2025 in review.

career (44), blog (21), year-in-review (8)

Yet another edition of my annual recap! This year brought my son to kindergarten, me to forty and to a new job at Imprint, my fourth book to bookstores, and a lot more time in the weeds of developing software.

Previously: 2024, 2023, 2022, 2021, 2020, 2019, 2018, 2017

Goals

Evaluating my goals for this year and decade:

  • [Completed] Write at least four good blog posts each year.

    Moving from an orchestration-heavy to leadership-heavy management role, Good engineering management is a fad, What is the competitive advantage of authors in the age of LLMs?, Facilitating AI adoption at Imprint

  • [Completed] Write three books about engineering or leadership in 2020s.

    This year I finished Crafting Engineering Strategy with O’Reilly. This is my third engineering book in the 2020s. More about this in the Writing section below.

  • [Completed] Do something substantial and new every year that provides new perspective or deeper practice.

    After almost a decade of not submitting a substantial pull request at work, I’ve been back in the mix since joining Imprint. I’ve submitted a solid handful of real pull requests that implement production features, and have used Claude Code widely in their creation. I’ve missed this a lot, and have learned a bunch about developing software with LLMs.

  • [In progress] 20+ folks who I’ve managed or meaningfully supported move into VPE or CTO roles at 50+ person or $100M+ valuation companies.

    This is a decade goal ending in 2029. I previously increased the goal in 2022 from 3-5 to 20. In 2024, the count was at 10. Things haven’t moved too much since then, but I’ll refresh next year.

    I think that I’m on track, but I will say that I think getting into these roles is markedly harder than it was three years ago. There are just fewer of these roles available recently, and they tend to be both more demanding and more difficult than the standard VPE/CTO role a few years ago.

For backstory on these goals: I originally set them in 2019, and then revised them in 2022. I’ve come to believe that I should be revising these every year, but also that it’s not that interesting to revise them every year. I’ll revise them again in a few years.

Writing

I finished my fourth book, Crafting Engineering Strategy, and wrote some notes on writing it. I’m really excited for this book to be done, because I think it’s been a missing book in the industry, and I hope it will change how the industry thinks about “engineering strategy.” In particular, I hope it’ll pull us away from the frequent gripe that “we have no engineering strategy!” You do have an engineering strategy, it’s just not written down yet.

As part of finishing this book, I’ve also recognized that if I write another book, it will be far into the future. After publishing four books in six years, I’m booked out, and I’m pretty sure I’ve tapped out my last decade’s path of writing books to advance the industry. I’ll definitely keep writing, but it’ll be posts focused on the stuff I’m concretely working on, without trying to map them into a larger book structure.

(Last year I mentioned adding The High-Context Triad to a second edition of Staff Engineer, which I still plan to do, but I’m not quite sure when. Probably in a few years.)

Work

I left Carta in May after two years there, and joined Imprint. Imprint has just been a lot of fun for me. I’ve written a small number of real pull requests that implement meaningful things. That’s something I haven’t done since working at Uber, and aligns with my desire to be working in the details again. There’s nothing more energizing to me than getting to solve real, concrete problems, and that’s exactly the sort of job Imprint has been for me. I just haven’t been spenting time on stuff like implementing internal workflow agents or automatically merging Dependabot pull requests in a long time, and I missed it.

It’s also, after some years spent on making teams more efficient, been an opportunity to really hire again, which I haven’t gotten to do since my first couple years at Calm. It’s never easy working at a fast growing company, but you do learn a lot, and quite quickly.

Family

My son entered kindergarten this year. I turned 40. My wife is starting to explore the world of fractional software development, and she’s figuring out its rules. We’ve had a fair amount of health issues in the immediate and extended family, but altogether everything is going well.

Speaking

I didn’t do much public speaking, although I spoke on Book Overflow about Staff Engineer, which was a fun discussion.

I also spoke at several private events, and recorded practice runs on YouTube of Good engineering management is a fad and CTOs must earn the right to specialize. Those are very similar talks, where I’ve been iterating on the core idea of how engineering managers need to adapt to the current era.

Reading

In 2024, I read 27 profession-adjacent books. In 2023, I read 11. I’m not quite sure how many I read in 2022, because I put together a 2019-2022 professional reading recap, but it was about 50 over four years. This year I didn’t do much professional reading, mostly because I was too busy with the new job and polishing my most recent book.

What I did read was:

  1. AI Engineering by Chip Huyen
  2. Recoding America by Jennifer Pahlka
  3. Facilitating Software Architecture by Andrew Harmel-Law
  4. Turning the Flywheel by Jim Collins

It’s interesting to note the drop in volume, but I feel fine about it. I don’t read to hit a goal, I read to learn or understand a particular problem, and found myself mostly working on topics that didn’t align well with that approach this year.

If you’ve written something about your year, send it my way!