The Obstacle is the Way

By Ryan Holiday

(Download .pdf synopsis.)


A Stoic guide to turn your toughest trials into your greatest triumphs.

Key Takeaways:

— Within every obstacle is an opportunity to improve your condition. “Obstacles are actually opportunities to test ourselves to try new things, and, ultimately, to triumph.” The obstacle is in advantage, not an adversity.

— “The impediment to action advances action. What stands in the way becomes the way.” - Marcus Aurelius

— Three steps to overcoming obstacles: Perception, Action, Will

Part I: Perception

— “To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives.”

— What matters most is not the obstacle, but how we see (perceive) and react to it.

— When faced with a seemingly insurmountable obstacle:

- Be objective

- Control emotions

- Choose to see the good

- Steady your nerves

- Ignore what disturbs/limits others

- Place things in perspective

- Revert to the present moment

- Focus on what you can control

— “Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.” Marcus Aurelius

— Relinquish perception: By themselves, situations can’t be good or bad. This is a judgement that we bring with our perceptions.

Apatheia: The calm equanimity that comes with the absence of irrational or extreme emotions. (This allows you to focus on solving the problem instead of reacting to it.)

“…The most harmful dragon we chase is the one that makes us think that we can change things that are simply not ours to change.” (Focus on what is within your power.)

Part II: Action

— Action is commonplace, right action is not.

— “Persist and resist.” - Epictetus (Persist in your efforts. Resist distraction and discouragement.)

— “When you play all the way to the whistle, there’s no reason to worry about the clock.”

— Failure is a feature.

— Being trapped is just a position, not a fate.

— Learn to continue forward when everyone arounds you sees disaster.

— Prepare for none of it to work:

“Perceptions can be managed. Actions can be directed. We can see things clearly, respond creatively. Look for opportunity, seize the initiative. What we can’t do is control the world around us—not as much as we’d like to anyway. We might perceive things well, then act rightly, and fail anyway.”

Part III: Will

— True will is quiet humility, resilience, and flexibility. Will is fortitude and wisdom.

— Will (ie. Willing and able) allow us to remain calm and continue, even during the unthinkable.

— Manage expectations: Your world is ruled by external factors. Your plan and the way things turn our rarely resemble each other. Don’t set yourself up to fail. If your ready to be disappointed, you won’t be.

— “We don’t get to choose what happens to us, but we can always choose how we feel about it.”

— Persist and persevere: Persistence is an action. Perseverance is a matter of will.

— Stop inflating your role and importance. Be selfless.

“Stop pretending that what you’re going through is something special or unfair…[it’s] not some unique misfortune picked out especially for you. It just is what is…We’re not special or unique simply by virtue of being.”

— Death makes life purposeful, not pointless. Treat your time as a gift.

What I got out of it:

An extremely powerful book, drawing on wisdom from the ages.