#18 Ryan Holiday

James Altucher interviewed Ryan Holiday (@RyanHoliday) to talk about his book, The Obstacle is The Way and about the application of stoicism to our lives. Stoic thinking is like a lever on a fulcrum, helping us lift any obstacle out of our way. I’m a subscriber to stoic thought and enjoyed Holiday’s book, so consider my bias in these notes.

At the start of the interview Altucher and Holiday head off together, like a three-legged-race team at the picnic of starting businesses. Holiday comments that things don’t need to be perfect to start a business and that they rarely are. His book lists ones started in depressions or downturns; Coors, Costco, GM, United Airlines, Microsoft and many more. Altucher agrees and Holiday says that a crisis are beneficial because they “force us to do things we wouldn’t have done.”

A crisis also provides moments to move forward, moments of challenge. Shane Snow – a past guest – writes that we need challenges, not matter the size, to make our lives meaningful. Snow uses the examples of the first men to walk on the surface of the moon. Buzz Aldrin struggled upon returning to earth while John Glenn succeeded. To Snow this means that the former didn’t find new obstacles. Aldrin didn’t answer the question of what you do after walking on the moon as well as some of his compatriots.

The stoics suggest that while having obstacles is important, immediately conquering them is not.  One of the most famous stoics, Marcus Aurelius wrote, “don’t go expecting Plato’s Republic; be satisfied with even the smallest progress.” Even finding your life’s goal may not be that. Carol Leifer told Altucher about the time that Jerry Seinfeld reminded her that a current success was only one of many. She may have been in her current dream job, but that doesn’t mean another dream job isn’t around the corner.

Holiday tells Altucher that stoicism is an attitude about not being put out of shape if things don’t go our way and he wrote the book to correct that. Some of those attitudes that Altucher suggests are unemployment, debt, and stagnation.

 “This is what successful people do. Period. They don’t get impeded by things, in fact, when bad things happen they get better.” – Ryan Holiday

Another stoic – they are everywhere once you start looking – and favorite talisman here, is Nassim Taleb. Stoic thinking is antifragile because it separates the what happened from the how I react to it. A fragile mindset is one that gets more fragile as the winds of change blow. It’s losing control and yelling about rain at a picnic. The antifragile, and stoic perspective, is to see that rain as a chance to do things in the rain.

Our family faced this “rainy picnic” on a recent trip where we had two hours until our flight boarded. This would have been fine for me, I could do some reading, but our six and four year old daughters weren’t going to sit still. Instead the three of us explored the airport together, and it was fun. I saw the time as chance to explore with my daughters rather than them nagging and me answering “no that’s not our plane.”  To get to this point, Holiday writes we should examine how to look at a problem. “We will see things simply and straightforwardly, as they truly are— neither good nor bad. This will be an incredible advantage for us in the fight against obstacles.”

Another stoic story – everywhere I told you – is from Malcolm Gladwell, who wrote an entire book about this idea of seeing things straightforwardly. One puzzle Gladwell tries to piece together is why some dyslexics are successful. Gladwell suggests that the obstacle (a problem with reading words) forced these people to get good at other things (like reading people, learning learning shortcuts, and more). He topples the idea that I can’t read so I can’t learn like a metaphorical Goliath.

Returning to the interview, Holiday says, that even random bad things are a chance for us to get used to a world where bad things happen. Altucher agrees and tells Holiday that he must have done incredible research for the book. Holiday reads a lot and shares the books he reads on email list. If you like to read check it out.

About the bad things, we can often extract some bit of learning for the future. Holiday says that minor obstacles can be practice for bigger ones and it’s an idea that Alex Blumberg has shown. Blumberg – a past guest – told Altucher that he’s had to be “stupidly optimistic” and when pressed about how he solves problems he says he doesn’t know. One recent example is when his podcast team misled a mother and her son about their interview. Mother and son thought they were doing an interview for This American Life, but really they were in an advertisement for Squarespace. The imbroglio ended up teaching Blumberg a lesson and he got a podcast episode out of it. By moving forward, overcoming each thing through a combination of grit, experience, and time Blumberg acted stoically.

Sometimes stoicism gets a bad rap as being something unemotional, indifferent and fatalistic. Stoics consider the bad things to help appreciate the good, and as Holiday points out in the interview with James, this is a good idea.

In Thinking Fast and Slow, Daniel Kahneman explains the pre-mortem. “Imagine that we are a year into the future. We implemented the plan as it now exists. The outcome was a disaster. Please take 5 to 10 minutes to write a brief history of that disaster.” In the book he writes about sharing this idea at Davos and one CEO of a major company said this idea alone was worth the trip.

Altucher sums up stoicism as being a realist/optimist philosophy. Another way to say it is finding the good in everything. Even loss, Holiday says, can be freeing. He tells Altucher that he worries about losing clients but when that actually happens he feels better. Holiday says, “our attitudes and our intentions they can never be stopped, they can only be rerouted.” A river may get dammed up and stop flowing in one area, but that doesn’t mean the water stops. As any building owner with a basement can attest, water will not be stopped. Holiday suggests that neither can our intentions.

The interview continues to move through many other examples about things that appear bad on the surface but are quite good in the long run. About this Marcus Aurelius wrote, “And when we describe things as ‘taking place,’ we’re talking like builders, who say that blocks in a wall or a pyramid ‘take their place’ in the structure, and fit together in a harmonious pattern.” At the moment of each event will have trouble imagining how all the past and future pieces will fit together. Looking back though how many people say they wouldn’t change a thing? How many high school heartbreaks would we change?

One of Holidays many examples is the tribulations of Abraham Lincoln, but he’s not the only one to focus on our presidents. Another guest – Daniel O’Brien – tells Altucher that many presidents persisted through troubles to succeed politically. Having an easy road is the exception, not the rule.

To act with a philosophy is like choosing our own governance. Epictetus taught that “each human being is primarily a citizen of his own commonwealth.” Marcus Aurelius says it slightly differently, “Lift me up and hurl me. Wherever you will. My spirit will be gracious to me there – gracious and satisfied – as long as its existence and actions match its nature.” Both stoics knew that our spirit is the only thing we control entirely and it will serve us well wherever we are.

The stoics most often cited are from a wide range of history. Marcus Aurelius was emperor of Rome, Seneca was a successful businessman, Epictetus a slave. Each found a way to apply the lever of stoic thinking to their own set of problems. Holiday says that Aurelius had “difficulties of abundance.” We may think that money solves our problems but if you had Kim Kardashians money, would you take her life as well? Holiday guesses that if he were 10X more successful he wouldn’t be any happier. Happiness is non-linear, or as Taleb might say in Brooklyn English “Two weekends in Philadelphia are not twice as pleasant as a single one – I’ve tried.”

The interview concludes with Holiday giving advice about how to react to crappy people. If people are rude to us, we can see that as a situation where they underestimate us. Marcus Aurelius takes the less practical, more philosophical tinge to ask who is hurt when someone insults you. Rather than the insult, consider the type of person who might say that. His logical conclusion is that if a person chooses to insult you, is that a person who’s opinion you should consider?

Altucher asks if Holiday practices stoic thinking consistently to which he responds, “I practice it in my life but I am admittedly not anywhere near as good as it as I’d like to be.”

As the introduction noted, I’m a big fan of stoic thinking. Here are suggestions for further reading:

This version of Meditations (and suggested by Holiday) is my favorite book of all (one of Bill Clinton’s too). It is very accessible. These books from Epictetus are a bit more style than substance, this book from Seneca is more substance than style.

Holiday’s own book, The Obstacle is The Way is also very good, just not an original source. A Guide to the Good Life is another good, non-original source.

If you want more general examples of “the obstacle is the way” mentality read both Gladwell’s David and Goliath and Megan McArdle’s The Up Side of Down.

I always like talking about stoicism and these posts..  Connect via text (559) 464-5393, in the comments, or on Twitter (@MikeDariano).

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