It Always Takes Longer Than You Expect (Even When You Take This Into Account)

Ryan Holiday
4 min readJul 14, 2023

When I finished my first book, I hired a publicist.

I was 25.

It cost $20,000 and was, to that point, the most money I had ever spent in my life.

As part of the scope of work, they had me put together a list of my top twenty or so media targets — –what I thought I had a reasonable shot of getting and what would be good platforms with the book.

Pretty much none of those opportunities happened. It wasn’t the publicist’s fault–they did a good job. It was that I had been preposterously unrealistic. You have these high hopes, you think this is my shot and of course, it turns out that the world has other plans.

You’re going to get everything you want when you want it?


If you really want something, you better be ready to hurry up and wait.

That was especially true for me then, since I was a kid, already getting to publish my first book far earlier than most people get to dream of.

All of this came back to me as I was flying home from New York from the launch of The Daily Dad. I had just done The Daily Show, CBS This Morning, and a daytime talk show in the span of a week. Which meant that 11 years and 14 books later, I was finally making a serious dent in the list that I had made back then. It had sometimes seemed like slow going, but then in the span of just a few days I had crossed off the best and hardest-to-get outlets.

There is this law called Hofstadter’s Law which says it always takes longer than you think it’s going to take. Even when you think it’s going to take a long time. Even when you take Hofstadter’s Law into account.

I started blogging in 2005. My first book came out in 2012. The Obstacle is the Way came out in 2014…and took six years for it to hit any bestseller list. I didn’t hit the New York Times Bestseller list until 2019, on my 13th book.

If you had told me that’s how long it would have taken, I might have been able to endure it. But Tom Petty was wrong. Waiting is not the hardest part. It’s the not knowing when the waiting is going to end.



Ryan Holiday

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’