29 Lessons From Owning A Bookstore

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. Every morning, I send out the Daily Stoic and Daily Dad emails to over 500,000 people. I put out a podcast that’s had 80 million downloads. As satisfying as it is to reach large numbers of people through the enormous scale of the internet, there is even more satisfaction in doing something in real life, for real people, even at a much much smaller level. Every time I walk by or to the bookstore, I think, Wow, I made that. 

– I think one of the best decisions we made was making our book tower. It’s 20 feet tall and made of some 2000 books, 4000 nails, and 40 gallons of glue. It was not cheap to do. It was not easy to do. It took forever. We had to solve all sorts of logistical problems to make it work. But it’s also probably one of the single best marketing and business decisions we made in the whole store. Because it’s the number one thing that people come into the store to take pictures of. 

– You want to have a unique proposition. You want to have something that only you could do. Most bookstores have thousands and thousands of books. But what we decided here was that we’d have only a couple hundred books, only my absolute favorite books, only the books I put in my Reading List Email. It would only be those books. So not only did this make it cheaper and easier to run the bookstore, it makes us stand out. 

– There’s this great story of when Jeff Bezos had the idea for Amazon. He was working on Wall Street at the time. He and his boss go for a walk in Central Park and after he tells him his idea, his boss says, “that sounds like a great idea for someone who doesn’t have a job.” Meaning that somebody else should do it, not Bezos. If there’s something crazy that you’re thinking about doing, maybe you should get serious about actually doing it. On the other side of the risk and the crazy leap can be something that changes your life, that changes your community, that changes the world.

– Doing something cool means risk…but just because you take a big risk doesn’t mean there aren’t lots of little ways to take risk off the table. My office is above the bookstore. I rent part of the building out to another business, etc. 

– There are lots of easier ways to make money than a physical bookstore in 2022…so everyday I try to remind myself this project was not about making lots of money. 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 don’t lose lots of money, that’s a win. 

– Start small. The problem is when you have really high standards, when you expect a lot of yourself, it’s hard to be comfortable with something that’s kind of crappy or mediocre or not all the way there. But there’s a reason most tech start ups think in terms of a minimum viable product. 

– Related to that there’s a great Hemingway line—we actually have a shirt with it, and I have a print of it on my wall—it’s one of my all-time favorite quotes: the first draft of everything is shit. I love how The Painted Porch is now, but it took weeks and months to get it to where it is. It’s been a continual process of improvement and growth and making changes.

– Lengthen your timeline. I mentioned Hofsteader’s Law above—it was important to remind ourselves many times that the building we were in was nearly 150 years old. It can be very easy on a project to get caught up in the immediacy of what’s in front of you…but you miss the big picture and you miss the reality that most things that work are set up to work for a long time. We sell books in our store that were written 2,500 years ago! Who cares if the project took 13 months longer to open than we thought?

– As Zeno said, books are a way to have conversations with the dead. You can learn from people who came before you. They can also inspire and reassure you. Some books I leaned on often throughout this were The War of Art by Steven Pressfield, Meditations by Marcus Aurelius, and A Calendar of Wisdom by Leo Tolstoy.

– One of the things I did while I was kicking around the idea is I looked up how expensive it is to start a bookstore. Search results said it was hundreds and hundreds of thousands of dollars—way more expensive than I was interested in. But then I wanted to question whether that number was real. So then I went and looked up how expensive it was to start an ecommerce business—something like Daily Stoic. Search results said it was hundreds of thousands of dollars more than I’d spent to start Daily Stoic. That was really helpful—to learn, oh, these people don’t really know what they’re talking about. Or that there’s a cheaper way, a different way to do it. You don’t have to do it the way that everyone else does it.

– Steal like an artist (also a great book we carry). We got the idea for the bookshelves in our store at someone’s house for a toddler’s birthday party. They had built them themselves, we took a picture and had our contractor do his own version. The book tower was roughly inspired by The Last Bookstore. Even the idea to carry fewer titles and put them face out was partly inspired by Amazon’s physical bookstores. Take from many influences and make them your own. 

– One of my favorite parts of the whole experience has been watching my wife work her magic. Not only was the original idea to do the store hers, but almost all the big design ideas were hers too. We have very different styles of working but collaborating on this challenged me to see the wisdom in her approach on a humblingly regular basis. 

– When you get criticism, when you get information, when you get facts—and of course you have to look for those things—you have to take them with a grain of salt. You have to put them up to the test, as the Stoics say. You have to question some of the assumptions out there. You might just find, as we did, that instead of something being way too expensive, it is actually doable for you to do it.

– Think of it as an experiment. When I was thinking about opening The Painted Porch, I asked Tim Ferriss for advice. “Think about it as an experiment,” he said. “How are you going to know if it’s something you want to do if you haven’t tried doing it?” The decision to see it as an experiment, not as a permanent life choice, was so freeing. It allowed me to go into it knowing that I was going to commit to it for the next two years, and then, I can reassess, I can change my mind.

– Confidence is earned. People talk about trusting their gut. But that’s something you have to earn. I talk about this in Ego is the Enemy—there’s a difference between confidence and ego. Ego thinks, whatever I want to do, of course I’m going to be successful. Confidence is something you earn, something you earn over time. It’s something you earn through having an idea and bringing it into reality. It’s learning what you’re capable of, learning what’s possible, learning why you do deserve to trust yourself. Confidence is on the other side of having done a scary thing, a thing that a lot of people said wasn’t a good idea.

– In Letters From A Stoic, Seneca says he pitied the person who’s never gone through adversity, who’s never done anything difficult. Because they don’t know what they’re capable of. Well…cue March 2020.

– Help yourself by helping others. When I first started my Reading List Email in 2008, the idea was that I wanted to celebrate other people’s works. To me, the bookstore is an extension of the idea of celebrating other people’s work. And when you do that, when you create value for people, when you’re generally a positive force in your industry, in your space, you develop a reputation. People want to support you. People want to help you.

– Robert Greene’s metaphor for mastery (if you haven’t read Mastery, you must) is being on the inside of something. When we start a new sport, when we get a new job, when we approach a field we haven’t yet studied, we are on the outside of. But as we put in the work, as we familiarize ourselves with every component, as we develop our intuitive field, we eventually make our way to this inside. This is a metaphor I think about constantly with the bookstore.

– Permission assets are everything. All my success as a writer, right down to this bookstore, has been rooted in the email lists and social media accounts I have built. When you have direct access to people who like what you do, everything is more affordable and more scalable. When you don’t? Everything is harder and requires so much more luck. 

– Just do the right thing…the rest doesn’t matter. That’s what Marcus Aurelius writes in Meditations. We delayed opening during the worst days of COVID—we didn’t need to, so why contribute to the problem? We paid people to work remotely instead. We kept up safety protocols even after the state of Texas washed its hands of its responsibilities last year. We did it even though people got mad at us for it, even though it probably cost us business. My conscience is clean and that’s what counts. Keeping your community and your staff safe is good for business in the long run anyway. 

– If it makes you a worse person (parent, neighbor, writer, whatever), it’s not success. On a note to myself when we were opening the bookstore in the middle of the pandemic, I wrote, “2020 is a test: will it make you a better person or a worse person?” That was the test that I reminded myself of over and over again: will this make you a better person or a worse person? If starting a business makes you a worse person—if it stresses you out, if it tears your relationships apart, if it makes you bitter or frustrated with people—then it doesn’t matter how much money it makes or external praise it receives. It’s not successful.

– As we were going through it, my wife and I asked ourselves, what does success look like? And we decided that success was going to be: becoming more community minded, becoming more responsible, becoming better organized, having more fun, making a positive contribution.

– Physical experiences matter more in a digital world. If people wanted a book cheaply, they’d buy it online. There has to be a reason people would drive out and come to your business.  We made a lot of our design and marketing decisions around that idea.  

– It would be wonderful of course if marketing didn’t have to exist. If things could be bare-boned. If presentation and packaging didn’t matter. That’s just not how life works—never has and it never will. You have to do interesting stuff. You have to make remarkable things, as Seth Godin writes in Purple Cow, you have to do remarkable marketing. Do stuff that commands attention. Draw attention like a magnet. These things cannot be underestimated.

– COVID has been tough. Even as I was working on this piece, we had to close because people got sick, even after all our precautions and we couldn’t stay open. That was expensive and it was scary for everyone. But we took it one day at a time, we adapted, we adjusted, we figured it out. Which is all you can do. .

– In The Obstacle is the Way, I quote this Haitian proverb that I like: behind mountains are more mountains. That’s just how life is. You don’t overcome one obstacle, you don’t get through the first year of your business, and then suddenly, you’re magically done with obstacles. No, that’s not how life works. Life is one obstacle after another. You just have to keep going. 

– I mentioned Austin Kleon’s book Steal Like An Artist earlier but his book Keep Going was even more relevant to this journey. 

I happened to be writing Courage is Calling during most of the crazy period of putting this book store together. Obviously, starting a small business is not the same as running into a burning building or onto a battlefield, but one thing you can’t escape noticing when you read history or biography is just how badly we need people to step up, to put themselves out there, to pursue their crazy ideas. All of human progress—big and small—depends on that. 

If you’re thinking of doing something, if you feel called to do something…well, maybe you should do it. Just remember to…

    • Start small.
    • Be patient.
    • Think of it as an experiment.
    • Do it the way only you could do it. 
    • Find ways to take risk off the table.
    • Define what success means to you.
    • Question some of the assumptions out there.
    • See adversity as an opportunity to find out what you are capable of.
    • Keep going—behind mountains are more mountains.

Anyway, come visit us on Main St. in Bastrop sometime…or support the store online at thepaintedporch.com! Some of the most popular books in the store are Empire of the Summer Moon by S.C. Gwynne, The Library Book by Susan Orlean, and The Tiger: A True Story of Vengeance and Survival by John Vaillant. We’ve also had many of my favorite authors stop by and sign copiesof their books, such as: The 48 Laws of Power by Robert Greene, The Subtle Art of Not Giving a F*ck by Mark Manson, From Strength to Strength by Arthur Brooks, and Finding Ultra by Rich Roll. If you buy from those links, your books will be shipped from us here in Bastrop, Texas!

Written by Ryan Holiday