If you're feeling stupid, ashamed, full of regret, or just out of hope today, this one's for you. I've been all four. I'm writing this from a first-class lounge waiting on a flight, and I'd like to tell you how I got from there to here, because the road is shorter than it looks from where you're sitting.
The creek wasn't a creek
My dad worked for USAID when I was small, and we lived in some of the poorest countries on earth. I learned early that the creek by the house was not a creek. That was my introduction to open-air sewers. Lesson learned.
Back in the States I watched him have great jobs and lose them — once when a government contract ended, and once because his boss asked him to lie at a congressional hearing and he said no.
That Christmas he went to work at the local mall demonstrating the Veg-O-Matic, in front of people who used to work for him. He told me years later he felt humiliated. My mother took me to see him. I was about ten. She says I pointed at him and announced proudly to the whole store, that's my dad.
There were times in the late 1960s when my parents had to borrow from my piggy bank to buy groceries. They were open with me about it, and I was a proud kid to help. We had a black-and-white television with four channels. No phone in a pocket, no streaming, no YouTube. Frontier days.
Potomac, and the lawn chairs
The family finances came back, and then some. We moved to Potomac, Maryland — one of the wealthiest places in the country, where a lot of famous people lived. And I got my second education. A lot of outwardly successful people there were miserable humans. As a teenager, I was invited inside by friends. Some of them slept on lawn chairs or in sparsely furnished rooms inside the house, because all the money had gone to the outside and cars.
I didn't have words for it at twelve. I do now. One of my core beliefs came out of that experience: we learn more by observing than by judging or worrying. BE AN OBSERVER.
And here is where I want to stop and say something to a particular reader, because a lot of you found me on Substack and you're carrying a different kind of balance, an emotional balance.
You have a number on a dashboard that isn't what you hoped. You've refreshed it today more times than you'd admit. You look at the writers with the big numbers and feel behind, and a little stupid for caring, and then you care anyway.
I have two publications. One has more than 16,000 subscribers and adds about fifty a day on its own, because the network hands it readers for the category it's in. The other, this one, has about 2,200, grows slowly, and is the one I actually love writing — and in a few days I'm going to cut that number roughly in half on purpose, by removing the people who never open it. Life taught me not to care about the numbers. If you'd asked me which publication I'd keep, I wouldn't need to think about it. It’s this one.
That big number is the lawn in Potomac. You can't see who's sleeping on the lawn chairs. Your small number is measuring the category you chose and the people you're proud to call subscribers — friends, really — — it isn't measuring you, and it isn't measuring whether the thing you're making is any good. The people who did subscribe did it because of who you are. That is the only part of this you get to keep, and you already have it.
My first emergency
Let's jump ahead to my first credit card. It was for emergencies. Who knew that my turn to buy the beer would be my first emergency.
Then I got my PhD in life. In the late 1980s I left a comfortable, stable job in medicine to chase my dream of a real estate development business, using the method of the day: other people's money. I did not see the economic headwinds coming. In 1990 I filed bankruptcy.
It was the lowest point of my emotional life. It was also the best thing that ever happened to me.
Don't waste a perfectly good mistake
Another of my core beliefs: there's no sense wasting a perfectly good mistake. So instead of hiding, I got curious. Why wouldn't creditors take my money after bankruptcy? How does a person actually rebuild? Within a couple of years I'd bought a house at market rates and financed a new car at prime. Bankruptcy didn't destroy my finances. It did play with my head.
And out of that experience I started helping people who were where I'd been. That was 1994. I've never stopped. I give away everything I know for free — every weekday I write about what people need to know about their money, I do a weekly podcast and a daily deep dive on credit and debt, and I sell no services. My biggest financial failure became the thing I've spent thirty years being useful with, through television, syndicated columns, books, and GetOutOfDebt.org, for more people than I could ever count.
But I don't want you to hear a miracle story, because it wasn't one. I spent four years after that bankruptcy feeling sorry for myself, being depressed, calling myself a loser, and holding on to the shame like it was mine to keep. Then one day I just thought: F that. And I got busy with another core belief — if you do good things, good things happen.
From four channels to the lounge
So flash forward from the kid with the black-and-white television to the guy in this chair, running three companies from his phone with AI, waiting for a flight. Everything else is doing well too.
What I'm clumsily trying to say is this: your lowest point deserves to be celebrated, because it is going to be the biggest and best learning moment of your life. It is all up from here — once you learn the magic of saying F it, stop caring what you think other people think of you, and get on with the wonderful, glorious, amazing life waiting for you around the corner.
That goes for the balance on the card and the number on the dashboard both.
Five mottos that have served me well
Don't be a dick.
As long as you are not on fire, it is a good day.
There is no sense wasting a perfectly good mistake.
Do it now.
It's much better to fail than to never try.
And two things I heard along the way that still hold me up. From a movie: it's better to get busy living than to get busy dying. And from I don't remember where: I'd rather be seen than viewed.
Life is a one-way journey, and the future is yours to write. Go do it.
If today is your bottom, I'd like to hear about it — reply, or comment, or just tell one person. That's how mine started to turn.
Steve
P.S. I believe in you.