How to stop letting fear make financial decisions for you

Every time I feel fear trying to hold me back from something I know I want, whether it’s a new opportunity, a big leap, an investment, or a next-level decision, there’s one question I always come back to:

Then what?

It’s simple, but also powerful.

I imagine the worst-case scenario that could happen if I go after the thing I’m afraid of. Then I ask myself — okay, then what?

And I keep asking.

Then what?

Then what?

Then what?

I follow the fear all the way down until I run out of “then whats.”

Then I walk back through each of those scenarios and ask, "Is this even true?" And even if it is, has anyone else ever been in this situation and still made it?

Because if I can find even one person who has faced that fear and still succeeded, then that fear can no longer be my truth. Now I have evidence that another outcome is possible.

Let me give you an example.

Let’s say I want to start a business selling hats, but I’m scared no one will buy.

So I ask myself:

If nobody buys from me, then what?

Then the business fails.

If the business fails, then what?

Then I lose the money I put in.

If you lose your investment, then what?

Then I go get a job or pick up extra work.

If you have to go back to work, then what?

Then I rebuild my savings.

If you had to rebuild your savings, then what?

Then I try another strategy to sell hats better.

By the time you have completed this exercise, you'll realize, I’m not actually afraid of failure. I’m afraid of the story I’m telling myself about failure.

And when I look around and find someone else succeeding in the same space — someone selling hats, or writing books, or building courses or earning multiple six-figures — then I can no longer say “it won’t work,” because clearly, it has.

So the next time fear tries to stop you, take out a piece of paper and write down every “Then what?” you can think of.

Keep going until you run out.

Then walk it back with truth, logic, and evidence.

I promise, you won’t find a single “Then what?” you can’t either handle or invalidate.

Inside Sprint to Surplus Challenge, I give you the exact prompts I use to work through limiting beliefs about money — the ones that keep you stuck in survival mode, afraid to have more, do more, or become more.

Listen to it here.