There’s a question that creeps up quietly, often when things slow down — on long walks, in the shower, or during those stretches of silence between emails.
“Would I make that decision again?”
Sometimes the answer is immediate. Other times, it’s slippery. Because the real question beneath it is harder: Do I regret it? And even more than that: What did I learn from it?
We all carry decisions that sit uneasily with us. A job we took. A person we let go of — or held on to for too long. A conversation we didn’t have. A risk we didn’t take. Or one we did, and paid for.
And when we look back, we don’t just see the decision — we see the consequences. And we may judge ourselves.
But here’s what I’ve learnt: We don’t evaluate past decisions with the thinking we had back then. We judge them using the thinking we have now. Which means we’re often holding our past self to a different standard.
Daniel Kahneman, the Nobel Memorial Prize winner best known for his work on the psychology of judgment and decision-making as well as behavioural economics, called this hindsight bias — the illusion that once we know the outcome, we believe it should’ve been obvious all along. It makes us feel like we should’ve seen it coming — and erases how uncertain things really felt in the moment.
Kahneman however also pointed out something subtler:
when we remember, we remember the feeling of the outcome more than the quality of the process.
Which means regret can be misleading — because it’s often driven by how something ended, not how well we thought it through.
I catch myself asking (more often than I’d like), “I should’ve known.” “Why didn’t I see that coming?”
But the truth is, I didn’t know. Not because I was blind or careless, but because at that point in time, I was doing the best I could with the facts I had access to and understood.
Would I make the same decision today? Maybe. Maybe not. But that’s not failure — it’s evolution.
That’s the part we forget to notice: The distance between who we were when we made the decision — and who we are now, able to see it differently.
So no, I don’t always make peace with every choice. Some things still sting. But when I ask, “Would I make the same decision again?” — I try to answer with more curiosity than criticism.
Because every “no” is also a quiet sign that I’ve grown.
Anu D’Souza
Anu D’Souza runs Bricoleur Consulting, a leadership coaching and recruitment company focused on the digital and technology industries. A thought leader on innovation, transformation and leadership, Anu has spent many years with companies like Unilever, Ogilvy and BBDO and has lived and worked in multiple cultures. Anu is also the author of ALIGNED Why CEOs need Company Brand Alignment in the Age of a Questioning Workforce. You can reach her on anu@bricoleurconsulting.com or book a call here.
