How do the biggest names in comedy navigate intense self-doubt, failure, and the pressure to succeed immediately?

In this On Purpose episode, Jay Shetty sat down with Judd Apatow, director, screenwriter, producer, and comedian. He opened up about his career and life, as described in his recently released memoir, Comedy Nerd: A Lifelong Obsession in Stories and Pictures. Apatow talked about using his humor even in the darkest of times and about succeeding in a competitive industry.

From Mediocre to Fame

Judd Apatow admitted to Jay Shetty that he believed he was a mediocre student. Growing up in Long Island, his school used formal tests to determine students' intelligence, and then placed them into track one (smartest), track two (regular), and track three (children with problems). For Apatow, being placed in track two at age 12 limited his perception of himself and his potential, and it bugged him that track one teachers seemed "cooler" than others.

Yet, despite being placed in the mediocre box through the school's assessment, Apatow went on to study screenwriting at USC film school. However, he secured his acceptance by writing a genuinely funny essay describing which buildings he would build, instead of relying solely on his grades. Apatow has always had a strong sense of humor that he was aware of, which helped him navigate official systems.

Learning From Comedy Icons

One of the foundational elements of Apatow's comedy education came from his high school radio station run by his friend Jack de Macy. De Macy suggested that Apatow treated the radio station like it was the real deal, while another friend told him to try interviewing established comedians. So, starting at age 15, Apatow conducted about 500 interviews in high school with legendary figures such as Steve Allen, Howard Stern, Sandra Bernard, Jerry Seinfeld, and Jay Leno.

Apatow told Jay Shetty that these interviews were crucial in shaping his career; he was amazed when professional comedians would try to make him laugh. Jerry Seinfeld offered him lessons on writing jokes and gave him examples of jokes he was actively developing, which fascinated Apatow at the time. This exposure to consecrated comedians made him feel safe about getting into this business, as he knew there were also kind people in the industry.

Competition vs. Collaboration

Apatow was determined to find a path into the comedy world. He told Jay Shetty that, initially, he saw the comedy world as consisting of only about 100 people, and this made him believe it was an achievable dream.

When he started his career, Apatow viewed other comedians like Jim Carrey and Adam Sandler as allies rather than arch-rivals. He told Jay Shetty that he never felt competitive because he recognized them as very special people and was extremely honored by the possibility of hanging out with them. Despite sometimes feeling depressed or not good enough, he cherishes the opportunities he had, such as assisting Jim Carrey with writing jokes and punching up scripts.

Judd Apatow stayed motivated to write and create, and he began writing for HBO specials and worked with Roseanne Barr and Tom Arnold. Then he collaborated with Ben Stiller to create The Ben Stiller Show. The drive behind this collaboration was his desire to find a community of like-minded people to have fun with.

The Seven-Year Rule

When he started interviewing other comedians, Judd Apatow received advice from many of them. He shared with Jay Shetty that they told him it took about 7 years to find your voice, and so he internalized this timeline and would give himself grace when things would not work out on the first try. He started at 17, and so he expected to become great around 24; if he were terrible at 19, he was happy because he knew he still had time to perfect his skill.

Judd Apatow believes that his philosophy was necessary for survival in Hollywood, where things can change at any moment. Even when The Ben Stiller Show was cancelled after only 12 episodes, he was still proud of his achievements up until that time. It takes time for the world to truly decide if someone has succeeded or failed, and Apatow believes that, sometimes, delaying something would only make you better, more mature, and give you more to say.The Creative Process

Apatow told Jay Shetty that the main bar for his creative process is always his personal belief: if he likes it and is proud of it, he considers it good. However, he understands that creativity is not a one-way street but a dialogue with the audience. If the audience doesn't love your work, or if they aren't emotionally touched or laughing, then you have failed.

Balancing artistic integrity with audience reception is delicate, as some ideas are recognized as niche and are meant for a small crowd, while others are aimed at a mass appeal. Apatow explained to Jay Shetty that he avoids chasing trends and prefers focusing on doing something truly unique instead. In his opinion, good comedy must first work as a drama. So, he focuses on the emotional story, trusting that situations in life that sometimes feel awful are often really close to funny.

Parenting Philosophy

Judd Apatow and his wife Leslie Mann prioritize raising their daughters to chase their passions rather than focusing obsessively on grades or discipline. To him, the core hope for a child is that they possess a strong desire to chase a dream and the energy to take a risk and go after something.

Many young people today feel pressured to become successful right away. However, Apatow and Jay Shetty believe that's a mere illusion. Apatow remembers when he was young and lived with Adam Sandler that he could experiment at clubs, without being recorded on camera and judged in digital forums or the comment section.

He explained to Jay Shetty that it was a type of freedom that allowed a gestation period in which they could just be really funny, take chances, and allow themselves to fail from time to time. Apatow believes the young people's need to put everything online immediately is detrimental because it's also fun to fail when nobody is watching.

Judd Apatow taught his daughters that the most important thing to care about is the work, and be passionate and proud about what they're saying. He advised them to focus on expressing something meaningful rather than taking jobs merely for career advancement. To him, it's important to take risks because the creative life always consists of inevitable highs and lows.

Achieving the Flow State

Apatow admitted that he always works hard to achieve a flow state, yet his process evolved over time. When he was younger, he used to do other things during the day and only focus on his work late at night from 8:00 PM to 2:00 AM. Watching TV during the day and having a relaxed dinner helped his brain relax enough for ideas to surface in the evening.

However, after having children, he had to change his schedule to accommodate being a father. He had to intentionally carve out creative slots and gradually train his brain to become creative during these times, although, naturally, creativity doesn't follow a strict schedule.

Additionally, Apatow took a class on flow states, which taught him simple, effective methods to improve his creativity, such as avoiding distractions by limiting news intake and phone usage. He told Jay Shetty that he had to protect his mental state from outside problems, which had the potential to put him in a bad mood and dissipate his imagination.

Apatow admitted to Jay Shetty that he had to find a balance between staying informed about the world and protecting his creative focus. As a storyteller, he is fascinated by world politics, corruption, and the choices people make, yet he knows the input is often too much. So, when he is in a good writing groove, he limits his consumption to maintain focus and makes up for it by engaging in philanthropic activities.

Understanding Himself Through Comedy

Humor is often seen as a coping mechanism for deeper pain. When he's writing, Apatow often tries to figure out his own thoughts, explore struggles or questions. Recurring themes in his work are high school, college, marriage, or sickness, drawing from his personal life, which help him cope with reality in a creative way.

When writing, Apatow frames it around an emotional core that defines a character's emotional problem. Then, he figures out what would have to happen for the character in order for them to hit bottom enough to make a change, and then decides what that healthy change would look like. According to him, comedy is a road to understanding yourself.

Apatow confessed to Jay Shetty that he abandoned stand-up comedy early in his career because he didn't believe in himself and felt like it left him with more questions than answers. He admits that when writing, he sometimes struggles with the critical voice that makes him feel like he would lose it all today.

Therefore, he has to implement mental tricks such as opening a simple Word document and forcing himself to write without punctuation for 10 or 15 minutes in a state of pure spewing, allowing his subconscious to speak freely.

Therapy Triggers and Honesty

Judd Apatow told Jay Shetty that he has been going to therapy for decades now, which opened his horizons and revealed new insights. Five years ago, he learned about trauma responses and the way people changed their lives to avoid past pain, and that we often live in a state of fight, flight, or freeze.

One major breakthrough was realizing that he projected his childhood (divorced parents) onto the network executives who'd rejected or abandoned him, he told Jay Shetty. When rejected, he would react illogically, feeling they were trying to destroy him. This insight allowed him to take that irrational energy out of his creative relationships and enabled him to calm down.

To Appatow, this realization is a key to successful long-term cooperations, such as working with Universal Studios executives. He told Jay Shetty that part of the success is picking your collaborators so that you can have a healthy conversation.

The Work of a Lifetime

Apatow is well aware of the importance of healthy relationships and support systems in his life and career. The secret to his fulfilling partnership with his wife is really enjoying each other and being amused by one another. He explained to Jay Shetty that marriage is a lot of work and requires the courage to be honest about what's happening. Moreover, their marriage is also a creative partnership because they make movies as a family as well.

Garry Shandling was Apatow's mentor who offered him numerous opportunities, including writing jokes for the Grammys and hiring him for The Larry Sanders Show. He acted as a paternal figure and said yes to every one of Apatow's requests over 10 years, giving him both lessons and opportunities alike. Now, Apatow told Jay Shetty he is trying to become a mentor himself for the next generation and finds it fun to work and give his wisdom to inspire people and help ease their journeys.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode “Judd Apatow: Fear of Rejection Holding You Back? THIS Trick Will Silence the Inner Critic & Help You Feel Confident to Create” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.

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