In 2013, Jay Shetty sat in his childhood bedroom with a mountain of student debt, more than 40 unanswered job applications and a growing sense that his skills from being in the monastery didn’t count for much in the corporate world.

“No-one looks at a resume and is impressed when they see ‘monk’,” Shetty tells The CEO Magazine. “There I was living at my parents’ house with no prospects and US$25,000 in college debt, while most of my friends were well on their way to establishing themselves in their careers. It was discouraging to say the least and a real blow to my confidence.”

That’s the part of his story most people don’t see when they scroll past one of his viral clips or hear his voice on his hit podcast On Purpose. Before the two The New York Times bestselling books, the podcast empire and sold-out stadiums, there was just a 20-something wondering if he’d made the wrong choice.

The gap between rejection and recognition is where Shetty found the lessons that now shape how he lives, leads and teaches.

“I worked through it with a combination of persistence and patience,” he recalls.

“Instead of sitting around and focusing on how badly I felt, I started going to the library to feed my love of learning and I continued my meditation practice. Having that structure in my life and engaging in things that were self-supportive sustained me until I finally got that job offer.”

Redefining success

Long before the setback, Shetty had already been wrestling with the question of what success should look like.

“When I was a child, I thought success was trying to make my parents happy,” he shares. “When I was a teenager, I thought success was trying to impress my friends. When I was at university, I thought success was getting a good job. It all changed during my time at the monastery.

Shetty gives the Class Day Commencement Speech at Princeton University on 26 May 2025. Image: Sameer Khan

“When I was a monk, I learned that success was self-mastery and service to others. This definition became the new foundation of my work.

“Success to me is meeting a 21-year-old college student, a 30-year-old Navy SEAL, a 40-year-old single mom and a 50-year-old nurse and hearing how my work has impacted them – only for me to remember that their stories inspire me,” he says.

When purpose called

Ironically, the global bestselling author and Chief Purpose Officer of mental health and wellness company Calm never set out to trade his suits for robes. Instead, his decision to become a Hindu monk began with a last-minute invitation to hear one speak. That single event ignited a sense of purpose he couldn’t shake.

Jay Shetty on Tour in Los Angeles at the Greek Theatre. Image: Matty Vogel

During university, he continued his studies. But every vacation was spent in India living with monks, immersed in their teachings. After graduating with honors from Cass Business School in 2010 with a degree in Management Science, Shetty remained driven by a deep desire to positively impact those around him.

But he felt uncertain about how his degree aligned with his purpose. It was then that Shetty made the decision to embark on a three-year journey as a Hindu monk in India and the United Kingdom.

“When I would come back from the monastery, I would be inspired, enthused and feel alive,” Shetty says. “I knew I wanted to make it my path after I graduated. There is a lesson here, which is: It is only by action that we will find our direction. There is only so much you can figure out in your head.”

Even before that, growing up as a shy child gave him lessons in empathy.

“I was bullied for my weight and the color of my skin,” he says. “I learned that bullying and making anyone feel inferior was never the right choice.

“It gave a sense of perspective and compassion for those who are also treated this way. But it did not make me want to prove the bullies wrong – it made me want to support those who are picked on.”

The power of humility

Fast forward to today and Shetty, now the Chief Purpose Officer of Calm, Co-Founder of the adaptogenic tea brand Juni — launched with his wife in 2023 — Appointed Relationship Advisor at Match, and a purposeful voice for Kenneth Cole, has sat across from some of the most influential leaders in business and culture. Through On Purpose, he has interviewed Bill Gates, Michelle Obama, Tom Hanks, Oprah, Kobe Bryant, Kim Kardashian and more.

What struck him most, however, wasn’t their celebrity or intellect – it was their ability to adapt.

“From interviewing Bill Gates and the Co-Founder of Netflix to Brian Chesky, the Founder of Airbnb, I have learned that pivoting is the most important business move,” he explains.

Shetty with wife and Juni Co-Founder Radhi Devlukia Shetty. Image: Kayla Mendez

“It wasn’t a failure, it wasn’t the end. It was prioritizing the pivot. Your mission can stay the same, but your path can change. Don’t be fooled into thinking there is only one way to that goal.”

But for leaders, agility alone isn’t enough.

“The smartest person in the room doesn’t have all the answers – they ask the best questions,” he points out.

“They are not scared of looking unintelligent or less informed because they realize that is the only way of growing more. Ego pushes people away from helping and supporting you and creates friction between you and your collaborators and competitors. Humility can come across as weakness, but it is truly the greatest superpower.”

Keeping energy alive

And that mindset is especially relevant for entrepreneurs. Building something from the ground up requires constant learning, asking questions and being open to feedback. There’s no room for ego – only curiosity. And with no clear ladder to climb or titles to chase, that curiosity, Shetty says, can keep a passion from starting to feel like a grind.

“Every year, I divide my time by what I love, what I am launching and what I am learning,” he says.

“What I love makes me happy, what I am launching makes me feel like I am starting all over again and what I am learning makes me excited. This way, my year is full of all the amazing emotions that entrepreneurship allows me to experience.”

Image: All is Amazing

In practice, Shetty breaks it down into percentages. “I have a rule I follow – 75/25. That means 75 percent of my time is spent doing my day-to-day tasks and roles and 25 percent of my time is invested in fresh thought, innovation and learning new things.”

Interestingly, he reveals that this formula is also something he applies to his social interactions.

“Seventy-five percent of my time is with the leaders inside of our company and 25 percent is with people I am curious about – who I can ask lots of questions to or are in completely different industries,” he says.

“Just this week, I spoke to a professional skydiver, an AI company founder and a Formula One racecar driver.”

Standing out authentically

All of these experiences have led him to believe that when it comes to AI and content overload, leaders must become sharper – not louder.

“Say less, mean more,” Shetty says, echoing Einstein, who famously said, “If you can’t explain something simply, you don’t understand it well enough.”

“AI can generate endless words. But using your uniqueness and the power of AI to distill your mission into a few meaningful words changes the game,” Shetty adds.

He points to Apple’s iPod as the gold standard.

“Think Steve Jobs’ one thousand songs in your pocket,” Shetty says. “And remember to share the scar tissue, not just the success. In a world where AI can make everything perfect in a matter of seconds, true human imperfection will shine through. Your vulnerability will continue to be a strength.”

The leaders of tomorrow, he believes, won’t be the ones with all the answers.

“Learn to ask better questions. AI already has all the answers (and will have more soon), so the best leaders won’t have all the best solutions, but they will be focused on solving better, bigger problems,” he says.

Something totally new

Despite reaching more than 60 million people worldwide, Shetty insists he’s just getting started.

“I’m excited about the innovation we’re bringing to the world of podcasting and media,” he enthuses. “I cannot wait to share the new ventures we have been working on in the coming months.”

And if, for some reason, he wasn’t doing this work? The mission wouldn’t change – only the medium.

“For me, it’s always about feeling that call to service,” he says. “But I’d be attracted to doing it in a completely different way than I’ve done before.

“That would be exciting for me. There’s a statistic that in 10 years, 60 percent of the jobs that will exist haven’t been created yet. So I feel like whatever it is, it would be something totally new.”