What Regret Can You Live With?

I’m not a natural risk-taker. I like stability, predictability, the comfort of knowing what comes next. Nor am I a purist or rigid conformist — I bend, negotiate, and adapt.

And yet, life has pushed me to crossroads that changed me. Moments where every choice felt like a gamble, where hesitation carried its own cost, and stepping forward meant leaving almost everything familiar behind. Choices that shook me, demanded more courage than I thought I had, and left me different.

Yes, there were moments of fear — anxiety, palpitations, even tears. But I rode the storms. I’m no superman, far from it, but courage isn’t the absence of fear. It’s moving forward while your heart races, while doubt shouts, while nothing feels certain.

Some time ago, someone sent me an article about Søren Kierkegaard, the 19th-century Danish philosopher. He suggested that whatever you choose, you’ll regret it: marry — regret, don’t marry — regret, leap — regret, wait — regret, stay — regret, let go — regret. Some form of regret seems to follow every choice.

At first, I thought it was bleak. Life seemed like a string of impossible choices, each shadowed by doubt. I lingered on the roads I didn’t take and the steps I hesitated to make.

Then I remembered Robert Frost and his famous poem The Road Not Taken. Two paths diverge in a wood, and we must choose one. The path we walk becomes real — messy, stubborn, imperfect. The one we didn’t take? Perfect only in memory and imagination.

That tension is the human condition. That is what it feels like to choose. And then it struck me: perhaps Kierkegaard wasn’t being pessimistic. Perhaps he was being honest.

Regret is part of life. There is no perfect decision. No step that leaves every door open. The real question is not how to avoid regret — it is which regret you are willing to carry.

I’ve faced that question twice in my professional life. First when I left Allahabad for Pune, and later when I moved from Pune to the UAE. Both decisions carried risk, and both carried quiet regret at the time. What if it doesn’t work out? What if I’ve taken a step backward?

Yet both moves proved right. They pushed me farther than I imagined. They reshaped my life. Sometimes stepping into the unknown is the only way forward. Yes, a step back is always possible. But a step forward can carry you miles beyond what you imagined.

Every yes closes doors — but every yes also opens thousands more.

I’ve seen this truth beyond my own choices: married people pretending they’re happy, bachelors quietly aching, leaders agonising over strategy, executives second-guessing every hire. The pattern is the same: all choices carry regret.

Human beings are terrible at choosing if we expect perfect clarity. But we can be remarkably good at choosing the regret we are willing to live with. That is courage. That is freedom.

Regret born from fear lingers. Regret born from courage settles. One shrinks you. The other deepens you.

Leadership, in the end, is not about avoiding regret. It is about asking one simple but uncomfortable question: which regret can I carry and still respect myself?

Can I live with the regret of trying and failing? Or will I struggle more with the regret of never stepping in? Because not choosing is also a choice — and it has its own cost.

When the season ends, and every season eventually does, what version of you will you respect more — the one who protected comfort, or the one who protected conviction?

The perfect choice never existed. The perfect road never existed. All that truly exists is the courage to say yes anyway — and the regret you are willing to live with.

Every yes closes doors. But every yes also opens worlds you could never have seen from where you once stood. You cannot see them all. You cannot guarantee success. But stepping forward — fully aware of risk and regret — is what moves life, leadership, and the self from something small and safe to something real, alive, and unforgettable.