EPISODE · Jun 18, 2025 · 1H 33M
Exit Interview: The Loneliness of Leadership with Carrie Siubutt
from Conversations with Offor · host Offor
Carrie Siubutt, former CEO of SimpleHealth, shares what happens when personal resilience meets professional burnout—and why stepping away can be the strongest decision you make.Carrie's journey spans from being diagnosed with a rare neurological condition at 11, to building a $75M telemedicine company with 200 employees, to facing regulatory changes and market turbulence that forced devastating choices. She opens up about the isolation of CEO leadership, the unique pressures facing leaders of color, and how wanting to be liked became her greatest vulnerability.We dive deep into what Carrie calls "the work twisties"—those moments when high-performing executives lose their footing and can't see a path forward. She reveals the physical and mental toll of executive burnout, the 12-month recovery process that followed, and how she's reinventing herself in an entirely new industry. This isn't about bouncing back—it's about the wisdom that comes from breaking down.Key topics:How disability became her leadership superpowerThe double standards facing CEOs of colorWhy wanting to be liked became her biggest weaknessLeading through regulatory crisis and market collapseRecognizing the signs of executive burnoutThe cost of caring too much about your teamBuilding sustainable recovery habits after traumaThis conversation reveals why we need honest stories about executive mental health and the courage it takes to choose recovery over revenue.
What this episode covers
Carrie Siubutt, former CEO of SimpleHealth, shares what happens when personal resilience meets professional burnout—and why stepping away can be the strongest decision you make.Carrie's journey spans from being diagnosed with a rare neurological condition at 11, to building a $75M telemedicine company with 200 employees, to facing regulatory changes and market turbulence that forced devastating choices. She opens up about the isolation of CEO leadership, the unique pressures facing leaders of color, and how wanting to be liked became her greatest vulnerability.We dive deep into what Carrie calls "the work twisties"—those moments when high-performing executives lose their footing and can't see a path forward. She reveals the physical and mental toll of executive burnout, the 12-month recovery process that followed, and how she's reinventing herself in an entirely new industry. This isn't about bouncing back—it's about the wisdom that comes from breaking down.Key topics:How disability became her leadership superpowerThe double standards facing CEOs of colorWhy wanting to be liked became her biggest weaknessLeading through regulatory crisis and market collapseRecognizing the signs of executive burnoutThe cost of caring too much about your teamBuilding sustainable recovery habits after traumaThis conversation reveals why we need honest stories about executive mental health and the courage it takes to choose recovery over revenue.
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Exit Interview: The Loneliness of Leadership with Carrie Siubutt
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