If you’ve been following along here for any length of time, you know I’m obsessed with goals. Big ones. Audacious ones. Goals that most people would say are “unrealistic” or “too ambitious.” But here’s the funny thing: I’ve found that when I set targets that make me uncomfortable – goals that stretch my imagination and force me to grow—I not only rise to meet them, I often end up arriving much sooner than expected.
Since 2012, I put five of those audacious goals down on “paper” (it was all digital). They became my compass for the last decade:
- Pay off our mortgage in seven years. We bought our first house at 28, and I wanted us debt-free by 35.
- Make the C-Suite by age 30. I was already 26 when I wrote this down.
- Build a $10M net worth by age 48. At the time, this felt like a 20-year marathon.
- Start, scale, and sell a business. My rough sketch was five years to build, followed by three years of transition with the acquirer.
- Transition to full-time capital allocator. I figured this would naturally follow the $10M milestone. (I’m starting to see this as more of a full-time resource allocator, recognizing that the allocation of TIME, especially in this next chapter, is even more important than the allocation of CAPITAL.)
Those five goals gave me clarity, direction, and motivation. But if there’s one theme that keeps repeating in my life, it’s this: timelines collapse.
Beating the Clock
- I thought it would take seven years to pay off the mortgage. We did it in just over four.
- I thought it was aggressive, but I made the C-Suite by age 30 nonetheless. Most people, if they ever make it, don’t hit the C level until their late 40s or 50s, after spending 25+ years climbing the ladder and “paying their dues.” I did it eight years into my career after graduating college – a fraction of the time.
- I thought building a $10M net worth would be a 20-year grind. It took seven years.
- I thought building and selling a business would take eight years. We sold the first 60% after just 33 months, and the remaining 40% 15 months later.
Looking back, each of those timelines collapsed not because I had some secret cheat code, but because compounding kicked in – on effort, on relationships, on knowledge, and on capital. Once momentum builds, it’s like gravity pulling you forward faster than you ever thought possible.
Wealth as an Accelerator
When I first became an entrepreneur, I thought of the business as a stepping stone. A tool to help me check the $10M box on the net worth scoreboard. What I didn’t realize until I was in it was that the business itself was a wealth accelerator. It didn’t just help me achieve the goal—it rewrote the trajectory entirely.
That’s when I made a new commitment to myself: I wanted to be done by 40. Retired. But not in the traditional “sit on the beach all day” sense (I’m not built for the pro-leisure life), but done in the sense that I was officially work optional, thereby divorcing my future decisions from the need to make money. I’m AMBITIOUSLY LAZY, not lazy.
I gave myself eight years. Start to finish.
And now here we are. Staying on brand. Finishing early. Again.
Why I Call It My “First Retirement”
In 100 days, at 39 years old, I’ll officially step away from the business that has been my life’s work for the last six years and 11 months.
I’m calling it my first retirement for a couple of reasons:
- I don’t think I’ll ever truly “retire” in the conventional sense. I like building, creating, investing, and competing too much.
- This feels less like an ending and more like a transition—from operator to investor, from active income earner to full-time capital allocator.
The freedom isn’t in stopping work. It’s in choosing work.
For me, retirement isn’t about checking out of the game. It’s about gaining control of the scoreboard.
I get to be a full-time opportunist!
Lessons From a Decade of Acceleration
As I reflect on the last ten years, here are a few themes that stand out:
- Clarity compounds. Writing goals down, even if they seem crazy, has a way of pulling you toward them.
- Momentum matters. Once you start stacking wins, they reinforce each other. That’s why I’ve consistently ended up ahead of schedule.
- Relationships are rocket fuel. Every major acceleration point in my career involved the right people at the right time.
- You can’t time everything, but you can compress time. Effort, intensity, and focus create optionality – and optionality creates speed.
What’s Next
So, what happens after this “first retirement”?
- I’ll still be plenty busy – as a husband, a dad, an investor, a writer, and probably (eventually) as a builder of something new.
- But for the first time, I’ll be operating from a place of complete freedom. TIME FREEDOM. LOCATION FREEDOM. FINANCIAL FREEDOM. Not because I hit some arbitrary number, but because I’ve built a life where my time is mine again.
A decade ago, these were just bullet points in a notebook on the screen. Today, they’re my reality. Faster than I ever thought possible.
And in 100 days, I’ll step into the next chapter.
Not done. Just free.
– Gen Y Finance Guy
