LESS regret.

Regret is a two-sided coin. Let’s call “heads” the things we regret doing and “tails” the things we regret not doing. Which would you call? Heads or tails? Before you answer, let’s add another game to the mix – a spin of my namesake coin, the copper penny.

According to Perci Diaconis, a professor of mathematics and statistics at Stanford University and former professional magician, the likelihood of heads versus tails is not a 50/50 proposition as one may think. Flip the copper penny into the air, and over time, the toss will favor heads 51%. However, spin the same coin on the table, let it land, and tails will prevail 80% of the time, because the weight of Lincoln’s head is slightly heavier than his memorial on the opposing side.

I selected this moniker-friendly metaphor as my own personal tolerance for regret. Yes, I have done some spectacularly-stupid things in my life, of which a very small percentage, let’s say 1% have created an unintended effect on someone else. One percent may seem an acceptable margin of error, yet when it comes to hurting others, it deserves reflection.

On the other hand, when it comes to regret for things I haven’t done, my personal penny indeed lands on tails 80 percent of the time. Just recently I regretted not having the confidence to voice an opinion contrary to well-respected experts, especially when the opinion proved correct. The regret isn’t about being seen as right, it’s about not challenging a point that would have saved everyone some time and angst. But this example will quickly fade in the grand cadence of life.

The 80 percent of things we regret not doing usually have much broader consequence. People who wait too long to retire and miss a season of happiness with those they treasure. Those who yield professional opportunities to preserve a more comfortable and predictable path. The ones who suffer death by 10,000 paper cuts over missing one of those tragically short windows of emotional boldness.

A few years before my late father’s death, he surprised me with his own story of regret. He shared with me that he had wanted to be a pastor, but with a wife and two children to support, he knew there was not enough time and money for him to attend seminary. He found myriad ways to share his deep faith with others, including me; but I have to say that the world missed out on one incredible pastor.

What is it that you may live to regret? Not spending enough time in the office or not spending enough time with your children? Not being richer than your neighbors or not lifting up a neighbor in need? Looking a bit foolish for trying something you’ve always wanted to d

o or wishing you had been brave enough to try? Contentment with the good business/life/family you’ve created or remorse for never pushing to make it truly great?

I can live with regret for what I have done, knowing that the vast majority of time, it will be of little consequence and also knowing I have the humility to atone for the occasional times my actions are misguided. But I don’t want to come to the end of my days with a disproportionate number of times when the coin of regret landed on tails. When time gets too short to change the outcome, I’d much rather boast my mistakes than lament chances missed.