Skip to Content

What Ryan Holiday Taught Me When I Visited Him

Some people teach best working face-to-face. Then there are those who teach volumes with broad messages that apply to everyone on a personal level. New York Times bestselling author, Ryan Holiday, is one of the later.

In my last article I gave you a tour of the United States from Green Bay, Wisconsin to Bastrop, Texas. This central continent backbone of the country contains natural wonders too many people still think is flyover country. The people are even greater than the natural beauty of the central United States.

My ultimate goal was to visit Ryan Holiday’s independent bookstore, The Painted Porch Bookshop, in Bastrop. From this beginning premise I decided to visit clients along the way. It was natural to start dreaming of meeting Ryan Holiday in person.

Authors are the most interesting people to meet. They are always well read which means they are very intelligent and a wealth of knowledge. Spending time with an author, any author, is a very sweet nectar, indeed.

Some authors are more accessible than others. Usually their level of sales determines how easy it is to shake their hand.

Attending conventions the author will be at is a great way to meet the published. My wife, Sue, and I attended four or five science fiction conventions per year back in the 90s. We got to meet many of the great names from the Golden Age of science fiction.

As I mentioned in the previous post, I started my journey with a visit to Jim Collins, another bestselling author, this time in the personal finance/investing arena.

Now I wanted to meet Ryan Holiday. And as always, Holiday was full of surprises and I never actually met him. But, boy, the lessons learned. And I still might get to meet him!

Ryan Holiday and Calendar Anorexia

Holiday is a prolific writer. He pumps out the Daily Stoic, Daily Dad and posts on numerous websites, including his own blogs, plus a book every year. The article of interest to us here involves time management, calendar anorexia (a more detailed description later) and the cost of saying yes.

Every business owner, especially tax professionals, know to build walls. If you don’t the non-stop interruptions will destroy your business while causing massive stress. You cannot(!) be fully accessible at all times. In fact, to be successful you need to make yourself very inaccessible. And the more successful you are the more inaccessible you need to be. If you ignore this lesson, the crush of people, most well intentioned, will drown you.

I had to learn this lesson the hard way when Mr. Money Mustache, a high traffic blog, gave me a push. It almost turned into a push off a cliff. I was unprepared. Adequate walls were not in place and my gatekeepers were crushed from the onslaught of humanity wanting me, and only me, to do all their financial and tax work.

This is the lesson Ryan Holiday taught in his article. He says he has calendar anorexia. He keeps plenty of open space on his calendar so he has time to create and think. He warns us to about people who want “just 15 minutes of your time.” In my profession we call this the “quick question.” And as every seasoned tax professional knows, quick questions do not have quick answers. And there goes another day, a day you never get back.

That brings us to where we left off in the last blog post.

Sue and I are in Bastrop, Texas enjoying the ambiance of The Painted Porch Bookshop. I ask the woman at the bookshop if Ryan is available and she said, “He is, but he is in meetings all day. If he becomes free I will let him know you are here.” Her gatekeeping skills bring a tear to my eye. Professional and to the point.

All of that and I actually saw Holiday twice. I could have made a massive mistake and forced a meeting for “just a minute.” At first I kicked myself for not taking the shot. After time to think about it I knew I made the best choice.

You see, I did not get to shake Ryan Holiday’s hand and thank him for his work. But that opportunity might happen anyway. Details below.

Ryan Holiday's Painted Porch Bookshop in Bastrop, Texas.
The Painted Porch Bookshop in Bastrop, Texas. Every book on the shelf is must-read material.

Ryan on Holiday

The gatekeeper told the truth. She also didn’t look like someone who would take crap from anyone attempting to force a meeting. She provided a wall for her employer. That is her job. She was friendly, professional, honest and straight to the point. Breaking in would introduce me to Texas law enforcement. Not the meeting anticipated.

I could hear Ryan speaking with someone in a back office of the bookstore. I browsed the selection of books, took pictures, made a short video and made a purchase. Then I noticed Ryan was out in front of the bookstore! He had someone recording him. I see his work on social media. I was privileged to see how he structures time to produce informational and marketing content.

And then he was back in hiding.

Around lunchtime I stepped out of The Painted Porch Bookshop. Sue was inside still browsing books. And then, out of nowhere, there he was! Ryan Holiday was on the street! Walking to a corner street vendor. I started to walk toward him and instantly stopped.

Yes, I could have walked up to the street vendor, ordered a hot dog and got a brief meeting with Ryan Holiday. It would have been an appropriate encounter.

But I stopped and refrained from my instinct. I know all to well what it is like to have people consume my lunch break or any other free moment I have. Scarfing down food because there is a lineup in the waiting room is not something I enjoy. Obviously, I don’t have calendar anorexia.

I can set the clock by the lunch hour. The phone starts ringing non-stop at noon. People feel I have a free moment and they have, ahem, a quick question. So they call on their lunch break. Or pop in for a moment.

I know what it feels like when it is done to me and had no intention of paying that BS forward.

Soon Ryan was off the street and safely behind his walls. My opportunity was lost.

My first thought was I made the right decision, but later kicked myself a bit. Now I firmly believe a forced encounter would have been meaningless and would have left a bad impression. And you never know when someone ends up in your life later. And it looks like later will come a lot sooner than I expected.

The front view/entrance of The Painted Porch Bookshop. Why do bookstores have such an allure?

Holiday Gifts

Ryan has a new book coming out! Discipline is Destiny. You can pre-order your copy on the Daily Stoic. (Ryan is selling copies for less than Amazon!)

If you buy your copy directly from the Daily Stoic you also get some gifts. Buy one copy for $20 ($30 autographed) and get two bonus chapters, an extended bibliography of the books that went into the making of Destiny and the Spotify playlist Ryan listened to while writing the book. (Bet there are Iron Maiden songs on the list.)

If you buy 5 copies you also get a signed and numbered page from the original manuscript and a live Q&A moderated, we are promised, by someone cool.

This is where it gets interesting. If I buy 120 copies I get all the other gifts, plus a philosophical dinner at The Painted Porch Bookshop. What’s not to like?

I don’t know how your heart is doing, but mine is racing thinking about it. It will set me back $3,360 for 120 autographed copies. Many people might consider this a steep investment. However, I drop $10,000 to $20,000 every year testing new outsourcing ideas in my industry. Most don’t work! To me, $3,360 is a cheap investment, especially considering I get to meet Ryan Holiday and listen to him speak to all the other 120+ book buyers. I might even get a chance for a conversation with him. How cool is that?

This is where you come in, gentle readers. These 120 books will be used to promote this blog. Once the books are in my paws I will give away one copy a day from the list of subscribers to this blog. You want to subscribe to get a chance at winning a free autographed copy of Ryan Holiday’s new book and so you do not miss my blog post of my meeting with Ryan and his biggest fans.

That concludes everything I wish to share from my road trip. I know many of you were cheering me on in my attempt to meet Ryan personally. Everything happens for a reason. This will be better than a brief introduction.

Thanks for reading to the end.


Thursday 1st of September 2022

Lol, I'm one of those readers who doesn't like others having walls, but understand they are necessary. Like now, I came to read your road trip article with the full intention of asking a completely different question...sorry... I just wanted to confirm my understanding that after the new Inflation Reduction Act became a law, the Backdoor Roth IRA method of saving for HI people survived and they are safe to continue funneling $6k/year to their Roth IRA this way. Could you please confirm this? Or do you think the gov't might surprise people later and would need to undo the contribution for 2022?


PS. I liked your road trip but I think I would take it much later in my retirement when I begin disliking airports and hassles of air-travel completely. Luckily I'm not there yet, but I don't fly often either either.

Keith Taxguy, EA

Thursday 1st of September 2022


The Mega Backdoor Roth dodged a bullet this round. We got a corporate minimum tax instead.

I like road trips more because I can go at my pace and make changes along the way. That, and getting sealing in an aluminum can with my 300 closest friends for several hours always gets me excited.


Friday 26th of August 2022

Great read--I love hearing about other people's road trips. I, too, love off the wall destinations and the stories we get from being there. I look forward to updates on this one!


Friday 26th of August 2022

Awesome. Love Holiday's books. Ego is the Enemy is my current favorite. Easy to read in that you can finish in a day but the impressions stay with you forever. Hoping to be a winner of a copy but if not appreciate the opportunity.


Friday 26th of August 2022

Great. Love your thinking and actions in this case.


Friday 26th of August 2022

Great idea Keith. What a great way to pay it forward as a prize for readers. I'm sure Ryan will enjoy meeting you as much as I enjoy reading your articles.

Keith Taxguy, EA

Friday 26th of August 2022

Michael, I will provide updates on the Facebook page and group and Twitter feed for this blog. There is no date for the dinner yet.