In this Art of Charm podcast episode, Jay Shetty, a former monk who now creates online videos and hosts the On Purpose podcast, explains why self-doubt shows you care, how to strengthen your own conviction when others question you, and why upskilling, experimenting, and a trusted inner circle help you move forward.
Listen on: YouTube | Apple Podcasts
Key Takeaways
- Jay Shetty says self-doubt is a sign that something matters to you, because he does not doubt himself about things he does not care about.
- He treats doubt as a checking system: ask what the doubt points to, then decide what you can put in place to improve it.
- Self-doubt often comes from not having researched, practiced, or watched people who are already good at the skill, so learning and upskilling are how it fades.
- When family or friends doubt your path, he suggests strengthening your own conviction instead of trying to weaken their arguments.
- Do not let proving people wrong become your motivation, because then that person still controls you, and respond to the people who already support you instead.
- Aim for work that is true to you but also resonates with others, and accept that a finished 75 percent is better than waiting for a perfect version.
- Find your passion by testing a process you would love to do every day, such as shadowing someone for a day, rather than chasing a result like fame.
- Build an inner circle with both peers who understand your field and grounded people who remind you of your roots, and let each person play their own role.
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Who is Jay Shetty?
Jay Shetty is a former monk, online storyteller, and host of the On Purpose podcast. He was born and raised in London, and during his university years he spent summers split between working in the world of finance in London and living as a monk in India. After graduating he chose life as a monk, studying texts that are around 5,000 years old, and returned to everyday life about three years later. He says he has coached thousands of people one on one and in groups over about 13 years and has spoken to audiences ranging from empty rooms to thousands. He joined social media in 2014 and posted his first YouTube video in January 2016. Four videos he made for HuffPost reached 100 million views. At the time of this conversation he was working on a book.
Episode Chapters
- 00:00 From Monk to Online Storyteller
- 03:33 Why Stories Break Through
- 09:42 Choosing the Monk Experiment
- 14:23 Handling Doubters and Toxic People
- 21:06 When Family Doubts Your Path
- 27:22 Perfectionism and the 75 Percent Rule
- 30:28 Building a Relationship With Self-Doubt
- 35:38 Getting Comfortable Being Yourself
- 40:18 Finding Passion and Purpose
- 45:29 Experiment Like a Beginner
- 52:42 Building a Trusted Inner Circle
- 59:22 Books and the On Purpose Podcast
How did Jay Shetty go from monk to online storyteller?
Around 00:00 in the episode
Jay Shetty wanted to make 5,000 year old wisdom relevant, accessible, and practical for anyone, so after years of speaking in person he began posting video online in 2016. He aimed to make wisdom entertaining rather than feel like a class.
The episode opens with the question many people have when they first meet Jay Shetty's work: how does a monk end up telling stories on social media at such a large scale? Jay explains that when he became a monk and had the chance to study texts and books that were 5,000 years old, he kept asking how to make sense of them for someone with no background in them. He pictured the eighteen year old he used to be in London, someone being bullied at college, or someone who hates their job.
He says he saw huge benefits in his own life from living those principles, but he knew not everyone would run off to a mountain and live as he had chosen. So his goal became making the ideas relevant, accessible, and practical. Before going online he had already spent a long time creating content and speaking at universities, schools, and companies, testing what resonated and what connected with people.
He joined social media in 2014 and launched his first video in 2016. He describes reading a study saying more people own a mobile phone than a toothbrush, which convinced him that video was the best way to reach anyone with a phone. He jokes that his first upload seemed to do well mostly because he kept refreshing the page and watching the views climb.
Within about three months, he says, someone showed his video to Arianna Huffington at Davos, and her team asked him to create a series for HuffPost. He made four videos, and they reached 100 million views, which he describes as a big turning point for his trajectory. In 2017 he began focusing on his own channels. The through line he names is making wisdom entertaining, practical, accessible, and actionable so people can live it that same day.
Why does storytelling connect with people so deeply?
Around 03:33 in the episode
Jay Shetty says a story that is real and genuine breaks through pain and connects people. He learned this from monks who were storytellers and from years of sitting with people's struggles.
Asked whether he was always a storyteller, Jay says he was and still is a big introvert and was the shyest kid in school. He credits Eminem for his love of English, describing how he enjoyed bending words, searching a thesaurus for synonyms, and looking up deeper definitions so words could rhyme or mean something else. He became fascinated with spoken word around age 14.
He adds that he cannot take all the credit. As a monk, much of what he learned came through ancient, timeless stories, and he was surrounded by incredible storytellers. His job was to tell their stories in a way that felt relevant today. Over roughly 13 years he has coached thousands of people, and he says that sitting with people's pain taught him that a story, when it is real, is what gets through.
To show what he draws from old stories, he tells one attributed to Alexander the Great, while noting he is not sure how factual it is. On his deathbed, Alexander is said to have made three wishes: that the best doctors carry his coffin, that the path to his funeral be laid with all the riches he had gained, and that his hands be left outside the coffin. The meanings were that even the best doctors cannot save you from death, that you cannot take anything with you, and that we arrive and leave empty handed.
Jay says he tries to live by the belief that we all have a finite number of breaths and a chance to make them count. He also cites a thought from Maya Angelou, that people will forget what you did and said but never how you made them feel. For that reason he says his videos are about how he makes people feel, whether that is self-worth, growth, confidence, or self-esteem.
How do you make a big life change like becoming a monk?
Around 09:42 in the episode
Jay Shetty treated it as an experiment. He split his summers between finance in London and living as a monk in India, then compared the two, and he recommends testing ideas through action instead of only thinking about them.
Jay explains that we all look for role models when we are growing up. His were celebrities, CEOs, and entrepreneurs, but at 18 he met someone who was truly happy, and he says that is rare. Many people he met had money, success, or admiration and were still sad. He was captivated by this person's happiness and simply decided he wanted it.
He describes how we tend to want whatever we feel in the room: around someone with followers, we want followers, and around someone with a yacht, we want a yacht. He was fortunate, he says, to be in a room where the most desirable thing was happiness. From ages 18 to 22 he spent his summer holidays half working in bars, steak houses, and finance in London, and half living as a monk in India. He calls it his first split test, and after four years he was convinced the monk life was more meaningful, more purposeful, and made him happier.
His advice is to experiment with things: live it for a week or a weekend instead of just thinking about it, and get out of your head and into action. He says that if he had only thought about it, he probably would not have done it.
Asked what he saw in that person, Jay names three things. First, the man did not try to justify his success; Jay learned only later that he had given up jobs at Google and Microsoft. Second, he was totally himself and looked comfortable in his robes, even though a room of young people was not going to be impressed by robes. Third, Jay felt he genuinely meant what he said. When Jay later saw him in India, he was exactly the same, and Jay points out how rare it is to stay the same whether you are with a crowd or one person.
How do you deal with toxic people who doubt your path?
Around 14:23 in the episode
Jay Shetty says build the other side of the bridge first, so leaving doubters is easier. He also avoids making proving people wrong his motivation, because that gives them control, and he spends his energy on the people who already support him.
Jay recalls that when he decided to become a monk in 2010, the reactions from friends at university were that he had gone mad, been brainwashed, or worse. Everyone was confused because he had seemed normal in every other way, and he was giving up a path to a bank or a tech company. He says he was so sure of what he wanted that he would not let other opinions break him down, even though it was uncomfortable at first.
He uses a bridge metaphor. Toxic relationships are hard to leave when you have not pictured the bridge you want to cross and have not built the other side. Over four years he had built great relationships with monks and a solid practice, so stepping away from the negativity was not hard. Without that other side, he says, it would have been super tough.
On people who doubted him and later wanted back in, he says he has tried to remove the thought that he has to prove anyone wrong. If proving them wrong is your motivation, that person now controls you and you keep seeking their validation. He keeps his distance from people who left and returned, trusts those who stayed, and sees the situation as showing him his true friends, including friends who said honestly that they did not understand him but would stick around.
He also describes a habit of attention. We amplify the one negative comment out of a hundred positive ones, so he replies to people who are already positive, because responding to positivity increases it. He skips over negative comments, takes feedback on board when it is useful, and does not try to change the minds of keyboard warriors. A story shared in the conversation about spending a day and a half replaying a pointless, critical dinner conversation underlines how much time that kind of rumination can waste.
What should you do when family doubts your big decision?
Around 21:06 in the episode
Jay Shetty suggests asking whether the person is invested in your future, will be there when you struggle, or pays your bills, and asking whether you would resent them on your deathbed. Then strengthen your own conviction.
The conversation turns to doubt that comes from people who love you. Jay says it was hard. He graduated but did not attend his graduation ceremony because he went straight to India, so his mother has no photo of him holding his degree, and that mattered to her. His parents were fairly liberal and supportive, he says, while it was his extended family who had more opinions and stirred things up.
To decide whose opinion mattered, he used a three part check: is someone invested in my future, will they be there when I am struggling, and are they paying my bills. He also asked himself whether he would look back on his deathbed and feel that his parents had held him back, and whether he might become bitter toward them. Since he never wanted to feel that about his parents, he decided to take responsibility for making the shift.
He argues that when we feel people are holding us back, it is often us not taking responsibility to push forward. If someone told you there was a million dollars waiting in New York, nobody would say their parents cannot afford it; you would get on the plane. He adds that he did face people who said he would fail, that nobody would hire him, and that he would be socially dead. It did not get amplified because he was strong in his conviction.
His main advice is to keep strengthening your conviction instead of trying to weaken the argument, because other people's opinions weaken when you strengthen your own. The discussion also stresses that people who truly love you keep their door open if you fail. Jay shares that when he came back from being a monk after about three years, some said they had told him so and others asked why he was back so early, and it felt like failure. Still, he asks why anyone wants people around who only love them when they do what they are told.
How do you beat perfectionism when creating content?
Around 27:22 in the episode
Jay Shetty aims for every video to be 75 percent complete, because waiting for perfection means never publishing. He also tries to create work that is true to him and still resonates with an audience.
Asked about perfectionism and the pressure to have a huge impact, Jay describes types of creators. The sellout creator only goes with what the audience wants and drops anything they care about. The selfish creator only makes things for themselves, and often nobody wants to watch. He aims for the middle: every piece of content should be true to him, but it should also resonate with people and make a difference.
He then explains a goal he set early on. He says he has said it often on stage but not on a podcast before. Every video is only 75 percent complete, which means he sometimes messes up words, mispronounces something, or forgets a shot, and he lets it go. He realized that if he waits for 100 percent he will be waiting forever, and his team releases three videos a week.
The conversation agrees that 75 percent is realistic and still means quality, because you are not settling for less. The discussion offers a music example of someone who wants to keep adjusting a mix for months, and the advice there is to finish it and put it out so that the audience or critic can respond.
my videos are only 75% complete
How do you handle self-doubt and videos that do not hit?
Around 30:28 in the episode
Jay Shetty treats self-doubt as proof that he cares and as a checking system for what to improve. He says it never fully goes away, so build a positive relationship with it and cut it down by learning and upskilling.
Asked about videos that flop while unexpected ones take off, Jay says he has reconciled himself to not always knowing what will work, and finds it liberating to give up that control. He works strategically and effectively, but sometimes the place he puts the most energy does worst while something on the side blows up. He warns that focusing on one thing that is not working can make you miss nine other good things happening around you.
He says he still gets self-doubt before a post, a video, or his podcast launch, and asks himself whether people will care. He is glad of it because it means he is human and that the work matters. He gets nervous when speaking at conferences because he cares, and if he ever stopped being nervous, it would mean he no longer loved what he does. He notes he does not doubt himself about things he does not care about, like a recipe for a dish.
His second step is to treat doubt as information. If the doubt is that not enough people will listen, ask how to make the content or conversation better. If it is that people may not like a topic, ask which themes he is good at. He calls it a great checking system, and says it is never going to go away, so build a positive relationship with it instead of avoiding it.
Finally, he says most self-doubt exists because we have not researched, built knowledge, or built expertise. To be a good interviewer, watch good interviewers; to be a good stage performer, watch good ones; to be a good monk, watch good monks. Today there are courses and podcasts to learn from. As he puts it, self-doubt is cut by the sword of knowledge and upskilling.
self-doubt can only be cut by the sword of knowledge
How can you be more authentic and comfortable being yourself?
Around 35:38 in the episode
Jay Shetty says get comfortable with yourself first, since we live in a perception of a perception of ourselves. Notice when you feel at your best and test what works for you.
The hosts mention an Instagram survey Jay ran asking whether people know the real him, where about half said yes. Jay says he is not surprised. We are told as children to fit in, stand in line, and wear the same uniform, then told as adults to stand out and be ourselves. People fear being themselves because it may turn others off, and we carry conditioning about what is normal and acceptable. He recalls that the first time he wore robes on a street was scary.
For those who answered no, he says the first step is getting comfortable being you, because nobody will be comfortable with you being you if you are not. He shares an idea from a writer named Cooley from the 1900s: I am not what I think I am, and I am not what you think I am, I am what I think you think I am. In other words, we live in a perception of a perception. His suggestion is to step away from that and ask how you feel about yourself when you are by yourself and no one else is around.
The conversation notes how exhausting second guessing can be, and that it rarely happens around old friends but creeps in around strangers we want to impress. One tip shared by a host is to treat people as if they are already your friends and already like you, which reduces the facade.
Jay's other practical tip is to observe when you feel uncomfortable and when you feel at your best. He has noticed that at events he prefers finding a one on one conversation in a corner and going deep over circulating through popular circles, so he gives himself permission not to network the usual way. Finding what works takes testing, and sometimes you have to do the thing that is not you once to learn that.
How do you turn passion into purpose?
Around 40:18 in the episode
Jay Shetty defines passion as for you and purpose as for others. Find a passion, get undeniably good at it through hard work, then use it to help others, and purpose follows naturally.
The conversation moves to purpose, with a note that many people lose sight of who they are after years of outside influence from marketing and expectations. Jay defines it simply: your passion is for you, and your purpose is for others. Purpose appears when you use your passion to serve other people.
He says the part usually missed is getting really good. You can be as passionate as you like about tennis, but if you are not good at it nobody will care. Turning passion into undeniable expertise takes hard work, work ethic, early mornings, and training. When you combine passion and skill you become successful, but he says you are only happy when you use that success to help others, at which point it switches into a purpose automatically.
He observes that people often do things they are not good at and do not love, or things they are good at but do not love. His encouragement is to move toward things you love, get really good at them, and explore widely, since you can explore almost anything today.
Asked about his own path, he credits his parents for sending him to public speaking and drama school from 14 to 18, even though he was shy and had no interest. He had the tools but nothing to speak about until becoming a monk gave him a subject he was passionate about: philosophy, science, culture, life, growth, and the mind. He has spoken for more than three hours a day for 13 years. Early on he was invited to speak at a university for no pay, nobody showed up on two occasions, and he practiced his talk to the empty room as if it were full.
How do you find your passion if you cannot go to a monastery?
Around 45:29 in the episode
Jay Shetty says to stop asking what result you want and ask what process you love. Use evenings and weekends to shadow or try the work for a day, and look at what people did when they started.
Asked what advice he has for listeners who cannot go off to a monastery to detach and explore who they are, Jay says we are trained to focus on results, and that asking what you want is the worst question because ads come in: the car, the home, the body. He prefers asking what you want to wake up and do every day, and what process you are in love with.
He gives a personal example. He is very passionate about soccer and loves the game, but he does not want to wake up at 4 a.m. to play on a rainy pitch or spend four hours a day in the gym. He would happily meditate for hours a day, and he is not envious of athletes because it takes a different mindset. Do not decide you want to be a singer because you want to be a famous singer; ask whether you love singing every day.
To find a passion, he suggests using weekends and evenings to test things: take a course, try it once, or shadow someone who does it. If you want to be a podcaster, shadow a podcast team for a week, then try the schedule of someone you admire for a day, and if you love it do another day. He thinks this is smarter than only sitting and reflecting. He adds that you should focus on what successful people were doing when they started, not what they do now.
The discussion links this to results being like chasing ghosts, since each win becomes a step toward something else, and to losing track of time when you are doing work you love. Jay says he gets more wins because he gets more failures, trying many things and seeing only the one that works. He points to Steve Jobs as a role model who failed many times, as described in the biography by Walter Isaacson, and says that when you are messing up you are on the same path as everyone you admire.
How do you build an inner circle you can trust?
Around 52:42 in the episode
Jay Shetty builds his circle through collaboration and reaching out without asking for anything, mixing peers who understand his work with grounded friends who remind him of his roots, and he trusts his intuition.
Asked how people who will say that an idea is bad ended up in his inner circle, Jay admits it is hard. You have to surround yourself with peers who understand you and do not see you as competition. He believes collaboration wins, so he regularly reaches out to people he admires to say he would love to get to know them and be a friend, not to ask them to teach him. If it grows into more, great; if not, he has a good friend who gets him.
He makes friends in two areas. One is people who do something similar, because conversations with them are great, and he gives Lilly Singh, a recent podcast guest and friend, as an example. The other is people outside media, like the monks in India, who remind him of his roots and the truths that bring him back. He says he spent a month in India meditating again for about 21 days.
He also relies on intuition. He may decide in a single meeting whether to speak to someone again, and he encourages listeners to trust their gut instead of letting their head make things up.
He tells a story, relayed from an interview of India's Prime Minister at Facebook, in which Mark Zuckerberg said that when he struggled with Facebook's direction in 2009, his mentor Steve Jobs advised him to spend time in an ashram in India. Jay says successful people surround themselves with differing beliefs, and mentions an MIT research study finding that more innovative people knew people who did not know each other, which avoids an echo chamber. He closes with the idea that everyone plays a different role in your life, such as his mother caring mainly about his health, so do not expect everyone to play the same role.
What books and goals does Jay Shetty share?
Around 59:22 in the episode
Jay Shetty recommends The Journey Home and the Bhagavad Gita, and says his On Purpose podcast aims to build depth with his audience and take guests beyond their professions into their purpose.
Asked for a book that changed him, Jay recommends The Journey Home by Radhanath Swami, an autobiography about a man who hitchhiked from America and London at the age of 19 in search of the truth. He describes it as a true story with travel, sacrifice, and a real desire to seek truth and find yourself.
He also recommends the Bhagavad Gita, the book he studied as a monk. He describes it as 5,000 years old, the story of a warrior getting advice from a divine coach, and a classic of India. He says that much of the knowledge he reads today seems to stem from it, though it is not the easiest read and is best approached with someone who knows it well.
On his podcast, called On Purpose and available on every platform, he says videos give scale, touching many people for a few minutes, while he wanted depth. He wanted people to know him better and to know them better. He also wanted a show where friends and guests could go beyond their profession and into their purpose.
He mentions guests so far including his wife, Russell Brand, Novak Djokovic, Giselle, and Rob Dyrdek, along with clinical neuroscientists and, soon, his mother. He says he grew tired of mainstream interviews that only focus on numbers, results, and success, and believes many people want to talk about purpose, passion, and meaning. The episode ends with thanks and a hope to do more together.
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Frequently Asked Questions
Who is Jay Shetty?
Jay Shetty is a former monk, online storyteller, and host of the On Purpose podcast. He grew up in London, spent summers during university split between finance and monk life in India, and became a monk after graduating. He began posting video online in 2016 and was working on a book at the time of this episode.
What did Jay Shetty say about overcoming self-doubt on The Art of Charm podcast?
He said self-doubt shows you care about something, so treat it as a checking system rather than something to avoid. Ask what you can improve, build knowledge by learning from people who are good at the skill, and recognize that doubt will not fully go away, so build a positive relationship with it.
How does Jay Shetty deal with people who doubt him?
He tries not to make proving people wrong his motivation, because that gives them control. He builds the other side of the bridge before leaving a situation, strengthens his own conviction instead of weakening other arguments, skips pointless negative comments, and spends his energy on people who already support him.
What is the 75 percent rule Jay Shetty mentions?
Jay says his goal is for each video to be only 75 percent complete. He accepts small mistakes, such as a mispronounced word or a missed shot, because waiting for 100 percent would mean never publishing. He releases three videos a week and sees 75 percent as realistic without settling for low quality.
How does Jay Shetty define passion and purpose?
He says passion is for you and purpose is for others. Find something you love, get really good at it through hard work, and then use it to help other people. In his view you do not have to find your purpose separately, because it develops naturally from passion combined with skill and service.
How can you be more comfortable being yourself, according to Jay Shetty?
He suggests getting comfortable with yourself first, since we often live in a perception of a perception of ourselves. Ask how you feel when you are alone, notice when you feel at your best, and test what works, even if it takes trying something that is not you once.
Resources Mentioned
- Jay Shetty's Podcast
- Jay Shetty on Instagram
- Jay Shetty on Twitter
- Jay Shetty on Facebook
- The Journey Home
- The Bhagavad Gita
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