In Over Your Head? You’re on the Right Track

Guy Raz Newsletter – September 19, 2024

There’s a common belief that before starting something new—whether it’s a business, a project, or a big change—you need to have everything figured out. That you need to have every detail, every strategy, and every possible scenario mapped out in advance.

And sure, preparation is important. But sometimes, we can overthink ourselves right into not starting at all.

This week’s episode with Bonnie Harvey and Michael Houlihan of Barefoot Wine is a perfect example of why that’s not always necessary. 

When they entered the wine business, they had no experience and almost no money. They didn’t know the “rules,” and in some ways, that was their greatest advantage. Because they didn’t know how things were “supposed” to be done, they were free to create a business on their own terms.

They didn’t wait until they had every detail worked out. They took the leap—before they were ready.

Bonnie and Michael knew nothing about terroir or vintages or noble grapes.

They couldn’t tell you the difference between…