In 2012, we were a few years out of the financial crisis. The world was still recovering from the aftershocks of the Great Recession. Occupy Wall Street had recently taken over a park in Manhattan. Gotye had the best-selling single in the country with Somebody That I Used To Know. (Taylor Swift had her first #1 on the Billboard Hot 100). HBO's Girls had just premiered. Obama was seeking re-election in a contentious race.
I remember that time very vividly (hey, it's Ryan) because I had just started to work on the book idea that would become The Obstacle Is the Way. In one sense, it was a totally different world and I was living a very different life: I wasn't married, didn't have kids, and was an editor-at-large at the New York Observer. By the time the book came out in 2014, a conflict in Ukraine was beginning, there was war in the Middle East and a scary outbreak (Ebola) was dominating the news.
Instability. Uncertainty. Danger. Division.
The more things change, the more they stay the same. This is one of the most consistent themes of Meditations, the way that events flow past us like a river, the way the same things keep happening over and over again. That's what history was, Marcus Aurelius said, whether it was the age of Vespasian, his own, or some time even more distant—it was "people doing the exact same things: marrying, raising children, getting sick, dying, waging war, throwing parties, doing business, farming, flattering, boasting, distrusting, plotting, hoping others will die, complaining about their own lives, falling in love, putting away money, seeking high office and power."
It was a surreal experience recently to go back to The Obstacle Is the Way to work on this new 10th-anniversary edition (we have a few numbered, signed first editions left—grab here). So much has changed over the course of a decade…so little as well. I got married, had kids, opened a bookstore, lived through a pandemic. Everything seems different…yet everything also seems the same.
Re-reading a book you wrote when in your early twenties feels weird. The words are the same, but the person who wrote them is not. The words are the same but the context around them is not. And now that book itself is being changed, updated, improved to fit the moment and future moments. When I wrote the book 10 years ago, I was focused on the obstacles I could see and had experienced. I was applying those Stoic lessons mainly to the challenges of navigating the early stages of my career. Today, I'm drawing on those same principles to navigate the complexities of fatherhood, running multiple businesses, and the perils of having donkeys as pets.
Despite all of the ways my life and the world have changed, as I went back through the pages of The Obstacle Is the Way for this expanded edition, the core principles still hold up—just how I apply them is different. That's the idea that Marcus Aurelius talked about, that saying that Heraclitus famously coined, "You never step in the same river twice." Timeless wisdom doesn't change, but what you get out of it evolves as you do.
While I added new stories and insights I've picked up over the years, the core Stoic wisdom remains the same—those ideas are as relevant today as they were when the Stoics first wrote about them. It wasn't about a major overhaul but about refining, improving, and making subtle adjustments, much like life itself—a tweak here, a new perspective there. A deletion here, an addition there. Over the past decade, all the reading I've done and the experiences I've had have deepened my understanding of these principles, and that's what this new edition reflects. It's not a brand-new book, but it's not just a reprint either. It's an evolution—a continuation of the great conversation of Stoicism that has been going on for thousands of years, updated with the lessons I've learned since 2014.
If you've read the first version of the book (thank you for that!), the 10th anniversary edition has relevant and insightful lessons (including a new foreword) I couldn't have possibly written a decade ago. And if you've been following this newsletter for a while but haven't read The Obstacle Is the Way yet, this is a fantastic time and place to start—it will advance your understanding of the lessons of the Stoics and how to apply them to your life.
Own a piece of the enduring legacy of The Obstacle Is the Way by getting the signed, numbered first-edition copy we have exclusively at The Daily Stoic Store. We've also put together some bonuses when you order multiple books, including a signed manuscript page used during the audiobook recording (some with Ryan's handwritten notes!). These limited time offerings are selling fast and will not be restocked, so head over to the Daily Stoic Store to get yours today!
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