[COMEBACKS] Turn Your Existing Skills Into a New Career | Grace Abbott (How To Go Freelance)

This week, I spoke with Grace Abbott, founder of How To Go Freelance, about turning the skills you already have into a career, and how to modernize an existing business or brand without blowing it all up.We covered procrastination, niching down without shrinking yourself, making your work more visible, and knowing when to let go of clients, projects, and identities that have become too small. Grace also makes the case for trusting your soft skills, research, and taste in a changing job market and explains why sometimes the biggest thing standing between you and your next chapter is trying too hard to fix yourself.SHOW NOTES and RESOURCES:Learn more about Grace AbbottExplore how to go freelance on SubstackFollow Grace Abbott on IG @howtogofreelanceKatie's Substack | IG: @letitouttt + @katiedalebout | Zine shop is here!Explore my Creative Clinic

This week on COMEBACKS, I spoke with Elizabeth Schild Kott, host of Too Niche and founder of Club Artist Way, about starting over and how stopping is the most important part of figuring out what's next. We talked about the changing internet, creativity, jealousy, unfinished ideas, getting quiet enough to hear your intuition, and why sometimes the best comeback is simply putting one foot in front of the other. LINKS AND SHOWNOTES Elizabeth Online:  ELIZABETHKOTT.COM | Listen to: TOO NICHE? CLUB ARTIST’S WAY ☆ Fall sessions now open for enrollment! Register Here!!  Katie Online: Substack | IG: @letitouttt + @katiedalebout | Zine shop is here! Explore my Creative Clinic

From a marriage she knew was ending long before she admitted it to a 48-hour move from Silicon Valley to New York, Amber Rae and I talk about why some of us stay too long while others leap too fast. If you’ve ever wondered whether you’re honoring your instincts or just avoiding discomfort, this conversation is for you. You’ll discover: The question that reveals whether you’re staying from love, fear, growth, or guilt The surprising way a “safe” relationship can fuel creativity, risk-taking, and reinvention How voicing sexual fear, shame, and insecurity can become the beginning of real intimacy Amber also gets candid about control, body image, Adderall, eating disorders, and the shift from chasing outward approval to choosing what actually feels good. We unpack people pleasing, direct communication, friendship dynamics, and learning to tolerate the discomfort of disappointing others when you stop abandoning yourself. If you feel stuck between knowing and doing, keep outgrowing old patterns but hesitate to make the leap, or find yourself looking for help figuring out what you already know deep down, listen up. Amber left me with a simple but powerful challenge: face the hard truths you’ve been avoiding, and freedom is often on the other side. SHOW NOTES & RESOURCES: Follow Amber on Instagram @heyamberrae Learn more about Amber Rae here | Feelings Journal Sign up for Amber's Newsletter Katie’s Substack | Instagram: @letitouttt + @katiedalebout | Zine shop Katie's Creative Clinic If you liked this episode, try this one from the archive: Episode 477: Erin Claire Jones on Decision Making in Career & Relationships & How Human Design Can Help

This week, I sat down with Cosmic RX founder Madi Murphy. I met her when I wandered into the coffee shop she owned in Brooklyn nearly a decade ago, and since then, she’s launched her own show, The Cosmic RX, published her first book, and started a family. Madi’s comeback began when she decided to leave behind her brick-and-mortar businesses, stepping out of her comfort zone and into what she calls the “Cosmic Zone.” We talk about her trademark dispute with Starbucks over a drink she created, the public backlash that followed, and how that experience ultimately became the catalyst for greater confidence, visibility, and a completely different life path. Plus, she breaks down Saturn cycles and transits, the importance of embodiment over endlessly consuming information, and trusting your own timing. SHOW NOTES & RESOURCES: Learn more about Madi Murphy here Explore the Cosmic Revolution on Substack Follow Madi on Instagram: @iammadimurphy & @thecosmicrx Sign up for Madi Murphy’s newsletter Listen to CosmicRx Radio with Madi Murphy Katie’s Substack | Instagram: @letitouttt + @katiedalebout | Zine shop Explore my Creative Clinic If you liked this episode, try this one from the archive: Episode 335: But You’re Still So Young, Redefining Our 30s with Kayleen Schaefer

This week's conversation is with musician and writer Greta Morgan. Greta spent years touring professionally, including with Vampire Weekend, before losing her singing voice after developing a rare neurological voice disorder. We talk about grief, identity, creativity, silence, what healing actually means, and how sometimes the comeback isn't getting your old life back, it's building a new one you never would have planned. This conversation is thoughtful, grounding, and one I'll be thinking about for a long time. Let us know if you listen.  Show Notes/Resources: Learn more about Greta Morgan here Follow Greta on IG @gretamorgan & Twitter @gretamorgan Check out Greta Morgan's webstore Sign up for Greta Morgan's free newsletter and explore her other work HERE   If you liked this episode, try this one from the archive: Episode 471 - Mixtape of the Last Few Years with James McCrae

This week, I'm re-airing a conversation from the archives with designer Norma Kamali, whose 50-year career is as rich as her designs are iconic — and who, fittingly for the COMEBACKS SERIES, lost her entire company and built it all back. We get into her thoughts on her evolving industry, upcoming generations, falling in love at 65, and why experience is your greatest asset. She gently gives me advice, and shares the motto that's carried her through building her career more than once: The more you do, the more you can do. Show notes: - Find me on IG: @letitouttt + @katiedalebout | Substack     Norma on the Web | Instagram -book a call with me here - Check out the Let It Out Kits | Write Kit | Talk Kit Waitlist - Learn more about my creative consulting & if you'd like to book a free session, book here! - Learn more about "Soft Stories" If you liked this episode you'd like  Kayleen Schaefer's episode

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