2 Years Of Lessons From Running My Own Bookstore

Ryan Holiday
9 min readMar 27

It is only from doing hard things, the Stoics said, that we learn what we’re capable of.

A little over three years ago, my wife and I had the craziest idea we’ve ever had in our lives: to open a bookstore in Bastrop, Texas.

Opening a small business is always hard. But opening a small business during a pandemic in a small town in rural Texas? To call it a challenge would be an understatement.

We’ve learned a lot…about business, about books, and about what we’re capable of. Last year, I wrote a piece on the lessons we’d learned in our first year of business at The Painted Porch. Now, another year has passed and we have learned a few more…and re-learned some of the ones we thought we’d gotten the first time. I share them here so you can perhaps learn a little from my experiences and hopefully go create something cool of your own out of it.

[1] Anything can be a good business if you treat it like a business. Too many indie bookstores are started because people think they’ll be fun…or because they love books. No, you have to be serious. I learned this as a writer: treat it like a job.

[2] The bookstore of course is not just a bookstore. It is my office. It is my employee’s office. It is where I record podcasts and film YouTube videos. I rent part of the building to another business (a really cool record store called Astro Records). When you are thinking about taking a big risk, look for little ways to take some risk off the table. Find multiple uses, multiple options so that if one fails, you can still succeed.

[3] On the Daily Stoic podcast, Matthew McConaughey gave me a better framework for making big decisions. He told me he’s known in Hollywood as a Quick No, Long Yes. His No’s are quick. But before he says Yes to something, “I give myself about 2 weeks in each frame of mind — Yes I’m in, No I’m out — and then I measure what keeps me up at night.”

[4] Keep your eye on the prize. What is success to you? What metrics actually matter to you? Remembering why you did something and how you measure success helps you calibrate your decisions properly. I’m happy enough to be putting books out in the world, making this community better, having a physical space, challenging myself, etc…as long as I…

Ryan Holiday

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