29 Lessons From Owning A Bookstore

Ryan Holiday
11 min readApr 6, 2022

I’ve done some crazy things in my life, but as I’ve said, the absolute craziest was deciding to open a bookstore. Running a small business is always difficult, running a small business during a pandemic is damn near impossible but a small town book store in rural Texas?

But here we are, a year later, not just still standing but doing great!

We’ve learned a lot…about business, about books, and about ourselves.

I made a YouTube video about the experience, but I wanted to expand it here into a fuller explanation of all the lessons that The Painted Porch has taught me. I share them here so you can get something too — and perhaps learn a little from my experiences and hopefully go create something cool of your own out of it. Here are 29 lessons from the first 12 months of owning The Painted Porch.

– It always takes longer than you think it’s going to take. That’s Hofstadter’s law. From the moment my wife suggested we open a small-town bookstore, everything has taken longer and been harder than we expected. If you can’t pass the marshmallow test of delaying gratification and deferring things into the future, you’re just going to get crushed.

– For most of my life as an author and entre­preneur, my work has been digital. Close to half of the sales of my books are audiobooks and ebooks…

--

--

Ryan Holiday

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR