Thoughts on turning 50 and regrets

In early march I’ll hit the big half century mark, the big five-oh. I’m not one to be sentimental about birthdays; it truly is an arbitrary number determined by how often the earth gets around the sun (all of us would die before our “first” birthday on Neptune which takes about 165 earth years to complete an orbit). But birthdays help us mark – with a high degree of uncertainty, to be sure – how much time is left. And they seem to give truth to a pithy phrase I once heard that went like this: Life is like a roll of toilet paper … the closer you get to the end, the faster it goes. How true. 

Having the benefit of so many years behind me, I was thinking about the personal and professional things I wish I’d known earlier in my life. It occurred to me while deep in that reflection that whenever we say “I wish I’d known then what I know now,” we are speaking about an inflection point in our lives – a moment when knowing some additional information at a particular moment in time would have made us make a different decision and therefore change our future. In essence, moments like that are what we call “regret.” Some regrets are more meaningful than others. “I regret not buying Bitcoin a year ago” is in a different class than something like, “I regret not spending more time with my children.” The knock-on effects of the former are likely not nearly as damaging as the latter.

In an age of social media, I’ve found that it’s easier to have regrets. I have very successful friends from my college and MBA days and see posts they’ve made, posts others have made about them, or news stories that hint at their successes. I’d be lying if I didn’t say that every now and then I think to myself, Boy, I wish I’d gone into hedge funds. Of course, this is a fool’s thinking – it presupposes two things: 1) that I would do well in the hedge fund business and 2) that I’d like it. It also assumes that if I’d chosen that path, then there wouldn’t have been negative outcomes that would have offset any positive ones. What if a choice to go into investment management put me in one of the top floors of the World Trade Center buildings early on September 11, 2001? What if I’d gone to work for Toys R’ Us in 1999 (I had a job offer from them out of business school) and during the drive to their headquarters in New Jersey to start my new gig, I was hit by a drunk driver and injured severely? Or killed? These are dramatic outcomes to be sure, but the logic in the questions is sound. 

I think of our lives as very linear – a line progressing from left to right extending for as long as we live. The line gets thicker as our lives are enriched. A happy marriage makes it thick. Healthy children do too. Fulfilling work, enough money to feed and house ourselves, time to relax … all of these things make the line thicker. When we come to a decision point, we are trying to discern: which path will make my line continue to thicken? A wrong choice, and the line thins. This comes from hurting somebody we love, taking the wrong job, making a mistake. We all take steps backwards. But the key is to do things that give you more and better paths to choose from. In business we call this “optionality.” More forks in your line with options that have a high likelihood of increasing its thickness, the better. 

I’ve found that people who have personal and professional success are great “line-thickeners” and believers in optionality. Indeed, I think the two are related. Sure, we can never know with certainty where a given path ends. But if your line isn’t getting thicker as the years roll by, it’s time to give yourself some options; it’s time to find some branches to explore. You can only take one branch at a time, unfortunately. So, choose wisely. But don’t dawdle too long. Remember, that toilet paper roll disappears faster and faster.