In this episode of Time to Press Pause, host Ellen Williams welcomes two guests: executive coach and Morningstar Ventures CEO Andrea Chilcote, and philanthropic advisor Stephanie Borsari. Andrea explains three common reasons professionals “press pause” in their careers: being involuntarily forced into change (such as restructuring), retiring without clarity on the next chapter, or experiencing a slow values or lifestyle clash. Stephanie falls into the last category; though she had a successful career in executive management, she discovered her role was unfulfilling and misaligned with her deeper values. With Andrea’s guidance, Stephanie decided to leave her position and step back to rediscover what mattered most.
During her professional sabbatical, Stephanie tried out various creative pursuits—writing poetry, considering new hobbies, and reevaluating her work identity. Eventually, she discovered she wanted to return to philanthropy on her own terms, establishing an independent consulting practice that allows her to focus on connecting private foundations and donors to meaningful causes. Andrea notes that not everyone must become a business owner; what’s important is to discover the path that authentically aligns with one’s strengths and values.
Both Andrea and Stephanie emphasize the privilege of taking a reflective pause, underlining the honesty and integrity needed to answer difficult questions about one’s true calling. Modern leadership, Andrea adds, acknowledges no individual can have all the answers. Stephanie now embraces vulnerability and emotional connection as key to her identity, and they both advise leaders to press pause the moment they discover they are no longer their best selves or are working for the wrong reasons.
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