I am sorry: this might be the slap that was not expected.
The Mathematics of Regret
Here’s a truth backed by actual research from Cornell University’s Gilovich study on regret:
People don’t regret the things they did and failed at. They regret the things they never tried.
The business not started. The trip not taken. The conversation not had. The love not declared. The dream deferred until it died of neglect.
Your deathbed self won’t think, “I’m so glad I played it safe.”
But they might think, “Why didn’t I just try?”
The Indian Paradox: Risk-Averse Yet Entrepreneurial
India produces more engineers than any country on Earth. We’re brilliant, hardworking, and educated.
Yet we’re also the nation where parents plan their children’s lives from conception to retirement. IIT-IIM-MBA-MNC-Marriage-
But something’s shifting.
Vineeta Singh was a topper at IIM Ahmedabad. She had offers from every consulting firm that mattered. Instead, she started SUGAR Cosmetics from her living room, faced rejection from 200+ investors, and kept going.
Today, SUGAR is valued at over ₹3,000+ crores.
Falguni Nayar left a cushy Managing Director position at Kotak Mahindra after 19 years—at age 50—to start Nykaa.
At fifty. When most people are thinking about retirement portfolios, not retail disruption.
Nykaa went public at a valuation exceeding $7 billion, making Falguni India’s wealthiest self-made female billionaire.
What did these people understand that you don’t?
They understood asymmetric risk. They played a game where the downside was bounded but the upside was limitless.
A Few Global Wake-Up Calls: When Courage Compounds
Sara Blakely cut the feet off her pantyhose, thought “this could be something,” and invested her $5,000 life savings into prototyping Spanx. No business experience. No fashion background. Just an idea and audacity.
She’s now worth over $1 billion.
Jan Koum was a Ukrainian immigrant living on food stamps in America. He taught himself computer programming, worked at Yahoo, then quit to pursue an idea: a messaging app with no ads. WhatsApp.
Investors laughed. Facebook offered him a job. He declined.
WhatsApp sold to Facebook for $19 billion.
The pattern? None of these people had a safety net made of gold. They had calculated risk tolerance and irrational conviction.
They asked themselves: “What’s the worst that could happen?” And the answer was never death. Just discomfort. Embarrassment. Starting over.
The Risks You’re Not Taking (And Why You Should Be)
Career Risks
- Asking for the promotion you deserve
- Leaving the soul-sucking job for the uncertain venture
- Speaking up in meetings when you have the better idea
- Starting the side project you keep postponing
Worst case? Temporary setback. Ego bruise. Resume gap.
Best case? Career transformation. Financial freedom. Purpose.
Relationship Risks
- Telling someone you love them
- Ending the relationship that’s draining your life force
- Setting boundaries with toxic family members
- Apologizing when you’re wrong
Worst case? Rejection. Loneliness for a season. Uncomfortable conversations.
Best case? Deep connection. Self-respect. Peace. Love that actually nourishes you.
Creative Risks
- Publishing your writing
- Sharing your art
- Starting that YouTube channel
- Launching that podcast everyone says “is saturated”
Worst case? Crickets. Criticism. “I told you so” from skeptics.
Best case? Impact. Income. A body of work you’re proud of. Legacy.
The Action Protocol: How to Take Intelligent Risks
Step 1: Define the Worst-Case Scenario
Write it down. Be brutally honest. What’s the actual worst that happens? Not your anxiety-brain version. The real version.
Step 2: Ask “Can I Handle This?”
If yes, continue. If no, adjust the risk.
Step 3: Define the Best-Case Scenario
Dream big here. What happens if this works?
Step 4: Calculate the Asymmetry
If the best case is 10x better than the worst case is bad, you’ve found your Goldilocks risk.
Step 5: Set a Deadline
Courage without timeline is just fantasy. Pick a date. Do the thing.
The Indian Classical Example: Arjuna’s Dilemma
The Bhagavad Gita—our own ancient text—is literally a conversation about taking the right risk at the right time. Most of you would be very aware of this already.
Arjuna stands on the battlefield, paralyzed by fear disguised as ethics. Krishna doesn’t tell him to be reckless. He tells him to act according to his dharma, to take the risk that aligns with his purpose.
“You have a right to perform your prescribed action, but you are not entitled to the fruits of action.”
Translation? Take the intelligent risk. Detach from the outcome. But take the risk.
The Question; The Introspection
Here it is. The question that will either haunt you or liberate you:
“Five years from now, will I regret not trying this?” –If the answer is yes, you already know what to do.
In Signing Off
You’ve read this far, which means part of you knows you’re playing too small.
You know there’s an ask you need to make. A leap you need to take. A conversation you need to have. A business you need to start. A relationship you need to end. A dream you need to chase.
You know it.
And you’re still here, reading, because some part of you is looking for permission.
Here it is: You’re allowed to want more. You’re allowed to try. You’re allowed to fail. You’re allowed to succeed.
The world doesn’t need more people playing defense with their one precious life.
It needs people who understand that the biggest risk is risking nothing at all.
The Risk That Doesn’t Kill You Might Just Make You a Legend
Somewhere between the coward who never leaps and the fool who jumps without looking, lives the sweet spot of risk. It’s that rare kind of risk where the worst case scenario is more like a bruise than a breakup, and the best case? A life-flip so dramatic it leaves you blinking in disbelief.
Look for risks where you won’t be crushed if it backfires, but you’d be blown away if it pays off.
Most people don’t take these manageable risks. Why? Because risk whispers 50/50 but fear shouts 100/0. So, they settle for “safe.” Safe is polite but painfully dull. Safe rarely breaks headlines or molds legends.
Go on, ask your crush. Pitch that experiment your gut swears will work. Write that book, start that venture. With a safety net beneath you, the falling isn’t fatal—just a chance to rise smarter, quicker, sharper.
The Parting Shot
If your heart doesn’t race a little when you consider your next move, you might be standing still on the sidelines of your own life. Don’t be that person.
Remember: The best bets are ones where losing doesn’t break you but winning redefines you.
Take the shot. Risk the small to win the large. Be the legend who dared where others paused.