On this episode Ryan and I have an extended conversation with Kendra about how she restructured her life to become significantly happier, how she has been affected by her controlling parents, and the unwritten rules that are negatively influencing our lives.  We also share: how to find your passions, how to deal with criticism, how to learn from others, as well as the stories of some the the greatest days of our lives.  Ryan shares a few travel stories including his skinny dipping experience in Thailand, and we play a high intensity question game that leads to Ryan talking about how his involuntary celibacy is affecting him, and I tell a story that brings me to tears.  Thanks for listening 🙂


  • Intro by Charlie [0:00]
  • Who is Kendra, why is she in Dallas? [4:08]
  • Dealing with strong parental pressure/living through your children [5:50]
  • How Kendra decided not to become a doctor [8:50]
  • How Kendra became more independent of her parents [12:00]
  • How Ryan and Kendra’s siblings influenced their childhoods/parents [14:30]
  • Kendra’s recent journey to to happiness [17:40]
  • How to find your passions [24:10]
  • What Kendra did to make the transition from unhappiness to happiness [31:05]
  • What invisible and unhelpful rules do we follow that are harming us? [40:50]
  • What invisible rules do we see ourselves struggle to stop following? [52:10]
  • Dealing with Criticism  (Note: Ellen and Amelia thanks for the constructive criticism :).  I’m not talking about you guys in my anecdote) [59:30]
  • How to learn from from people without mimicking their negative traits [1:06:00]
  • The stories of some of our best days ever [1:11:50]
  • Taste censorship & shamelessness [1:23:35]
  • What annoys you the most about others that you see in yourself? [1:29:30]
  • If we died today, what is something we wish we would have done?/Ryan’s skinny dipping story [1:40:55]
  • How do we want to be remembered after we die? [1:44:00]
  • What keeps us from committing suicide? [1:47:00]
  • The Uncomfortable Question Game [1:52:15]
    • When did I realize I was depressed/how did I overcome my depression? [1:52:50]
    • How is Ryan’s recent lack of sexual intimacy affecting him as a person? [1:56:15]
    • How would Kendra’s life change if her parents passed away? [2:04:25]
    • Why didn’t Ryan ask out a cute girl from the cross-fit gym today? [2:07:45]
    • How afraid is Kendra that she might lose a portion of her life following her parents desires instead of her own? [2:12:15]
    • Who would I rely on if I became disabled? (my emotional story about mental illness) [2:15:30]
  • Homework [2:27:20]


  • Ryan’s homework:  Next time you talk to a girl do an experiment that you would have never done unless you thought of it as an experiment.
  • Charlie’s homework:  Share, unironically and non defensively, something embarrassing that I liked and changed my life.
  • Kendra’s homework: Sharing her website of doodles.

Selected Links for the Episode:

Selected Quotes from the Episode:

  • “If you’re talking shit about somebody, you probably shouldn’t be hanging out with them.”
  • “You should only help people as long as you enjoy helping other people.”
  • “I think it’s great to shamelessly imitate people, but you have to take the good and leave the bad.”
  • “Is it weird or is it so?”
  • “These guys were grasping to this personality that they had and as soon as they let go and just lived in the moment they were able to become themselves.” – Ryan
  • “By letting go they were able to become themselves” – Ryan