How will you fail this year?
I hope you fail more this year than last. Seriously.
I hope you find the courage to try something new. I hope you embrace failure for what it is: the only route to success.
With that in mind, I offer you three quotes to kick-off 2023. My hope is that these words help push you forward when you stumble this year. And since these quotes come from three giants, I’ve included some background you should know.
“If you aren’t thinking back to who you were a year ago and grimacing, you aren’t growing fast enough.”
- Ray Dalio
Background: In 1974 Ray Dalio was a young investment broker at a firm on Wall Street. One night a group of colleagues went out drinking. Dalio got drunk and punched a superior in the face. He was soon fired from the firm. He then started his own firm. It was so small he couldn't afford office space for years. But over time it grew. Today Bridgewater Associates is viewed as one of the top investment management firms in the world.
“Success is all about going from failure to failure without losing enthusiasm.”
- Winston Churchill
Background: After graduating from university Churchill wanted to join the Royal Army, just like his father, grandfather and great-grandfather. But Churchill failed the entrance exam. Then he failed it a second time. On the third try, he was permitted to join the infantry but denied entry into the cavalry, which was viewed as more prestigious. The letter his father wrote him is startling for its cruelty. He tells his son Winston that no teacher has ever given him a good report. He says that Winston is “leading an idle useless unprofitable life.” He warns Winston that he risks “degenerating into a shabby, unhappy and futile existence.” Then he signs the letter “Your affectionate father.”
Winston Churchill went on to play a central role in saving the world from Nazi rule. But that letter left a lasting impression on him. He quoted it from memory 37 years after his father sent it to him.
“Many great projects go through a stage early on where they don't seem very impressive, even to their creators. You have to push through this stage to reach the great work that lies beyond. But many people don't. Most people don't even reach the stage of making something they're embarrassed by, let alone continue past it. They're too frightened even to start. Imagine if we could turn off the fear of making something lame. Imagine how much more we'd do.”
- Paul Graham
Background: In middle school Paul Graham and a friend made a map of the school cafeteria ranking the tables by popularity of the kids who sat at each. “We sat at a D table, as low as you could get without looking physically different.” His 2003 essay “Why Nerds are Unpopular” runs over 5,600 words, suggesting he was still processing the sting of his middle school years well into his 30s. That said, Why Nerds are Unpopular is a valuable essay, particularly for teenagers. The quote above is from another excellent Paul Graham essay called Early Work.
Today, Paul Graham is a kind of oracle of Silicon Valley having founded Y Combinator where hundreds of companies began, including Stripe, Instacart, Doordash and Rippling.
Everyone fails. Life is about getting back up off the ground.
Five questions for failing better this year:
What did you want to accomplish in 2022 but didn’t because you were afraid of failure?
How can you redefine success? How can you craft micro-goals to move you towards a first version?
Have you written down your micro-goals? Where? When will you review them?
Who is your advisory board? Who can you trust to give you feedback? To give you encouragement?
What will motivate you to push ahead when you feel like you’ve failed? A visual reminder on your desk? A playlist?