Big life choices are rarely between something that’s clearly good and something that’s clearly bad.
Almost everyone who’s started a company has had to decide if and when to give up their stable (and often lucrative) career and take the leap of faith. When Amazon’s Jeff Bezos was looking out over the cliff edge in 1994, he was comfortably employed by an investment management company in New York.
Bezos had a successful career. To make matters worse, leaving in the middle of the year would mean leaving his bonus on the table. On the other hand, the promise of the Internet was growing by the month, and Bezos had the chance to write the rulebook for online shopping.
We often see the same pattern:
- Staying at your current company and role is the low-risk, low-reward choice. It can offer a great quality of life, but your progress will remain very linear.
- Jumping on the new opportunity has the potential to change your life. At the same time, there’s a huge risk of putting in years of work and ending up with nothing to show for it.
We know how the story ended for Jeff Bezos, but what’s more interesting is the way he made the decision. He imagined himself looking back at age 80, asking himself which decision he would regret the most. As Bezos put it in Brian Christian’s book, Algorithms to Live By:
“I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried.”