But achieving that kind of success has come at a cost: Stewart believes the idea of perfectly balancing work and life is a myth.
“There is no such thing as balance—just get that through your thick skulls,” Stewart said earlier this month in conversation with Vivian Tu, who runs the social media account ‘Your Rich BFF’. “You can’t balance it. It doesn’t balance.”
Major life events, including marriage and divorce, inevitably throw things off course, Stewart said. And while she acknowledged that some people may occasionally manage to strike a balance, she isn’t convinced it’s the norm.
“This thing about balance, I don’t know who thought about that—but it just doesn’t work,” she said. “Maybe infrequently—and I’m jealous of those people—but they’re also boring.”
Even at 85, Stewart shows little sign of slowing down. She wakes up at 4 a.m., reads the entire New York Times, and heads to Pilates or a session with her personal trainer. By 7 a.m., Stewart is at work on projects ranging from her lifestyle brand to an AI startup—and expects her staff to be working, too.
Stewart staged a career comeback by embracing change: ‘I have choices.’
For Stewart, success also means seeking out excitement and embracing the unexpected.
She brushed off the idea of her career being described in major “pivots”—in fact, she said she “hate[s] the word pivot.” Instead, she prefers to think of her journey as a series of metamorphoses, an idea inspired by author Franz Kafka.
“Why be bored?” Stewart said. “If you even feel a moment of boredom or you can’t get up for some reason—because you don’t want to face the day—that is not good.”
Stewart said if something no longer excites her, she always finds something new to pursue rather than resign herself to boredom.
“When I get up in the morning, I have choices,” Stewart said. “I can do whatever right now I can do anything I want to do every day but I like being able to look forward to what’s going to happen in the day, and the surprises are also good.”
Her affinity for freedom may come as no surprise considering Stewart knows what it’s like to have it restricted: she served five months in federal prison for crimes related to an investigation into a stock sale. But since being released in 2005, she has notably staged a major comeback in rebuilding her public profile and expanding her brands.
From TIAA’s CEO to Barack Obama, leaders agree with Stewart that work-life balance isn’t always possible
While work-life balance remains a top priority for many aspiring young professionals, Stewart isn’t alone in arguing that the ideal is often impossible to achieve.
TIAA President and CEO Thasunda Brown Duckett made a similar case on Fortune’s Titans and Disruptors of Industry podcast earlier this year.
“Work-life balance is a lie. It never reconciles…so get rid of that,” Duckett told Fortune’s Editor-in-Chief Alyson Shontell.
For Duckett, that realization came during her time working at JPMorgan Chase, where she had climbed the corporate ladder to CEO of Chase Consumer Banking. Long workdays and commutes left her struggling to make time for her family, leaving her feeling as though she was falling short in every part of her life.
“I was feeling like I was failing my husband, I was failing my children, I was failing my mom, my dad, my brothers, everyone,” she said. “I was just not winning, and I needed a win.”
The answer, Duckett, said, was to stop trying to make sure every part of her life fit neatly into balance. Instead, she learned to accept that some periods would inevitably demand more of her attention at work, while others would allow her to focus more on family.
Former President Barack Obama has offered a similar perspective, arguing that excellence often requires periods of intense focus at the expense of other priorities.
“If you want to be excellent at anything—sports, music, business, politics—there’s going to be times of your life when you’re out of balance, where you’re just working and you’re single-minded,” Obama admitted last year on The Pivot Podcast.
