Heather and Alan sit down with writer, lyricist, editor, and creative force Kara Cutruzzula—whose winding, multidimensional career is a masterclass in following curiosity, embracing uncertainty, and letting creative energy lead the way. Kara shares how a series of “sliding doors” moments shaped her path from journalism to essays, from writing short plays to crafting musicals, and how she learned to stop treating choices as “right or wrong” and instead as opportunities to experiment, evolve, and discover what’s possible. She opens up about the power of self-belief, the importance of external accountability for big creative projects, her life as a manifesting generator (which Alan and Heather have thoughts about), and her brilliant system for managing ambition without burning out. We also dive into her upcoming Off-Broadway–focused publication The Hat, her musical Marathon, the joy of collaboration, the magic of mixing mediums, the necessity of tender self-compassion, and yes… the many unexpected life lessons learned from Wendy’s, Cracker Barrel, and saucy nugs. Connect with Kara: Brass Ring Daily newsletter: https://brassringdaily.substack.co Marathon the Musical: https://instagram.com/marathonmusica Open Skies creative brainstorm sessions: Link available via her Substack or Instagram bio Connect With Us: 📩 Email us at wasitchancepodcast@gmail.com 🎧 Follow Was It Chance? on your favorite podcast platform 📱 Connect with us on TikTok and LinkedIn ✨ More about Heather at her website, subscribe to her Substack and on LinkedIn, YouTube, and more EPISODE TAKEAWAYS There’s rarely a “wrong choice” — only the next choice. Kara reframes creative decisions not as irreversible forks in the road, but as directions you can always step away from or return to later. Follow what feels just out of reach. If a project feels a little scary, a little too big, or slightly beyond your current skills, that’s Kara’s signal to lean in — not run away. External deadlines are magic. Kara thrives when she brings in collaborators, contests, classes, or structures that help propel her forward when self-created timelines aren’t enough. Curiosity is a compass. Every major shift in Kara’s creative life — from journalism to plays to musicals to newsletters — began by following a spark of interest and treating it like an experiment. You don’t have to do the same thing twice. Kara intentionally avoids repeating what she already knows how to do; new mediums energize her and expand her skills. Self-compassion is a creative tool. “Tender self-compassion” helps combat the guilt loop of not doing enough. Kara normalizes renegotiating commitments with yourself and starting again tomorrow. Small steps matter more than perfect plans. Whether it’s a “things I can do later” list or writing tomorrow’s newsletter today, she reduces overwhelm by shrinking tasks to their next actionable piece. Failure is data, not a dead end. Kara embraces the idea of “first attempt in learning”— seeing setbacks as rerouting toward opportunities she couldn’t have anticipated. Community fuels creation. From the BMI workshop to launching The Hat, Kara continually builds and collaborates with creative networks that energize her ideas and keep momentum alive. Creative lives aren’t linear. Kara’s journey shows that weaving between mediums, interests, and roles doesn’t dilute your path — it is the path. Learn more about your ad choices. Visit megaphone.fm/adchoices
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