When Julia Hartz, co-founder and CEO of Eventbrite, reflects on her two-decade journey from idea to IPO, she pauses on a truth that feels both personal and systemic.

“I wonder if there’s just way too many off-ramps for women in that process—where you could be either implicitly, explicitly, or very often your own worst enemy, and saying, maybe I’m not the one for the next chapter.”

That single thought captures the invisible tug many women feel when they reach the edge of a new stage. It’s not always an overt rejection or a glass ceiling—it’s often a subtle whisper that questions whether we still belong in the room. Hartz’s reflection isn’t just about entrepreneurship; it’s about leadership at every scale. Whether you’re leading a company, a division, or a personal reinvention, every growth spurt brings checkpoints that demand we re-evaluate who we are and who we’re becoming.

The Shifting Checkpoints of Scale

In our recent CEO Perspectives salon, Hartz describes the path of building something enduring—from a “germ of an idea” to a business, then to a public company. What she calls “natural checkpoints” are moments when a leader must reassess and reimagine their skill set. They’re not failures or crises; they’re developmental leaps that require new muscles.

The entrepreneur who scrapes together an MVP isn’t the same leader who manages a 700-person global team. The executive who thrives in a crisis might stumble in a season of stability. Hartz admits that each phase forced her to learn faster, to outgrow her own habits. “There are these natural checkpoints along the way,” she says, “where one has to reassess and reimagine their skill set, to commit to learning more quickly.”

It’s a pattern that repeats in nearly every woman’s career. We master one level, and the next one arrives with new expectations—strategic instead of tactical, external instead of internal, visionary instead of operational. Somewhere in that transition, many of us step away, consciously or not.

The Off-Ramps That Appear Along the Way

Some exits are loud. They’re structural, visible, and all too familiar: pay inequity, venture bias, the impossible calculus of caregiving, boards and investors who underestimate female founders. When Hartz left television for tech, her first offer at a San Francisco startup came in thirty percent less than her previous salary. She hesitated—and that hesitation, like so many women’s, wasn’t about confidence. It was a turning point, the pause that redirected her path entirely.

Other exits are whisper-quiet. They hide inside self-doubt, or the well-trained instinct to please. Hartz calls herself a “natural people pleaser” and “very good at taking direction”—traits that made her exceptional early in her career, but which could have become constraints as she moved into leadership. At each stage, women are socialized to adapt, to smooth edges, to say yes. But every new chapter requires a willingness to unsettle, to take up uncomfortable space, to risk being unlikable for a while.

And then there are the invisible cultural exits—the ones baked into our definitions of what leadership “looks like.” Empathy, curiosity, and relational intelligence are often dismissed as soft, yet they were precisely the instincts that powered Eventbrite’s rise. When the company began, Hartz spent hours reading through customer service emails from early users, finding in them what she called “a treasure trove of stories and archetypes.” She personally called frustrated customers, listening, learning, and turning their pain points into better product design. That was product-market fit born of empathy. Yet, too often, women are told those instincts are secondary to strategy, rather than the engine of it.

Even success can be its own off-ramp. Hartz built one of the few tech companies to reach gender parity at both the C-suite and company levels. But even in that triumph, she saw the complexity of balance. “There were times,” she said, “when there were literally no men in the room. We had to make sure the men’s voices were being heard.” True equity isn’t about optics; it’s about wholeness—keeping everyone’s voices safe in the mix.

And of course, there’s the personal toll. Hartz describes the last five years—the pandemic and its ripple effects—as “an earthquake followed by powerful aftershocks.” The only way she made it through, she says, was by focusing on what she could control. When her daughter observed, “Mom, you’re really good at taking care of yourself; that’s why you can take care of so many others,” Hartz recognized the truth in it. Caring for herself wasn’t self-indulgence—it was strategy. Energy is a resource; leaders who don’t protect it eventually exit by exhaustion.

Staying In When It Would Be Easier to Step Out

Hartz’s antidote to off-ramps isn’t bravado—it’s practice. She builds staying power through small, consistent behaviors that make resilience less about personality and more about design.

One of those behaviors is the way she thinks about mentorship. “There’s no such thing as one mentor,” she says. “Find many smart people and ask them great questions.” For Hartz, mentorship is less a hierarchy and more a constellation—a mosaic of advisors she can call when the map gets foggy. During early COVID, she buried her imposter syndrome and called everyone she could think of. “There was literally no phone call or request to talk that I made that I got turned down for.” Each conversation added a new lens, a new way to frame the crisis. The lesson: don’t look for a single guide; build a network of insight.

Another pattern she returned to, again and again, is reflection under pressure. In the bleak early days of 2020, when Eventbrite’s revenue went negative, Hartz gathered her team for what she called a “rebuild it from scratch” exercise. If they could start over, what would they do differently? That conversation became their roadmap. It shifted them from panic to possibility, from duck-and-cover to design-and-build. Staying in the game often starts with asking, “What would we do if this were Day One again?”

And beneath all of it lies her relentless empathy—an instinct she once thought might be an Achilles’ heel. “It’s hard for me to be in a room with someone and not feel their energy,” she admits. But that emotional sensitivity became her edge. It helped her read between the lines of customer frustration and recognize patterns others might miss. When women learn to operationalize empathy—to turn it into insight, process, and design—it stops being soft. It becomes strategy.

Finally, there’s her quiet discipline: the daily recalibration of what’s in her control and what isn’t. In the chaos of disruption, Hartz’s stoic lens narrowed her focus. “I’ve benefited massively from focusing on the things I can control,” she says. In other words: when the landscape shakes, control the controllables—decisions, standards, communication, energy. Everything else is noise.

The Inner Audit for What Comes Next

If the question is how to stay, the answer starts with awareness. Hartz’s story suggests that the path to the next chapter begins with self-inquiry. Ask yourself:

• When was the last time you named the checkpoint you’re actually in—not the one you wish you were in? Are you still leading like the version of yourself who built the first iteration, or have you evolved with the work?
• What’s the story you’re telling yourself about why you might not be “the one for the next chapter”? Whose voice is that? And what evidence do you have that it’s true?
• Where are your insights still private—living in your head instead of out loud in the team or company? If empathy lives only inside you, it can’t scale.
• Who’s in your mosaic? Do you have a diverse chorus of thinkers who can challenge and expand you—or just familiar voices who keep you comfortable?
• What decision are you avoiding because it feels scary to own? 

As one of Hartz’s mentors told her in those early pandemic days, “There is no Plan B. You will make it.” Sometimes the difference between an off-ramp and a breakthrough is a single, brave decision made fast.

You Got Here. You’ll Get There.

Julia Hartz’s story is not just about founding a company; it’s about refusing to outsource belief. When every reason to exit appeared—investor rejection, self-doubt, crisis, fatigue—she chose to stay in motion. She sought new teachers, rebuilt the map, and re-hired herself into the next version of the role.

Her closing advice, to women redefining leadership in midlife and beyond, lands like both reassurance and a rallying cry:

“You got here somehow, you’re going to get to the next place. Honor and respect and have such immense pride in the gifts and the struggle that got you here, and know that those exact same traits and skills are going to get you to the next place—even if that next place is not clear and even if it’s really scary.”

There will always be off-ramps—some external, some internal, some paved with good intentions. But the next chapter doesn’t need someone else. It needs you, just updated.

So when you reach the next checkpoint, and that small voice asks if you’re really the one to lead through it, try answering as Hartz does: not with certainty, but with curiosity, courage, and the simple, radical act of staying in.