This is 50

This is 50

This summer, I will celebrate a major birthday milestone, one that has been looming on my calendar for quite some time. The “Big 5-0” – the half century, the back-nine, the one that sends us crashing over the hump and sliding downhill into our dotage, where “softening” Zoom filters become suddenly necessary, and reading glasses with which to find said filter. “Middle-age” always seems like a bit of a misnomer since few of us will actually live to see 100. But I suppose “three-quarter aged” just doesn’t have the same ring to it, or feel-good factor. 

Along with AARP membership comes a certain amount of reflection on the great passage of time. How am I doing? Have I used my time wisely? What’s left to do? Am I going to be okay? Overall, I am very grateful for the life I have and the opportunities it has given me. I’m lucky to have a home, a family and a career I love. Thankfully, I still enjoy good health which is the single greatest gift of all. Having lost both my parents, and seen others die before their time, I know what a privilege it is to even get older.

That being said, a proper accounting of the last 50 years would not be honest if it didn’t contain at least some regret. In his latest book, The Power of Regret: How Looking Backward Moves Us Forward, author Dan Pink offers a very thoughtful examination of regret as a learning tool, one whose power we might actually harness for good. Because, according to Pink, “The only people without regret are two-year olds, people with brain damage, and sociopaths!”

For this book, Pink set up a large-scale human experiment entitled “The World Regret Survey.” In it, participants were invited to share anonymously their biggest regrets in life. About 16,000 people participated across 105 countries, giving him a panoramic X-ray (and useful database) of human longing and aspiration. Not surprisingly, there were certain commonalities in all countries. Human beings, it turns out, are not all that different the world over. What he found was that people’s regret tended to fall into four major categories.

1. Foundational Regret

These regrets are rooted in the more foundational aspects of our lives, including things like education, career, health, finances, etc. Choosing the wrong career, or maybe choosing the right career but for the wrong reasons. Not taking care of our health, not working harder in school, not saving enough money. In some way, all of these are different expressions of the same basic regret: “I wish that I had been more responsible. I wish now that I had done the work.”  

2. Boldness Regrets

Fairly obvious, but these are usually regrets of “inaction” – and tend to be the most painful, often involving issues of love, romance, or personal ambition. It is “the one that got away,” the person we didn’t ask out because we were too shy, the business idea that we never pursued, the time we wanted to speak up but did not. According to Pink: “One of the most robust findings is that over time, we are much more likely to regret the chances we didn’t take, than the chances we did. What haunts us most is the inaction itself.”

3. Moral Regret

These are regrets that tend to needle our conscience late at night, involving times when we may have made morally dubious decisions. These might involve things like infidelity, betrayal, bullying, cheating of any kind. Those times when we failed to live up to our own moral or ethical code of conduct.

4. Connection regrets

As most will agree, it is really our relationships that tend to give our lives the most meaning and value over time. If the first half of life is “acquisitional”– then the second half tends to be more “relational.”

Why then, do so many of us let these connections “slide” as we get older? A lot of human regret and loneliness comes from our fractured relationships with others. If only I had spent more time with my children/parents/spouse/friends. If only I had been a little kinder. If only I had reached out when it mattered. If only I had taken the time to get to know my coworkers. If only….

With this in mind, one of the ways I am celebrating this upcoming birthday is by writing 50 letters in 50 days. The idea is simply to “reach out” to certain people and let them know how much of a difference their presence has made in my life. Yes, it has been onerous, slightly awkward, humbling, even tedious at times, but also very rewarding. Some of the responses I’ve gotten have been surprising and very heartwarming.

As for Dan Pink, I think we can take his findings one of two ways. We can curl up in a ball of self-recrimination. Or the way I see it – this is incredibly consoling and useful information to have. It proves we are certainly not alone.

Because regret, if we can actually sit with it for a while, in all of its knotty discomfort, is really the signpost for where we want to go. We just need to be able to name it (either to ourselves or to others), and then show self-compassion for what we’ve learned through our experience, knowing that “to err is human, to forgive divine.”* And if there is ever an inkling of doubt, always take that shot. Speak up. Make that call. And start now.

*“Regrets” by Jasper Johns MOMA