From Agartala to Fortune 500 rooms

The first time I sat across from a client whose annual budget was larger than the GDP of the town I grew up in, I spent the first ten minutes worried about my shoes.

Not the deal. Not the roadmap. My shoes. Whether they were the right kind of shoes for a room like this, with its frosted glass and its single, expensive plant in the corner. I’m from Agartala — capital of Tripura, tucked into a corner of Northeast India most of my colleagues couldn’t find on a map without help. I didn’t leave for Bangalore or Delhi like the ambitious-kid script demands. I left for Chennai at sixteen, a stranger to the language, the food, the unspoken rules. And here I was, years later, in a room full of people who had clearly never once wondered about their shoes.

That voice — you don’t belong here, and any minute now they’ll find out — has a name now. We call it impostor syndrome. Back then I just called it Tuesday.

The voice doesn’t leave. It just changes outfits.

Here’s the lie nobody warns you about: you assume the voice goes quiet once you’ve “made it.” It doesn’t. It just upgrades its wardrobe to match the room.

In my first small businesses through college, the voice said you’re a kid playing at this. At IIM Lucknow, it said they let you in by mistake. Leading product teams at a US SaaS company, managing relationships worth more than I could comprehend, it said you’re a small-town boy in a borrowed suit, and the borrowing is about to be noticed.

The content was always the same. Only the production budget went up.

What took me an embarrassingly long time to understand is that the voice isn’t a glitch. It’s a tax. Specifically, it’s the tax you pay for standing just outside your comfort zone — which, inconveniently, is the only place growth actually happens. If the voice is quiet, you’re probably not stretching. The discomfort isn’t proof you’re a fraud. It’s proof you’re in the right room.

The impostor voice is loudest precisely when you’re doing the most important work. It’s not a stop sign. It’s a mile marker.

Why “fake it till you make it” never worked for me

The standard advice is to manufacture confidence. Stand in the power pose. Talk louder. Project. Fake it till you make it.

I tried. It’s exhausting, and worse, it’s brittle. Faking confidence is pure willpower — you’re forcing yourself uphill against your own design, and the moment you’re tired or caught off guard, the performance collapses and the voice comes roaring back with receipts.

Anything that runs on raw willpower costs you every single time and never compounds. What I needed instead was a different default — a way of walking into those rooms that made the right behaviour the easy one, so I wasn’t burning willpower in every meeting. The trick, it turned out, is to push only until the hard thing becomes automatic, and then let it carry you.

That default turned out to be preparation, not performance.

What actually moved the needle

Three shifts, and none of them are about feeling more confident. They’re about needing confidence less.

1. I stopped competing on polish and started competing on preparation. The McKinsey graduates in the room had a fluency I’d never out-perform on charm. So I quit trying. I’d walk in having done the unglamorous homework nobody else bothered with — the client’s actual numbers, the thing their CFO was quietly afraid of, the question behind their question. You can’t fake your way past a man who’s read the brief three times. Polish is a fragile thing; being the most prepared person in the room is not — and it doesn’t require me to feel anything in particular.

2. I reframed the outsider thing as the asset. For years I treated “small-town, Northeast, came up the hard way” as the thing to hide. Then I noticed: I saw problems the insiders were blind to, because I’d never been told they were unsolvable. My curiosity about anthropology — about how different people see the same thing differently — wasn’t a quirk. In a Fortune 500 room full of people who all went to the same five schools, being the one who thinks sideways is not a deficit. It’s the entire reason you got a seat.

3. I let commitment carry the days when confidence wouldn’t. Some mornings the voice wins the first round. Interest is fleeting; it evaporates the instant a meeting goes sideways. Commitment is duller and far more useful — it’s what gets you into the chair on the day you feel least like a CEO and most like the kid worrying about his shoes. You don’t need to feel ready. You need to show up committed, repeatedly, until showing up stops costing you anything.

The room was never the test

Here’s what I’d tell the version of me staring at his shoes: the boardroom was never the real test. The real test was whether I’d let a voice — one I inherited somewhere between Agartala and Chennai, that has nothing to do with my actual competence — quietly negotiate my ceiling on my behalf.

That voice will never fully shut up. I’ve stopped expecting it to. Mine still pipes up before big rooms, and I’ve come to read it the way a pilot reads turbulence — uncomfortable, informative, not a reason to land the plane. The work isn’t silencing it. The work is refusing to let it sign your decisions.

If you’re the first in your family to be in rooms like this — first-generation businessperson, first to leave the small town, first to sit at a table where everyone else seems to have a manual you never got — I want you to hear the one thing it took me twenty years and a whole book to be able to say plainly: the discomfort is not a verdict. It’s the entry fee. You belong in the room not despite the unlikely road that got you there, but because of it.

I built a set of free tools and trackers for exactly this kind of work — the slow, unglamorous job of turning the things that cost you effort into things that eventually run on default. Because the goal was never to become a person who feels no doubt in the big rooms. It was to become a person who walks in anyway, prepared, and stops checking his shoes.