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Stories about Failure

How a Windy Day Defeated Steve Jobs

Origin: From the book Becoming Steve Jobs by Brent Schlender 

Lesson: In any dynamic organization everyone is vitally important

Character: Steve Jobs

Synopsis: After being fired from Apple, Steve founded a company called NeXT. As the world had said many times, he was a genius. Doubtless, he would create the next big product. He poached some great people and they got to work. Though he was a genius in creating products, he had a lot to learn in running a complex business. Here he gets a big dose of reality, from the wind.


A Tale of Two Beavers (A Fable about the Downfall of A&P Grocery)

Origin: From the book Good to Great by Jim Collins

 Lesson: Evasion is the way to destruction

Character: Two Beavers

Synopsis: Ever wonder how large corporations can get stuck in old ways that eventually destroy them? This is a classic example. A&P Grocery was once the largest grocery chain in the world. But in the 1970s buying behaviors began to change. A&P tested the market and discovered this to be true. What they did next brought about their downfall.


The Wizard’s Magic 

Origin: From the book The Obstacle is the Way by Ryan Holiday

Lesson: Find the joy in all things

Character: Thomas Edison (The Wizard of Menlo Park)

Synopsis: For most people, if they life’s work were to become engorged in flame, they would rail and wail against the injustice and unfairness. Men like Thomas Edison, act in the most bizarre way possible. He found the joy in it.


Some Assembly Required

Origin: From the book Mastery by Robert Greene

Lesson: Fail your way to success

Character: Henry Ford

Synopsis: Before the assembly line, before the Model T there was the Quad and Quad 2.0. Early prototypes to the vehicle that would make Ford famous. His vehicle, and the assembly line were not creations of a moment of genius, but rather necessities arising from numerous failures on every single front.


Son of a Con Artist

Origin: From the book The Obstacle is the Way by Ryan Holiday

Lesson: Rise above the chaos

Character: John D. Rockefeller

Synopsis: Rockefeller’s father was a con artist. He cheated his neighbors and his family. What Rockefeller could have learned was how to swindle people. Instead, he learned how to evaluate the actions and intentions of the men around him, so that he could rise above.


Contracting Hepatitis saves a life

Origin: From the book Springboard: Launching Your Personal Search for Success by G. Richard Shell 

Lesson: Learn to recognize the importance of symbolic actions in your life

Character: G. Richard Shell

Synopsis: Sometimes hitting bottom in one's life can be the biggest boon. When Professor Shell was a young man his life was leading him nowhere, so he left America for a trek around the world. It was when he collapsed on the side of a road in Kabul that he realized the status quo was intolerable and it was time for a change.


If you ask it

Origin: From the book Springboard: Launching Your Personal Search for Success by G. Richard Shell 

Lesson: Learn to ask the RIGHT questions at the RIGHT time

Character: Eric Adler

Synopsis: Eric Adler wanted a change from teaching. He decided to pursue an MBA at the prestigious Wharton school of Business. As his fellow students became swept up into consulting jobs, so to did Eric. But he was no consultant. He washed out. Finally, he realized he had been asking the wrong question. He’d been asking, “what should I do?” Instead, he started asking another question, and the question blossomed into a thriving enterprise that won him an interview on Oprah.


Coriolanus for President!

Origin: From the book The 48 Laws of Power by Robert Greene 

Lesson: Too much talking can bring you harm. Learn to say enough but not too much.

Character: Coriolanus (an ancient Roman General and statesman)

Synopsis: Coriolanus began his political career as the greatest Roman general and war hero of his generation. The people loved him. But then he began to speak.


The Proud Immigrant

Origin: From the book Basic Economics by Thomas Sowell

Lesson: Search your own background for special knowledge and skills you can use to create something unique 

Character: Amadeo Giannini

Synopsis: An Italian immigrant moves to America for a better life, but rather than feel ashamed of his heritage he embraces it. In his culture, he found the seed to a multi-billion dollar venture.


“Steve Jobs is crying in the parking lot”

Origin: From the book Becoming Steve Jobs: The Evolution of a Reckless Upstart into a Visionary leader by Brent Schlender.

Lesson: Always remember when judging public icons, there’s more to the story.

Character: Steve Jobs

Synopsis: The image of Steve Jobs as half genius/half asshole, comes primarily from his tempestuous youth. Yet, even then he understood how he came across to people. When only 24 years old he was already the poster-child of the personal computer revolution, and CEO of the greatest startup ever. Yet he still had not learned how to work with people who did not recognize his superiority. It would take numerous doses of medicine, to which this story illustrates one.


To the Summit and Beyond

Origin: From the book Delivering Happiness by Tony Hsieh

Lesson: Be willing to invest everything

Character: Tony Hsieh

Synopsis: After selling LinkExchange to Microsoft, Tony Hsieh was searching for something to believe in. He found purpose in But, to attain the heights he desired, he had to be willing to invest everything he owned. Failure would have meant starting over from the beginning. He invested.


The Boxer’s Advantage

Origin: From the book Mastery by Robert Greene

Lesson: Adapt and flourish 

Character: Freddie Roach

Synopsis: Freddie Roach was a washed out boxer. Rather than surrender to destiny, he decided to adapt. He transformed his love of boxing into coaching. He would one day transform the sport and coach the greatest boxer of our generation.


A Million Dollar Education

Origin: From the book Think and Grow Rich by Napoleon Hill 

Lesson: Before you decide to quit something, remember, you may be quitting only three feet from gold

Character: Mr. Darby

Synopsis: This is a classic tale from Napoleon Hill about a man who begins digging in the mountains for gold. After finding some he attracts some investors, but soon the mountain stops delivering gold. He digs and digs. And then he gives up. After selling his equipment to a local man, the man goes back to dig, only to discover that Mr. Darby stopped digging three feet from a massive gold vein.


Avianca Flight 052 

Origin: From the book Outliers: The Story of Success by Malcolm Gladwell 

Lesson: Empowering your subordinates can save your business… and your life

Character: Avianca crew, captain, and co-pilot

Synopsis: In 1990 the Colombian Avianca Flight, 052 was low on fuel. Despite inclement weather, the procedure was standard. Yet, inside the black box was revealed a flaw that has since served to explain the true cause of plane crashes.


Peter Thiel’s Triumphant Failure

Origin: From the book Zero to One by Peter Thiel

Lesson: The more you compete, the less you gain 

Character: Peter Thiel, co-founder of PayPal

Synopsis: Peter Thiel was on track to become a successful attorney. But one failure destroyed his dreams of being the top in his industry. The failure, however, brought an opportunity. He decided to start a little company that allowed people to transfer money using their emails. PayPal became a sensation. It never would have happened had he won the top spot as an attorney.