure any of us would know how to fix it.

Gracie is still quite old, but having more good days than bad. The good days are not as good as they were 6 months ago, but she’s got some happy life left in her.

It makes things like what happened this morning so much more meaningful to me. She has gone through many phases of level of independence– sometimes never being ok being alone, other times liking to be on her own. When she was first getting sicker, she spent quite a bit of time alone on the second floor in the living room. She was tired and seemed less interested in everything. It was one of the signs that felt like the end was near.

Lately, while still tired, she’s spending most of her time during the day with me. This morning, even with her grandma on the second floor eating and messing around in the kitchen, when I left from upstairs to get a coffee, she followed me to the second floor. When I returned, she waited at the stairs to see if I was going up, and when I did, followed me right into my office.

She didn’t want to be pet or paid attention to– or at least she didn’t give any indications of that. She just wanted to lie down in one of her three spots (in her bed, by my feet under the desk, or across the doorway) while I do my thing.

There are lots of ways that dogs can show their love and affection. Gracie is different with Elsa than she is with me. She’s different really with everyone. Her spending time with me is the perfect way to show her love. I’ve always been a “quality time” person. Somehow, she gets that about me.

This month I’m corresponding with Jacob Mishook

Jason,

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

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

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

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

Jacob

Hi Jacob,

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

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

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

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

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

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

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

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

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

Jason

On margin, I think it’s great that we’re unwinding COVID spending. It was a miracle there was actually support for very big investments during COVID to keep people above water, but that support was tenuous and may not have been present with a democrat in office.

Allowing pandemic and emergency spending to go away is critical to ensuring we can keep doing emergency investments when necessary in the future.

Imagine how much worse COVID would have been for people’s families and lives if every single step along the way (even more than it felt like this was true), the GOP would have been fighting that if they give this relief now, it’ll never go away.

Crisis spending is meant to help resolve the crisis. And while we continue to live with a new, frightening disease, we are no longer in the crisis we were in before.

On matters like student debt relief, the child tax credit, supplemental spending in education and at child care centers, the crisis funding should stop.

We can argue for each (or all) of those supports as a part of our permanent social safety net, but we should not be fighting for them as part of COVID or the crisis that was.

Here’s the thing– politically, this additional spending does not have the support it needs to be sustained. Fight for that, don’t try and win on fragile technicalities or twist a quick response system into permanence.

That last blog post did something I have been playing with but never articulated.

A lot of folks seem stressed about writing titles to blog posts. Short posts are mostly title-less, and there’s this sense that picking a title is a point of friction. There’s also a concern that no one clicks links or keeps reading.

I think that’s all a bit silly, but I know that my own absence of some kind of hangup around writing titles doesn’t mean that others don’t feel it.

But there’s already a native social form for long posts that are supposedly “title-less” that many folks clearly read. And mostly, when they read those long posts, they’re doing the equivalent of clicking through, so that’s clearly not a barrier.

We call these long posts “threads”, but really, they’re just a series of sentences or paragraphs where the lead in sentence is meant to draw folks into what you’re about to say and warn them it will span more than once 280 character block.

We have another term for an initial short sentence or phrase that draws people in and warns them there’s more than 280 characters to follow – titles.

I wish folks who adopted long form, title-less writing would learn from threads on other social platform and just make their opening sentence or so the title of their post. That’s what the first post in a thread always was, and it gives me far more to go on than a randomly truncated paragraph. You can certainly craft a 200 character or so sentence or title to start your post. You probably already did. Just make that the title.

Repeatedly watching smart people get tripped up on Mastodon, the Mastodon API, and ActivityPub has changed my opinion on the complexity of these services.

I have long thought the “Mastodon is hard” folks are being silly, but now I think they’re right. The conversation around interoperability and standards causes people to completely misunderstand what is possible (or even desirable). The ways in which Mastodon is not only or entirely ActivityPub confuses people.

The folks who seem attracted to Mastodon in the first place who are non-technical are sold a bill of goods about what is possible, not understanding protocols, APIs, federation, self-hosting, and all the ways they interact, along with the myriad of non-Mastodon services and how they can or can’t interact with each other and Mastodon.

What we used to call “prosumers” are getting killed by all of this mess.

Mostly they should just write on their blogs and forget about it.

I’ve talked about this exact idea before:

But if we see all the dogs running in one direction, especially if it’s towards us, we should take note.

A huge part of my own evolution and change in consciousness came from trying to be aware of where the dogs are running. When an idea is abhorrent to many people I respect, I try and pay extra attention to what my own bias may be doing or the interests of the people making an argument.

Yes, we need to learn from those who leave movements. And when people tell us who they are and what their project is, we should believe them. And when people tell us those things in the context of trying to convince us their politics are acceptable politics, we should apply caution. And when the dogs are running toward them, well… then we know what’s happening.

I also find the notion of a center situated above the political spectrum captures an incredibly dangerous idea. It’s one of those enticing ideas people with a certain level of intelligence fall into. “My politics is to look at the evidence on each issue and go with what that tells us.” This is a thing I’ve said, I’m sure. It’s a thing a lot of “Rockefeller Democrats” have thought describes them. It’s an idea every young libertarian dipshit thinks after their first economics class and reading one Robert Nozick essay. Basically, this is the explicit strategy designed to generate Ben Shapiro’s “high schooler who read Fountainhead” intellectualism.

But of course, none of us are above and separate from ideology. Our biases are a part of us. The biases of others are a part of their communication and their program. Underlying all evidence is a set of belief and theory to describe the world that embeds values.

There is no view from nowhere, there is no objective, values-neutral evidence on social activity. This ideal exists like a perfect sphere rolling down a frictionless inclined plane. Those who claim it’s mantle know exactly what they’re doing. Do you know what they’re doing?

Hi Jason,

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

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

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

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

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

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

Simon

Hi Simon,

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

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

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

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

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

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

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

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

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

Jason

Meta: This month I’m corresponding with Simon Woods

Hi Jason,

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

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

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

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

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

Speak to you soon, Simon

Hi Simon,

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

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

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

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

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

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

Jason

Ever have a fair amount of energy to do something, like write a long blog post or tackle a long term project for work and get interrupted just 10 or 15 minutes into the flow and completely lose it?

I was really getting going on something that I’ve wanted to do for a while, and all it took was Elsa asking me to help her with something for a minute and I’ve lost all motivation.

I don’t blame her– I was helping her do something that falls right into this category of a project we’ve been putting off (although in this case, it was something that literally took less than 20 minutes) that needed to get done.

But it’s so frustrating how fleeting energy and attention can be.

I’m not sure if it’s just the nature of my brain, the nature of knowledge work, a symptom of burn out, or what. But some projects just take a special combination of time and energy that cannot be conjured, just used when it it hits.

All summer there’s been construction work along Falls Road. Early on in the project, I thought about how much they were ripping up the street and hoping that we’d finally get something better than a thousand bits of patchwork and properly repave the street. To my surprise, a few weeks back, they cut the telltale grooves into the street that indicated we were going to get fresh, curb to curb, asphalt.

Imagine my delight when we had new street after extensive construction.

This has only been met by sheer rage, as just a few weeks later, a new crew shows up and cuts a huge trench right down the center of the road. They have been laying down metal plates since, and I’m sure when they’re done they’ll fill it like a pot hole.

This entire road was torn all the way down for work, and no one could coordinate with the next guys? They just show up a few weeks later and fuck it up?

This kind of every day incompetence in planning and coordination by local governments drives me insane. It’s the kind of low quality services that are unacceptable at $22.48 per $1000 property tax rates.

We need people who care enough about government services to do them better.

Police don’t solve crimes. They don’t prevent crimes. They mostly pull over black people for traffic violations.

In 2019, 88% of the time L.A. County sheriff’s officers spent on stops was for officer-initiated stops rather than in response to calls. The overwhelming majority of that time – 79% – was spent on traffic violations. By contrast, just 11% of those hours was spent on stops based on reasonable suspicion of a crime.

Reuters

Hi Jason,

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

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

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

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

Lee

Hi Lee,

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

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

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

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

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

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

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

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

Jason

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

Hi Jarrod,

Thanks for the kind words.

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

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

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

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

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

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

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

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

I look forward to finding out.

Jason

Hey Jason,

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

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

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

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

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

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

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

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

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

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

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

Thanks for coaxing these thoughts out of me.

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

Until next time,

Jarrod

For all the criticism about school opening or closing decisions, my impression is largely that districts were responsive to their parents. The thing is, not every district serves the same parents, and with big race, income, an education differences in preferences a lot of folks got really confused reporting on these stories.

Most of the tensions about school opening and closures came from one set of parents arguing what should be done for an entirely different set of parents.

A strong public health response, both in terms of what we did to help people not get sick or die from COVID and educating the public, would, hopefully, have smaller gaps between parent groups and their preferences for reopening. At the same time, in a country as large as the US, there were very few moments where a single response or narrative made sense in all places at all times.

I’m left thinking about the classic conundrum taught in every single education survey research course. Ask someone about how public schools are doing, and they’ll tell you they’re terrible. But ask someone about their neighborhood school, and satisfaction always seems quite high.

I bet the COVID response largely functions the same way.

There are basically two things that are interesting to me about Threads so far:

1. I’ve discovered more photographers¹ on there in one week than I have after years on Instagram and my year on Glass.

2. Some friends of mine are posting there who never “got” Twitter, but their posts would have been great tweets.

Hi Jason,

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

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

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

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

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

Lee

Hi Lee

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

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

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

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

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

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

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

Jason

And now for something not entirely completely different…

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

Hi Jarrod,

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

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

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

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

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

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

Looking forward to our month.

Jason

Hey Jason,

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

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

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

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

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

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

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

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

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

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

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

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

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

Talk to you again soon,

Jarrod

This month I’m writing letters with @leeS.

Hi Jason,

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

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

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

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

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

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

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

Looking forward to hearing from you.

Lee

Hi Lee,

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

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

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

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

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

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

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

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

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

Jason

I’ve been using the Godspeed caps for a really long time. It was time to clean them up, so I decided to switch keycaps for a bit. Feels weird.

Before

After

Riccardo Mori often has something interesting to say. He recently took a bit of a hiatus, and in his return post he wrote:

A tweet from back in March — So much tech today feels more focused on the creation of ‘digital toys’ more than on innovation that can actually, unequivocally positively help and advance humankind. And [I feel] that a lot of resources are being wasted on things whose real usefulness is debatable, e.g. self-driving cars.

A lot of unease I’ve been feeling in recent times boils down to what I perceive to be a widening disconnect between the tech sphere and the world at large, the real world that is going to shit and down the drain day after day.

The tech sphere looks more and more like a sandbox for escapism. Don’t get me wrong, some escapism is always good and healthy as a coping mechanism, because otherwise we would be in a constant state of depression. But — and I may be wrong here — the kind of escapism I feel coming from the tech world is the sort of ‘bury your head in the sand’, ‘stay entertained and don’t worry about anything else’ escapism that want people to remained hooked to gadgets and digital toys in ways that at times feel almost sedative.

I think this all comes down to software. Marc Andressen’s well-known article, Why Software is Eating the World, from 2011 is often cited, but I think that Ben Thompson is the much better read on this topic. In 2019, Ben asked, What is a tech company? and identified five key features:

Note the centrality of software in all of these characteristics:

• Software creates ecosystems.
• Software has zero marginal costs.
• Software improves over time.
• Software offers infinite leverage.
• Software enables zero transaction costs.

The question of whether companies are tech companies, then, depends on how much of their business is governed by software’s unique characteristics, and how much is limited by real world factors.

There’s a pretty broad set of industries that were full of distribution and production costs that software can eliminate. That’s been the primary engine of economic growth and “innovation” for the last 30 years. On the back of manufacturing breakthroughs in battery and semiconductors, computers kept getting more powerful, less expensive, smaller, and connected. With each step change in general purpose capability and availability, a new set of industries and practices became vulnerable to being eaten by software.

The last decade we have begun to see the end of this parade. Companies often claiming to be software companies these days often do so to pad a longshot investment thesis (the motivation for Ben’s article), but we’re well into the long tail of the “real world” that is not so easily disrupted by bits.

We saw when Apple and Microsoft and Amazon were exciting and watched them topple past giants in money, power, and cultural influence. But they’re big and mostly boring now. It may be some time before more exciting stuff starts to happen, and maybe they’ll never be as financially valuable as the first set of companies to ever dominate a zero marginal cost, zero transaction cost market, but they will exist.

It’s true that we build a lot of digital toys. I don’t bemoan the toys. They’re not interesting, but capitalism builds lots of toys hoping for a market. It’s been the easy path to money. ¹ But I also think that it’s easy not to see some incredible things happening.

I remember in the mid 90s when my grandfathers both needed angioplasty and stents put into their hearts. These were routine, but quite serious surgeries. They were life saving technologies not available to even their parents. But they were in the hospital for days and it was quite nerve wrecking. These days those procedures happen in a catheter lab as soon as problems are noticed. We check your heart and just fix things up while we’re in there and send you home just a couple of hours later. Advancements in laparoscopic surgeries are incredible. mRNA vaccines are real, big time, and absolute remarkable. Solar power has gone from something people laughed at Jimmy Carter about to the most cost effective source of utility scale power that you can also install on your home roof.

There have been advancements in science and technology.²

The problems we face as a society and a culture are not software or hardware problems. Our challenges are fundamentally rooted in hierarchy, power, and inequality.

We’re not really lacking in some fundamental technology we need to address climate change. We lack will. We lack the ability to convince others. We lack the ability to combat misinformation and fight a system that fails to incentivize the longer term and the bigger picture.

We’re not lacking in some fundamental technology to address inequality.

We’re not lacking in some fundamental technology to address racism, homophobia, and an anti-trans movement.

The “technology” we lack is empathy.

I’m disappointed in our society and technology is no longer an effective place to distract myself with optimism and a sense of progress. Riccardo laments, “the kind of escapism I feel coming from the tech world is the sort of ‘bury your head in the sand’” – but hasn’t that always been true? Maybe Riccardo had a different experience with technology than I did. Or maybe he bought into some of the industry hype that rang hollow for me. But I just feel like if what you’re worried about is that “the real world that is going to shit”, and I am worried about that, I’m not sure why you’d look to the computer technology sector for solutions.

Tech world has no solutions for our bigger problems. Tech world is all about making it easier, faster, and cheaper to impose our will in the world. But our social-political-cultural problems are matter of what we will, collectively.