The Obstacle is the Way

Author: Ryan Holiday
Title: The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
Published: May 1, 2014

I’ve been a huge fan of Holiday’s work since I first stumbled across his blog. I thoroughly enjoyed his first book, Trust Me, I’m Lying: Confessions of a Media Manipulator, and his short primer on Growth Hacker Marketing. Having read quite a bit of his work, I always appreciate his unusual aspect on various subjects. When Holiday announced that he was putting out a new book concerning overcoming obstacles and guidance from his favorite Stoic authors, I was intrigued.

The book is largely based on the philosophy of Stoicism, which is a practice of deep reflection, emotion regulation, and focused action used to appreciate, benefit, and dominate the world around you. Holiday draws on examples from famous historic figures like Ulysses S. Grant and George Washington. He references the work of Marcus Aurelius and Epictetus. In each case, Holiday is helping readers to understand how even the most horrid of situations can be flipped to become an advantage. Take, for example, the story of Thomas Edison:

At age sixty-seven , Thomas Edison returned home early one evening from another day at the laboratory. Shortly after dinner, a man came rushing into his house with urgent news: A fire had broken out at Edison’s research and production campus a few miles away.

Fire engines from eight nearby towns rushed to the scene, but they could not contain the blaze. Fueled by the strange chemicals in the various buildings, green and yellow flames shot up six and seven stories, threatening to destroy the entire empire Edison had spent his life building.

Edison calmly but quickly made his way to the fire, through the now hundreds of onlookers and devastated employees, looking for his son. “Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.” (Kindle Locations 1777-1783)

Despite that setback that year, Edison went on to generate a revenue of $10 million from his lab, quite the comeback from having everything you’ve ever worked on burned to the ground.

Holiday outlines how to overcome obstacles we will all face in our own lives in three parts:

  1. Perception – Flipping how we see and understand what is happening around us
  2. Action – How to create directed action to achieve what we’re looking for
  3. Will – How we keep moving forward even when it seems like we have no control over the situation and our backs are against the wall

Per the usual for Holiday’s writing, the work is absolutely filled with research and references. I always appreciate how well he backs up his thoughts with quotes and anecdotes from the past. Don’t go into this book expecting a step-by-step solution to getting what you want. Instead, Holiday presents a framework designed to help you change how you approach situations and how to make the best of the worst circumstances.

At a time where it’s easy to feel overwhelmed and helpless against powerful opposition, this book is a roadmap for achieving. I’d highly recommend it to anyone looking for a new perspective on how to shape your thoughts and actions to be more successful.

Reading Notes

Our actions may be impeded . . . but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting. (Marcus Aurelius)

Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings.

Carter did not have much power, but he understood that that was not the same thing as being powerless

There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve. With enough exposure, you can adapt out those perfectly ordinary, even innate, fears that are bred mostly from unfamiliarity.

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion.

Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.

Emerson put it best: “We cannot spend the day in explanation.”

Behind the behaviors that provoke an immediate negative reaction is opportunity—some exposed benefit that we can seize mentally and then act upon.

As a discipline, it’s not any kind of action that will do, but directed action.

We must all either wear out or rust out, every one of us. My choice is to wear out. —Theodore Roosevelt

genius often really is just persistence in disguise.

Stop looking for an epiphany, and start looking for weak points. Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.

Like any good school, learning from failure isn’t free. The tuition is paid in discomfort or loss and having to start over.

We are A-to-Z thinkers, fretting about A, obsessing over Z, yet forgetting all about B through Y.

Don’t think small, but make the distinction between the critical and the extra. Think progress, not perfection.

Part of the reason why a certain skill often seems so effortless for great masters is not just because they’ve mastered the process—they really are doing less than the rest of us who don’t know any better. They choose to exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics.

Remember, sometimes the longest way around is the shortest way home.

Perceptions can be managed. Actions can be directed.

“If you’re not humble, life will visit humbleness upon you.”

After you’ve distinguished between the things that are up to you and the things that aren’t (ta eph’hemin, ta ouk eph’hemin), and the break comes down to something you don’t control . . . you’ve got only one option: acceptance.

It is the act of turning what we must do into what we get to do.

How can we use this situation to benefit others? How can we salvage some good out of this?

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