I tried to figure out my whole life alone. It was the most expensive thing I ever did.

I told you Friday I’d be back today.

What I didn’t tell you is the part I’m actually embarrassed about. Losing almost everything at 21 wasn’t the worst of it. The worst of it was that there wasn’t a single person on earth I’d have listened to even if they’d tried to stop me.

I didn’t have anyone across the table.

I grew up around good people. My parents loved me as completely as parents can love a kid, hardworking, selfless, the kind of humans you’d be lucky to know. But they couldn’t guide me toward money or building something, because they’d never stood where I was trying to go. You can’t get directions to a place someone’s never been. That’s not a knock on them. It’s just true. Love and the right counsel are two different things, and I spent years confusing them.

So I did what a lot of driven people do. I decided I’d figure it out myself. All of it. Money, business, my body, my own head. I wore it like a badge.

That badge cost me a fortune. Figuring everything out alone is the most expensive thing a person can do, and the bill doesn’t come in dollars. It comes in years you don’t get back. Opportunities that walked past while you weren’t looking. Stress someone could have lifted off your shoulders in one honest conversation. The 21-year-old me didn’t lose almost everything because he was dumb. He lost it because he was alone and certain. There is no more dangerous pair of words in the English language.

It took me many years to learn the thing that would have saved me in twenty minutes. The smartest people I know aren’t smart because of what’s in their own head. They’re smart because of who they let into the room when the big decision is on the table. Every leader needs leaders. Every mentor needs a mentor. The ones who get destroyed are almost always the ones who were sure, and surrounded by no one willing to tell them otherwise.

Here’s the kind of thing I mean. Someone comes to me excited about a company everyone’s buzzing about, a valuation that, in my honest read, has gotten way ahead of the business. The easy move, the one that keeps everybody happy and keeps me liked, is to nod and say go for it. That’s what most people on the other side of that table do. They stay agreeable because they want to keep you.

I’ll tell them to wait. I’ll say I think the price is stretched and I’d rather watch how the thesis actually plays out than chase it here. Maybe I’m wrong and it runs without us. I can live with that. What I can’t live with is being the guy who saw the edge of the cliff and stayed quiet because the truth was awkward.

That’s the whole thing I do now, and it’s the thing I wish someone had done for 21-year-old me. I call it putting the relationship on the line. Telling you the truth straight, no fluff, even when it’s the harder conversation, and being just as willing to hear it back. Calling each other out, with love, only ever to make the situation better for everybody at the table.

Because the biggest decisions of your life, the ones about money, your health, what you build, where you point the next ten years, were never meant to be made alone. They’re too big, too emotional, too close to your own heart for you to see them clearly by yourself. That isn’t a weakness in you. It’s true for every one of us.

It took me almost losing everything to believe it. You don’t have to learn it the way I did.

If there’s a decision sitting in front of you right now that’s too big to be making by yourself, that’s exactly the kind of conversation worth having out loud.

Talk Friday.

— Mateo