May 26, 2025

How to Playfully "Date" Potential Careers and Callings | Charlie Gilkey

Have you ever felt stuck pursuing a path that didn't truly resonate with you? A career, creative endeavor or major life change that you committed to fully, told the world it’s what you were doing, and who you were now…only to realize it wasn't what you really wanted?

Today, we're going to explore a more forgiving approach - one that allows you to experiment and gather critical data before going all-in.

Imagine if you could "date" a potential pursuit, getting to know it intimately, before deciding whether to take that next step. What if the weight of having to definitively choose was lifted, allowing a sense of playfulness and curiosity to guide your exploration?

My partner in conversation today is Charlie Gilkey, a strategic advisor, executive coach, founder of the Productive Flourishing consultancy, and author of the multi-award-winning book, Start Finishing and Team Habits. Charlie brings a wealth of wisdom for trying on new identities through low-risk projects and experiments.

Find Charlie Gilkey | Website

Host: Jonathan Fields, creator of Good Life Project podcast and the Sparketype® Assessment ,

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