The woulda-coulda-shouldas mess with us - here’s how to reframe regret to help

Image of blue and purple circles out of focus with text overlay The Woulda Coulda Shouldas How to Reframe Regret by Rikki Goldenberg Executive Leadership Coach, Career Coach

Have you ever heard yourself saying, “if only I had done XYZ, I’d be so much [happier/successful/proud/etc]”?

Regret is a tricky thing. It fills our brains with all kinds of wild emotions. We travel back in time, consider an alternate path and then decide how we would be so much better off if only we had done things differently.

It shows up in our careers, finance, relationships, where we choose to live or go to school… you name it, there’s regret hanging out.

So… do we have to try to get rid of regret?

TLDR: Nope, we simply have to learn how to reframe the feelings of regret and recognize when and how it can be useful and when it isn’t.

So let’s get into things.

We’ll talk about….

  1. What is regret? What are the types?

  2. How does regret impact us and our lives?

  3. Give it to me straight - what can I do about it?

Thanks to Daniel H. Pink’s The Power of Regret: How Looking Backward Moves Us Forward, we’ve got all kinds of great answers here!

What is regret? What are the types of regret?

How to define regret?

Spoiler alert! No one really agrees on this one!

Psychotherapists say it’s:

The unpleasant feeling associated with some action or inaction a person has taken which has led to a state of affairs that he or she wishes were different

Management theorists:

Regret is created by a comparison between the actual outcome and that outcome that would have occurred had the decision maker made a different choice

And the philosophers:

A feeling of unpleasure associated with a thought of the past, together with the identification of an object and the announcement of an inclination to behave in a certain way in the future

But Daniel H. Pink highlights it as “the combination of time travel and fabulism.” Go ahead and try out regret in two easy steps!

Step 1: Go back in time and compare what happened versus what didn’t even occur, while negating the past experience and contrasting it with a current present of what could have been if something had changed

Step 2: Assess blame - you also decide the regret is your fault, was in your control, and you’re the cause of your own suffering

You did it!

What are the different types of regret?

Okay but more seriously, Pink through his massive regret survey found that there are really four types of regret: Foundation, Boldness, Moral, and Connection type regrets.

They live in two categories: Low opportunity (ones that can’t be fixed) and high opportunity (ones that technically can be fixed, they’ll just be uncomfortable. FYI: We spend more energy and mental time on low opportunity regrets because they plague us more deeply!

What do they look like in action:

Foundation Regrets - the regrets of failure in foresight and planning. It sounds like “if only i’d done the work!” Usually they have to do with things like your health, finances, education - and they sneak up on you over time in how much they bum you out. Foundation regrets stem from a desire for stability.

Boldness Regrets - the regrets about playing it safe. It sounds like “if only I’d taken that risk!” These are usually around moments that you avoided being disruptive, or a challenger. Boldness regrets stem from the human desire for growth.

Moral Regrets - the regrets that are about doing something wrong. Usually around fairness, loyalty, purity, things like that. Moral regrets stem from the human desire for goodness.

Connection Regrets - the regrets that had us missing out on connecting. It sounds like “if only I’d reached out!” These usually come from avoiding potential awkwardness or discomfort - choosing not to ask that person out on a date, giving a compliment, reconnecting with an old friend. Connection regrets stem from the human desire for love.

Which ones feel most connected to you?

How does regret impact us and our lives?

Think about your emotions as a portfolio. Some are negative, some are positive.

As humans, we prefer to want the positive emotions - optimism, joy, gratitude - and we want to avoid or dismiss any negative emotions… but, it’s a portfolio. Of course we want to have the positive emotions outweigh the negative emotions, but those negative emotions are powerful, too. They tell us how to think about risk, how to learn from mistakes, how to get better.

Regret is one of negative emotions that we almost all feel and dislike, but also value, because we can learn from it.

Regret can be super beneficial. It can:

  • Help us improve decisions by sharpening our decision-making skills

  • Boost performance by increasing persistence which often results in elevated performance

  • Deepen meaning by helping us connect to ourselves, our community, our desires and wants

And, it can also be dangerous. When regret becomes ruminative it can reduce life satisfaction, anxiety, oof.

But, if we work with regret as an emotion, as a behavior that we can work with rather than a judgment on who we are… it can become an opportunity.

I know I know, now you’re like, so tell me HOW. Let’s do it!

Give it to me straight - what can I do about it?

Pink breaks it down for us: what do for regrets about actions you took, and, what to do for regrets in general, along with additional techniques that might help. Let’s cover them all! Why not.

For Action Regrets

Step 1 - Undo it, if you can. Simple enough, right? I’m just kidding. But truthfully, it’s about trying to make things happen. Think of the chinese proverb - the best time to plant a tree is twenty years ago. The second best time is today.

Step 2 - “At Least” it. Rather than “if only” thinking, try shifting to “at least.” What this looks like in action, using the real example that Pink has of going to law school was a mistake? That could look like shifting from if only I hadn’t gone to law school I’d have -> Law school was a mistake but at least I met my wife!

Try asking yourself these questions to help:

  1. How could the decision I now regret have turned out worse?

  2. What is one silver lining in this regret?

  3. How would I complete the following sentence? “At least…”

For Any Regret

Step 1 - Self Disclosure: Relive and Relieve. It’s important to not hide away from the regret but to truly spend time with it. That could look like…

  • Writing about your regret for 15 minutes over 3 days

  • Talking about your regret into a voice for 15 minutes over 3 days

  • Discussing your regret with someone you know in person or via phone - with a time limit, say, 30 minutes? To avoid brooding and repetition

Step 2 - Self- Compassion: Normalize and Neutralize. Regret is very real, very human experience. So let it be! Some questions that might help are:

  • If a friend came to you with this same regret, how would you respond? Respond to yourself the same way!

  • Is this regret completely unique to you - you’re the only one to ever experience it, or, is it more likely that others have felt this regret, too - not just you?!

  • Does this regret represent a moment of unpleasantness, or does it define your entire life and existence? If it feels all defining, try bringing in a neutral third party.

Step 3 - Self-Distancing: Analyze and Strategize. It’s hard to examine regret when you’re in the emotions. But, when you separate yourself out, it’s easier to find neutrality and compassion, and take action if you need to! Some tactics to try:

  • Pretend you’re a fly on the wall rather than your perspective - is this regret still such a huge deal?

  • Visit the future - pretend it’s ten years from now - does this regret resonate?

  • Try language tricks - talk about it in third person to yourself (thanks Ethan Kross!)

Even mooooore tactics!

  • Create a regret circle. It’s like book club. But not.

  • Write a failure resume. It’s not so bad, is it?

  • Study self compassion. Kristen Neff is a great start!

  • Pair your New Years Resolutions with Old Years Regrets - we keep growing!

  • Mentally subtract positive events. Remember It’s a Wonderful Life? When we’re feeling doom and gloom, it helps to recall how each instance in life is important!

  • Adopt a journey mindset. Keep creating and learning

  • Participate in Pink’s World Regret Survey

That’s all we’ve got folks. Good luck on trying these things out to move out of the self-shame and frustration, and reframing regret as something that you can learn from and take action on!

And of course, if you want help with any of this…

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