REGRET: YOUR SUPERPOWER

Who hasn’t thought, ‘If only I’d made a different choice…’? Regret stings. But it also reveals something positive and powerful — a desire to do better. Beneath the discomfort lies fuel for growth: personal and organizational.

Ignoring regret holds us back

In this age of relentless positivity, we’re often told to ‘move on’ and to ‘stay optimistic’. But pretending everything is always fine doesn’t always help. It doesn’t teach us anything. 

Too much positive thinking can lead to missed signals - brushing past mistakes we were meant to learn from. Regret, if acknowledged, can become a teacher. A guide. Sometimes even a turning point.

The hidden wisdom in regret

Author Daniel Pink believes we should reframe regret not as a trap, but as a tool. Research he has conducted highlights four core types of regret that show up in nearly everyone’s life:

• Foundation regret – ‘If only I had prepared better…’
• Boldness regret – ‘If only I had taken that chance…’
• Moral regret – ‘If only I had done the right thing…’
• Connection regret – ‘If only I had reached out…’

But for Pink these aren’t just feelings. They’re signals — showing us where we’ve drifted away from who we want to be. Psychologist Tory Higgins explains it like this.

Inside all of us are three versions of self: who we are; who we want to be; and who we think we should be. Regret surfaces when those versions don’t align — especially when we miss the chance to live up to our ideal self.

And it’s important to remember that even the most successful people harbour regrets. The difference? They use them to their advantage, as the following two examples show.

From mistake to momentum

GoPro came to the marketplace offering tiny cameras capable of capturing almost any activity. But as it grew more successful, the company expanded too fast, chasing trends with more expensive drone technology and offering its own media platform as a rival to such others as YouTube. As CEO and founder Nick Woodman said later, “We went wide instead of deep.” So he admitted his mistake and refocused the company on what it did best: action cameras. And it was this move that helped it recover.

Starbucks was known as the place to meet away from home and work. A social space, serving good coffee. But as success grew, that core offering changed. A Starbucks app was introduced, to help customers order coffee to go. Prices rose. The ‘local coffeehouse’ atmosphere faded. Recognising this error, CEO Howard Schultz closed underperforming stores, and refocussed the Starbucks chain to regain that feeling of a community hub.

These two individuals didn’t ignore their regrets. They learned from them — and recalibrated.

But what about companies?

Can companies regret?

They’re made up of people. So yes — they can, and should, reflect on their actions with the same honesty as individuals. They should do so because, too often, the ‘fail fast’ business concept – that companies should use a trial-and-error approach and move on quickly if something doesn’t work -  becomes a slogan rather than a practice. They don’t stop to think about what went wrong. And that’s a mistake, because real learning requires courage — to admit what didn’t work and why.

So here’s how Daniel Pink’s regret framework applies to teams and organizations:

• Foundation regret – ‘We rushed to the market without enough testing…’
• Boldness regret – ‘We played it safe and missed the moment…’
• Moral regret – ‘We didn’t act in line with our company values…’
• Connection regret – ‘We neglected key relationships…’

Every one of these regrets holds a lesson. The question is: are we willing to look? And if we are, then what do we do next?

Turning regret into action

Here are four simple, powerful ways to put regret to work:

• Create Team Regret Logs – Document, and learn lessons from, decisions that didn’t pan out.
• Hold monthly Reflection Sessions – Create space for open, blame-free sharing discussions.
• Build Failure Libraries – Build a knowledge base that details past missteps.
• Reward reflection – Celebrate honesty and insight, not just outcomes.

And always remember: this isn’t about dwelling on the past — it’s about learning. Together.

Regret isn’t weakness. 

It’s awareness.

Regret shows we care — about our choices, our values, our impact. And that means we still have the power to shape what comes next. So instead of hiding our regrets, and ignoring them, let’s honour them. Learn from them. Grow through them.

Because the most meaningful change — in life and leadership — often starts with a simple question: 

‘What will I do differently next time?’