Ideas from the book The Obstacle is the Way by Ryan Holiday

“Obstacles are actually opportunities to test ourselves, try new things, and, ultimately, to triumph.” - Ryan Holiday


  • When faced with insurmountable obstacles we should try to:
    1. Be objective.
    2. Control emotions and keep an even keel.
    3. Choose to see the good in the situation.
    4. Ignore what disturbs and limits others.
    5. Focus on what can be controlled.
  • We decide what we make of each and every situation.
  • The observing eye sees simply what is there. The perceiving eye sees more than what is there.
  • Take your situation and pretend it is not happening to you. Pretend it is not important and that it doesn’t matter.
  • Is your perspective truly giving you perspective or is it actually causing you problems?
  • Focus on what you can change.

“The trick to forget about the big picture is to look at everything close up” - Chuck Palahniuk

  • Focus on the moment not the monsters that may or may not be up ahead.
  • Obstacles illuminate new options.


  • Doing new things invariably means obstacles. A new path is by definition uncleared.
  • It’s okay to be discouraged. It’s not okay to quit.
  • Settle in for the long haul and then try each and every possibility, and you’ll get there.

“What is defeat? Nothing but education; nothing but the first steps to something better.” - Wendell Phillips

  • Lessons come hard only if you are deaf to them.
  • Failure shows us the way by showing us what isn’t the way.
  • Excellence is a matter of steps. Excelling at this one, then that one, and then the one after that.
  • Even mammoth tasks become a series of component parts.
  • Take your time, don’t rush. Some problems are harder than others.

“Whatever is rightly done, however humble, is noble” - Sir Henry Royce

“The cucumber is bitter? Then throw it out. There are brambles in the path? Then go around. That’s all you need to know.” - Marcus Aurelius

  • Do the best with what you’ve got.

“I don’t care if the cat is black or white as long as it catches mice.” - Deng Xiaoping

  • Start thinking like a radical pragmatist.

“Whoever cannot seek the unforeseen sees nothing, for the known way is an impasse” - Heraclitus

  • Sometimes the longest way around is the shortest way home.

“You never want a serious crisis to go to waste.” - Rahm Emanuel

“In the meantime, cling tooth and nail to the following rule: not to give into adversity, not to trust prosperity, and always take full note of fortune’s habit of behaving just as she pleases” - Seneca

  • We must be willing to roll the dice and lose. Prepare at the end of the day for none of it to work.


  • Always try to:
    1. Prepare yourself for more difficult times.
    2. Accept what you are unable to change.
    3. Manage your expectations.
    4. Persevere.
    5. Learn to love your fate and what happens to you.
    6. Protect your inner self and retreat into yourself.
    7. Submit to a greater, larger cause.
    8. Remind yourself of your mortality.
  • Have a premortem for your projects. Look at what could and will go wrong before you start.
  • You must never lower yourself to becoming a person you don’t like.
  • Don’t inflate your role and your importance.