EPISODE · Jun 22, 2026 · 1H 11M
[COMEBACKS] How to End Well So You Can Begin Again: Megan Hellerer on Grief, Self-Honesty & Directional Living
from LET IT OUT · host Megan Hellerer, Katie Dalebout
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
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What this episode covers
I spoke with my longtime friend, Megan Hellerer, career coach and author of Directional Living. We talk about directional living versus destination living, why clarity comes from action (not thinking), grief, reinvention, productivity, self-honesty, and what happens when you've outgrown a version of yourself but aren't quite sure what's next. Somewhere along the way, Megan ends up coaching me through my own comeback in real time. This one is thoughtful, practical, emotional, and honestly a little therapeutic.
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[COMEBACKS] How to End Well So You Can Begin Again: Megan Hellerer on Grief, Self-Honesty & Directional Living
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