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Jay Shetty PodcastKENDALL JENNER: “I Lost Myself Trying to Please Everyone!” – WATCH This To Take Your Power Back
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CHAPTERS
- 0:00 – 7:07
A Manifested Meeting and a Warm Start
Kendall Jenner and Jay Shetty trade stories about how the interview came together, each feeling it was meant to happen. They talk about admiring people like Michael Singer and Wim Hof, her love of working on herself, and her wish that sharing it never feels like a pity party.
- •Kendall says she manifested the interview after seeing Jay at a friend's house
- •Jay explains he reached out directly because personal connections feel better than PR-driven ones
- •Kendall admires patient, determined people like Michael Pollan, Michael Singer and Wim Hof
- •She has started cold plunges and loves self-care
- •She shares tips like deep breaths, walks and journaling to be helpful, not to throw a pity party
- 7:07 – 13:49
Formal Introduction and Horses
Jay gives the formal introduction to Kendall, and they talk about the synergy of the connection. Asked about her horses, Kendall describes growing up in a horse community and feeling like a child again around her horse Delandra, and Jay shares his horse-carriage proposal story.
- •Jay introduces Kendall and thanks Simeon Hayes for the connection
- •Kendall grew up in a horse community and has loved horses since she was very young
- •Standing in her horse's stall can leave her teary-eyed because of their wordless connection
- •Jay's wife turned out to be allergic to horses on the day he proposed
- •Jay talks about cows in India and gorillas in Rwanda as animals that have moved him
- 13:49 – 18:41
First Jobs, Solitude and Craving Simple Things
Kendall recalls being a disciplined child who walked dogs for her first job and preferred time by herself. She explains how she has returned to enjoying her own company and says she craves simple days and a small core crew despite her busy, social career.
- •Her first job was dog walking, with flyers she put around her community
- •She was a disciplined kid who put herself to bed at 7 PM
- •She loved Sims, video games and time with horses, while her sister Kylie was the social butterfly
- •The pandemic helped her re-enjoy being alone
- •She describes her ideal day and says she craves simple routines
- 18:41 – 21:35
Proudest Achievement: Setting Boundaries
Asked about a proud moment, Kendall points to her determination to become a model and, above all, the self-work she did after years of overwork. Around age 23 she set boundaries and began saying no. She says this lets her show up better for herself and others.
- •She decided at 14 to become a model and kept at it until about 24
- •For about five years she said yes to everything and became overwhelmed
- •She set boundaries at about 23, prioritizing her happiness and wellbeing
- •She says she now shows up better for herself and the people around her
- 21:35 – 26:33
The Courage to Put Herself First
Jay asks where she found the courage to step back in a competitive industry. Kendall says she felt she would lose herself if she went any further, even though some people around her pushed her not to stop. She used the time to take it slow with wellness practices and to return to her horse.
- •Jay notes that stepping back is harder when you have everything to lose
- •Kendall says she knew she would lose herself if she kept going
- •Some people who worked for her did not want her to stop
- •She trusted she would be okay if work slowed down
- •She took things slowly rather than trying every wellness practice, and bought her current horse around then
- 26:33 – 29:26
Protecting Happiness and Her Higher Self
Jay says a core belief in her life is that it is important to be happy. Kendall says she does not want her happiness to depend on others, and she talks about living as her higher goddess. She uses words of affirmation in the mirror to counter false narratives.
- •Kendall says happiness that depends on others leaves you at the mercy of things you can't control
- •She and her therapist talk about her higher self, or higher goddess
- •She uses affirmations in the mirror
- •She says her friends, family, dog and horse know who she is, and everything else is noise
- 29:26 – 32:16
Perception, Multifaceted Humans and Cooley's Insight
Jay shares an exercise he does with clients using a leaf to show how multifaceted people are. He quotes Charles Horton Cooley on living in a perception of a perception of ourselves. They agree that people dislike being seen in a singular way.
- •Jay's leaf exercise shows that things are often different from how they look
- •People are easily boxed in by a singular view from social media or one interview
- •Cooley's quote: "I am what I think you think I am"
- •Jay says the empowering answer is to look to how you and the people who know you feel about you
- 32:16 – 34:00
Honesty, Breathing Room and Family Overwhelm
Asked about habits behind her good relationships, Kendall points to honesty and open communication. She also says it is okay to step away, even to the bathroom at a family dinner, and breathe when overwhelmed. Jay praises how simple and accessible that habit is.
- •Kendall values honest, healthy, communicative relationships
- •She steps away during family gatherings to take a few breaths
- •She says her feelings are valid and sometimes her family is a lot
- •She is prone to anxiety and tries not to react, then returns calmer
- •Jay notes it requires no new meditation practice
- 34:00 – 40:09
Grief and Remembering Virgil
Jay brings up Kendall's loss of Virgil and shares his own losses of his spiritual teacher and his best friend as a monk during the pandemic. Kendall describes the shock and the unfairness of losing such a light. They talk about how gratitude and generosity defined both men, and how remembering them gives comfort.
- •Jay lost his spiritual teacher and a monk friend to cancer during the pandemic
- •Kendall asks why it is always the best people who are lost
- •She found it meaningful to share the grief with so many people
- •Both describe Jay's teacher and Virgil as grateful and giving even through illness
- •Kendall says Virgil fulfilled the purpose he was meant to
- 40:09 – 44:57
An Evolving Purpose: Spreading Love and Positivity
Kendall says her purpose has evolved from her career toward tuning into her higher goddess and sharing tools to help others feel love. They discuss staying away from negativity on social media and why people gravitate to bad news. Both want to see good in the world.
- •Kendall's purpose now centers on her higher self and connecting with others
- •She wants people to feel love and says she was placed here to share and smile
- •She stays off social media because it can feel negative
- •Jay posts daily fun videos hoping to bring someone joy
- •They agree we need to retrain our brains away from negativity, and Jay says it starts with how we see ourselves
- 44:57 – 46:42
Inner Child Work and the Mirror Photo
Kendall describes inner child work with her therapist, inspired in part by a TikTok trend. She found a Polaroid of herself as a little girl and put it on her bathroom mirror. When she's tempted to be negative about herself, she looks at the photo and reminds herself that she's talking about that child.
- •Her therapist suggested placing a childhood photo on her bathroom mirror
- •She found a Polaroid she had never seen before in her memorabilia closet
- •She talks to the photo and tells her younger self she is dope and loved
- •Jay calls it a great tool and says his team made a humorous version of the trend
- 46:42 – 49:43
Feeling Heard and Our Shared Humanity
Jay asks what Kendall hoped to share and whether she feels heard. She says she wanted to share a vulnerable side of herself and hopes it brings comfort. They reflect that everyone shares the same emotions, and that kindness starts with being kind to yourself.
- •Kendall wanted to share a side of herself that is sometimes scary to share
- •Jay says the closer you get to people, the more you see how similar everyone is
- •Everyone feels their own guilt, pressure and challenge regardless of money or fame
- •Kendall says we are all having a human experience and should be kinder to each other
- •Jay says he stopped judging others once he stopped judging himself
- 49:43 – 53:58
Final Five and Closing
Kendall answers Jay's rapid-fire Final Five questions about curiosity, self-work, founding 818, what she no longer values and her one world law. Jay then thanks her and invites listeners to share what resonated with them.
- •She is curious about meditation and is reading Michael Singer's The Surrender Experiment
- •She is working on boundaries and on stressing and controlling less
- •She loves being her own boss and being creative with 818
- •She no longer values validation, or at least tells herself so
- •Her proposed law is to spend part of Sunday, or the full day, off your phone
