The Obstacle Is The Way by Ryan Holiday

The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday is a self-help book published in 2014.

When something stands in our way, humans have a tendency to blame anyone and anything but ourselves – our bosses, economy, politicians, other people. In contrast, many great individuals throughout history found a way to transform weakness into a strength. Earlier generations faced worse problems with fewer safety nets and fewer tools – the reality is that most of the time nowadays, we aren’t even in horrible situations, just minor disadvantages. 

The Obstacle Is The Way aims not only to make facing and dismantling stumbling blocks a little easier but to show how to turn every obstacle into an advantage. As Andy Grove, the former CEO of Intel, says, “Bad companies are destroyed by crises. Good companies survive them. Great companies are improved by them.”

PERCEPTION

“Nothing is either good or bad, but thinking makes it so” – Shakespeare 

• Perception shapes meaning
  • Events are neutral; perception defines them as good or bad
  • We create or remove obstacles through our viewpoint
• Choose your response
  • Choose not to be harmed = you won’t be
  • Control how events appear; reactions and beliefs are always under your control
• Steady your nerves
  • Calm > talent in critical moments
  • Emotional overreaction clouds judgment
• Control your emotion
  • Getting upset doesn’t improve clarity or options
  • Real strength = feel emotion but choose your response
  • Let go of unhelpful thoughts, not through false positivity
• Practice objectivity
  • Remove ego to see clearly
  • Give yourself advice as you would a friend
• Alter your perspective
  • Break fear into manageable parts
  • Shrink problems by scaling them down
• Focus on what’s up to you
  • Can’t change past or most external factors
  • Direct energy only toward what you can control
• Live in the present
  • Past and future are sources of stress
  • Act in the now
• Think differently
  • Beliefs shape outcomes
  • Believe in the goal more than the obstacle
  • Find opportunity in obstacles
  • Bigger struggles = bigger growth
• Prepare to act
  • Step 1: Control emotions
  • Step 2: Flip perspective – spot opportunity, not threat

ACTION

• Directed action
  • Be strategic: avoid brute force, go around obstacles
  • Apply pressure only where it matters
  • Use obstacles against themselves; sometimes inaction is best
  • Be patient — not every fight is worth it
• Get moving
  • Just start; fear of imperfect conditions causes paralysis
  • Create momentum yourself
  • Initiative + energy often determine success
• Persistence
  • Most failure comes from quitting too soon
  • “Persist and resist”: resist distraction and discouragement
• Adapt
  • Failure = learning
  • Ask: What went wrong? What can I improve?
  • Pay the “tuition” of mistakes and keep learning
• Follow the process
  • Big goals = small steps; focus on the next step
  • Trust steady progress
• Do your job, do it right
  • Take pride in each task, no matter how small
  • Give full attention to what’s in front of you
• Seize the offensive
  • Crises = hidden opportunities
  • Act boldly when others retreat
• Prepare for failure
  • Even right actions may fail
  • Use failure to grow; practice humility, patience, and acceptance

WILL

• Will is power
  • Will is the one thing we completely control
  • True will = quiet, resilient, flexible; not bluster or ambition
  • Will is unbreakable, even if actions are constrained
• Build your inner citadel
  • Strength comes from within, not by changing the world
  • Toughen yourself; don’t expect the world to soften
• Negative visualization
  • Plan for setbacks; expect things to go wrong
• Be real
  • Acknowledge limitations without letting them define you
• Love it all
  • Embrace what comes with cheerfulness, not regret
  • See challenges as opportunities to prove yourself beyond others’ expectations
• Bigger than yourself
  • Recognize struggles aren’t unique; many have faced worse
  • Perspective reduces personal hardship
  • Focus on what truly matters
• Prepare to start again
  • Obstacles are never-ending; each conquered challenge leads to another
  • Every attempt improves you; don’t fear or be overwhelmed