What a year.
If I'm honest, from the day-to-day perspective, 2025 felt like a non-stop stream of uncertainty and struggle and just...ugh.
It came from all directions.
The general economy was...let's go with "choppy" - with tariffs and shutdowns and budgets cuts, oh my. AI rapidly morphed from a new and exciting efficiency booster to a possible existential disruption to our entire field. And in our own little world, Highline battled with a bit of an identity crisis - who are we and, more importantly, who should we be?
It was all a bit discombobulating.
That's not to say everything in years prior has been rainbows and unicorns. We've had trials and obstacles. But 2025 was a struggle. No doubt about it.
Isn't that what makes the journey meaningful though?
With the benefit of a few days of rest and reflection, as I look back at the year, I'm probably more proud of this year than any other in terms what we've learned and built, how we've adapted and changed course, and how we've stayed true to what we believe in and we're all about.
Here are my three favorite highlights from this year...
Highlight #1: In January, we launched Highline Coding Academy. After the pandemic forced so much of our lives into the virtual realm, our hope was to bring people of all ages out into the physical world to connect and build and learn and have a little fun. In this first year, we offered 21 different events and classes, facilitated by about a dozen different presenters and teachers, and welcomed 500 unique registratrants. Pretty great start.
And it was never about the money - which is a good thing, because (shocker!) we learned quickly that the economics of in-person education are not what you would call "strong". Instead, it was about planting the seeds of inspiration and creativity, and allowing for the serendipity of real world interactions. In terms of both of those, our little Coding Academy was a big success. Hearing from a few kids about coding projects they started on their own was a delight. And our professional events allowed us to make some connections and re-connections with friends and other like-minded builders.
Lastly, it also gave us a chance to eat some amazing Rockaway pizza on the regular.
Highlight #2: Bootstrapping a company isn't easy. 7 years ago, when it was just me, I was stressed to the MAX about what a late or no-payment would do to my family's personal finances, or what would happen if that next contract didn't come through. And this stress obviously didn't abate as we on-boarded employees and contractors over the ensuing years. Understanding and managing cash flow is a scary thing - especially when your degrees are in philosophy and information systems, not business.
In 2025 though, after 6 years of business frugality, Highline finally got to a place of solid financial stability, and all without any investment or debt. With the help of some great advisors (and a few business self-help books), I now lose ZERO sleep about late or no-payments - though, to be clear, I still want us to be paid!
This stability allowed us to do some new things - for example, this year we put into place a concept called "bench insurance", where full-time employees pay a small percentage of their billable rate into what we call a "bench pool", which we manage in a prescribed and transparent way. We've since accrued enough in our pool to allow for a guaranteed month worth of bench compensation for every employee, which gives a little peace of mind when contracts wind down.
Highlight #3: On the delivery side, while I can't share too many of the nitty gritty details, in 2025 we delivered some truly great projects for our clients. In the spring, we assembled a strike force team to build a mobile app and admin console for a client in the health care space. The timeline was extremely tight, the scope a bit murky at the start, and the deliverable crucial for their business. Highline delivered on time, on budget, and even took on a bit of extra scope. One of the best team efforts I've been apart of.
For other clients, we contributed to dozens of releases of different applications, services, and pipelines that helped their businesses in innumerable ways - like eliminating manual data entry for office staff, giving and tracking refunds for customers, helping to streamline the delivery of food to patients in long-term care facilities, and a ton of other great things.
TLDR; we built some really cool shit.
Well, now I'm on a roll...but I'll stop at these 3...though I have to say, I'm also super grateful for the awesome new people we've welcomed on board in 2025 as well as the equally awesome people we helped transition to full-time roles at clients.
Maybe it's just a function of this cozy time between holidays when work ebbs and stress fades that's adding a degree of sentimentality, but honestly as I look back, 2025 was, after all, pretty great. Despite all challenges, we persevered.
It wasn't about revenue numbers or profit margins - it's that we continued to build quality software and also stay true to what we're about: rewarding those doing the work and enjoying the collaborative process with people around us.
No matter where AI takes things, we'll be siding with the humans.
In the end, I'm super grateful for everyone who took a chance on our little company, for all the great work they do, and the professionalism and commitment with which they do it.
Happy New Year!
