3 embarrassing moments that changed my life

Shaan opens by saying the episode contains three embarrassing moments that changed him. In social situations, he believes he is fundamentally trying to avoid embarrassment—possibly even more actively than he avoids pain or death, which he does not think about as much. Embarrassment still finds him often, though, and once the sting fades it usually leaves behind learning, growth, or some other benefit. His framing for the episode is that “sometimes the wound becomes the door.” The first story begins after Shaan sold a company for more money than he had ever made. Unsure what to do next, he hired a life-direction coach, who gave him an unusual personality test and asked him to answer honestly across work, personal life, and relationships. When the coach showed him the results over Zoom, Shaan had low scores in most categories but scored 110—or possibly 115—on a narcissistic personality-tendency scale. His immediate reaction was itself narcissistic: “That’s right. I win.” Then he became embarrassed and wondered whether the coach was effectively calling him arrogant or narcissistic. The coach explained that the trait was not simply an insult, but something Shaan needed to understand.

The coach told Shaan that people high in this trait tend to feel special and believe their lives will be special, so ordinary averages, rules, and norms do not fully apply to them. Shaan recognized himself in that description: he had always taken pride in rejecting an ordinary life and assuming that general statistics would not apply to him because he was an outlier. The coach agreed that this belief had served him, but warned that what serves someone can also harm them—the “dose makes the poison.” It can motivate someone to start a company despite the statistic that 90% of businesses fail, but it can also make them ignore useful limits. The distinction from ordinary self-confidence, the coach said, is that narcissism often involves a vague belief that something about you is special without knowing exactly what it is. Because the belief is fuzzy, the person seeks confirmation from other people through social media, content creation, public speaking, or similar activities. Shaan recognized all of those behaviors in himself. External validation creates a high when people affirm your specialness and an unusually deep low when they simply fail to notice you—not only when they criticize you. He connected this to hosting an event for roughly 30 exceptional founders. Even while the event was going well, he could feel insecure and want the attendees to know how impressive he was. He described the experience as having “gone to heaven” but feeling “hell” in his own head. The coach’s remedy was awareness first, then clarity about what is genuinely special about you, so you can fill your own cup rather than waiting for other people to do it. Shaan says he has not fully reached that state, but seeing the score gave him a mirror and let him adjust.

Shaan’s second recent embarrassment came through a blunt phone call from Scott Harrison of Charity Water. Shaan says they know each other but are not friends and had not spoken by phone in about ten years. Harrison said he had been listening to Shaan’s podcast and thought Shaan did a good job, but asked whether Shaan wanted to become great at podcasting. When Shaan said yes, Harrison told him to stop saying “like” so often. Harrison estimated that Shaan said “like” roughly 500 times in an episode. He told Shaan the problem was fixable: pay attention to it, work on it, and the podcast would improve, especially because Shaan was already doing many other things well. Shaan felt two reactions at once. He was embarrassed to be called out for a verbal tic by a podcaster, but he also appreciated the feedback because Harrison was not trying to gain anything from it. Harrison had simply noticed a problem and made sure Shaan knew about it. Shaan treats the call as an example of the value of people who will tell you the truth in an uncomfortable, non-self-serving way. He thanks Harrison and says he is still working on the habit. The larger lesson is that an embarrassing correction can be a gift when it identifies something concrete that can be improved.

At 21, Shaan and two friends decided they would build the next Chipotle, Subway, or Five Guys—but for sushi. Shaan admits he was not a foodie, sushi chef, or someone who had grown up eating sushi; he had only tried sushi a few months earlier. Still, he had the confidence of a beginner and believed he knew what he was doing because he had won a business-plan competition. The group cold-emailed founders of restaurant chains, and the founder of Noodles & Company invited them to lunch. For three months, Shaan interpreted hard work as planning rather than testing the idea. The group created forecasts, financial models, employee uniforms, promotion systems, and other operational details. They printed a roughly 250- to 300-page business plan and brought it to the meeting, expecting to impress the experienced founder. When he flipped through it quickly, Shaan realized the meeting was going badly. The founder was not rejecting them angrily; he appeared to be searching for a polite way to explain how hopeless their preparation was. Shaan finally told him to be direct. The founder said the plan was “nothing” and not how a restaurant is started. He said they should find a location, sign a lease, put down a deposit, set a 90-day opening target, start serving customers, and learn how to make them happy. The three friends returned to the basement where they were living, sat silently in the car, and recognized that they had spent five months getting no closer to a restaurant. Shaan says they had lost little besides their dignity, but the embarrassment showed them they had been avoiding the real work.

After the restaurant meeting, Shaan and his friends procrastinated by watching a Seinfeld episode in which George Costanza decides his life has gone wrong and that he should do the opposite of his usual behavior. George changes his regular chicken-salad order to tuna on toast and approaches a woman by presenting himself honestly as a single man who lives with his mother. Shaan used the episode as a model for his own reset. He asked what the group had been doing and concluded that they had been planning endlessly to impress people instead of taking action. From then on, he decided the company would be about doing the thing rather than making the plan look impressive. He says he became “a man of action,” effectively worshipping at the “Church of Action”: whenever action and inaction were alternatives, he chose “tuna on toast.” The change served him. A year later, the founders found a mentor, acted on his advice, and returned roughly 48 hours later with results, lessons, and next steps. After repeating that process three times, the mentor wrote publicly that he did not know whether their idea was good, but they had the highest bias for action of any founders he had met. For Shaan, that public observation validated the lesson from the embarrassing meeting. The point was not that planning has no value, but that planning had become a safe substitute for validating the business. The wound forced him to start learning through contact with reality.

Shaan’s third story comes from adolescence, when he was extremely shy. His older sister called him “the laugh track” because at school he was not the main character, love interest, or even sidekick; he was background noise with a few friends. He liked a girl and wrote what he calls a note—probably a poem—describing how wonderful an unnamed girl was. He arranged for the girl to find it by their lockers. She read the note and asked who it was for. Shaan says the two of them were so far apart emotionally that she could not imagine it was about her. Although he considered admitting the truth, he panicked and invented a girl he had met at a competition who attended another school. The girl then asked for updates for the next six months, forcing Shaan to maintain the lie. He says he dug himself deeper until his family moved from Houston, Texas, to China and he left for a new school in 10th grade. On the flight, his sister told him that nobody at the new school knew him. When he responded skeptically, she explained that this meant he could be anybody. She asked who the coolest person at his old school was, and Shaan named Casey Priseman, a class clown who was athletic, kind, and friendly. His sister told him he could simply be that person at the new school. Shaan took the idea seriously: in each situation he asked what Casey would do and did that. What initially felt like acting became a new way of behaving, and he learned that reinvention starts with a decision.

Shaan generalizes the China-school experience into a broader claim: people do not need to move countries to reinvent themselves. They can decide that an old identity describes who they were, then begin acting as someone else. He calls the decision “upstream of all action.” In his account, choosing a new identity makes different behaviors available, and repeated behavior eventually makes the identity feel real rather than performed. He says he has reinvented himself several times by stripping off old labels and applying new ones. Before launching his podcast, he thought of himself primarily as a technology entrepreneur and received his value from that role. Then he decided he wanted to be like Tim Ferriss: someone who could entertain people while giving them enough insight that they would want to listen again. He was not yet that person, but he believed the identity and acted from it. The next day, he asked what Tim Ferriss would do, decided that person probably would not spend the day in meetings, created a show, booked a studio, and recruited a friend as the first guest. That became episode one of My First Million. He closes by returning to the three wounds. The useful question after losing dignity is not only what was lost, but what was gained: awareness of a damaging need for validation, a bias toward action, or permission to reinvent yourself. The gain may be hidden at first, but answering what it was is how embarrassment becomes growth.