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Episode 58: Can Getting Lost Lead to a Breakthrough?
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Creative Work Hour Podcast – Episode 58
Can Getting Lost Lead to a Breakthrough?
Released: July 5, 2025
Crew: Alessandra, Greg, Devin, Shadows Pub, Michael J, Bobby B, Wai Ling, Hillary
Episode Summary
On this post–July 4th episode (or as Greg jokes, “Treason Day”), the Creative Work Hour crew dives into the idea: Can getting lost or veering off track actually lead to unexpected breakthroughs in creative work and life? Each member of the roundtable shares honest stories of confusion, detours, and how embracing the “messy middle” has led to new skills, insights, or even joy.
Highlights & Takeaways
Alessandra
- Takeaway: Getting lost is part of any creative or ensemble process—especially in music performance. Alessandra describes marking her scores with “I got lost here” not as a failure, but as a reminder to listen to others and let go of control.
- Quote: “It’s important I loosen my grip a little bit so I can fly into something much bigger. Because creative work isn’t about being right—it’s about what wants to be said and how it wants to be said.”
Greg
- Takeaway: Sometimes the best discoveries come from wandering off the map. Greg draws a parallel with travel, noting that his favorite destinations appeared when he got lost and just kept going.
- Quote: “Some of the most interesting places I ever found were the result of getting lost. But I kept going on. Let’s see where we end up.”
Devin
- Takeaway: Letting yourself wander can bring you somewhere unexpected—and better. Devin shares his journey from resisting technology (clinging to a flip phone) to building a career in app development, thanks to encouragement from Alessandra.
- Quote: “I wandered a bit and got lost in technology just enough to learn something new. That put me on a different, good path.”
Michael J
- Takeaway: Randomness is vital for creativity. Michael brings up the “20% bees” story: most bees follow the queen, but some go off on their own—and those are the ones who keep the hive alive by finding new food sources.
- Quote: “Wandering the track a little bit, letting your mind explore—often, what feels random leads to something valuable and energizing.”
Bobby B
- Takeaway: It took Bobby time to risk getting lost creatively, especially with memory challenges. Now, intentionality and “humble confidence” help him try new things and find joy in the unexpected.
- Quote: “Intentionality with humble confidence gives you strength to let go and realize you’re going to be fine. And remember to giggle.”
Wai Ling
- Takeaway: Getting lost is both paralyzing and freeing - especially during big projects like a dissertation. Wai Ling uses the idea of “tiny experiments” from Anne-Laure Le Cunff’s book to manage ambiguity and embrace exploration.
- Quote: “There’s virtue in getting lost… I’m learning freedom can be intoxicating and paralyzing at the same time. Tiny experiments help manage that.”
Shadows Pub
- Takeaway: Shadows Pub rarely worries about being lost; she follows whatever path feels right in the moment, always ready to reconnect with her purpose if needed.
- Quote: “Maybe it’s deliberately losing myself. If I connect back to what I’m doing—great. If not, oh well, I wonder.”
Hillary
- Takeaway: Sometimes mistakes or detours produce unexpectedly great results—like her accidental “cream of chicken” manicotti that turned out phenomenal. Hillary admits she struggles not to lose valuable ideas when wandering off course but tries to capture them for later use.
- Quote: “With every pivot or mistake, sometimes you get something even better than what you planned. The trick is not losing track of those gems along the way.”
Episode Themes
- The “messy middle” - why uncertainty is an essential part of creative work.
- Letting go of perfectionism and control.
- Embracing randomness and detours as opportunities for discovery.
- Practical strategies: marking where you get lost (Alessandra), taking baby steps (Wai Ling), intentional risk-taking (Bobby), capturing side ideas (Hillary).
- The value of community practice (“Practice Not Perfects”) and sharing creative struggles.
Listen & Connect
What about you? Has getting lost ever led you to something better? We’d love to hear your story.
Visit us at creativeworkhour.com
Subscribe to Creative Work Hour wherever you get your podcasts - and join us next week for another thoughtful conversation.
Keep wandering. You never know what you’ll find.
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