Alexis T.'s Key Ideas from The Obstacle is the Way
by Ryan Holiday

An ancient Zen parable features an almost identical line of thinking, stating: The obstacle in the path becomes the path…Within every obstacle is an opportunity to improve our condition.

Stoicism and Marcus Aurelius’s wisdom motivated men and women throughout history, helping to spark the Renaissance, the Enlightenment, the Industrial Revolution, the US civil rights movement and Silicon Valley’s amazing high-technology advances.

Stoicism addresses real-life issues that confront everyone: “Are you worthy?” “Can you get past the things that inevitably fall in your way?” “Will you stand up and show…what you’re made of?”

Obstacles can provide benefits. First, you must move beyond typical responses to trouble, including “fear, frustration, confusion, helplessness, depression” and “anger.”

Marcus Aurelius’s courage and self-knowledge enabled him to transform trouble and tragedy into triumph. Achieve similar results by adopting the vital Stoic lesson: “The obstacle is the way.”

Marcus defined the methods to overcome obstacles: “Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance – now at this very moment – of all external events. That’s all you need.”

• How you see the world provides meaning to the events of your life. Don’t assign “good or bad” labels to events.
• Put aside your fears and prejudices. See things for what they are. See the truth, not a biased interpretation of it.
• How you think about and react to obstacles while maintaining your composure defines you.

The American industrialist John D. Rockefeller once worked for just 50 cents a day as a bookkeeper in Cleveland, Ohio. As an investor, he rode out major national financial crises in 1857, 1873, 1907 and 1920. Where others saw catastrophe and chaos, the objective, unemotional Rockefeller saw valuable lessons and opportunities.

So much so, that by 1877, his perception and his nerve helped him corner “90% of the oil market.”

During the 1960s, Rubin “Hurricane” Carter was a leading middleweight title contender. Carter was unjustly convicted in a triple-homicide case. In jail, he never ceded power to the warden or guards. He maintained his independence and his identity. Carter – and not the authorities – held control over his mind and spirit. He spent his time in prison working on his legal case.

After 19 years, Carter got his verdict overturned. Once released from prison, he never looked back.

 During the US Civil War, General Ulysses S. Grant always seemed completely nerveless. Once, a shell exploded near him, and killed a horse right next to him. Unfazed, Grant calmly surveyed the battlefield through his field glasses. He saw that his troops were removing supplies from a steamship when it exploded.

Everyone ducked for cover except Grant, who ran toward the shattered steamboat to help the survivors.

NASA trained America’s first astronauts to remain cool under pressure and to avoid panic. The agency had the astronauts practice every aspect of their space flight “hundreds of times,” until the routines became commonplace. Comprehensive training eliminated the unfamiliarity of spaceflight.

Tommy John pitched in Major League Baseball for an astonishing 26 seasons. John always asked himself: “Is there a chance?” “Do I have a shot?” “Is there something I can do?” When he was 45 years old, the Yankees cut John. Unfazed, he appeared as a walk-on at the team’s next spring training. He worked hard, made the team and pitched the season opener, a win over Minnesota.

Stay objective. When necessary, change the way you interpret what you see. Don’t agonize over the past or worry about the future. Focus your thoughts and actions on the present. Find the good in the bad. Stay bold.

When you are deliberate, bold and persistent, you are better prepared to take “right and effective” actions. Use the “creative application” of action to dismantle obstacles.

Set out to develop the “Minimum Viable Product,” as identified by Silicon Valley’s iterative MVP philosophy. Remember the engineering touchstone: “Failure is a feature.” Learn from every failure. Treat your job like the most important work in the world. Stay aware that sometimes a flank attack will work better than a head-on charge.

The world can knock you down and break your heart. But if you harness your willpower, no knockdown blow can deter you. Your will – not anyone else’s – puts you firmly in charge of your life and accomplishments. Proper willpower is steady, not blustery.

You connect to your internal power without braggadocio; the best strength of will springs from “humility, resilience and flexibility.”

Postmortems are useful; so are pre-mortems – thinking in advance about “what could go wrong.” Sometimes you must simply acquiesce when things don’t go your way. 

Across the centuries, academics in their ivory towers tried to assume ownership of philosophies such as Stoicism and tried to guard it as part of their exclusive domain. As developed by Seneca, Zeno and others, the philosophy of Stoicism was never intended to be isolated as remote, sterile intellectualization.

Those sages first promulgated Stoicism as “an operating system for the difficulties and hardships of life,” and that is how it should remain.