633 episodes
Encore: Jenna Kutcher on Taking Your Dreams Off the Shelf and Embracing the “What Ifs”
16/10/2026 | 48 mins.Description:
Jenna Kutcher was a few years into a corporate career at Target when her boss slid a five-year plan across the desk. A promotion, more money, more responsibility, all mapped out by somebody else, and every step of it was something she did not want. She did not know yet what she wanted instead, but she knew exactly what she no longer wanted. So she bought a camera off Craigslist for $300.
We’re in the middle of our Courage to Change: Do It Scared series, and I’m bringing back this conversation from January 2023, when it opened our For the Love of What If series. Jenna walks us through how that camera became a photography business, then the Goal Digger podcast, then the New York Times bestseller How Are You, Really?, and why she built the next thing quietly on the side while the paycheck was still coming in. We talk about what happens when more money doesn’t buy the life you’re longing for, why time became her real currency, and the question she asked me that I could not shake: not how does it look, but how does it feel.
Stay for the end, because something happened after this tape. On the last day of 2025, after 968 episodes, Jenna paused Goal Digger while it was still going strong. She meant every word she said here.
Thought-provoking Quotes:
Her question is yours now. Not how does it look. How does it feel. (Jen Hatmaker)
That is what courage to change actually looks like most of the time. Not a blaze of glory. Not a resignation letter thrown in the air. (Jen Hatmaker)
A woman asking an honest question, hearing an answer she did not love, and then doing something about it anyway. (Jen Hatmaker)
You are not in prison. You made that rule up, and you are allowed to change it. (Jen Hatmaker)
Resources Mentioned in This Episode:
How Are You, Really? by Jenna Kutcher - https://bookshop.org/book/9780063221949
A New Chapter for Goal Digger - https://jennakutcherblog.com/a-new-chapter-for-goal-digger: Jenna on why she paused the podcast
Leave us a voicemail - https://jenhatmaker.com/podcast: Tell us about the safe thing you walked away from, or the one you’re thinking about leaving.
Guest’s Links:
Website - https://jennakutcher.com
Instagram - https://instagram.com/jennakutcher
Facebook - https://facebook.com/jenna.kutcher
Connect with Jen!
Jen’s Website - https://jenhatmaker.com/
Jen’s Instagram - https://instagram.com/jenhatmaker
Jen’s Twitter -Description:
Barbara Kingsolver got the offer on her first novel the same day her first daughter was born. She came home from the hospital to a blinking answering machine, and the book came out the week that same baby learned to walk. Almost forty years later, she has a Pulitzer Prize, the National Book Foundation’s medal for a lifetime of work, and a recovery house for women in Lee County, Virginia, built with her Demon Copperhead royalties. She has been one of my literary heroes and true life mentors for decades, and I still cannot believe I got to talk with her.
We talk about what publishing looked like in 1988 versus now, why a slow-building career was a gift to a young mom, and the stubborn hand condition we both live with that ended her public book signings. She walks us through October on her farm in southern Appalachia, where the tomatoes are canned, the peppers are roasted, and she is the one who gets the call when a lamb gets stuck. And she makes the case that rural people are close to half of this country but almost none of what we see on screen, which is why she writes books that work as mirrors for her neighbors and windows for everybody else.
Then we get into Partita, her new novel. Livia was a piano prodigy from east Tennessee who became a small-town piano teacher instead. In her fifties, the first love who derailed her calls and asks to see her, and she has seven days to decide. Barbara built the whole book like a Bach partita, with movements named for old dances and a listening list in the front. She tells us how a small-town girl fell for classical music on her living room floor, why nobody in America wants to talk about class, why revision is where art lives, and about the practice room scene her pianist friend had been waiting her whole life to read.
Thought-provoking Quotes:
I became a novelist and a mom the same day. (Barbara Kingsolver)
I need my hands to write books. If you let me keep them, I will write you more books. (Barbara Kingsolver)
Rural people are close to half of the population of this country, but we are just about zero percent of what you see on television, in the movies, or in the news. (Barbara Kingsolver)
I want to write these books that are both mirrors for the people who need to see themselves and windows for the people who don’t know. (Barbara Kingsolver)
When you’re in the flow state making something beautiful, that is love too. It’s another kind of love. (Barbara Kingsolver)
I love revision. I feel like revision is where art really lives. (Barbara Kingsolver)
When I’ve finished a book to my absolute satisfaction and send it out into the world, the work of it is only half done. (Barbara Kingsolver)
When I closed Demon Copperhead, I remember thinking, I have just read a masterpiece. (Jen Hatmaker)
Some people ask me, how can you be optimistic in these times? And I say, look who I’m dealing with. (Barbara Kingsolver)
Resources Mentioned in This Episode:
Partita by Barbara Kingsolver - https://bookshop.org/book/9780063577541: Barbara asks you to buy it from your local independent bookstore. The listening list is in the front of the book.
Labor: One Woman’s Work by Dr. Mary Fariba Afsari - https://bookshop.org/book/9781668015407
Higher Ground Women’s Recovery Residence in Pennington Gap, Virginia, founded with Demon Copperhead royalties
Barbara’s earlier books we talk about: Demon Copperhead, The Poisonwood Bible, Animal, Veg ...Description:
This episode is sponsored by Function.
October is Menopause Awareness Month, and every time we talk about midlife bodies on this show, what you write back to me isn’t really about hot flashes. It’s about being dismissed. Walking into an appointment, saying something feels different, and being told it’s normal. Dr. Tiffany Lester, a board certified integrative medicine physician and the Women’s Health Medical Director at Function, has built her career on refusing that answer.
We get into the wellness trend she went all in on and walked away from (and why so much of the research behind it was built around men), the moment her own lab results told her perimenopause had arrived, and what a standard annual physical tends to miss. She explains why markers like ApoB and fasting insulin matter so much in our forties and fifties, whether knowing this much about your body makes you healthier or just more anxious, and where the line sits between owning your health data and needing a doctor across the table. I share what happened when I brought my own results from Function to a new doctor, and we talk about who gets left out of conversations like this one and why health equity is so personal to her.
Thought-provoking Quotes:
As Dr. Stacy Sims likes to say, we’re not little men. We are separate. And that’s okay, it’s not a bad thing. (Dr. Tiffany Lester)
I knew intellectually that this transition was coming. But I still wasn’t ready for it somehow. (Dr. Tiffany Lester)
We have in some ways been conditioned to accept the bare minimum. (Dr. Tiffany Lester)
It’s much harder to dismiss a woman when she’s there with black and white data. (Dr. Tiffany Lester)
We do not have to just grin and bear it. (Jen Hatmaker)
A lot of people don’t even know what they don’t know. But once you see it, you can’t unsee it. (Dr. Tiffany Lester)
It starts with knowing your numbers and not guessing, because you can’t manage what you don’t measure. (Dr. Tiffany Lester)
Resources Mentioned in This Episode:
Function - https://functionhealth.com/FortheLove: Join and use code FORTHELOVE25 for a $25 credit
The work of Dr. Stacy Sims on women’s physiology
Guest’s Links:
Website - https://drtiffanylester.com
Instagram - https://instagram.com/drtiffanylester
Substack - https://drtiffanylester.substack.comPeople tell me I’m brave all the time. About the divorce, about the book, about rebuilding my life while everybody watched. And every single time, I feel a low-grade panic, because I know what it actually looked like from the inside: sitting in my parked car for 45 minutes because I could not make myself walk in, typing one sentence and deleting it 15 times, sobbing in the parking lot outside my brand new financial planner’s office. I was not brave. I was scared, and I moved forward anyway.
We’re kicking off our October series, Courage to Change: Do It Scared, and today it’s just me and you. I’m handing you a much smaller word than “ready.” Ready is a feeling, and you can’t schedule a feeling. Willing is a decision, and you can make it on a Tuesday while you unload the dishwasher. We’ll sort fear into two piles: the warning you should heed and the fee you simply have to pay. And I’m going deeper on two stories: the months I waited too long to face what was happening in my marriage, and the years I coddled my fear before publicly changing my theology on LGBTQ inclusion in 2016. That was the best fee I ever paid.
Coming up this month: Barbara Kingsolver, Kim and Penn Holderness, and Sarah Stewart Holland and Beth Silvers of Pantsuit Politics. You’re not going to feel ready. But you can get willing, and willing is available to you in the next ten minutes.
Thought-provoking Quotes:
In my life, ready never came. Not one time in my entire life did readiness already exist before the hard thing.
Ready is something like a feeling, and you can’t schedule a feeling. Willing is a decision. Willing is a choice.
Fear is not measuring whether or not you should. It is measuring whether or not this thing matters.
There is fear that is a warning that should be heeded. And then there is fear that is just a fee. It’s just a cost that you’re going to have to pay.
The first one has a real object, but the second one has an audience.
The fear was a fee. It was not a warning. And I did have to pay it. It’s the best fee I ever paid.
I may not be ready, but I am willing.
You’ve done harder things than this. And you did those things scared too.
Resources Mentioned in This Episode:
Awake: A Memoir by Jen Hatmaker - https://bookshop.org/p/books/untitled-memoir-jen-hatmaker/22287565
Join the AWAKE Collective on Letters from the Middle - https://jenhatmaker.substack.com
October AWAKE Collective Reflection Guide, with this month’s writing prompt: “The Thing I Would Do If I Were Not Scared”
Leave us a voicemail - https://jenhatmaker.com/podcast: Tell me the change you’re scared of, or the one you already did scared.
Connect with Jen!
Jen’s Website - https://jenhatmaker.com/
Jen’s Instagram - https://instagram.com/jenhatmakerThis month’s Jen Hatmaker Book Club pick is The God of the Woods, and Liz Moore joins Jen straight off the set of the Netflix series she is co-showrunning in the Adirondacks. Liz talks about the family cabin with no TV and no internet where she read every old book in the house, her early years singing in New York clubs while working weekends at a guitar store, and the practical family that taught her to keep a day job. She explains the difference between a TV writer and a showrunner, why she loves casting local square dancers and first-time actors, and how the cast is deepening the characters she wrote. Plus how she starts a four-year novel knowing only the people, the place, and the first problem, her worries about what AI will do to developing brains, the title her publisher vetoed, the hand-drawn map at the front of the book, and what she is reading right now.
Thought-provoking Quotes:
You have to know people, you have to know place, and you have to know problem.
You just sort of whittle down what feels right emotionally until you get to a place that feels right emotionally, and then that’s the end of the book.
You have to experience frustration in learning and then get past it in order for the brain to grow.
I want the title to have multiple meanings, and for those multiple meanings to become apparent as the reader moves on.
I have too many jobs that I love, which is a huge blessing in life.
Resources Mentioned in This Episode:
The God of the Woods by Liz Moore
Long Bright River by Liz Moore (and the Peacock series)
The Words of Every Song by Liz Moore
Raven Black by Ann Cleeves
London Falling by Patrick Radden Keefe
Get Down by Asali Solomon
Sing Sing (film)
Louis L’Amour westerns
Temple University MFA in Creative Writing
Guest’s Links:
Website - https://www.lizmoore.net/
Instagram - https://www.instagram.com/lizmoorebooks/
Twitter - https://x.com/LizMooreBooks
Facebook - https://www.facebook.com/lizmoorewriter/
Connect with Jen!
Jen’s Website - https://jenhatmaker.com/
Jen’s Instagram - https://instagram.com/jenhatmaker
Jen’s Twitter - https://twitter.com/jenHatmaker/
Jen’s Facebook - https://facebook.com/jenhatmaker
Jen’s YouTube - https://www.youtube.com/user/JenHatmaker
The For the Love Podcast is presented by Audacy.&nbs ...More Relationships podcastsTrending Relationships podcastsAbout For The Love With Jen Hatmaker PodcastNew York Times bestselling author Jen Hatmaker has arrived in the middle years, and she couldn't be happier about it.Jen has navigated the ins and outs of life, from career to parenting, marriage (and divorce), spiritual evolution, and the joys of being a hardcore Gen Xer.With each weekly episode, Jen serves as our "everywoman" guide to all the seasons, past, present, and future, as she walks excitedly and tenaciously into the second half of life.Some weeks, Jen brings her perspective straight to you, just her and the mic, talking through the things we're all navigating. Other weeks, she pulls up a chair for some of the most interesting and accomplished guests around, plus a few of her favorite friends, bringing insight, expertise, and a whole lot of heart to the most relevant topics of our time.While Jen has plenty of wisdom to share (and some pretty hilarious stories, too), she doesn't claim to know it all. From her honest solo reflections to her compelling conversations with guests, she's here to reassure you that you're not alone in this game of life.It's "For the Love" of all that is good, justified, exasperating, exhilarating, real, fun, and so much more.Listen to For The Love With Jen Hatmaker Podcast, Let's Be Honest with Kristin Cavallari and many other podcasts from around the world with the radio.net app

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