In 1998 I was living in Key West, working as a gardener, and everything was going to plan. After saving up from a job at Lloyd’s of London, I’d bought a ticket to Australia and had a one-year working holiday visa waiting. The arrangement was simple enough. Spend 90 days in America first, meet my girlfriend in California, fly across a few islands, and land in Australia ready to start the next chapter.

Clean, logical, sorted.

Then Hurricane Georges showed up and none of that mattered anymore.

The Problem With Having a Plan

When the government advised people to evacuate Key West, most people had somewhere obvious to go. They had family to call, friends to stay with, some kind of network that would absorb them while the storm passed.

Being a young British bloke travelling completely alone, thousands of miles from anyone I knew, none of those options existed for me. No contacts, no safety net, no obvious next move on the board.

Most people in that situation would have sat tight, weighed things up carefully, maybe called home, and waited to see what developed. Probably the sensible thing to do. Instead, I was halfway through a book that was about to change how I thought about decisions entirely.

The Dice Man

The Dice Man by Luke Rhinehart follows a character who abandons conventional decision-making altogether and starts rolling a dice instead. Six options written down, one roll, whatever comes up is what happens next, no going back and no second-guessing.

It sounds absurd on paper, but sitting in that dormitory in Key West with a hurricane on the way and no obvious plan, it made a strange kind of sense.

So that’s what I did. Wrote down six American cities, rolled the dice, and got number four. Chicago. No dramatic moment, no rush of excitement, just a kind of flat acceptance that this was the answer and it was time to move.

Went straight to the Greyhound bus station and bought a one-way ticket before I could talk myself out of it.

48 Hours Going Nowhere Planned

The journey took about 48 hours, changing buses in Atlanta somewhere along the way. This was 1998, so no smartphones, no internet, nothing to keep you company except your own thoughts and whatever was passing outside the window.

A lot of the journey was dark, the landscape was pretty when you could see it, and mostly I just sat with the strange reality that I had absolutely no idea where any of this was heading.

Arriving in Chicago late at night, I found a motel near East Ohio Street downtown, run by a large Irish woman who had very little interest in my situation. Paid for a full month upfront, which left me with about $80 to my name. My flight out of LA wasn’t for almost three months.

What Happened Next

The morning after I arrived, I walked around restaurants asking for work and eventually landed a job as a waiter at a diner called Johnny Rockets. That was the beginning of something that took me all the way across America through one of the most extraordinary stretches of my life, and yes, I did make it to LA in time. Australia happened. T

he original plan, eventually, came together.

But none of the interesting parts of that story exist if I’m still sitting in Key West trying to figure out the perfect move.

The Thing Most People Get Wrong

After years of working with people trying to build something online, the pattern I keep seeing has nothing to do with knowledge or skill. Most people who are stuck aren’t stuck because they don’t know enough. They’re stuck because they’re waiting for conditions that never quite arrive.

The right moment, the right level of confidence, enough information to feel certain, some sign that it’s finally safe to go.

They’re standing in Key West watching the hurricane come in, still trying to plan the perfect evacuation route.

The dice roll wasn’t clever. It wasn’t a framework or a strategy, just a commitment to move and figure the rest out on arrival. That’s what actually made the difference. The method was ridiculous, but the commitment was real, and the commitment is the only part that matters.

You Don’t Need a Dice

To be clear, making business decisions by rolling a dice is not the lesson here. The lesson is that imperfect action beats perfect inaction every time, and the people who build things aren’t the ones who waited until everything lined up.

They’re the ones who got on the bus, arrived somewhere unfamiliar, and went looking for work the next morning.

Whatever you’re trying to build, you probably already know roughly what it is. The conditions aren’t perfect and they’re not going to become perfect. At some point the deliberating has to stop and the moving has to start, because the hurricane doesn’t wait for you to feel ready.