Steven Bartlett - Jack Whitehall

1) Comedian Jack Whitehall reveals that his comedy inspiration came from his father, Michael Whitehall, who was someone who could command the attention of a room through stories. However, Whitehall did not think of comedy as a career path until he saw comedians perform stand-up at the Edinburgh Festival in his teens, which inspired him to pursue it professionally. His parents, who had experience in the film industry, discouraged him from pursuing a career in the arts but ultimately, they pushed him towards comedy, despite it being a competitive industry. Whitehall reflects that it all worked out in the end, and he doesn’t begrudge them for their decisions.

2) Jack Whitehall talks about his family and his experience at boarding school. He shares that despite having an unusual relationship with his family, they have always been close, even when he was away at boarding school. He also reveals that he was sent to a boarding school in Oxford after struggling at a previous school and that he was initially upset about it. However, he eventually found that it was a better fit for him and it allowed him to cultivate his passions and interests. Jack also talks about his brief experience as a child actor, including an audition for the role of Harry Potter.

3) Jack Whitehall talks about his lack of self-belief as a child due to various knockbacks and the desire to earn his father's approval. Whitehall mentions that he had problems with confidence due to his buck teeth, cowlick, and glasses, which made him an unfortunate-looking child. He also talks about his father, who had been dismissive of his acting ambitions and was tough to please. Whitehall then went on to do comedy after going up to Edinburgh with two of his schoolmates and performing in a sketch. He climbed up the comedic ladder quickly, but his lack of confidence in his talents was a constant struggle.

4) Jack Whitehall opens up about his beginnings in stand-up comedy. He talks about how he had no performing experience and no idea what he was doing when he first started. Despite receiving negative reviews, a producer recognized his potential and gave him his first gig as tour support for Horn and Corden. This eventually led him to his first television gig hosting "Big Brother's Big Mouth." However, Whitehall admits that he was not ready for TV and had not yet found his comedic voice, which he struggled to find in his early years.

5) Jack discusses his early days as a comedian and performing in pubs with terrible sound systems, half-interested audiences, and disruptive noise. He admits that despite having many bad gigs, he was unburdened by the anxieties he would have now as a professional comedian and performer. He attributes this to his youth and being unencumbered by worries, unlike now when he feels the pressure and anxiety of professional expectations. Louis Capaldi shared similar sentiments in his documentary about missing the lack of pressure and expectations when he used to sing in pubs in Scotland.

6) Jack talks about his fear of failure and losing what he has built. He reveals that he feels more pressure now than he did in his early twenties and is worried that everything could disappear. While this fear can be prevalent in the corporate world as well, he knows that he must focus on what's essential, such as his work-life balance and relationships, to maintain his happiness and fulfillment. He also shares his thoughts on doing this podcast and expresses his surprise that it's become successful.

7) Jack opens up about the pressure of not having a playbook or rule book to succeed in his career and the feeling of comparing himself to others in his profession. He admits to being sensitive and vulnerable to rejection, bad reviews, and online trolls, which consumes him for days and causes him to lose himself in an internal dialogue. While he puts up a brave face and buries his emotions not to burden people, he often feels distant and not present in the company of friends and family.

8) Jack opens up about his work-life balance and how he struggles with it. He admits that he started working when he was just 17 and has always had a work-first mentality. However, with a significant life event on the horizon (becoming a father), he hopes that it will shift his focus and be a healthy change for his life. He also realizes that he needs to be more proactive in striking a balance between his work and personal life, and that having a child will give him a better perspective. Jack describes himself as being driven, but thinks that sometimes being "dragged back" might be a good thing.

9) Jack Whitehall talks about his desire to have children and his fear of the impact it could have on his career. He admits to wanting four kids and sees himself as a present father, but worries about the reduction in his career it would require. He mentions the practicality of it, and that there are only 24 hours in a day while he is already using all of it. While agreeing that something will have to give, Jack thinks realistically about the significant moment of change that his life will undergo and mentions his upcoming tour dates being added to and the difficulty of delegating all the production work.

10) Jack talks about his preference for doing stand-up comedy in short, condensed bursts instead of long tours because after a while he gets bored of his own material. He explains why he thinks actors want to be musicians and end up in bands, as it allows them to have the live experience and connection with the audience that is hard to replicate anywhere else. He also discusses how his comedy has changed with his new show "Settle Down" being about the transitional period in his life where he is settling down and becoming more of an adult, contrasting with his previous shows which were more focused on his 20s and the misadventures of being a man-child.

11) Jack Whitehall talks about the importance of surrounding himself with good people and having a good judge of character. He also discusses his work ethic, being successful in comedy, and the feeling of having imposter syndrome. Whitehall believes that his abilities lie in selling jokes and delivering them well and has a sense of awe for his craft. He admits to occasionally doubting himself and feels that someone might call him out and tell him to go back to telling inappropriate jokes.

12) Jack discusses the challenge of having to be happy when dealing with self-doubt and putting pressure on oneself that comes from being in the public eye, especially when giving interviews. He feels he often comes across as depressing in print interviews, and this can be frustrating as he does not see himself in that light. He prefers podcasting where the broader picture can be shared, and there is no editing. Connections are essential to Whitehall, and he feels it's vital to be open and authentic, which liberates people from thinking they are inadequate and flawed. Whitehall expresses his contentment with his recent movie experience, working alongside excellent people in a happy creative environment.

13) Jack discusses his fears about his father not being around when he has a child and strives to achieve in his career. He wants to do all of it while his father is still alive and wants him to have a relationship with his child. Jack's father's approval still means a lot to him and he often thinks about impressing him. Jack expresses his gratitude for having had the opportunity to work with his father and discusses the special dynamic of their relationship, which is very banterful on screen but doesn't involve them discussing their emotions. Even though Jack has never articulated his feelings to his father, he thinks his father knows how much he means to him.

14) Jack talks about his father's decision to wind down and spend more time with his kids, and how he wants to do the same when he becomes a parent. He also opens up about his struggles in communicating with his father and not having regrets about words unspoken. He says he wants to be more present and attentive to the people he loves, and pledges to change a nappy.