The Loneliness of Leadership: When Being Strong Becomes Your Weakness
The second episode of Exit Interview explores what happens when resilience meets burnout—and why stepping away can be the strongest move you make
At seven years old, Carrie Siubutt declared she would become a CEO by 37. She got a cash register for Christmas in Trinidad and told her mother exactly how her life would unfold: CEO first, then marriage, then kids. The CEO part happened right on schedule. What she didn't predict was how lonely it would be—or that walking away would require more courage than staying.
In this episode of Exit Interview, Carrie shares what it's really like to lead through crisis, why wanting to be liked became her biggest weakness, and the 12-month recovery process that taught her the difference between being strong and being whole.
When Disability Becomes Your Superpower
Carrie's leadership story begins with a diagnosis at age 11: dystonia, a rare neurological condition affecting one in 300,000 Americans. While other kids might have seen this as a limitation, Carrie saw it differently.
"Dystonia has been my superpower because it's given me grit, it's given me focus, it's given me discipline and it's given me resilience," she explains. "It never changed my North Star. I actually think it brightened that star a little bit."
This mindset—turning obstacles into advantages—would define her approach to everything that followed. From Wall Street to Stanford Business School to building SimpleHealth into a $75M telemedicine company, Carrie's condition taught her to work around constraints and find creative solutions.
But the same resilience that powered her success would later make it nearly impossible to recognize when she needed to stop.
The Double Standards of Leadership
As one of the few Black women CEOs in her space, Carrie faced questions that her white male counterparts rarely encountered. She describes the exhausting reality of having to prove herself repeatedly while managing a company through regulatory changes and market turbulence.
"It's a double standard for women, right? If I was a white male, half of that wouldn't have happened," she reflects. "I mean, it's hard enough to be a Caucasian woman CEO, and then you put a woman of color on it."
The pressure was compounded by her own personality. Carrie's biggest weakness as a CEO? Wanting to be liked.
"I wanted to be liked. It meant that it wasn't going to happen and I had to shift my thinking around that—that everyone had to show me respect and not like," she explains. "That shift was something that I learned the hard way."
This desire for approval made difficult decisions even harder, especially during the crisis that would ultimately lead to her exit.
When Everything Falls Apart
SimpleHealth had reached impressive scale—200 employees, $75M in revenue—when regulatory changes in 2022 cut their business in half almost overnight. The timing couldn't have been worse: the market was correcting after years of frothy investment, making fundraising nearly impossible.
"I just knew my whole world is about to turn upside down," Carrie recalls. "I'm too damn smart for my own good. I knew the market was going to collapse."
What followed were nine months of impossible decisions: layoffs, salary cuts, putting company expenses on her personal credit card. The woman who had always been four steps ahead found herself fighting just to keep the company alive one more day.
"Making payroll is my biggest nightmare," she says. "There's only so much you can do when you look in the bank account and don't have any money."
The Work Twisties
Like Kanya in our first episode, Carrie experienced what we call "the work twisties"—those moments when leaders lose their sense of position and can't see the path forward. But Carrie's version was particularly brutal: she literally forgot how to smile.
"My very best friend was like, 'You haven't smiled in months.' And I was like, 'I don't even remember how to smile,'" she recalls. "I would be physically there, but mentally I wouldn't be present."
The signs were clear to everyone around her, but Carrie couldn't see them herself:
Lack of joy in daily life
Social isolation
Physical symptoms (she stopped eating because stress eliminated her hunger)
Every day feeling like a chore just to get out of bed
"If lacking joy and every day is a chore for you to wake up and you literally, physically have to put one foot in front of the other to get out of bed, that's a sign that you're not on a good path."
The Cost of Caring Too Much
Perhaps the most devastating aspect of Carrie's experience was how much she cared about her team. The same empathy that made her a beloved leader became a source of torture during layoffs.
"You can't personalize these decisions. You can't think of, like, whether Bob can make rent or Suki and her kids," she explains. "That was a hard lesson for me."
Her empathy was both her greatest strength and vulnerability. Employees who understood how much she cared sometimes used it against her, knowing exactly how to manipulate her big heart.
"Once they knew I cared, they knew exactly how to manipulate me," she admits. "Those people will take your heart and take your empathy and just walk all over it."
When Stepping Down Means Standing Up
The end came in April 2023 when Carrie sold SimpleHealth's assets—not the triumphant exit she'd once imagined, but a necessary conclusion to an impossible situation.
"It was one of those feelings where I was sad that it ended, but I felt like I breathed for the first time in like a year," she describes the day she signed the papers. "I was elated that it was over, but I was sad that it ended that way."
The aftermath was dark. For months, Carrie had no plan—something that terrified someone who had always been a planner. She went through what she calls "burnout," a term she previously didn't believe in.
"Burnout is real. I never thought it was until this whole thing happened," she reflects. "You cannot rush the recovery process. You just can't."
The Recovery
Carrie's healing process took 12 months and required rebuilding basic habits she'd lost during the crisis:
Morning walks to watch the sunrise
Reading for intellectual stimulation
Prayer for spiritual grounding
Gratitude journaling
Learning to physically push negative thoughts away
"When that thunderstorm starts rolling in my head, I physically see myself pushing the boulder out," she explains. "I practice it now every day almost. And I can do it now."
What's Next: From CEO to Chief Accessibility Officer
Today, Carrie is pursuing a master's in cruise operations and working toward her next goal: becoming a Chief Accessibility Officer in the cruise industry. It's a role that combines her business experience with her lived experience of disability.
"I want to show people that people of color, women of color who are disabled could be CEOs," she explains. "These positions don't exist. I would make one up at some company because someone will see the value of that one day."
Her new vision is about opening markets, not just checking boxes: "It's accessing multiple markets. The money is there, but people don't feel like they're often marketed to or invited to that party."
Redefining Success
Perhaps the most powerful shift in Carrie's story is how she now defines success. The seven-year-old with the cash register thought becoming CEO would solve all her problems. The 49-year-old who lived through it knows better.
"Being a CEO didn't solve my problems. No matter how much money you make, you are the person you are," she reflects. "It was the most unhappy I'd been in years."
Now she's focused on stability, purpose, and sustainability—concepts that felt impossible during the chaos of rapid growth and crisis management.
"I don't want to worry about payroll. I don't want to worry about money in the bank. Those are things that's not my purpose in life. My purpose in life is to innovate, to talk about things, to change things, to be a change agent."
Why These Stories Matter
Carrie's story reveals truths about leadership that successful people rarely discuss publicly:
Resilience can become a trap when it prevents you from recognizing when to stop
Caring deeply about your team can make necessary decisions nearly impossible
The loneliness of leadership is real and can be devastating
Recovery from executive burnout takes time and can't be rushed
There are many ways to define success beyond the traditional CEO path
Her journey also highlights systemic issues: how leaders of color face additional scrutiny, how the desire to be liked can undermine authority, and how the mythology of entrepreneurship often ignores the human cost of building companies.
But perhaps most importantly, it offers a different model of courage—one where stepping away isn't giving up, it's making space for what comes next.
The Wisdom of Letting Go
"Sometimes the bravest thing you can do isn't persist," as we said in our first episode. "It's knowing when to let go."
Carrie's story proves this in the most personal way possible. The woman who turned a neurological condition into a superpower had to learn that being strong sometimes means admitting you're not okay—and that recovery is its own form of leadership.
Listen to the Full Episode
🎧 "The Loneliness of Leadership: Carrie Siubutt on Burnout, Recovery, and Reinvention"
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About Exit Interview
Exit Interview is a limited series exploring the entrepreneurial stories that don't make headlines—the complex realities of building, scaling, and ultimately stepping away from the companies you create. These are honest conversations about what it takes to lead when the stakes are highest, for founders, executives, and anyone facing decisions that will define their path forward.
About Carrie Siubutt
Carrie Siubutt is the former CEO of SimpleHealth, where she built a telemedicine company serving women's health needs. She's currently pursuing her next chapter in the cruise industry, working toward roles that combine business leadership with accessibility advocacy. You can follow her journey on LinkedIn at Carrie Siubutt.