My Year in Review: 2025
Series: reflections December 12, 2025
I was prompted to write a year in review and had to dust off this blog. I haven’t written here in five years! My last year in review was over 10 years ago…
At that time (2014), I was 25. I was working at SEP and had just finished grinding my “senior engineer” promotion. It was a big year for me as an engineer. I had built my first open source project (an RSS reader) that got any traction. I was in my peak blogging, reading software book, Hacker News posting era.
I would start that year doing Android development, with Ruby and Rails stuff on the side. That year would end with me working on-site (in another state), toiling away on a Java web app, constantly fighting with a team of literal “JavaScript bros”.
But I was really putting in a ton of work and leveling up. I don’t think it was burn-out, but I was very restless that year.
I nearly left my job (where I would remain for another seven years). I made it to late stage interviews at Buffer (at peak hype) and Know Your Company (splashy 37signals spin-off), but didn’t get either and felt pretty bad.
I have distinct memories of wondering why my colleagues did not have the energy or time to do more: more coding, more projects, more blogging, more company changes.
I get it now, I’m not the young guy on the team anymore, with no responsibilities and a chip on my shoulder.
As I write this now, in December 2025, I am 37.
Work
This year I finished Year 4 at Arrows (fully vested, baby!) and my third year as CTO. I’m enjoying my work and the people I work with.
This year I felt like I was working at a startup. The excitement of getting traction, the speed of shipping, the stress and pressure of a small company bending-but-not-breaking.
We’ve been mainly building our sales room product in 2025. Still on the lookout for a designer to join our team.
Big projects I tackled this year: AI suggestions and follow-up email generation, building a deep Salesforce integration (yuck), web research onboarding wizard
I am still writing code every day, but this is the first year I am lowest of the engineers on the raw “contribution” stats.
Arrows is doing great and reaching some fun milestones. We’re at ~10 full-time at the moment and I love that we punch above our weight.
We’re locking in for 2026 and I’m excited to see how much further we can grow with our core team. So much to build!
Personal
Happy and busy on the personal front! Around this time last year, I proposed to Kayla. She hates surprises so we both knew it was coming. Our wedding will be next May.
Wedding planning and ancillary events have taken up a big portion of our year. It’s fun seeing Kayla go into her classic deep-dive on every aspect and we’re excited to celebrate with friends and family next year.
After splitting time between houses in Anderson and Lawrence for most of 2024, one of our big 2025 projects was consolidating our real-estate empire. We spent the summer getting Kayla’s house sold, including unplanned renovations, dealing with inspections, and negotiating with realtors.
We’re enjoying our life together here at Historic Fort Ben. It’s a simple joy of mine to be able to get up from my office, pop in a podcast, and take Piper for a walk around the neighborhood every day.
I’ve spent more and more time cooking in 2025. We cook nearly every meal at home these days. This year I’ve been getting more comfortable using a wok and perfecting the art of the Brazilian picanha.
Miscellaneous projects
No major side projects ongoing. I find that Arrows is scratching most of my itches (Rails, product work, the siren song of AI) and feels like a high leverage place to be pouring any extra brain cycles into.
Writing has slowed, I published two articles to Boring Rails this year (but both were guest posts that I mostly just edited). Still posting on Twitter, but having achieved my personal goal of 10k followers, I’m not on the daily grind anymore.
One podcast appearance this year with my Rails buds Jeremy and Jess on IndieRails. Always game to hop on the mic!
I just wrapped up another profitable CFL (Canadian Football League) daily fantasy season. It’s a silly, obscure hobby of mine that I would be happy to talk your ear off about.
My current algorithm
I think your YouTube algorithm is a window into your deepest, truist self.
Here is what I’ve been consuming lately:
30-something cooking guys: Brian Lagerstrom, Ethan Chlebowski, InternetShaq
Tech comedy that your partner doesn’t appreciate: Alberta Tech, Alexis Gay
Personal solo pods from my internet friends: Caleb’s Notes on Work, Adam’s Morning Walk, Justin’s Breaking Change rants
Random rabbit holes: negotiating car sales, sports card vendor POV, classic hardcore World of Warcraft
Current music hyperfixation: Liquicity
Reading: The Hobbit, Lord of the Rings, Project Hail Mary, Bobiverse series
TV: The Rehearsal, Severance, Pluribus, Shoresy, King of the Hill (full binge)
Parting thoughts
Keep going…