2025 Year In Review

As has been my custom for the past fifteen years, I like to spend a bit of time at the end of the year reflecting on the year that has been, looking ahead to the year that is to come, and noting down these reflections for posterity.

Professionally

Stripe

This has been a big year of transition for me personally. When Stripe acquired Lemon Squeezy last year, I went from being a Staff Engineer/Tech Lead who happened to be called a CTO (i.e. had co-founder responsibilities) to an Engineering Manager at a "big tech" company. I've come to discover that, although there is some overlap in these roles, they are very different.

This year has very much been a year of two halves. The first half of the year was spent dealing with a tonne of inbound requests and work from other teams at Stripe. As you can imagine, a company like Stripe has very high bars for things like risk, security, compliance, etc. Our team was flooded with all sorts of demands, from increasing our security posture, to moving our vendor contracts to Stripe (via procurement), and trying to hire more engineers for the team. This was pretty frustrating as it came at the expense of us actively developing and shipping features for Lemon Squeezy. Despite this, however, we were able to start building out the new native MoR product for Stripe called Managed Payments. It launched to Private Preview over the summer and we're super excited about seeing this GA next year (here's a sneak peek).

While all of this was going on, I spent a lot of time learning the Engineering Manager (EM) role at Stripe. It took me a while to really figure this out with everything else going on. However, by the end of the summer I started to feel comfortable with the expectations of the role and started to hit my stride. My day-to-day now consists less of Staff Eng-type work, and much more EM-type work (quarterly planning & strategy, performance coaching and reviews, hiring, team execution, etc). My team has changed significantly over the year, but I feel like we have started to mature as an engineering team and are ending the year looking a lot more like a typical Stripe eng team compared to the start of the year.

I have always approached my time at Stripe as a huge learning opportunity and the experience so far has not disappointed. This year I've learned so much about how teams work together in big organisations. I've been keeping note of what works well, and what doesn't. I'm hoping this will stand me in good stead if I ever end up running a larger business in the future.

Overall, I'd say my experience at Stripe this year has trended positive. There are well documented upsides and downsides of working in a corporate environment. But the perspective and growth I've gained this year have definitely been worth it.

AI

I can't really write this review without at least mentioning AI and its impact this year. Not only have I been investing in it heavily through personal and side projects, but we've been diving into it at work and using it for all sorts of things (planning, coding, reviews, interviews, etc). It seems to me that the AI "revolution" is coming fast and is about to change the shape of the world, especially in white collar (knowledge worker) jobs. There's much to say here, but I'll leave that for another time.

Personally

Personally, this year has been much less eventful than last year, but has built on many of the same themes.

We celebrated all of the usual milestones this year. I turned 38, we celebrated our 15th wedding anniversary, and our kids turned 9 and 6 respectively. Life is as busy and chaotic as anyone with a young family, but it's also incredibly fun and fulfilling. I'm actively trying to remind myself that, despite all of the busyness and tiredness, we'll look back on this time of our lives and think that these were the highlights.

We had a bunch of great family trips this year. We took the kids and some of my wife's wider family to Disneyland in April. This turned out to be such a fun trip and the kids had a ball. We also did our regular break in Keswick in the summer, and visited a luxury lodge near Aviemore in November. Each trip was filled with family, fun and memories.

We also got a puppy at the start of the year. He's a Cavapoo called Vinnie. He's incredibly cute. The "puppy bites everything and wees everywhere" stage was a bit frustrating for a while, but that stage quickly passed and he's now just another member of our family.

I've continued on my wealth management journey, although it has not been all that eventful this year due to needing to keep funds liquid for our new house refurbishment. Back in September last year, we unexpectedly bought a lovely old house nearby. It has lots of space and some cracking grounds but needed some renovation. We ended up deciding to fully strip and modernize the interior and build an extension, converting the house from a 4 bed (1 up, 3 down) to a 5 bed (4 up, 1 down) with a large extension. Most of this year was spent working on plans with our architect, getting planning permission, and designing bathrooms and a kitchen. But in November work finally started on stripping the house, and we're very excited about moving in later next year.

Looking ahead to 2026

2026 is already shaping up to be another eventful year. We'll be launching Managed Payments to GA at Stripe, taking another family trip to the Netherlands in April, my sister-in-law is expecting another baby, and our house refurb project is due to finish in September (can't wait to finally move in!). Lots to look forward to.

As always, it is my prayer that in 2026, I will continue to walk closely with God and that he will continue to strengthen, encourage and grow me in spiritual maturity. I am so thankful to Him for how He has sustained us this past year, and I pray that he will continue to equip us for whatever 2026 might bring.

Wishing you all a Happy New Year and best wishes for 2026.