3 embarrassing moments that changed my life

Why does it matter? Because your biggest asset and your worst liability are the same trait.

Three embarrassing moments. Each one Shaan would have paid to skip. Each one cracked open something he had been running on without seeing it clearly.

• Narcissistic self-belief and the compulsive need for external validation are the same mechanism — the very thing that makes you start companies is what makes you emotionally hostage to follower counts and elite-room status
• A 250-page business plan is three months of productive-feeling avoidance — a single lunch with someone who has actually built something will expose it in sixty seconds
• Pity from an experienced operator is a more actionable signal than rejection — it means you are not even playing the right game yet, which is more fixable than playing and losing
• Identity change is a decision that precedes every behavior — not a gradual process you earn once circumstances finally align

The trait that makes you ignore failure statistics is the same one that makes you crave external validation

He scored 110 on a narcissistic personality tendency scale. His first internal reaction, by his own admission: that is right, I win. Which proved the coach's point exactly.

The mechanism is precise: people with this trait carry a vague, unshakeable conviction that the normal rules do not apply to them. That is the fuel — it gets you to blow past the '90% of businesses fail' stat and go anyway. But it is vague. "You don't know what it is that's special about you. There's a sense that something is going to happen, but you don't have any specificity on it." Because you can't name it, you go hunting for external proof. Social media, public speaking, elite rooms — anything that confirms what you feel but cannot define.

The trap is asymmetric. High highs when the validation lands. Lower-than-normal lows when you just do not feel seen as special — not even a criticism, just absence. Shaan hosts events with thirty of the most accomplished founders alive and still gets that pang of needing them to recognize him. "I've gone to heaven and I'm feeling hell."

What served you can also screw you. The dose makes the poison.

Pity from an industry veteran hits harder than rejection — and a 250-page binder will earn you pity every time

They cold-emailed every fast-casual chain founder they could reach. The guy from Noodles and Company replied. Shaan and two friends showed up with a 250-page binder — three months of financial models, promotion tracks, employee dress codes. The last thing they had done was talk to a real customer or sign a lease deposit.

Shaan names it honestly: "My version of hard work was avoiding the actual work and doing the flavor I felt safe in." Planning looks like grinding. It is not.

He had braced for rejection — had even been hardened to it from earlier pitches. What arrived was worse. He could see the man from Noodles trying to figure out how to be kind, because it was not rejection, it was pity. Pushed to speak straight: "This is nothing. I don't know what you're doing. This is not how you start a restaurant."

They sat in the car without speaking. That night, Seinfeld — the episode where George, having hit rock bottom, decides to do the opposite of everything. Chicken salad has got him here. Today it is tuna on toast. Shaan converted on the spot. A year later, a mentor wrote publicly that they had the highest bias for action of any founders he had ever met.

Identity reinvention is a decision you make before any behavior changes — not a reward you earn afterward

His older sister called him the laugh track — not even a background character, the noise behind the scene. He wrote what was probably a poem for a girl at school, she read it and asked who is this for, because it had not occurred to her it could be for her. He invented a fake girlfriend from another school to cover. Maintained the lie for six months. Then his family moved to China.

On the plane, his sister said: "They don't know you're the laugh track. They don't know who you are. So you could just be a different guy."

He picked a model — Casey Pruzman, class clown, athletic, genuinely liked by everyone — and at each decision point asked: what would Casey do? At first it felt like acting. Pretty quickly, it did not.

The same move fired again years later when he decided to start a podcast. Not "I will become a podcaster once I have something to show for it" — just: what would Tim Ferriss do today? He probably would not go to meetings. So Shaan booked a studio, called a friend, made episode one of My First Million. That is the origin story. "The decision is upstream of all action." It always has been.

One honest call from someone with nothing to gain is worth more than years of polite silence

Scott Harrison — Charity Water founder, not a close friend — rang Shaan cold. He had been listening to the podcast. One note: "You say 'like' like 500 times in an episode."

The embarrassment landed first. Then the gratitude overtook it. Shaan asked himself: how many people in his life would make that zero-upside, genuinely uncomfortable call? Almost none. Harrison just dropped something useful at the door and left.

The coach's antidote for the narcissism problem connects here. The fix is not humility — it is precision. Get specific about what genuinely makes you exceptional, concrete enough that the cup is already full before you walk into any room. "When you filled your own water cup, you're not sitting around waiting for the waiter to come back." Seek out the two or three people who will say the hard thing. When they do, respond with immediate gratitude — so they know the door stays open.

The wound only becomes a door if you stay in the room long enough to hear what it is showing you

Most people treat embarrassment as something to survive and move past as fast as possible. The through-line across all three stories is the same: stay in the room, get precise about what the moment is revealing, then make the decision that precedes every new behavior. Shaan still has not fully solved the narcissism. But knowing what the cup looks like is already halfway to filling it yourself.

That is the real advantage — not the absence of the flaw, but knowing exactly where to look.

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Topics: entrepreneurship, self-awareness, psychology, identity, bias for action, validation, narcissism, personal growth, embarrassment, reinvention, feedback, mental models