Overcoming Your Greatest Obstacle
PART 2 of the two-part series focused on one question: “What should I do with my life?” Start by reading The Most Common Question.
The fear of failure is one of the greatest obstacles we have. Whether conscious or unconscious, it’s important to know when we might be making a decision out of fear—especially a decision as important as the goals we’ll pursue for the rest of our lives.
I used to tell students not to fear failure; easy to say and hard to follow. Instead of continuing to give that useless advice, I developed five tangible methods to methodically break down your fears, analyze them with the conscious part of your brain, and conquer them.
Let go of outcomes, focus on effort and integrity instead
One of the very first investments I ever made was in a label printing company in Detroit. By all accounts, the investment was a failure. I gave investors back less money than they invested—it’s hard to consider that a success! The deal was structured such that my only compensation was on the gains on the investment, and pretty early into the deal, it was clear that there were not going to be any gains. But I dug in and worked hard, spending many weekends in Detroit, hiring a new management team, restructuring the company’s debt, and cutting costs. We improved the outcome from investors losing 100% of their money to losing “only” 30%. I learned a lot about investing and management in general. All but one of the investors in that deal invested into my subsequent investment.
For many years, I defined failure as a failure of outcome: I lost a race, we didn’t win a deal, a company we invested in underperformed, or a valuable employee left. After the Detroit investment, I was crushed.
Over time, I’ve come to focus more on two controllable variables and to let go of the outcome:
(i) Effort – Did I give my best?
(ii) Integrity – Did I show up as the best version of myself and handle myself with honesty and integrity?
We can control these two inputs. You will experience setbacks and events that challenge you from time to time, but if you maintain effort and integrity, you will walk away with your head held high. Let go of the outcome, knowing you gave your all, and shift the way you define failure.
Consider the worst case scenario and the wild asymmetry of the upside
Imagine you had the opportunity to bet $10 for a 30% chance to win $10,000. We would all probably take this bet. This bet presents wildly asymmetric outcomes—the gains on the bet and the losses on the bet are unbalanced. The worst case scenario is losing $10, most of us can get comfortable with that. The best case scenario you win $10,000, a far more compelling upside. Consider the three variables in this assessment: the upside ($10,000), the downside ($10), and the probability (30%).
“Most of us wildly underestimate the upside of spending our lives doing whatever makes us come alive.”
We would be well-served to evaluate decisions about our own lives through a similar lens. Let’s start with the upside—the $10,000 payoff. What is the upside of being able to live your life pursuing your dreams? Have you considered the upside of spending every day doing something meaningful that you love? What will you gain by throwing yourself fully into the pursuit, and in the process being able to learn and grow and become a better version of yourself? Most of us wildly underestimate the upside of spending our lives doing whatever makes us come alive.
What is the downside? What is the equivalent of the $10 you might lose? What if you don’t get what you’re looking for? What if you’re not successful on your journey or you can’t convince people to invest? What if you’re not good at the career you pursue?
I have a close friend, we’ll call her Sam, who started a company. She raised money, and for two years she threw every ounce of herself into the company. She hired people, developed code, and mapped out the product. She launched and pivoted and tried several versions. Ultimately, she didn’t get user traction, shut her company down, and lost money for her investors.
Shutting down the company was her “worst case,” her $10. Along her journey, she gave 110% of her effort and maintained her integrity, she was transparent with investors throughout, and she made the most of their investment.
What was Sam’s true downside? She taught herself to code, learned how to fundraise, developed a user interface, solved problems, hired and fired, and built a company for the first time. She couldn’t have learned these same lessons doing virtually anything else. She got paid to earn a business school education. Sam now uses these skills in her role as a very successful executive at another company.
When you play out the worst scenario and become comfortable with it, you’re free to take a path that might otherwise seem risky. You will probably realize that you’re making a wildly asymmetric bet and you’re risking a limited amount of downside for a lifetime spent pursuing the thing you’re most excited about.
Expect setbacks
When I started Alpine, I expected to follow a linear path up—and to the right. When I lost money on my first two investments, I wanted to quit. I thought I wasn’t cut out to be an investor, and these setbacks proved my inadequacy. As the two companies I invested in began to swirl down the drain, I watched my dream of starting an investment firm go with them.
Around the same time, a mentor of mine advised me to read the biography of Abraham Lincoln. I told him I didn’t need a biography right now—particularly a thick, hardcover Lincoln biography I had to lug onto flights. I needed someone to help me get relief from debt covenants for the two companies. Nonetheless, I plowed through the Lincoln biography and partway through I realized why he recommended it. Here is Abraham Lincoln’s path to the Whitehouse:
Lincoln’s Failures
1832 – Lost his Job
1832 – Defeated for state legislature
1833 – Failed in business
1835 – Sweetheart died
1836 – Had a nervous breakdown
1838 – Defeated for speaker
1843 – Defeated for nomination for Congress
1848 – Lost the re-nomination
1849 – Rejected for land officer
1854 – Defeated for U.S. Senate
1856 – Defeated for nomination for Vice President
1858 – Defeated for U.S. Senate (again)
1860 – Elected President
Approximately 66% of historians rank Lincoln as our greatest U.S. President. Lincoln kept the Union together, oversaw the victory of the Civil War, and led the abolition of slavery. If nearly any other man in history had been president in 1860, we may be living in a very different country today.
Lincoln was a great president, not in spite of all of his setbacks, but because of them. He proved to himself that he was resilient and capable of persevering through adversity; he developed confidence in his character and faith in his resolve; and he relied on this confidence to back his convictions even when nearly half the nation turned against him.
Most biographies of famous people read like Lincoln’s. Steve Jobs was fired unceremoniously—and perhaps deservedly—from the company he founded. Sam Walton’s business partner screwed him out of his first store; Walt Disney’s partner stole his initial animated characters; Elon Musk came close to going bankrupt in the recession; Oprah Winfrey was abused as a child; and so on. The protagonists face challenges, setbacks, and tremendous adversity. And they become stronger for them. Most great achievements take decades.
How long will you give yourself to pursue your dream? How long are you willing to persist? You will certainly face setbacks. And when you do, realize this is a normal part of taking a less-travelled path. Your ability to persist is not only a necessary part of your journey, but a welcome one. The confidence you gain will embolden you and permanently strengthen your character.
Ask yourself: If not now?
“The chains of habit are too light to feel until they’re too heavy to be broken.” — Warren Buffett
In over 15 years, no student has never said, “Graham, I just give up. I’m never going to pursue my dream.” Here’s what they say instead:
“Not now.”
“First I gotta...
...Make a little more money,
...Pay off a debt,
...Get more experience,
...Vest into this equity,
...Get through the holidays,
...Earn one more bonus,
...And on and on.”
Pretty soon, “not now” becomes “not ever.” And the burning flame becomes a flickering light and then a distant memory.
You become your environment over time. You become the people you spend time with; their goals become your goals; their values become your values. Every day you don’t leave it becomes harder to leave. You have more commitments and more money on the line, the inertia becomes more powerful.
Set a deadline for yourself. Put milestones in place. Tell friends, coaches, and mentors about your goals. Ask them to hold you accountable.
Taking action will feel uncomfortable. Driving toward your future will feel uncertain—it almost has to feel that way. The only truly certain thing is staying where you are. Recognize that you can’t know the answer or the outcome, nor would you want to.
But this life is not a dress rehearsal for life. This is life.
Don’t underestimate yourself
Think of a time when you felt like your absolute best. Everything went right. You were the version of yourself you wanted to be. Maybe you achieved something at work or in a sport or in a group or on a test. Maybe just how you showed up for a group of friends, a close loved one, or a mentee. How did you act when you were the best version of yourself?
That person is still in there. You still have all those attributes, skills, and characteristics. You are that person. When you pursue something you’re really excited about, you’ll get to be that person more often. And you’ll have a chance to become an even better version of yourself.
People overestimate the $10 cost and underestimate the $10,000 payoff, but they also underestimate the probability of winning. They haven’t factored in how they will show up at their best.
When you’re doing something meaningful, you perform differently. You show up differently. You get up early. You think of ideas in the shower. You are willing to persist until you win. As the Genie says, the road will be longer than you think, and it may be winding. But the probability of success is likely higher than you think. Particularly if you’re not in a hurry.
One of the most important things I’ve learned in my career is this:
The Genie is real.
The Genie is you.
You—and only you—have the power to grant yourself that wish.
I hope you will.
