The one bet that always pays off

The math is simpler than you think.

Author

Stephen Stanberry
September 19th, 2025

Hey friend!

I spent the entire night thinking about this:

Every important decision in my life has come down to the same thing:
Making a bet on myself.

When I quit my job to freelance, it wasn’t because I had savings stacked or a bulletproof plan.
It was a gamble.
On me.

When I said yes to my first ghostwriting client, even though I felt underqualified, it was the same.
Another bet.

Even when I launched my storytelling guide, I felt that nagging voice:
“Who’s going to buy this?”
I hit publish anyway.
Bet on myself.

And here’s what I’ve learned:

Every story worth telling starts with that kind of decision.
The messy, uncertain, shaky-hand moment where you could walk away, but don’t.

It’s what makes your story relatable.
It’s what builds trust with your audience.
Because people don’t connect to your highlight reel.
They connect to the risk you took to get there.

So here’s the lesson: if you want your content to resonate, don’t just share the win. Share the bet you made to get it.

That’s where the human part lives.

And here’s where it ties back to you:

Starting your business? Bet on yourself.

The details look different, but the story is the same.

But here’s the truth: progress isn’t guaranteed. It’s calculated risk.

And when you strip it down, the math is simpler than you think.

You don’t need millions to change your life.
You need enough steady wins to cover your base.

Let’s play it out:

  • 5 clients at $1k each = $5k

  • Or 3 clients at $1k and 10 people at $200 for a workshop = $5k
    Double those numbers, you’re at $10k.
    Keep going, and the growth compounds.

Here’s the framework I share with clients:
• A clear offer people need
• A way to share your story consistently
• The confidence to step forward when it feels uncertain

That’s it.

So let me ask you what’s the last bet you made on yourself?
And what story came out of it?

Talk soon,
Stephen

P.S. Hit reply and tell me one bet you’ve made that still makes you nervous when you think about it. That’s the story your audience probably needs to hear.

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