When I read Brené Brown’s wonderful Atlas of the Heart, the idea of having no regrets is one of the few things that she wrote that I didn’t entirely agree with. It’s possible that we just disagree on exactly what the phrase “No Regrets” means, but I think it’s a worthwhile aspiration.

First off, it’s Spoiler Alert™️ time: It’s not actually possible to have no regrets. If you read the words “No Regrets” as a statement of fact, then it’s just not true. This, I think, is where Brené Brown disagrees with the phrase. Also, she points out that regrets are a great opportunity to learn about who we are and what we want. I totally agree; more on this later.

But, as an aspiration, I think “No Regrets” is a great thing. When I think “No Regrets”, I don’t mean that I have no regrets; rather I mean that I intend to make choices in the moment so as to minimize regrets later. It’s an intention, a desire, a goal—not a statement of fact.

An example from my personal experience. When I was in grad school, I was riding the train home late one Saturday night, and there was a gorgeous young lady sitting across from me. She was getting hit on by some drunk guy, and was not even the tiniest bit interested. (Well, it was apparent to me that she wasn’t interested. Apparent to him, not so much.)

When we changed trains, I ended up sitting next to her and we chatted for a bit. It turned out that she was also a student at my school, and we ended up getting off at the same stop. As we were saying goodbye, there was a clear opportunity to ask for her number. But, because I was tired and afraid of rejection, I didn’t.

After spending the next few days kicking myself for not having gotten her number, I made the decision that I was never going to regret not asking someone out again. So, over the next few years, I asked out bunches of women. I’d ask someone out for any reason or no reason, if I thought there was even the slightest possibility of attraction or interest.

This was a great success, in that over that period I went on something like 30 first dates. Now, most of those went nowhere (over that same timeframe, I think I went on two second dates), but it was a tremendously valuable experience for me. I learned how to put myself out there. I learned a lot about my fear of rejection being ungrounded (I did get rejected, but not nearly as often as I was afraid of, and the consequences were not nearly as devastating as my earlier self had imagined they would be). And, I learned some things about dating.

The perspective of trying to minimize later regrets is not unique to me. Shirzad Chamine, in his book Positive Intelligence, talks about consulting your older, wiser self as a way to help make decisions or focus effort in the moment. “What would your older, wiser self suggest that you do?” is really just another way of framing the question “What action can I take now that I will regret the least down the road?”

But, the kicker here is that honestly and accurately answering either of those questions requires that you have the experience of doing something that you regret. As Brené Brown points out, the sad truth is that regrets are great teachers; they help us learn what we don’t want to do. By learning from the regrets, and by using them to guide our actions, we can start to avoid accumulating more regrets. And, unfortunately, if I haven’t had the experience of doing something, I may not know whether or not I will regret it.

Further, one of the characteristics of Shirzad Chamine’s “sage perspective” is the idea that every problem or setback can be turned into a gift or opportunity. I have had the experience of taking something that seemed like a horrible thing in the moment and turning it into a gift or opportunity later. But, once it has become a gift, or an opportunity, there’s much less room to regret it. Since I know this, it’s much easier to not regret even the things that seem to have not gone my way.

Similarly, in Richard Carlson’s Don’t Sweat the Small Stuff, he suggests imagining yourself at your own funeral. What do you want to be remembered for? What kind of impression do you want to leave on the world? If you’re not doing that today, what are you waiting for? It seems likely that you will regret it later.

So. I don’t actually believe that it’s possible to have no regrets. And, since I’m not perfect at anything, I’m not going to be perfect at avoiding additional regrets either. But, as an aspirational goal, I definitely try to avoid adding new ones. It doesn’t always work, but it’s a good target to shoot for. Thinking about how I’m going to feel about my choices later is a great way to start.