In 1994, Jeff Bezos was pursuing a career in software engineering. He had picked the finance and investing fields and lived in a nice apartment in New York. The internet was just starting to make waves--the average person barely used it and Google didn't even exist. Yet, Bezos had an inkling even back then that internet-based companies would change the world. (He is now the richest person in the world, by the way.)

In a recent interview he gave with his brother Mark, Bezos explained how he debated starting Amazon. He had recently gotten married, and since his career was already taking off, Amazon didn't seem like a smart risk at the time. Yet, he recalls imagining what his 80-year-old self would say looking back at his life. He wondered if he would be able to summarize his life by saying he had taken risks or just stayed safe.

"It would be a 100 percent chance of regret if I didn't try and a 0 percent chance if I tried and failed," he said, suggesting that it is a great way to make life decisions.

During the talk, I couldn't help wondering if this is also a perfect way to define success.

I've written about this topic many times, because I've experienced some success as a writer over the years. I've wondered at times if it is really all about perseverance--never taking no for an answer. I've wondered if it is luck and if being downsized from a corporate job back in 2001 was a wonderful gift that set a course for me so many years ago.

In listening to Bezos, I realized it is really about risk. It's about living in a way that suggests you will not have regrets--you won't miss an opportunity by looking the other way. 

For me, I've split my life into three distinct sections.

The first third was all about career building. I spent 15 years trying to make it big in the corporate world, eventually leading a large team at one of the most successful retail giants around. The second act was about my writing career. I've been a columnist now for Inc.com for over 10 years, but before that I toiled as a freelancer for several magazines and websites, some large and some small. It's been a wild run.

In the third installment, I know I will keep writing (in fact, my first book comes out this summer and I have no plans to abandon this column), but I also know that I'm starting to think more about mentoring and training the younger generation. I'm thinking about the impact I'm making. I see potential in folks who are 18 to 24. (Sadly, I don't think they always see this potential in themselves, so I am happy to point it out.) In many ways, it's become my passion to help people see their potential, and that is a heavy responsibility.

Why do I even care?

For me, I want to look back at my life when I'm 80 and think about the impact I've had as a writer and as a mentor. I won't think about the corporate job as much. It helped me support my family, and that's admirable enough. But I wasn't really making much of a difference in terms of influencing people outside of my own family. And, along with my wife, I'm now an empty-nester. I'm happily watching as my kids figure out how to become functioning adults. We hope that occurs fairly soon, but in the meantime, we're both looking for ways to have an impact outside of the home, to plant seeds in others and watch those seeds grow.

It's not an easy process.

In some ways, I'm already starting to look back and wonder, perhaps a bit like Jeff Bezos is now (we're about the same age), what would have happened if I had stayed in the corporate world and just kept collecting a nice paycheck and annual bonuses. In the interview, Bezos said if had not started Amazon he'd still be a software engineer. I'm not sure what I would have become. Depressed? More financially secure? (I hear people actually have pensions when they're my age.) Not sure.

I know it was a huge risk to start writing. It's another huge risk to mentor people who are young and inexperienced. To be honest, I don't know how the third act will pan out. Maybe I won't make it to 80--who knows? At least I can say I'm giving it a shot.

How about you? Have you taken risks that would make the future you proud? I'd love to hear what your 80-year-old self would tell you about success and risk.

Published on: Dec 14, 2017
The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.