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How regret helps us move forward

As absurd as this may sound, I was really excited to read “The Power of Regret” by Daniel Pink. I became a big fan when I took his MasterClass on sales and persuasion last year. He’s a great teacher and speaker and knows how to engage his audience. 

So even though I didn’t think “oh regrets, what a fun topic,” I knew I was going to learn something valuable — and thankfully, he didn’t disappoint. 

Similar to Brené Brown, he based his book on research. He conducted a World Regret Survey that collected regrets from more than 16,000 people in 105 countries. 

Daniel identified 4 main categories of regrets: foundation, boldness, connection and moral. Foundation focuses on core areas like health, finances and education. Boldness regrets are based on risks, the “if I’d only taken the chance” ones. Connection results are about relationships that drifted apart. And moral regrets are about things that conflict with our beliefs like stealing, lying and cheating.

Based on the research, one thing became apparent. Over time, we have more regrets about the things we did not do versus the things that we did do.

This makes sense. Our brains are wired to survive. When we start to consider trying new things, our brain activates a warning system because it’s moving out of a comfort zone — and “threatens” our survival.

We also live in a culture that is obsessed with positivity. It’s more acceptable to share happy moments and inspirational quotes than how we’re working through difficult times and feelings.

In fact, we take Herculean efforts to avoid rejection and failure. We would rather avoid a painful experience than to learn and grow. Of course we’re not all one way or the other. We take risks in some areas, but not so much in others.

When it comes to our careers, we might have regrets about staying in a job for too long, not pursuing a career change we really wanted, not going for a promotion or not speaking up enough.

I often hear a lot of “should’ves” when people walk me through their career. For many of us, we put our careers on autopilot, especially when we have big life events that require a lot of energy. And sometimes we just get comfortable and then 2, 5 or 7 years pass and we look up and wonder how we ended up in a role that doesn’t excite us.

Benefits of regret

Regret is a negative emotion that can lead to a positive impact. When we’re brave enough to explore our feelings of regret, we gain clarity and get to learn and grow. 


  • Teaches us what we want to change: when we’re tired and stressed, we might snap at our colleagues or loved ones. Later we feel guilty about it. We wish we weren’t so harsh or could have a do-over. This can lead us to learning new coping skills like taking deep breaths before we act or asking for some space.
  • Shows us what we want in life: when we feel like we missed out on an opportunity and can’t shake it, we learn what’s important to us. We can then proactively create an experience that we desire and feel even more grateful when it happens.
  • Makes us whole: when we embrace and process the full spectrum of emotions, including the negative, we tap into our authentic self. We feel light and free — which allows us to show up authentically. And it makes us even more relatable and likable. 

Steps to process regret

When we give ourselves the time and space to explore our regrets with non-judgement, we are able to let go of the hurt and pain and feel empowered. 

Here are some steps Daniel suggests to process regret.

  • Journal. Writing about negative experiences helps us make sense of the situation. It makes sense of the big and nebulous feelings we have and creates clarity. So write whatever comes to mind when you think of a regret. 
  • Write a failure resume. Make 3 columns. List things that you regret in one column. Write what you learned in the 2nd one. And then what you’ll do differently in the future in the 3rd one. This also helps us see how we’ve been able to overcome obstacles and move forward.
  • Share with others. Daniel says he’s a fan of regret circles — getting 5 or 6 people together and sharing a regret. The act of disclosure is liberating and feeling supported amplifies your healing. It’s also valuable to understand you’re not alone and that regret is a natural, and even an essential part of the human experience.
  • Practice self-compassion and kindness. We haven’t been taught how to deal with negative emotions, so we either ignore them or berate ourselves (which makes us not want to deal with them even more). Kristin Neff’s work on self-compassion shows that kindness is a powerful tool for building emotional resilience and reducing stress and anxiety. So please, be as kind and compassionate to yourself as you are to others.

Deep self-reflection takes a tremendous amount of courage. You already have everything you need to face your regrets, learn and embrace new challenges. Be brave, be bold and be kind, my friend. I believe in and support you!

If you’d like to learn more, here are some helpful resources:

Power of Regret by Daniel Pink

Dare to Lead podcast with Brené Brown

TedX: Self-compassion by Kristin Neff

If you’re ready to take bold action and make a strategic career move, watch our video and book a session with one of our job strategists. We’re excited to talk about your career goals!

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