07/11/2013 12:33 EDT | Updated 09/10/2013 05:12 EDT

Turning Regret Into Action

Man enjoying a view at sunset

"Regrets -- I've had a few," sang Sinatra. By a certain age, it seems we all have! Perhaps we think back on a relationship, or ponder the "one that got away." Or maybe it was an opportunity we turned down at one stage; to move, or accept a risky career opportunity. Hindsight is 20/20, as they say, and it's easy to look at something retroactively and think of all the ways that things could have been different, better even.

But I think we also all recognize that this is a destructive pattern, a shoulda-woulda-coulda way of existing that takes us out of our REAL LIFE and instead indulges an idealized alternate reality. If you're prone to dwelling on regrets, here are some things to help you snap back to reality:

1. Trust that you made the best decision at that time

Very often, we use our "current" self to judge decisions that we made in the past. But we weren't the same person then. Instead, try to get back inside the head of the "you" who made those decisions. You'll often find that you were making a fair and balanced decision based on the facts available to you at the time and the emotional space you were in.

Sometimes, the opportunity that came knocking 20 years ago was not compelling for a range of reasons that were, at the time, very legitimate. Perhaps you were making other priorities, or maybe there was a downside you weren't willing, or able, to handle at the time. Maybe you're seeing that opportunity as a missed one now because you're in a different position.

I think it's important to give yourself credit for doing the best job when you could. Even if you made mistakes, there were probably understandable reasons for making those mistakes and they probably acted as key learnings for the next stage of your life. Regrets can undermine our confidence and hold us up from moving forward, but if you reflect on the situation more neutrally, you may find there are aspects of your decision-making that you respect and were formative for you as an individual.

2. Don't romanticize the alternative

Romanticizing the alternative is an easy trap to fall into. Have you ever noticed that you dwell more on regrets when you're unhappy than when you're happy? For instance, the "one who got away" is only on your mind when you're feeling lonely or frustrated in your current relationship -- never when you're blissfully happy!

The truth is that all relationships and all opportunities have both their positives and negatives and you could forever rue the alternative no matter what decisions you made at the time. Again, I think the solution is to trust that you went with the most authentic choice at the time and to deal with the REALITY of your life, rather than taking refuge in idealized fantasies about what "could have been."

3. Understand we only live this life once

Life is short and you can only play out one set of options at a time. That may seem like a brutal fact, but it also means that we really have no way of knowing how all those little different choices might have played out. If we could look at our lives like a science experiment and run and compare every different alternative, sure then we'd be able to measure the most favourable outcome. But that's not how this life works. We're all mostly winging it, following the path that feels right for us and trying to find happiness along the way.

Some may find this distressing, but I find it liberating. There's no dress rehearsal, so you have to give up some control and trust the course you're on and also trust yourself. I do believe there's some kind of higher power helping us find the right direction, but I also believe that we can embody awareness and authenticity. If you work hard to be the best version of yourself at all times, that's really the most any of us can do. Instead of being hung up on the what-ifs and if-onlys, take a deep breath and be grateful for this wonderful life. Live in the present and dream of the future - don't get hung up on the past!

4. Refocus on what you can do here and now

That said, if you have a sincere regret, it may not be too late to do otherwise. Instead of dwelling on the regret, thinking about what aspect of the alternative is so compelling to you. Is it that you wish your relationship could be happier, more romantic? Or that your career could be fulfilling? Do you regret that you didn't travel more when you were younger? You won't get that time back, but you should make sure you don't compound that regret by wasting the time you have now. Instead, think constructively about what you could do today that could address some of those regrets. It may not always be possible to get everything back, but you might find a new way of enjoying your life now and in the real world.


Daydreams about what "might have been" fuel a kind of overly romantic and elated state of mind. But TRUE happiness -- which is what I think we all want -- is much more grounded than that. It's about when life truly hooks up to who we are, and what we really want, in a way that's real and true, rather than heady and idealized. If you find that you're hung up on regrets, switch gears and instead focus on what could make you happy in the HERE AND NOW. You never know, you might surprise yourself!