You Don’t Get the Map Until You’re Lost

I have a confession. I love a plan.

Give me a whiteboard, a fresh pack of markers, and a problem nobody has solved yet, and I will be happy for hours. I can map out a project so thoroughly that I never actually have to do it.

That last part is the problem.

Most of us are waiting for a map. We want somebody to hand us the route, the mile markers, and the gas stations before we pull out of the driveway. And we will sit in that driveway for years waiting on it.

Here’s what I’ve learned the hard way. You don’t get the map until you’re lost.

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The guitar problem

Nobody ever learned to play guitar by reading about guitars. You can memorize every chord chart on the internet and still sound like a raccoon in a trash can the first time you pick one up.

Starting anything works the same way. You cannot know how to start until you have started. That sounds like a riddle, but it isn’t. It’s just the order of operations. The knowledge comes from the doing, not before it.

The first book I ever wrote is proof. I honestly can’t even remember the title.

It was about the day I made $10,000 in the stock market. Part story, part beginner’s guide to investing. Was I an expert? Hardly. But I had an anecdote and a dream, and that felt like enough.

I didn’t type it, either. I yelled it into my phone. A friend of mine worked a boring overnight security job, and he spent his shifts typing up whatever I’d recorded that day. Honestly, it was a pretty good system.

Unfortunately, we didn’t know how to write a book. We definitely didn’t know how to promote one.

But we did it. And everything I know about writing books today started with that one, the one whose title I can’t remember.

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Build the ugly version

In the software world there’s a term I use all the time: MVP. Minimum viable product. It means you build the smallest, ugliest version of the thing that still works, put it in front of real people, and let them tell you what’s wrong with it.

Tech companies do this because they learned the expensive way that the plan is always wrong. Not a little wrong. Wrong in ways you could never have guessed from the whiteboard.

I have launched no fewer than 15 websites. The first one, I designed myself, and it was awful. Clunky. Basic. It was, to put it gently, a turd.

I launched it anyway. And that turd taught me the most important lesson I’ve ever learned about the internet.

Just because a website exists doesn’t mean anybody is looking at it.

If I had waited until I’d built the most beautiful blog in the world, I would have learned that lesson a lot later, and a lot more expensively. You can have a terrible website with people on it, or a perfect website with nobody on it. Only one of those is a problem you can fix.

Jesse Cole, who runs the Savannah Bananas, talks about this kind of thing all the time. When their merch went on sale, the demand crashed their website. That’s a great problem to have. They learned from it, and now the site stays up. But the crash only happened because the people showed up first.

Polish matters. People matter more. And you’ll never find out which one you’re missing until you launch the ugly version.

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I’m lost right now

I’m not writing this from the finish line. I’m writing a book called Cornered, and it is quite literally my life story.

You would think that would be the easiest book in the world to write. I don’t have to research anything. I was there for all of it.

And still, I get stuck. I sit down to write and it feels boring. I’m uninterested. It doesn’t jive. Something comes up. The stories just won’t come out.

Then, out of nowhere, I have a eureka moment and write five chapters.

I used to think the stuck days were wasted. Now I think they’re part of the trip. (Turns out nothing was wasted, including the detours.) You don’t get the eureka without the wandering. So I keep showing up, and I trust that the map shows up too.

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If you’re sitting in the driveway

Here’s how to get moving without a map:

1. Shrink the first step until it’s almost embarrassing. Not “write a book.” Yell one story into your phone. Not “start a business.” Ask one person if they’d pay for it.
2. Put a date on the ugly version. Planning expands to fill whatever time you give it. Give it less.
3. Expect day one to make no sense. Check back on day 365. It will look a lot clearer from there.

The map is real. It’s just printed on the back of the trip.