"Fewer & Fewer Regrets"

A helpful way to define 'success'

I came across this soundbite the other day: “For me, success is not a public thing. It’s a private thing. It’s when you have fewer and fewer regrets.”

This struck me as a pretty darn good way to look at it, the more I thought about it. I mean, sure, I’ve definitely considered the prospect of future regret — it’s figured heavily into my career decisions in the last decade — but I don’t think I’ve ever thought about actually defining ‘success’ along those lines.

After I heard the idea, I started thinking through its implications…

For starters, does it ring true? Does the end state described here -- the condition of having no regrets -- feel like an appropriate, sufficient definition of ‘success’?… I think it does, actually. If you add regret to any conventional success story (picture someone having all the money, status or accolades you could ask for), you no longer have a success story, you have a cautionary tale. Nobody wants to be the sad person on their deathbed, wishing they could trade their accomplishments for another chance at their past relationships, their health, etc.

Now if you picture someone having all those accomplishments and having no regrets, that seems like a great place to end up. But so does winding up totally content without any sort of notable fame or fortune. At the end of the day it’s contentment that everyone’s after, and whereas conventional forms of ‘success’ may or may not lead to contentment, accumulating a laundry list of should’ves is guaranteed to lead to the opposite.

So -- defining success by the absence (or gradual lessening) of regrets seems like a pretty good way to think about it.

Okay, so what does this view suggest about how to achieve success?

Seems to me the first -- and maybe trickiest -- part is to know what you’re going to regret in the future. That’s way easier said than done, given how much and how frequently your worldview changes throughout life. But if we’re going to define success in terms of our ability to have fewer regrets, that means that at a minimum it’s worth reflecting on this. I’ve always had the sense that most people don’t spend enough time thinking about what they’ll regret in future, so I think this is good guidance.

Next, supposing that you do know what you’ll regret in the long run, avoiding those things requires making good decisions about the big-picture life building blocks that set the stage for your story… things like marriage and family, occupation, lifestyle. Basically, how you spend your time and who you spend it with. Your choices in these areas need to be compatible with your long-run contentment, and it could be that evaluating your decisions through the lens of what you’re likely to regret (or not) in future is a helpful exercise.

Then, assuming you know what regrets you’re trying to avoid and you’ve generally set your life up to avoid them, there’s the million day-to-day / moment-to-moment choices you need to make to follow through on your plan. Failure to do so is not only likely to take you off the path of whatever you’re out to achieve, but it’s also likely to lead to some regret — so once again, this framing of aiming to have fewer regrets over time seems to make sense.

All in all, I think this is a pretty elegant framing of the nature of success. Succinct, poignant, humble. I dig it.