I Was There

A Night in NYC to See Ryan Holiday, My Favorite Writer


photo via @GCTech

“How did you first hear about my work?”

A book signing, just like any other meet-and-greet, is a weird exercise in small talk. It’s a manufactured encounter in which a group comes together to meet one person. That person is on display, but also tries to be as friendly and engaging as possible.

While flattering, I’m sure it’s also pretty weird to sit down at a table and look at a line of strangers waiting in line to parade past you and tell you how much they like you. It’s like an adult version of sitting on Santa’s lap. Also, it’s not as easy as it sounds. We’ve all read accounts from celebrities or prominent figures describing their hand cramping up or fans getting angry when they had the temerity to take a break.

It’s far from an ideal situation, but it’s usually still the best way for fans to meet their favorite artists and interact with them in person. And you never know if you’ll ever have the opportunity again.

With that in mind, when I learned that Ryan Holiday, my favorite author and thinker, would be speaking at an event in New York City, I immediately snatched up two tickets and planned to make a quick jaunt across the river. He lives in Texas, so it’s not like he always on the east coast.

A few days before the event, I received an email reminder that also informed me that we would be receiving a free copy of his new book, Perennial Seller. Since I had already purchased two copies the day it was released, there would now be four editions in our home.

On Monday, my wife picked me up at my office and we headed into the city. After (finally) parking and grabbing a quick bite to eat, we made our way to the event.

It was in a cool, hip tech space with minimal furniture, brightly colored walls, floor-to-ceiling windows, and a cadre of young people in casual wear sipping on beer and wine. We walked in and immediately felt like chaperones. This was not our scene. Ryan was standing near the door, casually chatting with a couple of people.

We found a pair of seats in the center a few rows back and settled in.

After waiting for a few minutes, the talk began and, having listened to nearly every podcast and interview Ryan has ever done, I was expecting it to be like the other Q&A’s he’s done to promote the book. However, the host/moderator – who is also the managing director of the company that hosted the event – asked how many people in the audience had read any of Ryan’s books and when nearly every hand went up, he decided to devote most of the time to audience questions that covered any number of topics, not just Perennial Seller.

It was a wise choice and made it more of a free flowing conversation as opposed to just a stiff interview.

I was about the eighth or ninth person to ask a question – the rest were all men – and as I was beginning, Ryan interrupted to say, “Sorry, but do we have any questions from any non-dudes?” When it appeared not, I said, “I guess I’m the dude” and asked him about how he feels when a publication like Gawker or online commenters lay into him, as they did for his open letter to his father regarding Donald Trump.

He answered that while it always sucks to have people say negative shit about you, you need to know who your audience is and is not and he’s not going to spend time worrying about people that don’t know him or his work or whose only goal in life is to criticize others.

The woman behind me asked the next question and then there was another question from a non-dude, thus finally breaking up the sausage party. After the talk wrapped up, Ryan made his way to a table near the door to sign books.

We were about fifth in line. I didn’t want to bother Ryan by asking for a photo with him, so I asked my wife if she’d take photos while he was signing and I’d just keep one of those.

When it my turn, he said, “Hey.”

I approached and said, “I’m a huge fan,” and we shook hands.

That’s when he asked how I had first heard of his work, I froze. I couldn’t remember.

I know he wrote a guest post on Tim Ferriss’s blog, but that wasn’t it.

I remember loving his “How I Work” entry on Lifehacker, but I had already been familiar with him before that.

I feel like it was the announcement of his first book deal, the one with the inflated number that Ryan himself put out there (as he admitted in his first book, Trust Me, I’m Lying). But I wasn’t sure. Moreover, when you’re in a line and you’re rushing, you panic and the last thing you want to be is long-winded. So I just blurted out, “Um, I think it was, like, 2010. Gawker published something bad about you and l was like, ‘I like this guy.’”

He laughed, but I felt like I had flubbed it. Damn it.

I thanked him for signing my book and slid over so that the line could move up. My wife was next and Ryan said to her, “Did he want a picture? Some people don’t like to ask.” I admitted that was the case. As ridiculous as it sounds at a meet-and-greet book signing, I didn’t want to impose.

I hate the way I look, but it’s still getting framed

He popped up out of his chair and we took the picture. I thanked him again. He signed my wife’s book and we were on our way.

As we were in the elevator, she said, “Well, you’re excited.”

I was.

I’ve often heard that you shouldn’t meet your heroes or people whose work inspires you but I’ve done it a few times.

And I could not disagree more.

Christopher Pierznik’s nine books are available in paperback and Kindle. His work has appeared on XXL, Cuepoint, Business InsiderThe CauldronMedium, Fatherly, Hip Hop Golden Age, and many more. Subscribe to his monthly newsletter or follow him on Facebook or Twitter.


By Christopher Pierznik

Christopher Pierznik is the author of 9 books and has contributed to numerous websites on a variety of topics including music, sports, movies, TV, personal finance, and life. He works in corporate finance and lives in northern New Jersey with his family. His dream is to one day be a member of the Wu-Tang Clan.

2 replies on “A Night in NYC to See Ryan Holiday, My Favorite Writer”

Hey man, loved how descriptive your encounter with Ryan Holiday was. Hope to meet him one day too. Btw, do you happen to read FarnamStreetBlog too? Ryan highly recommends them too 🙂


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