How Buying a One-Way Ticket to Rome is Unlocking Unexpected Opportunities

Evolving dreams, paneling at PickleCon, the nicest thing courtesy of an 11-year-old, authors and expectationless connections, and my bookstore date with Steve Carell.

The one-way ticket to Rome you buy at the same time you put your house on the market and put in notice at your job will, yes, take you to Rome. But you can’t even imagine where else it will take you, literally and figuratively.

The whole point of what I’m about to share is that sometimes deciding, and committing to a course of action, unlocks an unexpected other door. Not necessarily a different door. It’s just a door you didn’t expect but which may just open into an existing or expanded dream.

Let me explain.

When I launched this Substack, I had decided to focus on building out my career as a writer and speaker on the subject of intentional living: getting your money and life roots right, travel and life stories highlighting the wonder of wander, entrepreneurship, leaving jobs you’ve outgrown for more creativity/autonomy, the freedom found in getting out of debt, that sort of thing.

My second book, Dear Fellow Dreamer, was somewhere between Draft #2 and Draft #3, and I was doing some fi…