[COMEBACKS] How to End Well So You Can Begin Again: Megan Hellerer on Grief, Self-Honesty & Directional Living

This week I spoke with career coach, author of Directional Living, and my longtime friend Megan Hellerer. What started as a conversation about her book turned into a conversation about grief, endings, iteration, and what happens when you've outgrown a version of your life. We talk about directional living versus destination living, why clarity comes through action, the importance of self-honesty, productivity as a form of avoidance, and how to navigate the uncomfortable in-between when you know something needs to change but aren't sure what's next. In the second act of this episode, Megan ends up coaching me through my own transition from Let It Out into COMEBACKS, and we talk about how to let go of a chapter that no longer fits so you can begin again. SHOW NOTES:  Megan Hellerer   Directional Living: A Transformational Guide to Fulfillment in Work and Life by Megan Hellerer Katie's Substack | IG: @letitouttt + @katiedalebout | Zine shop is here! My Creative Clinic. If you liked this episode, try this one from the archive: Ambition Within Cynicism: Organizing Creative Chaos with Abbi Miller

This is the second episode of the COMEBACKS series, featuring Liz Tran. I loved getting to talk with her again in this new format. In this episode, Liz shares her experience with divorce, reinvention, dating, and what it actually takes to rebuild your life when the version you planned for falls apart. We talk about how loneliness can transform you when you stop trying to outrun it, the ways avoidance can masquerade as productivity, AQ (adaptability quotient), timelines, and learning to trust that your life can expand in ways you never could have planned for. SHOW NOTES: Explore more from Katie Dalebout: Katie Dalebout Substack + Let It Out Lists Katie's Instagram: @letitouttt + @katiedalebout My Zine Shop and My Creative Clinic Find Liz on the Web | Instagram | Podcast  Liz's latest book,  AQ: A New Kind of Intelligence for a World That's Always Changing  Liz's first book, The Karma of Success If you liked this episode, try this one from the archive: Karma Success with Liz Tran, Founder of Reset NYC

In this first episode of the new COMEBACKS series, I spoke with my longtime friend Jessica Murnane about reinvention, knowing when to move on, and why I tend to linger in the past too long. We talk about creative pivots, grief around letting go, and starting again—without forcing it. Jess shares how she’s built multiple careers, moved cities, why she’s not nostalgic, and the simple question she always comes back to when she’s stuck: What are you waiting for? Let us know if you listen. Key Insights:  Starting something new can be the fastest way to let go of something old. Reinvention isn’t always strategic—it’s often a gut feeling that it’s time to move on. Lingering (in careers, relationships, identities) is often about fear, not timing. Nostalgia can keep us stuck. Success isn’t recognition or fame—it’s often feeling financially and emotionally steady. Movement is one of the best ways to shift your mental state when stuck, even just a few minutes. Aging narratives are mostly cultural noise—you don’t have to opt in. And extremely boring. Show Notes / Resources / Mentions: Katie's Substack | IG: @letitouttt + @katiedalebout | Zine shop is here!Inside + Outside with Jessica Murnane Subscribe on Spotify, Apple Podcasts, or your favorite podcast player! If you liked this episode, try this one from the archive: The Art of Tending: Kerrilynn Pamer, Founder of CAP Beauty, Returns

This week, a very important person in my life—Sacha Jones—hosts the podcast. Every year for nearly a decade Sacha has come back on to host the episode the last week of April (the week of my birthday). This year she really outdid herself: she shocks me with questions sourced from my friends and family and a special guest joins us to host a special rapid-fire round.  Sacha is one of the most creative, wise, and gentle people I know and our annual catch-ups end up being time capsules of what we’re leaning this year. Prior to her surprises, we cover focus while being people who do many things. And how much the little things—like simple routines, mean to me. I will be back on the other side of the interview next week but until then I hope this conversation offers you something, that you come away from it feeling the energy of it. Or that it keeps you company you during your day. Show notes: - Subscribe to our newsletter to get show notes + essays, etc. sent to your inbox - Follow @letitouttt on Instagram. I'm @katiedalebout - Follow Sacha on Instagram - Sacha's general website | ceremonies website - The Let It Out Kits are 32% off with the code 32 - My episode with Derick Melander - My 2020 episode with Anjie Cho - Learn more about my creative consulting & if you'd like to book a free session, book here! If you liked this episode, try out: Episode 358: Two Saviors, Writing, Touring & Surfing with Musician Buck Meek of Big Thief

This week I spoke with Kyle (Smiling Strange) about generations, the internet then vs. now, how we discover music as we grow up, and what it takes to keep evolving instead of calcifying with age. We talk about his process of making videos while walking around his neighborhood, why authenticity cuts through the algorithm, and how culture is shifting faster than we can keep up. This one is eclectic—it goes from music to the internet to creativity to philosophy (and even economics). Kyle is super interesting and fun to talk to, and I left this conversation with a lot to ponder. I hope you do too. Let us know if you listen.   Show Notes / Resources More of Kyle: Hey Smily Strange: A podcast about DIY scenes, independent music, and the best uncslop available. Smiling Strange Patreon: Internet Busking + Exclusive Content Follow Kyle Rosse on IG @smiling_strange Also check out @__pileup__ and @yellowrooooom Explore more from Katie Dalebout—host of the Let It Out Podcast—including her writing, creative resources, and journaling tools: Katie Dalebout Substack + Let It Out Lists Instagram: @letitouttt + @katiedalebout My Zine Shop and My Creative Clinic If you liked this episode, try this one from the archive: Molting and Slow Growth with Andrew Bird [REAIR]

This week I spoke with Emmalea Russo about her novel Vivienne, the strange experience of putting art into the world right now, and what it means to create something that doesn’t try to make everyone comfortable. We talk about cancel culture, ’90s nostalgia, the difference between information and truth, discomfort in art (and growth), and how dreams can act as an antidote to the algorithmic age. This one gets a little philosophical—we go from astrology to internet culture to the writing process to dreams—so buckle up. Let us know if you listen ⭐️   Show Notes / Resources / Mentions: Vivienne by Emmalea Russo Dream School Emmalea Russo's website The Moon Papers, A Novel by Emmalea Russo Find Katie: Katie's Substack | IG: @letitouttt + @katiedalebout | Zine shop is here! My Creative Clinic. If you liked this episode, try this one from the archive: Collapsing Timelines with Holisticism's Michelle & Wallis

This is part two of my conversation with herbalist and writer Rachelle Robinett, recorded live in LA in a very intimate room full of friends while talking about her book Naturally. In this part, we get into our favorite themes from her book: pleasure, pain,  transformation, grief, and the ways creative expression helps us process. We also talk about sleep hygiene, the connection between slowing down and self-awareness, why knowing the state you’re trying to shift matters before reaching for anything, and how herbalism can help when you know what you’re actually seeking. Toward the end, we open it up to questions about adaptogens, nervines, kava, tinctures, fresh versus dried herbs, and what daily life looks like now that Rachelle lives in Costa Rica, where she says she’s practicing herbalism less like a system and more like a way of living.   Show Notes / Resources / Mentions: Learn more about Rachelle Robinett on her website: https://www.rachellerobinett.com/ Follow Rachelle Robinett on IG @rachellerobinett Grab her book Naturally on Amazon: https://amzn.to/3MOTEVS Find Katie: Katie's Substack | IG: @letitouttt + @katiedalebout | Zine shop is here! My Creative Clinic. Book Let It Out: A Journey Through Journaling   If you liked this episode, try this one from the archive: Desire, Dopamine, and Anticipation: Rachelle Robinett on Herbalism, Evolution and Redefining Ambition

This week is a little different: usually I’m the one asking the questions, but this time I’m on the other side. My friend Sophie had me on as the first guest to her new podcast, Late to the Party, where she interviewed me. This conversation ended up feeling surprisingly cathartic and was the most honest I’ve ever been while being recorded. She gave me a container to share and her genuine interest, thoughtful questions, and care gave me the confidence to open up about things I haven't. This episode fills in a lot of the story of what’s been happening with not only me these last several years but also tells the full story of the podcast,  from beginning to the middle, I'm still in now. Sophie’s show, Late To the Party is a perfect companion to this show, it’s for anyone who feels a little behind in love, work, or life, or is growing into something new. It was an honor to be her first guest and listen to all the episodes she's aired since.   Show Notes / Resources / Mentions: Late to the Party Podcast Instagram @latetotheparty_pod Sophie Ragir @sophragir Find Katie: Katie's Substack | IG: @letitouttt + @katiedalebout | Zine shop is here! My Creative Clinic. Book Let It Out: A Journey Through Journaling   If you liked this episode, try this one from the archive: Sacha Jones returns to interview me for a special birthday episode

This week I spoke with herbalist and writer Rachelle Robinett about her new book, Naturally, and some of my favorite ideas inside it: dopamine, novelty, primal motivation and strategies to regulate our nervous systems. We also talk about how the ways we distract ourselves are often attempts at a change in state and how knowing what type of state change we’re craving can help us determine not only which herb to work with, but what the desire under the craving actually is. We get into her favorite herb, how she uses it as an alternative to alcohol, as well as how she’s evolved within wellness culture and how she’s redefining ambition now.   Show Notes / Resources / Mentions: Learn more about Rachelle Robinett on her website Follow Rachelle Robinett on IG @rachellerobinett RSVP Here to a free live event with Rachelle, Herb Club LA, and me on March 9th at 6pm. Grab her book Naturally on Amazon Find Katie: Katie's Substack | IG: @letitouttt + @katiedalebout | Zine shop is here! My Creative Clinic Book Let It Out: A Journey Through Journaling   If you liked this episode, try this one from the archive: Supernatural Herbalism, Adaptogens, Trends, Productivity, Change + with Rachelle Robinett

This week I talked to attorney and writer Savala Nolan. Her newest book, Good Woman, which was named a Most Anticipated Feminist Book of 2026 by Ms. Magazine, is out now. I got to read an early copy and loved it. She writes with raw honesty about making herself smaller, both literally and metaphorically, in order to be a good daughter, a good wife, a good mother, and all the ways she allowed herself to be diminished to keep the peace, and how many others do this too. The 12 essays blend cultural commentary, personal experience, reportage, and history. We talked about the vulnerable process of writing a personal book of essays, including writing about divorce, motherhood, and the importance of respecting one’s appetite in every way, from creative to physical. I always love talking to Savala and loved getting to catch up with her here. Let us know if you listen.   Show Notes | Resources | Mentions: Follow Savala Nolan on IG and on Substack Good Woman: A Reckoning by Savala Nolan Website Find Katie: Katie's Substack | IG: @letitouttt + @katiedalebout  | Zine shop is here! My Creative Clinic.  Book Let It Out: A Journey Through Journaling   If you liked this episode, try this one from the archive: Don't Let It Get You Down: Savala Nolan Returns (part 1) 📖 Don't Let It Get You Down: Savala Nolan Returns (part 2) 🥖