A dispatch from the North Slope. The first entry in a 5-year plan to trade a life of obligation for a life of intention.
It’s mid-July, 2025. I’m on the job, about 600 miles from home, which gives a man a lot of time to think. Too much time, maybe. And there’s this one question that keeps rattling around in my head lately.
Is this whole 5-year plan… this idea to radically change my life and my family’s life to go sailing… is this a midlife crisis, or is it some kind of enlightenment?
I’m 38. The argument for “midlife crisis” is pretty strong, I’ll admit. I’ve been working my entire life, non-stop since I was twelve. Driving full-size semis in Oregon at sixteen. Working my way up to General Manager of a car dealership. It has always been about the grind. The next goal, the next paycheck, the next rung on the ladder.
So when a guy like me suddenly wants to drop it all for a boat, it looks like a classic cliché. It looks like I’m just trying to run away from the pressure of a lifetime of responsibility. And maybe, a part of me is.
But then I think about the other side of it. The “enlightenment” side.
This wasn’t a snap decision made after a bad day. This was a slow realization… a decision to stop living a life by default and start living one by design. It’s a choice to trade a life of accumulation for a life of experience. It’s about owning my own time, and being able to share that time with the people I love. It’s about building something real with my own two hands, not just managing the bottom line for someone else.
“It doesn’t feel like I’m running away from my life; it feels like I’m finally running towards it.”
And I am incredibly lucky to have a family that is willing and ready to take that leap with me.
So, what’s the answer? Midlife crisis or enlightenment? Maybe the line between the two is blurry. Maybe a crisis is just the messy, chaotic catalyst that forces you to finally search for a more enlightened path. The alarm clock you can’t ignore.
All I know for sure is that this plan feels more right than anything I’ve done in a long time. It feels like the first, most important step on our own long tack toward a worthy life.
If this story resonates with you, you’re in the right place. This is just the beginning. The best way to follow along is to join our email list and follow us on our socials. We’re building a community of people who believe in chasing a more adventurous life. Thanks for being here for the first entry.
-Daniel
