Dear Chelsea – “Twice with Mitch Albom”
Podcast: Dear Chelsea
Host: Chelsea Handler
Guest: Mitch Albom
Release Date: October 23, 2025
Episode Overview
In this heartfelt and dynamic episode, Chelsea Handler is joined by acclaimed author Mitch Albom to discuss the creative process, the making of his latest novel Twice, and his storied career writing both nonfiction and fiction bestsellers. Together with co-host Catherine Law, Chelsea and Mitch explore themes of second chances, the complexities of truth, coping with regret, and the art of writing itself. Listeners are also treated to Mitch's personal revelations and practical advice, making the conversation moving, inspiring, and insightful for readers, writers, and dreamers alike.
Key Topics & Insights
1. Mitch Albom’s Writing Career and Philosophy
- Tuesdays with Morrie: Origins and Impact
- Written to help pay his dying professor’s bills, the memoir was intended as a simple act of kindness but unexpectedly changed Mitch’s life and career.
- “I was trying to do something for somebody else, which is kind of one of the points of the book ... I gave Maury all the money and said, here, you don’t have to worry about when you die.” (08:45)
- The book’s success transformed Mitch from a renowned sportswriter into “everybody’s rabbi” (10:48).
- Transition to Fiction
- Post-Tuesdays with Morrie, Mitch shifted to fiction, beginning with The Five People You Meet in Heaven, pursuing themes instead of plots.
- Discusses publisher resistance:
- “All anybody wanted was Wednesdays with Morrie ... I said, I do have this idea for a novel...” (13:34)
2. The Power of a ‘Yes’ and Creativity Amid Rejection
- “It doesn’t matter how many people say no. You just need one person. All you need is one person.” (17:20)
- Both Chelsea and Mitch share stories about perseverance in the face of creative rejection.
- The importance of finding even one champion for your creative vision.
3. Thematic Writing & The Little Liar
- Mitch outlines his theme-driven writing approach—he starts every book by identifying a core idea, not a plot.
- “Most of my writer friends... come up sort of with a plot ... I always try to come up with a theme...” (18:35)
- The Little Liar drew inspiration from Holocaust survivor testimonies and reflects on the destructive power of lies, both historically and in contemporary society.
- “What if I make it a kid who’s never told a lie before in his life and he gets tricked into telling his own people that it’s okay to get on these trains?” (21:21)
- On researching:
- “Everything in The Little Liar is historically accurate ... I researched the hell out of that book.” (23:49)
- On fictionalizing Hitler as “the Wolf”:
- “I didn’t want his name in any of my books ... Everything is historically accurate except the characters who I invented.” (23:49)
4. Writing Process and Practical Advice
- Mitch describes his disciplined daily routine:
- Writes for two to three hours every morning, before looking at any media or devices.
- Leaves off mid-stride in a good passage so he’ll look forward to returning to the work (25:47).
- “You go until your tank is empty and then you come back and do it again.” (27:09)
- Advice he received:
- “Surround yourself with the best music, the best art, the best books, the best film, and everything else will take care of itself.” (27:59)
- Advocates osmosis—drawing inspiration from all forms of art.
5. Discussion of “Twice” and Deeper Life Lessons
- Premise of Twice:
- A boy, Alfie, discovers he can redo any life event—but only once, and he must live with the new outcome.
- Explores the “grass is always greener” syndrome and the lure (and danger) of trying to perfect life or love.
- “He has the power to do anything in his life again, but only one time ... and he has to live with the consequences the second time.” (36:09)
- On Regret and Life Lessons:
- Neither Chelsea nor Mitch shy away from admitting regrets, but both value what past mistakes have taught them.
- “All of the mistakes ... have taught me the things that I have learned now ... have shaped me into the person I am now.” (39:52)
- Mitch’s Personal Story – Finding Family in Haiti
- Shares how not having his own children led to “inheriting” an orphanage in Haiti, ultimately adopting a daughter and helping over 100 children.
- “To have that opportunity is a miracle ... but I don’t think it would have happened if I hadn’t made the first mistake.” (40:58)
- The Rule of Love in “Twice”:
- Alfie can redo moments, but not to get love back.
- “He can do anything twice except love. He can’t get somebody to love him twice ... I think, you know, that's kind of how it should be.” (49:37)
6. Chelsea & Mitch on Creativity Without Limits
- The dangers of being typecast, accepting only one’s “designated” creative path, and the importance of multiple evolutions.
- Story about Maya Angelou:
- “It’s the cruelest thing you can ever say to somebody ... It’s telling a bird that it shouldn’t fly.” (44:13)
- Story about Maya Angelou:
7. Reading, Inspiration, and Favorite Books
- Mitch’s bookshelf is filled with dog-eared, annotated books.
- “I destroy my books, but I’m good with that ... You devoured it ... You ate the whole meal.” (54:47)
- Favorite titles:
- Gilead by Marilynne Robinson
- History of Love by Nicole Krauss
- The Right Stuff by Tom Wolfe
- Praises writing that “packs a punch with sentences”
- Chelsea recommends Circe by Madeline Miller (55:09)
Notable Quotes & Moments
- On Becoming “Everybody’s Rabbi”:
- “You can’t just go ‘Patriots’ and go up the escalator ... you have to stop and you have to talk. And ... it’s sensitized me in a way to people.” – Mitch Albom (10:48)
- On Truth vs. Lies in Modern Times:
- “There shouldn’t be different views of the truth. The truth is the truth. But now there are multi–multiverses.” – Chelsea Handler (21:09)
- On Writing About Trauma or Family:
- “Everyone is entitled to tell their story and write their story ... By telling your story, you are helping so many people.” – Chelsea Handler (77:18)
Timestamps for Important Segments
- Mitch Albom’s Early Career & Tuesdays with Morrie: 08:45 – 10:48
- Transition to Fiction & Writing ‘The Five People You Meet in Heaven’: 13:34 – 17:17
- Publisher Resistance & the Power of 'Yes': 17:20 – 18:35
- Themes in 'The Little Liar': 18:35 – 23:49
- Writing Process & Advice: 25:47 – 30:22
- Premise and Rules of ‘Twice’: 36:09 – 39:52
- Regret, Life Lessons, and Mitch’s Haiti Story: 39:52 – 44:13
- Creativity & Not Being Typecast: 44:13 – 49:37
- Love, Rules in ‘Twice,’ and Writing for Loved Ones: 49:37 – 52:12
- Reading Habits & Book Recommendations: 52:57 – 55:28
Listener Q&A Highlights
On Getting Started as a Writer (66:31)
- Both Chelsea and Mitch stress the importance of writing first thing in the morning with a clear mind, avoiding media and distractions.
- Tips: Use note cards for scenes/memories, avoid strict chronology, allow free-flow.
On Writing About Family Trauma (77:17)
- Chelsea encourages honesty and self-protection:
- “You just have to be your own best protector and think of that little girl that you were ... and this is your job to protect her in this moment.”
- Suggests including a prologue to explain intentions and pre-emptively address controversy.
Memorable and Moving Moments
- Mitch’s story of running an orphanage in Haiti and the “miracle” of adopting his daughter (40:58).
- Chelsea’s emotional response to Mitch’s journey of personal growth and compassion:
- “What a model male human being. The opposite of toxic masculinity.” (59:11)
- The mutual admiration and invitation for Mitch to see Chelsea's live show in Detroit (59:03).
Episode Tone & Style
The tone is thoughtful, candid, and deeply human—balancing humor, personal stories, and powerful emotional revelations. Chelsea and Mitch’s rapport is warm, respectful, and full of mutual admiration, offering both laughter and wisdom to listeners.
If you’re a reader, writer, or simply interested in how people find meaning and purpose after setbacks, this episode is a must-listen: funny, real, and deeply inspirational.