What if letting go of the five-year plan is the first step toward actually feeling like yourself? In this soul-forward conversation, I sit down with Catherine Pao, a former tech exec turned holistic leadership coach who helps high-functioning humans make friends with their intuition. She’s also the incredible human who supported me last year through some of the most challenging parts of stepping into my next chapter (working title “former lawyer & spiritual weirdo overshares on the internet”). Together, we wandered through: * the moment she walked away from startup life and into a fog of uncertainty (and possibility) * how structure, when it’s not weaponized by your inner overachiever, can actually support your creativity * why “wintering” isn’t laziness, it’s preparation * the unexpected creative project that quietly re-lit her business (and her spirit) This episode is a must-listen for anyone navigating a transition or craving a life that feels more like them. Chapters 00:00 Nature's Influence and Personal Reflection 01:58 Career Transitions and Self-Discovery 04:01 Navigating Uncertainty and Trusting the Process 06:52 The Journey of Self-Discovery and Intuition 11:00 Balancing Intuition and Structure 18:51 Embracing Seasons of Life and Transition 28:13 Trusting Yourself in Times of Change Guest Info : Catherine Pao is a holistic leadership coach and creativity mentor who helps people integrate their intuitive, creative intelligence with their strategic, intellectual power. She works with ambitious creative spirits, executives, and leaders who desire living life from deeper alignment with their unique soul blueprint. Her work supports clients in reconnecting with their inner wisdom, unlocking creative flow, feeling a deep sense of thriving and trust in life, and experiencing life as effortlessly abundant—both in their work and within themselves. Catherine has coached founders, leaders, and teams at Google, Facebook, Pinterest, Twitter, Nextdoor, GitHub, Rippling, and numerous startups through executive coaching, group programs, and leadership development trainings. Formerly, Catherine led digital marketing and growth product teams at Blue Apron, DigitalOcean, Fab.com , and Microsoft. She holds a degree in Computer Science Engineering and Marketing from the University of Pennsylvania, is a certified Co-Active Coach (CPCC), and a 300-hour registered yoga teacher (RYT-300). Her current creative delights include: crafting collage mandalas, curating immersive Spotify playlists, dancing 5Rhythms, and exploring the ASTAR creative process. Learn more at www.catherinepao.com or follow her on Instagram @catherinepao . Music thanks to Mutual Benefit! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit alliecanton.substack.com
