The Tattoo, the Mountains, and the Truth About Success
A mountain trip, a conversation with a mentor, and a tattoo reminded me of what really matters
Two weeks ago, my wife and I took our first vacation in over a year.
We went to Estes Park, Colorado and I didn’t realize how badly I needed the break until I was standing beside a glass-still lake, surrounded by silence and mountain air. Something about that place made my brain relax in a way it hadn’t in months. Maybe years.
Leading up to the trip, I’d been sprinting… 10+ hour days, weekends spent working, building something on the side while still showing up fully for my job. And I like my job. The people are great. The culture is good. But deep down, I know it’s not forever. I’m not built to settle into a career and ride it out for 40 years. That’s not in me. I’m wired to keep growing. To keep building. To chase the next opportunity—not because I’m ungrateful, but because I’m unfinished.
While in Colorado, I finally got a tattoo I’d been thinking about for a while. Mountains… and the words memento mori. Remember you will die.
It’s a thought that’s lived rent-free in my mind for the past year. A strange comfort. A sobering reminder. Life is short, fragile, beautiful, fleeting. We walk around like we’re invincible, like there’s always more time. But there isn’t. And there won’t be.
During that trip, I had breakfast with a long-time client and now friend, Tim Stoddart. As we talked about work and life and figuring things out, he leaned back and said something that stuck with me: “Just yolo it, man.”
He was talking about how he and his wife made the decision to move to Colorado… to bet on a better lifestyle and just go for it. Just yolo it. That stuck with me, especially after getting a tattoo that reminds me daily that I don’t have time to waste.
Sure, Tim’s in a different season. He’s successful. “Just yolo it” looks easier when you’ve already built a runway. But it still made me think… what does that look like for me? What if I stopped overthinking and just moved forward?
The truth is, I don’t want to settle. I don’t want to get comfortable. I used to think success meant luxury… Lambos and travel and private jets. But the more successful people I meet, the more I realize that’s all noise. What they really want is freedom. Freedom to build. Freedom to choose. Freedom to live life on their terms.
Success isn’t about excess. It’s about intention.
I don’t know exactly why I chose to write about purpose… maybe because I needed to find my own. But over the past few years, I’ve realized something:
Purpose isn’t about you. It’s about what calls to you. What keeps you up at night. What only you can solve for someone else.
And you don’t need the whole map to start walking. You just need the next step.
Rumi said, “As you walk on the way, the way appears.” I’ve found that to be true. We want the entire staircase, but growth hides in the step right in front of us. Until you take it, nothing changes.
Maybe fear has been my fuel up to this point… fear of mediocrity, fear of wasting my shot. I’m okay with that. I know what I want to build. I know the road ahead is filled with boring, repetitive steps… systems, discipline, doing the work nobody claps for. But I’ve come to believe that those boring steps are the path.
After that breakfast, during the following week I burned through one of Tim’s courses on building a local SEO business. And honestly, even though it was tactical, it was also deeply philosophical. The biggest takeaway?
Entrepreneurship is boring.
It’s not the movie montage. It’s not the Shark Tank pitch. It’s consistent, methodical, unsexy work. And most people won’t do it long enough to win.
But I will.
Because purpose lives in the mundane.
Freedom is forged through repetition.
And the way appears… as you walk it.
Issac, great article and spot on about entrepreneurship. I also listen to the short podcasts you do. Great stuff. Very relevant. Keep it going!