When faced with a decision, a dear college friend would always remind us, “No regrets, man. No regrets.” At the time, it sometimes seemed like a nudge to do whatever it was I was thinking about. But now I look differently on the advice to have not regrets, and I remain grateful to my friend. 

I came to learn that regret requires two things.  First, and most obviously, regret happens when there is a negative or undesirable aspect of the outcome of a decision. No one regrets a decision when everything works out beautifully. The second factor has to do with how the decision is made. If one carefully considers and honestly weighs all the relevant elements that contribute to making the decision, even the hard ones and uncomfortable ones, then there will be no regret. You may wish things had worked out differently, but if you’ve truly made the best decision possible based on the all information that was available at the time, you may be sad about the outcome, but you won’t regret it.  But if you don’t consider a perspective that was available to you, if you don’t give appropriate weight to a perspective (perhaps because of its source), if you don’t listen to the still small voice that often guides us correctly, and the decision has negative outcomes that perhaps could have been avoided, then you may well regret it.  We regret what we did (or didn’t do) because we know in our hearts that we could have and should done better.  Regret is not only about the outcome, it about how we arrive at the outcome. 

An example. I grew up in Arkansas and went to college in Pennsylvania. A lot was new to me there, particularly carless access to big cities. During my first year in particular, I spent many hours on buses to Washington, DC, to protest ills that often didn’t get the same level of attention in my beloved home state.  I went so often that my mother said I was getting to be like Amy Carter.  

One of those trips was to a march against homelessness.  My friends and I brought poster boards and markers and arrived early enough to make signs before the march began. We sat on the grass trading ideas for what the sign should say.  I started one by writing “BUILD HOMES” across the top.“What should I add?”“Bomb Bush!” was one of many suggestions; it came from a cute junior I had a bit of a crush on. So even though the still small voice in my mind reminded me that I had no desire to bomb our president at the time (or any other) and that it was not my nature to promote violence, I wrote “BOMB BUSH” and my friend drew a small home.  As I remember, there was smoke coming out of the chimney. We joined the other marchers and I held my sign.

This was one one many marches I attended during my first year but it’s the only one I think about decades later.  That’s because I regret the sign that 17 year old made and held. I made the decision to include those last two words even though I knew at the time it was the wrong. Yet I proceeded.  

But what about the negative outcome, one might ask. There have been no external negative ramifications (as far as I know), but the internal one is real - after so many years that sign is still on my mind.  Certainly, that sign is not my only regret, nor is it my most serious one, but it serves as a useful reminder for what not to do in the future.