
October 5, 2026
The Safe Route Is a Game Too

I was coming up on twelve years in the army when the people around me started drawing the rest of my life for me.
Stay in. Do twenty. Get the retirement.
It was good advice from people who cared about me. It came with a finish line and a pension waiting on the other side of it.
And something in me kept saying the same quiet thing. I've got to go find my own path. I've got to go play my own game.
The hard part was that I didn't know what the game was.
A version of that moment keeps finding its way to me from people in very different rooms. The security and certainty is good. Some of the work is good too. Some of it doesn't feel like you at all. Underneath the math sits a quieter question.
Is this the game I want to play?
Here's what I've come to see. The safe route is a game too. It has its own rules, its own length and its own prize at the end. Somebody drew it long before you arrived. Most of us were playing it for years before we noticed we actually had a choice in the matter.
Once you see that, the question changes shape. "Stay or go" becomes "Whose game is this? Am I choosing it?"
Choosing it can be a beautiful move. Playing somebody else's game for a while, while you figure out your own, there's nothing wrong with that at all. A steady job can fund the experiments and buy you the time to see.
What keeps most people in place is the other side. They can't see where they'll land, so they stay at the edge.
I couldn't see it either. What I had was a short list of things to lean on: some savings, a twelve-month plan and the GI Bill for a while. I also had a gap I could name. I had no idea where I was going. Travel as a way of growing felt like a place to start. That was as far as the map went.
Everyone's list looks different. Your life chapter. Your relationship to risk. The advantages you already carry. The gap you can name. When you know what the gap is, you can move with it.
If you share your life with someone, the decision is shared too. A partner or a family has a say. Their fears and their relationship to the unknown sit at the table beside yours. Navigating those conversations is part of the dance.
The game I was looking for showed itself through playing.
A road trip through 37 states. A move to Panama. Courses, ebooks and dozens of experiments at every scale. Each one carried a resonance and a contrast. That feels like me. That doesn't feel like me at all.
For several years I did things I didn't like because I thought that's what you "had" to do. Even that was good data.
Every experiment moved me a little closer to something more me. That's how you write your own rules for the game: one alignment and contrast at a time.
Sometimes clarity comes from taking action. Sometimes it arrives on its own and pulls you into action. Both are part of the play.
The Infinite Game is the one you play to keep playing, where the structure keeps evolving as you do. That's why its rules get written along the way.
A more intriguing game can take longer to find its momentum, especially when people rely on you and money is involved. Welcome the mentors and the frameworks along the way. Be discerning with the advice you keep. There's no seven-step path. It's all remixed. We're all developing our own game, with plenty of overlap and plenty that's unique to you.
Here's the part I'd hand to anyone feeling that friction on a Monday afternoon.
The way you make decisions becomes your default. Decide from fear or the need for certainty again and again. That becomes the groove you run in. Make room for what feels Alive in how you decide, how you move and the goals you set. Over time that becomes the default instead. A way of being you no longer have to think about.
That practice starts smaller than a leap. One Alive Thing is one hour set aside on purpose for one thing that lights you up. It's the smallest experiment there is. You can run it from inside whatever game you're playing right now.
I'm freshly back from a month in Nepal. It was a really great trip. I'll be sharing more of it soon. The idea that travel could be a way of growing was where my own game began. It's still part of how the game keeps showing itself.
Lane
Enjoy the Journey
Something in you that wants to move? One Alive Thing is a free mini side quest, a finite adventure you choose inside the Infinite Game. Find it, name it and make it real in under an hour.
Start your One Alive ThingGet new writing by email
The whole essay, straight to your inbox. Plus a breadcrumb at the end.