Question The Self

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Bestselling author Jedidiah Jenkins goes behind the scenes of his epic 10,000-mile journey by bike in search of answers to some of the greatest—and hardest—questions we ask of ourselves. A special companion podcast to his bestselling memoir, To Shake The Sleeping Self: A Journey From Oregon to Patagonia, and a Quest For A Life With No Regret. (Available everywhere books are sold.)

Jedidiah Jenkins


    • Nov 17, 2022 LATEST EPISODE
    • monthly NEW EPISODES
    • 1h 4m AVG DURATION
    • 20 EPISODES


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    Latest episodes from Question The Self

    How This Man Snuck Into America to Escape Russian Oppression

    Play Episode Listen Later Nov 17, 2022 93:35


    I met him at a coffee shop. We started talking and his story knocked me over. Oppressed for being a minority, oppressed for being queer, and trapped in a country waging war and drafting its young men... Zhargal knew he had to get out of Russia and fast. So he watched YouTube videos on how to smuggle himself into America. It was complicated and sneaky. And he did it. This is his absolutely wild story of how. It was brave of him to say a lot of the things he says here, but you can hear that something compels him to keep sharing. I hope you'll honor his bravery by listening to his story. And I hope this gives you fresh perspective on what it means to live here and what it means when people do everything they can to come here.  *also, I say he snuck across the Rio Grande, which is wrong, it was the Colorado. Ok now go listen.*  

    Mom is Back: How Do We Love Family When We Have Profound Disagreements

    Play Episode Listen Later Sep 2, 2022 56:17


    What happens when you have deep disagreements with family? Rifts. Incompatible beliefs. Different political views. Faith or no faith. How do you stay in relationship? How do you love each other without pain? My mom and I have deep disagreements and we love each other. And in this episode, we try to get to the bottom of it all.

    Why You Should Write an Ethical Will with Rabbi Steve Leder

    Play Episode Listen Later Jul 12, 2022 56:24


    Why is it that when we die we leave a document that gives away all our stuff, but not our values, our beliefs, or our personality? Rabbi Steve Leder comes on the show to talk how to write an ethical will, why it should become a cultural tradition, and his new book 'For You When I Am Gone.' 

    Authenticity vs Selling Out with Cailin Russo

    Play Episode Listen Later Jun 20, 2022 65:56


    She writes with Kanye, she navigates the wilds of the Los Angeles music and party scenes, she sings her face off, and she finally feels like she knows what she wants to say. This is Cailin Russo, and we talk about her upcoming Album, being the only girl in Kanye's writing sessions, and how to be *very* online without losing yourself. 

    How To Get Published with Literary Agent Bryan Norman

    Play Episode Listen Later Jun 9, 2022 64:05


    This special episode is an interview I did with my agent Bryan Norman. He is a seasoned literary agent and knows every nook and crack of the book business. If you are a writer, or want to be, and wonder how to be noticed and get published, give this a listen. This audio is originally from an Instagram Live I did with him, so forgive the audio quality. I had to make this an episode because the content is just that helpful. It's required listening if you want to break into the world of authortown. 

    How To Make It As An Artist with Jack Garratt

    Play Episode Listen Later May 26, 2022 89:05


    Jack Garratt tells me how the music industry works, how record deals work, how to survive the pressure of success and expectations, and why old people music doesn't sound good... to me. 

    Deconstruction and Faith with Brit Barron

    Play Episode Listen Later Mar 14, 2022 63:57


    What is a deconstructed Christian? If the church has hurt me, why shouldn't I just chuck it all out? What happens when we don't integrate our past into our future? I talk with pastor Brit Barron about faith and what remains when we outgrow old ways of thinking. 

    How to be Gay, Black, Love Jesus, Free and a Dad with Griffin Matthews

    Play Episode Listen Later Nov 4, 2021 65:07


    The title says it all. Griffin is an actor (you've seen him on The Flight Attendant, Dear White People, and Ballers), a playwright, a singer, an activist, a husband, a dad, and a life long friend. He's always been one step ahead of me, or ten. And he's always been my funniest teacher. He also basically tells me step-by-step how to foster a kid. Did you know it's free? Enjoy. 

    Where is my person, my Big Love? The biological clock, adoption, and career with Connie Britton

    Play Episode Listen Later Oct 27, 2021 74:46


    What if I don't get the love I want? When will it happen for me? What if I don't have time for a family? Am I making enough space for love? Can I raise a kid alone? Should I adopt? These juicy questions guide my conversation with Connie Britton, my reluctant life coach who I hate. 

    Grief and Death Without an Afterlife with Sasha Sagan

    Play Episode Listen Later Oct 20, 2021 72:36


    How does a secular person think about death? How do you grieve the loss of a parent when there's no hope of seeing them again? How do you find meaning or beauty in a world without God? Author Sasha Sagan talks about losing her father, Carl Sagan, and what her parents taught her about grief and love and legacy. 

    Parasocial Relationships (one-sided internet relationships) and Scaring a Psychic Healer with writer Nada Alic.

    Play Episode Listen Later Oct 13, 2021 76:16


    What does it mean to feel like we have an intimate relationship with writers and podcasters and internet personalities? How does we curate our online personae and what does that say about who we are? What happens when a writer steals your idea? What is dopamine fasting and why should we all be doing it? Should Alan Watts be disqualified as a wisdom teacher because of the way his life ended? Why is Fran Lebowitz uncancellable? And when should someone be cancelled? As a writer and thinker in this modern age, Nada Alic is a delight. Process the world with us if you're nasty.

    How to Dress Beyoncé and Adele and Gaga and All The Greats, Part 2 with Daniel Roseberry

    Play Episode Listen Later Oct 6, 2021 63:32


    Part 2 of the best conversation. What it's like to dress all our faves. How do you even get the call to dress Gaga for the inauguration? What happens if you screw up?? And Daniel has three pages of questions for me.

    How to Find What You Love, Part 1 with Daniel Roseberry

    Play Episode Listen Later Oct 6, 2021 61:11


    What if you don't know what you're good at? We learn the journey to creative success with the designer who has dressed Beyoncé for the Grammys and Lady Gaga for Biden's Inauguration. Daniel talks about the power of negative reinforcement, i.e. learning from trying things and disliking them. We learn about his rise to becoming the Artistic Director at Schiaparelli, the haute couture house in Paris. How he handles critics. And how he has written fake reviews of future fashion shows, imagining what a reviewer might say in his fantasies, and then moving towards that vision.

    Belief and Death, The Soul and What Comes After - with Ruthie Lindsey

    Play Episode Listen Later Sep 29, 2021 59:43


    What do you say to a grieving friend? How do you process the death of a parent or a future you expected for yourself? What does spirituality look like after Evangelicalism? What is the 'baby' and what is the 'bathwater'? Ruthie is a memoirist, a speaker, and a guide for spiritual ceremonies. She's also one of my best friends. We don't always agree on the details, but we do on the heart. And she has a life story and hard-earned wisdom that continue to change my life.

    Bad Friendships and Finding True Community with Lauren Paul

    Play Episode Listen Later Sep 22, 2021 51:15


    How do you find kindred friends? How do you break up with a bad friend? Is it ok to have hard conversations over text message? (hint: yes). Co-founder of Kind Campaign, Lauren Paul has spent her adult life speaking to high schools about bullying and healthy relationships. And she also happens to be my friend-group's go-to therapist. If you want some delicious advice on building community and finding boundaries, we gotchu.  

    Vaccine Fears and Family with Jessica Rivera

    Play Episode Listen Later Sep 17, 2021 87:40


    Epidemiologist and Science Communicator Jessica Rivera joins me to talk about mRNA vaccines, why people are scared of them, how to make complex medical decisions for your kids, not 'having it all' as a professional and a parent, and why we should still invite our friends with kids to parties. We also talk about what to do if you fear coming out as gay to your family and how it feels when your career choice disappoints your parents. 

    Jon M. Chu on Work and How to Choose Your Path

    Play Episode Listen Later Sep 15, 2021 55:11


    Film director Jon M. Chu talks about his journey to Hollywood, making Crazy Rich Asians and In The Heights, and responds to questions like how to know if you have a calling, when to make a career leap, and how to overcome the pressure of expectations.

    Question the Self trailer

    Play Episode Listen Later Sep 8, 2021 4:32


    Welcome to season 2. Here's a wee preview of what's to come.

    My Mom

    Play Episode Listen Later Mar 6, 2020 52:18


    In episode 2, Jedidiah interviews his mom, asking her about their deep disagreements and what it’s like to raise a traveler.

    Meet the real Weston

    Play Episode Listen Later Feb 29, 2020 75:39


    Phillip Crosby is the real Weston. In this episode, we talk about the bike trip, our fights, psychedelics, and life after the trip.

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