Kyle Hebert

Hello and Welcome!

I'm Kyle Hebert, an engineering leader who spends a lot of time connecting dots. I work across multiple teams, focusing on technical health, system-level risk, and making sure product ambition lines up with what engineering can actually sustain. I’ve learned the hard way that authority isn’t the point—initiative is. I care about making good software, and even more about the people who make it.

In my spare time I dabble in a lot of hobbies like video and board games, reading (mostly fiction), and attending as many live music shows as I can sustain.

I live in Minneapolis, but I was born and raised in Louisiana. It's pronounced a-bear.

Here's what I wrote yesterday:

Weekly Retro #32

The week was about coming back, getting back to routine, and the comedown from the NYC trip. I was also getting over a cold that my wife eventually got.

It was an emotional week for me too. I’m not sure how much I want to get into the specifics, but I’ll talk a little about what I’ve realized as a result. The short version is I spend a lot of time, too much time, in the future. I get into this mode where I’m predicting what will or won’t happen, and things usually go negative fairly quickly. Sometimes, even after predicting a positive outcome, I’ll return to it later and go the negative route instead. It makes any moment of joy ephemeral—I almost immediately start thinking about how I can get that feeling again, and mostly assume I won’t be able to.

I tend to rehearse events ahead of time by going through the permutations of what I will and won’t say and trying to predict the responses to those things. Trying to glean information about something that hasn’t happened, and in some cases won’t happen, when there’s no real way to do that. So my brain invents. I run these experiments, though they aren’t really experiments because there is no actual data. It’s all imaginary.

This goes in reverse too. I revisit the past. I pick apart conversations and interactions trying to glean meaning or interpret intent when the present usually has the answers to those things.

The week was largely that, and frankly it’s exhausting. However, with my therapist and on my own I’ve realized two things: one, that this is happening, and two, that I’ve kind of found the solution: spontaneity and improv. Let me explain.

I noticed this first in NYC. We had some plans: a Broadway show, some dinner reservations, some destinations. Everything else was left open. We would walk to a destination, but if we saw something interesting we’d stop and do that. What that meant was that even though there were some unknowns—the kinds of things my brain tries to dissect and predict—the uncertainty is immediate and participatory. Participatory is the key. There’s something for me to respond to or interact with. Future uncertainty doesn’t provide that. There’s no data about the future. Nothing to interact with.

Good conversation can also do this. What I mean by good conversation is the kind that flows from one thing to the next, almost like a musical performance. Everyone is just riffing off of what the last speaker said. Not in an “I’m just waiting to speak” mode; it’s a listening and responding mode. Sometimes if I try to remember what those conversations were about, the details are fuzzy, but the impression they leave behind isn’t. Those conversations feed my soul, and I think it’s participatory improv that does it.

My therapist has picked up on this as well. She’s encouraged me in our last two sessions to pick up writing fiction again. I think it’s a good idea because it also taps into that same participatory improv. I have a destination in mind for the story and its characters, but I don’t actually know if I’ll reach that destination or what the characters will do or say.

I did some writing this week, and I’m trying to find space for more of it. Trying to find more participatory improv in general. Get out of my head, stop analyzing, participate rather than predict. That’s definitely what Mojo Kickball offers. I think it will be at least part of what the Kith + Kin chorus provides.

Things I enjoyed this week

  • My friends and I rolled credits on Big Walk this week. We’re not done—there are still more puzzles to solve, but wow, what an incredible experience. I won’t spoil it, but the final set of puzzles before the credits is among my favorite experiences in gaming.
  • I finished Kate Atkinson’s “One Good Turn” this week, and literally laughed out loud when I read the final sentence. No one does it better.

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