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


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

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

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

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

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


Hi Katie,

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

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

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

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

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

What’s got my attention…

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

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