I’m a little dismayed my blog has become a place where I just write annual retros, but I’m glad I still have a place to do it.
Themes for this year
Job transitions
That’s right, with an s. Multiple job transitions.
Leaving Motivo
I left Motivo, the company I cofounded, in March of this year. I spent a few months at a big tech company before going back to Motivo in November.
I left Motivo with no plan, but after a few months, I started getting some recruiter outreach from big tech companies. I ended up doing a small round of interviews and accepting an offer for a few reasons.
The most obvious ones were money and title. The money was really good, and this would’ve been my first Staff role at a big tech company. I wanted to prove that I could be an effective Staff Engineer at a big tech company (for reasons that are still not super clear to me).
The last reason was more subtle. When I left Airbnb back in 2020, I knew there was a good chance it was my last big tech job. Part of me wanted to find out if that was true, or if I could still thrive in a big tech environment for a little bit.
It turns out I could not. Even though my manager told me I was doing well enough, I felt it so difficult to get things done there. I never felt like I was doing enough, and I worked way too much to accomplish what I felt was the bare minimum I should be doing.
Returning to Motivo
Around the same time I decided I was done, the executive team at Motivo reached out to me about returning. Ultimately, I said yes for 2 reasons.
Firstly, I realized I had leveled up considerably since I’d left, specifically around AI use in both the development process and the actual product. I felt like I could use those skills to make a real difference at Motivo.
Secondly, I talked to my friend Louis about this decision. Louis is also in his 40s, and he talked about how valuable it is at our age to optimize for stories instead of more traditional markers of achievement. It would be much more compelling to talk about how I made a meaningful change in a company’s trajectory and a huge impact on my team’s professional careers than to say I helped ship some random feature for a big company.
So I’m back, and I feel pretty accomplished for just 2 months of being here. I brought AI tooling to the company in a huge way and it’s been an obvious improvement in the team’s velocity. I feel a noticeable shift in how the company thinks about our product team’s ability to ship. It was definitely the right decision for me, returning to the place where I could have the most impact for my time.
The best part of this is I never ended up having to update the subheader for my personal website.
Parenthood
This was the first year I felt like my wife and I were really in the thick of it with 2 kids. As of the end of this year, my son is almost 5 and my daughter is 16 months.
I feel like the best analogy for having a second kid comes from gaming. Having a second kid is like starting a New Game+ game. You keep all the skills and abilities from your first game, but the enemies are 4x harder and you have 30% of your old healthbar.
Of course there were highlights despite our exhaustion. My daughter took her first steps this year, and her personality has really started to develop. She’s fierce and assertive, able to communicate what she wants so well. It’s hard to believe that she was just kind of a blob at the beginning of the year.
As for my son, I’m routinely blown away as I see him pass through cognitive milestones. I’m routinely surprised by his level of understanding. He’ll randomly demonstrate his counting or math skills, or read something I had no idea he knew how to read.
(Developer) community
This year, I attended my first-ever developer conference, Commit Your Code. I also gave my first conference talk ever there.
I have a long and complicated relationship with teaching, writing, and being involved in the developer community in general. If you look at the publishing dates on my blog, it’s obvious my aspirations for writing exceed my motivation.
The trouble is, promoting my work is hard, and I don’t like social media. I want my teaching and writing to speak for itself, but I know that’s not how attention and the Internet work. I have a really hard time doing things unless I have an end goal. And I just don’t think I have it in me to commit consistently to having a real presence in the developer community.
So I surprised myself a little by booking a ticket to CYC. I continue to have no real aspirations to become someone in the developer community. But I decided to go to CYC and give a talk in order to…go to CYC and give a talk, with no goals of becoming an influencer, developer education specialist, or regular conference speaker beyond that.
I’m glad I went. I got to meet many awesome people from my developer community. I had an amazing time giving my talk, and I got some great feedback that it helped people think differently about programming. I’m not sure what more I could ask for from a trip like that.
Pessimism
I’ve read a lot of retrospectives similar to this one this year, and no one has talked much about the current state of the world. The level of fear and uncertainty seem higher than they ever have in my lifetime. I’m sure it’s affecting people.
I don’t necessarily want to dwell on it here either, but I’d feel a little disingenuous not acknowledging the low-level impact it’s had on my ability to hope for a better future. I wish I had a more uplifting ending to this section, but I don’t! We’ll just have to buckle up and see how things go.
Lessons learned
I am not my job
When I was deciding to go back to Motivo, a few of my trusted friends asked me if the things that had caused me to leave had changed somehow. It’s such a good question. If no one asks it, how could I expect the second time to be different?
I already knew the answer: I had changed, not Motivo.
In my first tenure, it was so important to me that my leadership represented my values. As the company and executive team grew, it became increasingly difficult for that to be the case. More execs means more opinions, and more employees means more paychecks means more pressure to make money. All of these things mean I don’t have as much control as I want over how the company operates.
In retrospect, it’s obvious I should never have put this much pressure on my job. Funnily enough, one of the first things I try to instill into mentees is that they should try and separate their ego from their work as soon as possible. Your job is always going to be at the mercy of forces beyond your control. I’m a little surprised it took me this long to re-learn this lesson in the context of leadership.
I like building things, not programming
This was the year I really bought into AI-powered software development. I experienced Claude Code coding entire tickets with a single prompt, answering every possible question I had about my codebase, and writing high-quality tickets and documentation.
When I first started experimenting with these tools late last year, I experienced an identity crisis. I spent my whole career improving my code-writing abilities: generating code efficiently, navigating to exactly where I needed to go in my codebase, and mastering keyboard shortcuts. These things are either unnecessary or can now be accomplished 10x faster while I’m not even sitting at my computer
I now spend most of my time deciding what to build, how to structure things, and how to get the AI to do things the way I want. As Kent Beck so eloquently put it:
90% of my skills are now worth $0, but the other 10% are worth 1000x
This shift forced me to reckon with what I actually like about this field. Was it typing things into my editor, or was it the final product? I’ve put countless hours into improving the typing code part, so it surprised me a bit that I am enjoying this new way of coding. For me, it turns out it’s always been about the finished product, how well that product is built, and how it solves people’s problems. The typing code skills were always a means to an end, a way to get the finished product faster.
One more thing I love about my career is how it encourages you to dig deep and understand how things work. AI tools, when used properly, accelerate this process. I inspect all AI-generated artifacts carefully and am endlessly inquisitive when I don’t understand something. Besides code generation, the ease of exploring new topics has been a godsend for me expanding my horizons.
I think one of the reasons AI coding discourse is so polarized is we are seeing the collision of people who want completely different things out of their engineering careers. Some people genuinely love the act of programming, and these tools are an affront to their craft, which I get, but it’s not a feeling I relate to. It’s been helpful for me to sit with my feelings about where my work is headed, and I feel hopeful these tools will continue to make me a more effective builder.
Some years are just about surviving
I’ve spent a lot of mental energy over the past few decades trying to improve myself in various ways, so it was strange to have a year where I did none of that. I had aspirations though — I bought a bunch of courses (AI, game development, web design) and ended up not even starting any of them. That’s pretty impressive.
This year was mostly about reminding myself that things will get easier as my kids get older. Remember that New Game+ analogy? The game isn’t 4x harder forever. Your abilities keep scaling, and eventually catch up to the new difficulty.
I’ll hopefully have more time for my goals every year from now on. More importantly, my kids are only little once, and I should appreciate this season for what it is, rather than dreaming about what life could be if I had more time.
2026 intentions
I’m hoping we’ll come out of survival mode a little bit this new year, but as I just said, who knows what will happen. I’m holding any intentions this year with an open hand, but here’s what I want from myself in an ideal new year:
Prioritizing my physical/mental health
You can tell a lot about my overall mental state by what I do right when I get back from dropping off my kids at daycare.
Meditate/work out = good
Open my laptop and start working = bad
This is by far my biggest priority. Taking care of myself gets so much harder as I get older, but this intention is just a matter of setting better work boundaries to not let it consume my entire day. I’m most excited to get things back on track here.
Nurturing my creative instinct
I’m leaving this vague because I think there are a lot of ways I can feed my soul creatively, I just haven’t been doing any of them.
Some possibilities:
- Playing music regularly
- Actually launching one of my half-built projects
- Writing
- Creating a video game
- Getting better at web design
I’ll be happy if I do any of these more intentionally this year.
I keep coming to my friend Louis’s advice about optimizing for stories. I spent this year surviving, and a younger me might have seen this as a failure: no courses completed, no side projects shipped, just getting through.
But, I feel incredibly fortunate that the stories unfolding in my life right now are really good. I love watching my kids grow up, and I’m making a meaningful difference at my company and in the lives of my team. Maybe the intention for next year is not just about creating new stories, but it’s about finding more energy to be present for the ones that are already happening. I’ll let you know how that goes.