You read stories of brave entrepreneurs taking bold career risks to reap outrageous sums of money. Secretly you despise or envy them, wondering why you didn't do the same. After all, you always have had an idea similar to Facebook or WhatsApp. But how can you seize an opportunity when you don't have the willingness to take risks?

How to Gauge a Person's Willingness to Take Risk?

When I meet new folks, I often ask them one question to gauge their willingness to take risk:

What is your favorite failure that later set you up for success?

Most of the time, I get bullshit answers along the lines of "Oh well. You know. One time I had an underperforming employee. So I made his life miserable by putting him on a Performance Improvement Plan (PIP). His work performance improved dramatically overnight. Next Monday he left the job and now he is a successful executive. I feel I played a strong and unappreciated role in his success..."

In 2018, I got an answer that shook me to the core!

The Cost of Not Giving Jeff Bezos a Ride to the Airport

"What is your favorite failure that later set you up for success?" I asked the product executive. The entire room went silent. 50 odd eyeballs gave me the death stare. It was supposed to be a casual Q&A between the product executive and the design team. My manager would have preferred if I had asked casual questions like, "What show are you binge-watching?", "How can design provide value to the organization?". But there I was defying the status quo (What's with treating Fortune 500 company executives as noble lords? They eat, shit, and sleep the same just like us mere mortals!)

"Before you were born, I was finishing up my MBA at the Harvard Business School," says the product executive. "Harvard would host a business case study competition where entrepreneurs would pitch their business ideas, and MBA students would give feedback on it. One time this entrepreneur pitched his idea of selling books online. Most of the students thought it was an outrageous idea. I thought it was a disruptive idea and gave positive feedback on it. The professor saw that and told me, 'You are my favorite student. Why don't you give Jeff a ride to the airport?' I told my professor, 'I am sorry I can't as I am running late for my next class.'"

The whole room exclaimed with surprise and astonishment. Did the product executive say no to the world's richest man Jeff Bezos?

"Since I turned down the opportunity, my friend jumped on it," says the product executive. "He gave Jeff a ride to the airport. During the ride, they bonded. He ended up joining Amazon and became an executive there. He left Amazon with stock options worth millions of dollars. This friend, later on, went to start Hulu. So, if anyone asks me for a ride to the airport now, I'll jump on it!"

How to Seize an Opportunity?

Does your career or lifestyle allow for time on weekends to work on side hustles? Do your finances allow you to work for free on promising projects in return for equity? Does your 9-5 job allow you time to tinker on side projects? If not, you must find a way to escape the 9-5 grind and design a lifestyle that enables you to take calculated risks.  

How to Overcome Regret?

Life happens, and you might miss out on opportunities of a lifetime. Because at the time, you don't know if it's a life-changing opportunity. Nobody fucking does! I missed out on a $212,333 investment opportunity. Trust me, regret will only take you further down the well of self-pity.

My friend Sung Kim believes that the only thing we can do to overcome career regret is to choose opportunity over money:

Train your mind to be open to spontaneity. Increase your willingness to take risk. Spend time with folks who are 30x better than you in the field of your interest. It will improve your decision-making process. Above all, trust your gut feeling. The Universe has a plan for you and communicates via this gut feeling.

What is your favorite failure that later set you up for success? Email me and tell me. I read every email :)