Product Hunt Book Club: The Obstacle Is The Way

I am excited to hear that my book The Obstacle Is The Way has been selected as May’s selection for the Book Club. They asked me to put together a quick introduction to the book to facilitate discussion and conversation. I look forward to talking to everyone on May 26th.

When most people think of “philosophy,” their eyes glaze over. It’s the last thing they want, let alone something they need.

But this, as you already know, is silly and naive.

Philosophy is not just about talking or lecturing, or even reading long, dense books. In fact, it is something men and women of action use — and have used throughout history — to solve their problems and achieve their greatest triumphs. Not in the classroom, but on the battlefield, in the Forum, and at court.

It was jotted down (and practiced) by slaves, poets, emperors, politicians and soldiers, as well as ordinary folks to help with their own problems and those of their friends, family and followers. This wisdom is still there, available to us.

Specifically, I am referring to Stoicism, which, in my opinion, is the most practical of all philosophies. It’s what I based my most recent book, The Obstacle Is The Way on and what we’ll be talking about in the Product Hunt Book club.

What Is Stoicism?

A brief synopsis on this particular school of Hellenistic philosophy: Stoicism was founded in Athens by Zeno of Citium in the early 3rd century BC, but was famously practiced by the likes of Epictetus, Cato, Seneca and Marcus Aurelius. The philosophy asserts that virtue (such as wisdom) is happiness and judgment be based on behavior, rather than words. That we don’t control and cannot rely on external events, only ourselves and our responses.

But at the very root of the thinking, there is a very simple, though not easy, way of living. Take obstacles in your life and turn them into your advantage, control what you can and accept what you can’t.

In the words of Epictetus:

“In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices.”

Amazingly we still have access to these ideas, despite the fact that many of the greatest Stoics never wrote anything down for publication. Cato definitely didn’t. Marcus Aurelius never intended for Meditations to be anything but personal. Seneca’s letters were, well, letters and Epictetus’ thoughts come to us by way of a note-taking student.

And so it was from their example, their actions, we find real philosophy.

Because other than their common study of the philosophy, the Stoics were all men of action — and I don’t think this is a coincidence. Marcus Aurelius was emperor of the most powerful empire in the history of the world. Cato, the moral example for many philosophers, defended the Roman republic with Stoic bravery until his defiant death. Even Epictetus, the lecturer, had no cushy tenure — he was a former slave.

And this shouldn’t really be that surprising…

The modern day philosopher and writer Nassim Nicholas Taleb defines a Stoic as someone who, “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.”

Using this definition as a model we can see that throughout the centuries Stoicism has been a common thread though some of history’s great leaders. It has been practiced by Kings, presidents, artists, writers and entrepreneurs. Both historical and modern men illustrate Stoicism as a way of life.

Prussian King, Frederick the Great, was said to ride with the works of the Stoics in his saddlebags because they could, in his words, “sustain you in misfortune.” The founding fathers were also inspired by the philosophy. George Washington was introduced to Stoicism by his neighbors at age seventeen, and afterwards, put on a play about Cato to inspire his men in that dark winter at Valley Forge. Whereas Thomas Jefferson had a copy of Seneca on his nightstand when he died.

The economist Adam Smith’s theories on the interconnectedness of the world — capitalism — were significantly influenced by the Stoicism that he studied as a schoolboy, under a teacher who had translated Marcus Aurelius’ works.

Today’s leaders are no different, with many finding their inspiration from the ancient texts. Bill Clinton rereads Marcus Aurelius every single year, while Wen Jiabao, the former prime minister of China, claims that Meditations is one of two books he travels with and has read it more than one hundred times over the course of his life. Tim Ferriss is prominent advocate of stoicism and the list goes on and on.

What Is This Book About?

This book is about a very specific line from Marcus Aurelius:

“The impediment to action advances action.
What stands in the way becomes the way.”

In his words are the secrets to an art known as turning obstacles upside down. Of acting with “a reverse clause,” so there is always a way out or another route to get to where you need to go. So that setbacks or problems are always expected and never permanent. Of making certain what impedes us, can empower us.

Let’s be honest: most of the time we don’t find ourselves in horrible situations we must simply endure. Rather, we face some minor disadvantage or get stuck with some less than favorable conditions. Or we’re trying to do something really hard and find ourselves outmatch, overstretched or out of ideas. Well, the same logic applies. Turn it around. Find some benefit. Use it as fuel.

Isn’t that the definition of entrepreneurship? To wake up everyday and make something where other people see problems and difficulties? Isn’t the definition of the lean startup model built around using as few of the “luxuries” that traditional businesses rely on as possible? That’s why you’ve seen stoicism make its way through Silicon Valley

It’s simple. Simple, but of course, not easy.

That’s what we’ll be talking about in this book club and answering in our discussions. Some questions it might be fun to kick around:

  • What’s the biggest obstacle you’ve faced? What benefits were you able to derive from it?
  • Is there anything so bad that it’s not an opportunity? Anything so bad that it is utterly without benefits?
  • How do you know when to stick and when to quit?
  • Why does philosophy feel so foreign and intellectual to most of us?
  • What’s the single most practical piece of advice you’ve ever heard?
  • What’s the most important part of an entrepreneur or creative’s mental toolkit? What do you wish you’d learned/added/been shown earlier?

For those of you who haven’t read the book, are looking for background on stoicism or just don’t have time, I will also suggest these resources below:

Thank you,

Ryan Holiday

Like to Read?

I’ve created a list of 15 books you’ve never heard of that will alter your worldview and help you excel at your career.

Get the secret book list here!

Like what you read? Give Ryan Holiday a round of applause.

From a quick cheer to a standing ovation, clap to show how much you enjoyed this story.