"Nobody should feel sorry for me. I was really stupid."

That's what I told the New York Times back in 2016. 

I meant it.

But there are things that happened to me I genuinely didn't see coming.

Things that broke me. Things that saved me.

And one thing happening right now that changes everything I've spent 13 years telling everyone.

1. I didn't expect to go from $15 million to $143 in a single summer.

I had a TriBeCa loft. Helicopters to Atlantic City. $100 tips to cab drivers. A $300,000 credit card just because I could.

And I still felt poor.

So I invested in everything. A device for deaf people. Internet stocks at the peak of the bubble. Zero of it worked.

The summer of 2000, I lost about a million dollars a week. Cash.

When it was over, I checked an ATM. $143. I stood there and cried.

2. I didn't expect to do it twice.

I clawed back to $10 million by 2007. Then 2008 happened. My fund collapsed. The columns got canceled. My marriage ended.

I moved back into the Chelsea Hotel. Same place I'd lived before the first fortune. The front desk guy looked at me and said: "You again."

No door on the bathroom. Old furniture. When my six-year-old daughter came to visit, I had to steer her around a used condom on the stairs.

3. I didn't expect to research ways to kill myself.

I'm not being dramatic. I had a $4 million life insurance policy. I calculated whether my daughters were better off with the payout than with me as their father.

Depression isn't sadness. It's not caring. About anything. About anyone. It's back to bed.

I tell you this because what happened next only makes sense if you understand where I was.

4. I didn't expect a ten-cent waiter's pad to save my life.

Walking on the Bowery one afternoon, I wandered into a restaurant supply store. Bought 100 waiter's pads for $10.

Next morning I wrote down ten ideas. Not good ideas. Any ideas.

Did it again the next day. And the next.

Move your body. Cut the people who drain you. Write ten ideas. Stop trying to control the outcome.

Four things. Sounds like nothing. It was everything.

5. I didn't expect a million people to need to hear it.

I wrote it all down. The ATM. The Chelsea Hotel. The web searches.

Put it in a blog, then a book I self-published on purpose—because the whole argument was that gatekeepers were obsolete, and I wasn't going to wait for one to approve it.

Choose Yourself sold over a million copies.

What I really didn’t expect: a search for "I want to die" once returned my blog as the second result on Google, right below the Suicide Prevention Hotline. In one month, nearly 5,000 people found me that way.

People were on the floor too.

6. I didn't expect the world to get harder after I figured it out.

Choose Yourself was the right philosophy. I still believe every word.

But it assumed something I never said out loud: that everyone had something to choose with. Some runway. Some margin.

Some ability to take a swing without drowning.

7. I didn't expect groceries to cost $220 more a month than five years ago.

That's not a statistic. That's a family doing arithmetic in the grocery aisle and putting things back.

8. I didn't expect the savings rate to fall to three cents on the dollar.

Three cents.

That’s how much the average family saves from their income.

How do you choose yourself—invest, risk, build, bet on your own future—on three cents?

It’s getting harder for most people to see a way out. 

9. I didn't expect Social Security to have a countdown clock.

Not a maybe. A scheduled event. Six years out. Automatic benefit cuts baked into the math.

Nobody in Washington doing anything about it.

10. I didn't expect to have to rethink everything.

The philosophy stands. Autonomy over dependency. Stop waiting for permission.

But before you can choose yourself—before any of it means anything—you need a floor.

Real income. Cash from the market that doesn't depend on a paycheck, a pension, or a politician.

That’s what I’m working on right now inside my network.

More soon.