How to think when you don't know what to do
With Ankur Warikoo · Hosted by Raj Shamani
Episode summary
Entrepreneur, author, and content creator Ankur Warikoo joins Raj Shamani on Figuring Out to talk about decision-making under genuine uncertainty — the moments where data runs out, advice contradicts itself, and you have to choose anyway. Drawing from his time as nearbuy.com's CEO, his post-exit reinvention as one of India's most followed creators, and the failures he openly documents, Ankur walks through his personal framework: the 10-10-10 rule, the regret-minimization test, and why most life-defining decisions should be made deliberately slow and most professional ones deliberately fast. The conversation is unusually personal — including how he decided to wind down nearbuy and what he'd tell his 30-year-old self today.
Key takeaways
- 1.Most decisions are reversible — the cost of acting fast on those is much lower than the cost of deliberating.
- 2.For the few decisions that are irreversible (marriage, kids, career pivots), use the 10-10-10 rule: how will I feel in 10 minutes, 10 months, 10 years?
- 3.Regret-minimization beats outcome-optimization — you can survive a bad outcome but not a regret you can't unmake.
- 4.Most career advice is survivorship bias — the people who give it succeeded, so they cannot honestly tell you what would have failed.
- 5.Public failure is a moat: when you document what didn't work, the lessons compound and competitors can't copy your scar tissue.
Full transcript
Transcript edited lightly for readability. Timestamps refer to the YouTube video above.
Ankur, the title of this episode is 'how to think when you don't know what to do.' Where does your framework even start?
It starts with asking one question: is this decision reversible? If yes, just decide. The cost of being slow is almost always higher than the cost of being wrong, because you can always change your mind. We waste enormous amounts of energy deliberating on things we could simply undo.
And for the irreversible ones?
That's where I use 10-10-10. How will I feel about this in 10 minutes, 10 months, 10 years? The 10-minute answer is usually fear. The 10-month answer is usually social pressure. The 10-year answer is almost always the truth. Most people optimize for 10 minutes and wonder why their life feels off.
You wound down nearbuy. Walk me through how that decision actually got made.
Slowly, and then all at once. For a year I was telling myself a story about why it could still work. Then one morning I asked myself: if I were starting today with the same cap table and the same team, would I start this business? The answer was no. The day you can't honestly say yes to that question, you owe it to everyone — your team, your investors, your family — to stop.
Why do you publish your failures so openly? Most founders hide them.
Because hidden failures compound into shame, and shame is the most expensive emotion an entrepreneur can carry. The moment I started writing about what I got wrong, two things happened: I stopped being scared of being found out, and the audience started trusting everything else I said. It turns out vulnerability is a content strategy.