If a top executive on your team, or better yet, a great friend, made a decision that didn’t pan out, would you expect them to dwell on it indefinitely? Or would you expect them to assess, adapt, and move forward with clarity and purpose?
Now, ask yourself: do you hold yourself to that same standard?
I have noticed that most people often carry regret like a hidden tax—quiet, persistent, and draining. It shows up as second-guessing, hesitation, or an overly cautious approach to future decisions. And no one seems immune – even the highest performers seem to be paying this tax.
But here’s a big “secret” I have discovered: regret is not a weakness. Regret is a data point. And like any data point, its value lies in how you interpret and act on it.
Regret signals that something matters – that you’ve grown and evolved in your knowledge and understanding of what is important to you. Through this lens, regret is simply a checkpoint along your path. The most effective leaders I know don’t avoid regret—they mine it for valuable nuggets of data. Questions like:
- What did this teach me?
- What systems failed? Or could a system have prevented this from failing?
- What assumptions went unchecked?
It can be super helpful in mining something that went sideways or maybe did not happen at all. Armed with new data points, the most effective leaders can move forward intentionally and confidently to make better decisions based on these new data points.
Suddenly, what was once a regret has been transformed, alchemized even, into a valuable learning opportunity.
As my dad would say, the process I laid out is simple but not easy to execute – this is where coaching or strategic thought partnership becomes invaluable. Not because you can’t figure it out alone—but because you shouldn’t have to. We humans are built to be in partnership. A trusted advisor helps you reframe the narrative, extract the insight, and accelerate the pivot onto a new path with more clarity.
Remember: your past doesn’t disqualify you. It equips you. Every misstep and missed opportunity is the raw material for a more resilient, intentional version of you.
So, the next time regret surfaces, don’t suppress it. Interrogate it. Learn from it and move forward with the confidence and clarity that only wisdom and experience can offer.
Ready to turn reflection into momentum?
If you are a reader like me, I recommend you check out the brilliant and hilarious “You Only Die Once: How to Make it to the End with No Regrets” by Jodi Wellman, MAPP.
Or the slightly more serious but equally valuable (in my opinion) The Power of Regret: How Looking Back Moves Us Forward by Daniel Pink.
Both books give the reader the opportunity to reflect on the past in the most productive ways to learn and “alchemize” the things you did not do and wish you had.
If you have reflected as much as you have on your own and are currently navigating a pivotal moment and want a thought partner to help you move forward with clarity and confidence, let’s talk. Email me at [email protected] to start the conversation.
