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Words of Wisdom for My Younger Self: Take More Risks

Most years, I have to be reminded that it’s my birthday. But this one felt different, and I saw it coming.

I recently turned 50, and 50 is a milestone birthday. It’s the age that I had always viewed as being old. While my mind feels sharper than ever, and my self-confidence and self-awareness are at all-time highs, my legs don’t move as quickly as they used to and my hair has just about left me altogether.

I’m also working through some family transitions. I have three daughters. My oldest recently graduated from college and is launching into adulthood. My middle daughter is pursuing her studies while also cultivating a dance career, and my youngest has begun her freshman year in college (though from home for the first semester due to COVID-19).

The intersection of this milestone and these transitions has moved me to pause in reflection. My reflection centers on things I know at this age that I wish I knew when I was the ages of my daughters. Three lessons in particular come to mind. Today, we’ll look at the first one, learning to take more risks.

I spent the past 25 years of my career with two large organizations. I worked hard, sought to make meaningful contributions, and was able to advance through the organizations pretty quickly. However, as I look back on my time in those two companies, I recognize how safe I played it, particularly once I had achieved a certain level of success.

About a year into my tenure at a Fortune 100 food distribution company, I was asked to be the President of one of their subsidiaries. This company had been recently acquired, and while it had a history of success and growth, that growth had stalled. We made some tough, bold decisions, including changes to the leadership team, but within two years we were back on track with record sales and earnings, as well as improved employee engagement. We sustained this growth for several years, even through changes and challenges in our industry and in our community.

So, what do you do when you achieve success? You make sure you never lose it; or so I thought at the time. When we were trying to rebuild the company, we were scrappy and bold; but once we were hitting on all cylinders, once we got used to earning bonuses and winning in the marketplace, we became complacent. We had doubled the size of the company and tripled its earnings, and we were afraid to lose what we had achieved.

We didn’t stay complacent. We were shaken free by some upstart competitors and annually increasing operating budgets. And while we regained our footing, I look back on that season with regret. Just like my 50-year-old body, it’s not as easy to get going as it used to be. I wish we had stayed fearless.

When I think about being brave and taking risks, I think about my daughter Kayla. Last year she did an exchange semester in South Africa and on one of her free weekends she decided to go on a tour that included the opportunity to go bungie jumping. The picture of her diving off the platform, arms spread, is one of my cherished possessions. When I asked if she was afraid, she said, “Yes, but I know I could never have an amazing experience like that if I didn’t take a risk.” May I never again fear that I have too much to lose to be willing to take a risk.

Stay tuned. In my next post, I’ll have more 20/20 hindsight to share.


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