I want to tell you about a door.

Not a metaphor. An actual door — though it became a metaphor later.

When I first came to the United States, I came the way I thought was the side entrance.

I started in Ottawa, Canada. By bus. Through Toronto. Past the mist coming off Niagara Falls. Across the border, past the American flag, and into Buffalo, New York.

It was November 1992. Thanksgiving week. Bill Clinton had just won the election, and the country felt like it was breathing out for the first time in a long time. The air at the Buffalo bus station was thin and cold, and nothing like the air I had left behind in Ottawa.

But I wasn't done yet.

From Buffalo, I boarded an Amtrak train. I rode it west through the long, flat dark of upstate New York, across the rust belt and into Chicago — a city I had never set foot in, with a few hours between trains and a sandwich I still remember the taste of. Then I boarded a second Amtrak and rode it across the plains, through the Rockies, through the desert, and out the other side into California.

I came down the train steps at Union Station in downtown Los Angeles, with two suitcases and a name nobody could pronounce.

A different climate — in every sense of the word.

I thought I had taken the back way.

I was wrong. It was the door.

I'm writing to you in the middle of a week that has me watching a lot of people walk through doors.

I'm in the middle of a 5-day challenge myself — learning a stack of AI tools that are rearranging how I work. Every morning this week, hundreds of us are showing up at 11am to learn something that didn't exist eighteen months ago. The people in that room aren't kids. They're educators, professionals, late starters, second-act builders — exactly the room you and I keep finding ourselves in.

And I'm noticing something I want to name for you.

The main entrance was a lie.

The story we all got told — the one I believed for a long time — is that there's a front door, and the front door is the only one that counts.

The right college. The right first job. The right company logo on the resume. The right introduction from the right person. The right moment, the right age, the right credentials.

Wait for the front door. Line up. Apply. Hope you get picked.

I tried that door for ten years. I waited for permission to start. I waited to be ready. I waited to look like the person who was supposed to be doing whatever I was about to do. I had a ten-year plan that started in my forties and ended somewhere in my fifties, and most of what was in the plan depended on a front door that had no interest in opening for me.

Then 2008 came. The door didn't open. The whole building came down.

And I had to find another way in.

I didn't find a new front door.

I found a side door.

And once I started using it, I realized something I now believe with my whole chest:

Every door I've ever walked through was the wrong one first.

The side door of a charter school in California, where I became a teacher in my fifties. The side door of a small real estate practice, where I learned the local market by knocking on doors nobody else wanted to knock on. The side door of a small Facebook group, where I met people who were building the kind of life I wanted to build. The side door of this newsletter, which I started with a hundred subscribers and no credentials other than forty years of living.

None of them looked like the main entrance.

All of them changed my life.

I want to say this to you directly, because I think some of you are standing in front of the wrong door right now.

You are not too old. You are not too late. You are not too under-credentialed. You are not too far gone. You are not the wrong kind of person to walk through the door that's actually calling you.

The door that doesn't look right is almost always the right one.

The door that feels too small is almost always the one that fits.

The door nobody else is lining up for is the door that nobody else will walk through, which is exactly the point.

This week, while you're watching the AI Secrets Challenge unfold, or doing your own work in your own room, I want to leave you with this:

Find the side door.

Don't wait for permission. Don't wait for the credentials. Don't wait to be ready.

Walk up to the door that doesn't look like the door you thought you'd be walking through.

Try the handle.

It's almost always open.

If you've been circling a door for a while — a vocation, a version of yourself, a project that's been sitting in your desk drawer for a year — I built something for exactly that moment.

It's called the Winstonism Life Audit — 7 Questions That Reveal If You're Living Someone Else's Life.​

Fifteen minutes. Seven questions. No fluff.

Most people tell me it's the first honest conversation they've had with themselves in years.

👉 Take the Life Audit → 7 Questions That Reveal If You're Living Someone Else's Life​

More soon.

Winston

P.S. — Tomorrow morning at 11am Pacific, Day 2 of the AI Secrets Challenge goes live. If you're not inside it yet, it's free. The link is in yesterday's email. The room is full of people who decided this was their side door. You can be one of them.

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