Lifestyle Design Fodder

As I mentioned in the last post, lifestyle design is both the beginning and the end of getting on The Highway to Yeah.

It starts with noticing the sparks—the urges toward things you want in your life.

Two exercises, in particular, helped move me toward my own version of radical lifestyle design:

1. Looking Back from 100 Years Old

At the time, I was working a job that had me traveling to small towns across two large states. The company had a library of books on tape—actual cassette tapes, which tells you where I was in life.

Somehow, I came across an audio program by Earl Nightingale. He had that old-school, wise grandfather voice—part philosopher, part newscaster. Weird stuff, but I listened anyway.

 One exercise stuck with me: imagine yourself near the end of your life, looking back at all the things you wanted to do—but didn’t. Which ones would you regret most?

He may have suggested listing 100 things you hope to do in your life. I aimed for 10.

That list has evolved, but I still revisit it. Some items, I’ve completed—like earning a PhD. Others, like biking across the U.S., I haven’t. But even that unrealized goal pushed me toward financial freedom. I realized: how else could I take three months off to do something like that?

2. The Big 3 Life Events

In this exercise, you divide your early life into three phases—pre-teen, teen, and early adulthood—and identify the most meaningful memory from each

Mine were:

1.     Horseback riding through Garden of the Gods

2.     Reading The Lord of the Rings

3.     Performing on stage

Then you revisit them.

When I re-read The Hobbit, the chapter on Rivendell struck me deeply. It became a new life goal: find the real-world version of Rivendell—or create one.

A few years later, I found myself at Esalen in Big Sur. My first thought: this might be the closest thing.

Looking back, these weren’t fully formed lifestyle designs. They were early signals—clues pointing toward the life I wanted.

Do the exercises. See what shows up.