The Power of Regret: 4 Ways Looking Back Can Move Us Forward

How often do you look back on your life and wish you’d done things differently?

Do any of these sound familiar and resonate with experiences you've had?

  • “I spent too much time trying to meet others’ idea of normal.”

  • “I regret following a career path for money instead of for my passion or work I would actually enjoy.”

  • “I have been afraid of failing and looking foolish, and, as a result, I did not do things I wish I had done.”

How often do you experience regrets?

Never? Occasionally? All the time?

Five-time New York Times bestselling author, Daniel Pink, asked that opening question to 4,500 people in 2021 as part of the American Regret Project in which he compiled more than 16,000 regrets from people in 105 countries.

While less than one percent of respondents reported never experiencing regret, 82% said they looked back with regret at least occasionally.

It turns out that we regret what we DIDN’T do more than what we DID do. Regrets of inaction are far more common than regrets of action.

Most of us tend to see regret as something bad, something to be avoided at all costs.

Think about the number of times you or someone you know has said the words: “No regrets!”

We take pride in living life to the fullest, never looking back and wishing we could undo things.

But what if regret could be a teacher? What if it could tell us something about ourselves that we could use to live differently moving forward as a result of looking backward?

When we reframe regret as an opportunity for meaning-making and better decision-making in the future instead of a threat or something “bad,” we can tap into the power of regret for good.

I read Dan's book, The Power of Regret, in the spring of 2022 and was drawn in because he’s one of my favorite authors. Not only that, but two types of regret he wrote about are directly connected to what it means to live an “unmuted” life. (I'll be interviewing him on my January 9th episode of UnmuteYourself right here on LinkedIn Live!).

According to Dan's research, it turns out that most regrets can be categorized in one of four ways:

1) Foundation Regrets: “If only I’d done the work.”

If only I’d taken care of my body and my health.

If only I’d eaten better and exercised more.

If only I’d watched less TV and slept more.

If only I’d saved more money. 

If only I had applied myself in school, with my hobby or in my job.

The tough thing about foundation regrets is there isn’t much we can do about them because they're the result of the accumulation of consistent habits over time.

We may not be able to undo those “If onlys,” but we can use that regret as fuel for the future. We can decide to live differently moving forward, rather than constantly looking back and staying stuck in the past. We can use regret as motivation to make different choices that will lead to a more stable, secure and hopeful future.

Maybe you haven’t been saving money or taking care of your body or applying yourself fully, but you can choose to do the work now.

Start today.

Take It One Step Further: Another book to check out that helps with foundational habit formation is James Clear’s Atomic Habits. Check it out!

2) Boldness Regrets: “If only I’d taken the risk.”

I wish I’d asked him out.

I wish I’d spoken up and been more assertive.

I wish I’d launched that business or written that book.

I wish I’d traveled and explored more and been more adventurous.

I wish I’d had the courage to be bolder earlier in my career instead of caring so much about what other people thought of me.

When I talk about what it means to live an “unmuted life,” I often use these words - “courageously expressed and boldly alive.”

When we mute ourselves, hold ourselves back and doubt ourselves, we tend to do it because it feels like the risk of speaking up and expressing ourselves, the risk of going for it, and the risk of going against what is considered “normal,” feels too great.

So we end up not taking action and living with regret. The roots of why we do that run deep.

In his book, The Myth of Normal, Dr. Gabor Mate writes about the two needs all humans have from the time we are born - the need for authenticity and the need for attachment.

If we believe or experience that being true to ourselves and being authentic will threaten our ability to be in relational connection with people, then we will choose to mute ourselves.

Being “bold” will feel too risky because it will threaten our fundamental need to be in connection.

Because of that, we will keep ourselves stuck and small and stagnant as a way to (from our brain’s perspective) keep ourselves alive. We will compromise authenticity for the sake of connection, and when we do that, we are more likely to become bitter, resentful and frustrated. It's deeply painful to be inauthentic, to play small when we want to be bold.

Take It One Step Further: What is one way you’re holding yourself back and what might become possible if you unmute yourself by taking a risk in that area of your life?

3) Moral Regrets: “If only I’d done the right thing.”

Some of the most prevalent moral regrets people shared included:

I regret being unfaithful and having an affair.

I regret bullying that kid in middle school.

I regret not serving in the military.

I regret ending my pregnancy.

I regret taking so long to come out.

Of the four core regrets, moral regrets comprise only about 10 percent, but they often “ache the most and last the longest.”

There is no universally agreed upon definition of the word, “moral,” but in his book, The Righteous Mind: Why Good People Are Divided by Politics and Religion, Jonathan Haidt found that beliefs about morality fall under five pillars:

  • Care / harm

  • Fairness / cheating

  • Loyalty / disloyalty

  • Authority / subversion

  • Purity / desecration

Take It One Step Further: As you think about your life right now, where are you feeling the pang of regret around not doing the right thing? What choice could you make today to right a wrong? To say sorry? To ask for forgiveness? To forgive yourself? To seek counseling or support?

Own your contribution to the situation and then make a choice to take action to do what you can to rectify it, starting today.

4) Connection Regrets: “If only I’d reached out.”

Connection regrets look and sound like this: 

I regret not saying “I love you” more.

I regret not being nicer to my mom.

I regret not taking the time to be a better friend, sister and daughter.

I regret not spending more time with my parents in their final days.

I regret not reaching out to check in on an old friend when she was sick, before she passed.

Relationships are one of the main areas of our lives in which we mute ourselves. When we feel shame or anger or resentment of bitterness, we mute ourselves, sometimes letting pride keep us silent and distant, rather than initiating contact with someone.

I was listening to Being Well, one of my favorite podcasts hosted by Rick and Forrest Hanson, and one of the questions Forrest asked stuck with me and is related to this core regret:

What are the undelivered communications in your life?

Think about it.

If you were given a terminal diagnosis tomorrow, what would you want to say and to whom? Who would you wish you’d spent more time with? Called back? Appreciated? Forgiven? Been more present with?

If we don't take action on those urges to connect, we'll be more likely end up experiencing regret.

Take It One Step Further: Think about the first person who came to mind as you thought about "undelivered communications." Reach out to them today with a call, a text, an email or a letter. Schedule time to get together with them, and be fully present when you are.


Now What?

Now that we have more clarity and language around the types of regret we experience, what can we do about it? Dan suggests three steps: looking inward, outward and forward.

  1. Look inward: Take a look back at your life and describe in two to three sentences one significant regret you have. Be kind and compassionate with yourself as you do this. The goal is not judgment but awareness.

  2. Look outward: When we disclose what we’re feeling through talking to a trusted person or writing about it, we remove some of the weight of the guilt or shame we feel. And as we share, we often realize that we’re not alone, that other people feel the weight of regret, too.

  3. Look forward: Create distance between yourself and the regret, viewing it more objectively. As you consider what to do differently in the future, ask yourself what advice you’d give a friend or frame the situation in third person, like this: “What would Rachel do?” Contemplate how you’d feel a decade from now if you made the decision you’re about to make as a way to anticipate regret in the future so you can make a different decision in the here and now.

Want to dig into the power of regret further? Check out this episode of my LinkedIn Live show, UnmuteYourself, as I interviewed Daniel Pink himself!

How Can I Help?

Over the last 15+ years, I’ve devoted myself to helping organizations, leaders and teams go from burned out and checked out to energized, motivated and connected. I've done this through interactive keynotes, workshops, leadership trainings and retreats onsite and virtually.

If you're interested in learning more about my services for yourself or someone else on the topic above or other topics, start here and we can find time to connect.

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