I just turned 40 and I'm freaking out - my 2025 annual review
A yearly look behind the curtain of my personal and professional life.
Welcome to my 2025 annual review.
This is my fourth time doing this - and my fourth year in business as a solopreneur.
I originally started writing these for myself. I’m in a season of life where I’m doing a lot of reflection and planning, because I don’t think you build an amazing life by accident. Like anything, you have to think about exactly what you want - and then use that vision to guide your actions. So I carve out time each year to look at where I’m at, what’s working, what isn’t, and what I want to lean into next.
In the beginning, I only shared these with my family and a few close friends.
Then I sent one to a couple of coaching clients. I was embarrassed to spend so much time talking about myself. But I quickly realized nobody was judging me - and that people enjoyed learning about my life. So I started sharing it more broadly.
Somehow it turned into an annual ritual that I genuinely look forward to.
And every year I get messages from people who say it helped them reflect on their own lives and careers, which is also really cool and fulfilling.
Especially now, when it feels like we’re all spending more time talking to robots and agents and less time connecting - it feels even more important to share something personal and human.
So without further ado, here’s my 2025 annual review.
What went well
In terms of stuff that went well, I’m proud of a few things.
The big-picture story of 2025 is that I made 18% more top-line revenue than last year.
But more importantly, this felt like a year where I invested in some new things that should tee-up an amazing 2026 (more on that below).
I have a long-term goal to build a more scalable business. Right now I have a great services business - which, if you’ve ever run one, you know basically feels like a job, not a scalable machine. So I spent a lot of this year laying the groundwork for what a truly scalable coaching business could look like.
Launched a new program
The biggest step in that direction was launching a new scalable program, The Growth Operating System.
I launched it over the summer and 33 people enrolled.
That’s fantastic.
But I’d be lying if I said I didn’t wish it were in the hundreds by now.
If you’ve ever launched a digital program, you know how hard it is to talk about it consistently, reinforce it, and sell it. So I’m grateful for where it’s at and proud of the traction so far. And I’m going to iterate on this more next year.
Scaled the podcast
I also invested heavily in the podcast this year, for the same reason.
I love the show (and I have a very exciting announcement coming in a few weeks about it) and I can see a future where it becomes a very large piece of what I’m doing.
But like anything worth building, it needs care, iteration, and constant improvement. If you’ve been following along, you probably saw the evolution I made on the thumbnail front, trying to level-up the packaging.
We went from this
To this:
And these (which I’m still experimenting with):
I also hired a podcast coach to help me take things to the next level.
Scaling a podcast is really hard - and I’ve never done it before. When you really get into the medium, there’s so much to learn about:
From titles to thumbnail design. Episode blocking and content architecture. Not to mention how to promote the show and get guests to share interesting information.
So when I thought about ways to grow the show, I figured there were two basic paths:
I could try to learn all this stuff myself, implement what I’m learning, make some mistakes, and eventually figure out what works and scale the show
I could find other people who’ve seen what the other side of this journey looks like who could accelerate my path to get there
That’s why I hired a coach to support the growth of the show.
I’ll publish a full piece about the changes soon, but the short version is: I’m rebranding the show with a new name, new artwork, and a slightly refined concept.
I’m excited to mix in some solo episodes with the interviews to share more of my expertise, too.
Improved my business model
I’ve spent most of my career optimizing other people’s growth models - but rarely touched my own.
So in 2025, I started doing a monthly review where I stepped out of the day-to-day role of “coach and advisor” and into the role of a Head of Growth who reports to the owner of a coaching business. And through that lens, it became obvious that I was leaving a lot on the table.
I’ve been so hesitant about coming off “too salesy” that I think I’ve actually undersold my expertise and underserved the people who want to hear from me.
So I built some simple email flows, nothing fancy, helping people discover more of my content and, if they want to work with me, making that path easier.
I also updated my bottom-of-funnel collateral.
I made a short video explaining what coaching actually is, who it’s for, and how it works. And another that I send before consult calls so folks know what to expect, what the offer looks like, and what questions to bring.
Those changes worked.
My LinkedIn reach was a little down this year. But I had my busiest year for new business anyways.
This year, I had 60 consults and signed 22 new coaching clients.
My roster was essentially full the entire year.
But with a full roster, I hit the natural ceiling of a services business. With two young kiddos at home, I couldn’t sell more of my time. So to scale from here, I have two options:
raise my 1:1 prices.
build something more scalable.
A group program is in the cards for next year.
I’ll be making more investments in that direction, especially because demand continues to rise and I only have time to support so many clients.
Camp Solo
Another highlight: I launched a second business with my good friend John Bonini, Camp Solo.
This was never meant to be a business; it kind of just… happened.
John and I have chatted monthly for years as two solopreneurs comparing notes.
At some point we created a Slack Channel, invited a few other high-ambition solopreneurs, and it grew into something special.
We eventually closed the group, made it private, and started charging.
It won’t ever replace my main business, but it’s become an important part of my life -and a really fun thing to build with a close friend.
I turned 40
On the personal side, life felt good this year.
I turned 40 on December 7th, which still feels wild. But forty sounds older than I feel.
At the beginning of 2025, I set a goal to enter 40 feeling in the best shape of my adult life. For context, in 2024 we welcomed our second baby Mia. All parents know how challenging that first year is. In the process between the lack of sleep, the late-night eating, and the lack of schedule, I basically stopped going to the gym and didn’t feel my best.
So I’ve been exercising four times a week. I’ve dramatically cut down on processed foods. And in the process, I’ve lost about 7–8 pounds.
I’ve also been doing sauna sauna and cold plunge a few times a week. I know that makes me a startup-guy cliché, but with two little kids and not much sleep… it works.
I feel good.
I golfed a lot
When I started my business, I set up a four-day workweek.
I spend my Fridays refilling my cup. I usually do something physical outside like snowboarding or hiking in the winter, and golf during the warm seasons. I took a few lessons this year, lowered my handicap by three strokes, and shot an 80 - my lowest score ever. Golf is outdoors, social, and grounding.
It’s as good for my brain as it is for my body.
Coached my son’s soccer team.
I’ve always pictured being a coach to my kids at some age but I didn’t plan on doing it this early in life.
But when the town sent out an email saying they were on volunteers, I figured the universe was sending me a sign.
I coached a team of eight 4-5 year olds. Our team name was the Black Ants. Although we didn’t technically keep score, I think we had a pretty good year
(no this picture isn’t AI - I blurred everyone except Cameron and I out of respect to the other families)
Coaching kids this young is hard, but also hilarious and rewarding.
I learned quickly the real job isn’t teaching soccer; it’s making the kids feel excited to come back and play more soccer.
So I gave lots of high-fives and tried to make it as fun as possible.
What didn’t go well
There were a few tough things this year - both personally and professionally.
My grandfather passed
My grandfather passed away this summer at 97.
He lived an incredible life and stayed healthy right up until the last week. He was a huge influence on me - both personally and professionally. And we talked almost every week.
In addition to being my grandfather, he built multiple businesses, including a leather tannery, a recycling business, and Granite Links golf course - which probably explains some of my love for golf.
And as an entrepreneur, he loved reading these annual reviews, and asking about my business.
His passing sucked. I got to say goodbye and we had a meaningful conversation before he passed. But I still miss him a lot.
Here’s a picture of him meeting my daughter (his great granddaughter) last summer.
Car Accident
My wife got into a scary car accident with both kids (on the highway) this summer.
She was going 70 mph when a large flatbed truck sideswiped her car. She spun 360 degrees across three lanes of traffic and ended up on the median. Somehow no one hit her in the process. The car didn’t flip. Everyone walked away uninjured.
But getting that call, knowing what could have happened, absolutely shook me. It forced me to slow down and remember what actually matters.
Ear infection drama
The third personal challenge: Mia, who’s now 18 months, was sick constantly.
She had seven ear infections this year.
If you’re a working parent with young kids in daycare, you know how brutal that is - the fevers, the pickups, the 3–4 days home each time.
My wife and I both work full-time. When I don’t work, I don’t get paid. So we spent a lot of this year juggling, falling behind, catching up, and doing it again. It was physically and emotionally draining.
Two unpaid invoices
On the professional side, I had two clients stiff me on payments this year.
One was a coaching client who had been paying me directly (vs having their employer pay for coaching). We’d been working together for 4 months when they were laid off.
I figured that would probably impact our engagement and I wasn’t going to be surprised if they needed to pause, or maybe end things.
But I didn’t expect what actually happened.
They immediately ghosted me. They canceled our meetings, stopped responding to my emails, and never paid for the last month of coaching (that I’d already delivered).
It wasn’t a massive amount of money, but it was disappointing on a human level.
The second was an early-stage advising client who (eventually told me) they didn’t close a funding round and couldn’t pay me.
Individually, neither situation was catastrophic. But combined, it was a pretty meaningful financial hit - and as a dad working to support a young family, it stung.
What I’m focused on next year
I’m genuinely excited about 2026.
At the end of 2025, I took time to revisit the growth model for my business. What I realized is that I want to make one major investment in each layer of that model.
1. Discovery
This is how people first find me. Next year I’m going all-in on YouTube. I’ve been dabbling already, and even with very light effort, I’ve had videos do 1000+ views and reliably drive 2–3 consults per month.
I like making video, but I can’t keep doing all the editing and thumbnails myself.
It’s too time-consuming. So I’m hiring help to improve production quality and buy back my time. YouTube has massive upside for my business, and I want to lean into it.
If you haven’t already, subscribe here.
2. Engagement
People primarily find me through LinkedIn (and eventually YouTube) but email is still the best way to build a long-term relationship.
I’ve been on Substack, but honestly, I’m underwhelmed.
It’s becoming another social network, and I can see the pay-to-play writing on the wall. So I’ll probably switch platforms in 2026 - either to HubSpot, or ConvertKit.
3. Conversion & Delivery
I’m working on a scalable coaching program. I’m not sure exactly what form it will take yet - but I’m leaning towards a live group coaching program so that people can learn from me - and from each other.
That’s something that I’ve heard a lot from my existing clients is they also want to build a sense of community and belonging with each other in a safe private place.
But that’s the direction:
YouTube → Email → Scalable program → 1:1 for the right people.
That’s the model I’m building toward next year.
Anyways that’s it for this year’s reflection.
Have questions or advice for me? Let me know in the comments. Otherwise, you can follow along right here.
Or view my previous reviews below: