Seven years ago, I was in the last step of selling my tech start-up. At the last second, I had an epiphany about my life priorities; I didn’t want to spend my 30s driving to an office park. I wanted to pursue my love of surfing. So I bailed on the deal and decided to move to LA.
In this COVID era, many people are re-evaluating their life. They’re making significant changes to give themselves a better chance to be happy based on their personal values rather than traditional definitions of success.
If you’re one of those people, I commend you. I know first-hand that it’s a scary process, and you might wonder how it will all turn out. Of course, no one knows. But I want to share my story with you in hopes of inspiring a little confidence.
Spoiler alert: I’ve found that choosing to improve the daily quality of my life was worth it, sustainable, and not at all “just a phase.” Life really is much, much better as a result.
That parking lot just didn’t feel right.
It was 2014, and we were already deep in the M&A process to sell my tech start-up, H Engage. My co-founder Kate and I were sitting next to each other on a flight back to Boston from San Francisco, where we had just met our future managers. The LOI was signed, and we were finalizing details like reporting relationships and salaries. Turning back seemed impossible.
H Engage wasn’t doing that well. We had some traction with big companies like Mcdonald’s, but I failed at raising money or spurring growth. Then, as our funds were running out, a terrific company wanted to buy us. The deal was for a good price, a life-changing amount of money, really, given we’d bootstrapped up until that point. I’d have immediate cash and a pretty solid future in Silicon Valley. For a Ukrainian immigrant living in Boston, it felt like a golden ticket to the kind of life my family dreamed of for me.
I was 29 years old. Our buyers had an office opposite Facebook with this parking lot out front. As the flight got closer to Boston, I kept imagining myself driving there every morning, parking, and walking into one of those bright office layouts with carpeted floors. For years. Four years probably. They knew how to work a deal, and I’d be wearing some solid golden handcuffs.
A feeling started dawning on me: regret for the life not lived…as a surfer.
Surfing felt more important than a big check.
At the time, I already loved surfing — a lot. Riding waves became a spiritual experience for me, something that felt like a life’s purpose. But I lived in Boston, I wasn’t very good at surfing, so I didn’t get to ride many waves.
Being 29 years old, I knew that I didn’t have much time left to get better.
Pretty much all I’d done up until that point was prioritize my career. I was in the start-up grind. I woke up early every day, made the walk to the office, and came back long after the sun had set. Before that, I was in the management consulting grind. I woke up early every day, made the walk to the office, and came back long after the sun had set.
On that plane ride, I realized that if I spent the next four years of my life in that office, I would blink, even more life would pass me by, and I would be one of those middle-aged people who imagined what could have been, what I could have done before my body gave out.
When I got home from the airport, I had a feeling that I couldn’t shake: Surfing was more important to me than Silicon Valley. More important than a big check.
A life-changing spreadsheet
I spent that night hunched over my laptop in my tiny Boston apartment. And as a beautiful snowfall started outside, I compiled a spreadsheet that would help determine the next phase of my life.
Each row was a place where I could live and surf. Columns included water temperature, number of coffee shops with five-star ratings, co-working spaces, and population density.
It was a somewhat desperate attempt to make my decision feel more calculated. I couldn’t yet admit to myself that “following my heart” was a valid enough reason.
Off that spreadsheet, I picked Venice, California, a neighborhood in Los Angeles. It had a surf break near the city, decent water temperatures, and lots of office space.
I called Kate and said, “Hey, what do you think about me blowing up this deal and us moving to Venice?”
Kate’s always been up for an adventure, and she agreed to go.
Seven years later
Not everyone has had the chance to assign an exact monetary value to something they love, but that day I did.
The opportunity for regret was unusually high. It’s been seven years. I have absolutely no regrets about the decisions I made that day.
I’ve become a pretty good surfer. I surf three to five times a week. Nothing in the world makes me happier or more satisfied than being in the water. I just turned 37 years old, and I know my years of getting better at surfing are numbered. And I’m proud that I took my early 30s to become good at something that wouldn’t be possible for me to do later in life.
We pivoted H Engage into a new venture and struggled for years. My job was really hard, and so was Kate’s. But through all that hardship, I never regretted our decision not to sell. Being true to my inner instincts about my values — no matter how crazy they seemed to the people around me — gave me peace.
Eventually, we created Airbo and are doing quite well. We’ve grown a lot in the last couple of years and recently crossed a pretty significant revenue milestone. We raised a bunch of money. I couldn’t be happier with my job or the people I’m working with at Airbo.
This is not a “happily ever after” story.
I don’t think the lesson here is “do what your heart tells you, and everything will be happy ever after.” I’ve had plenty of tough times after moving to LA.
I think the lesson here is more like, “do what your heart tells you, and the hard times will be worth it because you’ll be working toward your dreams.”
I’ve been an entrepreneur for over 11 years. I have failed many times on many dimensions. But my spiritual retreat wasn’t ever too far away. Whenever something goes haywire, I catch a wave, feel restored, and feel like I can keep going. I’m also reminded that no matter what happens, I don’t have to live with a cloud of regret, pining for what could have been.
I think a common misunderstanding about prioritizing lifestyle is that we view it as a tradeoff against career success. I’ve found the opposite. Surfing has not turned out to be a lifestyle choice at the expense of my performance as a company founder. On the contrary, it has enabled me to maintain a high level of performance when I otherwise would have quit.
COVID gave us the chance to go fully remote as a company, and I intend to keep it that way because being where you’re meant to be and living your happiest life shouldn’t be dictated by work.
I hope you find your Venice.