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 #33

Well, it was bound to happen, but I only just realized I forgot to write one of these last week. I’ll try to recap the last two weeks here, but I’ll be honest, even trying to recap a single week is hard enough.

Therapy has been going well. Once I came to the conclusion about participatory vs anticipatory uncertainty, the next step was participating more. What that means for me is staying in the moment and participating in what’s happening right now. I keep waiting for things to happen, or some perfect version of them to happen, when sometimes that thing is actually happening. I’m trying to keep myself in the moment and noticing how often I tend to go into the future. Even on my way to therapy on Thursday I caught myself preparing what I was going to say when I walked into the room. I stopped myself and said “No, just wait until you get there.”

The other side of that coin, though, is that I can now see why I go into the future so often: the present is full of unmet desire, and I’m learning that I don’t handle that very well. Not in an “I’m going to force this to become true” or “my desires outweigh all others” way, more in an “I can’t comfortably sit in a moment not knowing what comes next” kind of way. That’s when my brain kicks into problem-solving mode, mapping out outcomes and possibilities with little or no information. So the outcomes are negative, the possibilities go rotten, and I miss out on the good that’s already happening. Or even the bad. That’s important. It’s not all good, and that’s okay.

I can start to see how I wound up in the box that made my life feel so small. A life on rails has no desires. And of course that’s awful too. What I’ve learned, or at least what I’m learning, is that I’d rather have the bigger life with unmet desires. Now I just need the tools to handle that better than I have been.

This week we wrapped up three weeks of John Hughes films at a theater near our house. One film a week for the past three weeks. We saw “Pretty in Pink”, “The Breakfast Club”, and “Ferris Bueller’s Day Off.” Of the three, the only one I’d ever seen in its entirety was “The Breakfast Club”, but I knew the bones and structure of the other two. I enjoyed all three, but I’d probably rank them in the same order as we saw them.

We also saw Phoebe Bridgers this Thursday on the Saint Paul stop of her Lost Weekend tour. It was incredible. I was worried her songs wouldn’t translate to an arena show, but she managed to pull it off. The show had some of the best lighting and stage design I’ve ever seen, and, of course, Bridgers was great. The best part, though, is I don’t have any photos or video of the show because the tour is a “no phones” tour. When you enter the arena they seal your phone in a pouch that doesn’t unlock until the show is over. It meant people were talking to each other before the show, making friends, and when the show started we all just watched with our own eyes and listened with our own ears. No one pulled their phone out to record the cool moments, of which there were many; instead we all just experienced something amazing together, and you literally had to be there to see it.

Things I enjoyed this week

  • We started watching the TV show “Furious” and it is living up to the hype. Thrilling, well-acted, full of great characters.
  • We finished DTF St. Louis this week, which started oddly but finished strong. It’s a dark comedy that deals with some heady themes, including loneliness, which really resonated with me.

Continue reading →