August 2026 | Leadership

An Entrepreneur Among Executives

When the participants in Wharton Executive Education’s Executive Development Program (EDP) were divided into teams for a business simulation, Carrie Eberly found herself in unfamiliar territory. Her team’s fictional company was performing well, and most of her teammates agreed there was little reason to change course. But Carrie saw an opportunity they weren’t considering.

She and another teammate argued that the company should be sold — a move no other team in the simulation was even contemplating. It wasn’t the safest decision, but it would test assumptions, spark discussion, and reveal what happened when leaders were willing to take a calculated risk. Eventually, they persuaded the rest of the team to give it a try. Looking back, Eberly laughs at the memory. “We were the only company that sold,” she says. “Nobody else even entertained the idea.”

The decision paid off, but the victory wasn’t the outcome of the simulation. It was that Eberly had found the confidence to make her case in a room full of accomplished executives. Only months earlier, she wasn’t sure she belonged there.

An accidental entrepreneur who runs two growing businesses she founded — a travel advisory firm and SitReps, a veteran recruiting company — Eberly wears every hat. But despite her success as a leader who juggles marketing, operations, strategy, finance, and customer service, she arrived at her first Wharton Executive Education program carrying a familiar burden. “I was dealing with imposter syndrome,” she says, “wondering if I belonged.”

That uncertainty quickly gave way to something far more valuable than reassurance. Through two Wharton Executive Education programs, the weeklong Business Essentials for Executives followed by the EDP, Eberly discovered not only new business frameworks, but also newfound confidence in her own judgment.

Finding Your Voice

Like many entrepreneurs, Eberly had learned business by doing. She knew how to solve problems, build relationships, and grow companies, but she wanted to understand the principles behind the decisions she had been making intuitively. “I loved learning the why behind what I was already doing,” she says. “Experience had taught me what worked. Wharton taught me why it worked.”

Some of the subjects she expected to find most intimidating turned out to be among the most rewarding. Finance and accounting, in particular, became accessible in ways she hadn’t anticipated. Rather than presenting abstract theory, Wharton finance professor Michael Roberts connected concepts directly to real business decisions, giving her tools she could immediately apply.

That practical approach carried into the EDP, where participants were challenged to apply what they were learning in the classroom to complex business problems in the simulation. “That was where it all clicked,” she says. “Coming from a small business, I'd never experienced that kind of cross-functional teamwork. Seeing how every part of the organization depended on the others and the importance of effective communication was incredible.”

Just as important was learning from people whose experiences differed dramatically from her own. Her teammates included seasoned corporate executives, finance experts, military leaders, and MBA students. Their different perspectives often challenged her assumptions, while her entrepreneurial mindset encouraged the group to think beyond conventional approaches. “Being an entrepreneur made me more comfortable questioning the obvious answer,” she says. “Sometimes you have to be willing to try something different and see where it leads.”

The programs also helped Eberly confront something that many accomplished professionals experience: hesitation about speaking up. In partnership with her executive coach (EDP pairs every participant with one), she identified a personal goal of contributing more actively in class discussions and group work. Feedback from colleagues before the program had reinforced what she already suspected — she often had ideas to share but kept them to herself.

“One of the biggest changes after the program has been that I’m no longer afraid to speak up,” she says. “I still like listening and learning from other people, but when I think I have something valuable to add, I’m much more willing to say, ‘Hey, my turn.’”

That shift extended well beyond the classroom. Today, she continues to make it a goal in meetings, collaborative projects, and graduate school discussions to contribute with greater confidence.

Learning That Lasts

The impact of Eberly’s Wharton experience didn’t end when the programs concluded. Inspired by her time in the classroom, she decided to pursue an MBA. The transition back into academic life felt much smoother because she had already reestablished the habits of learning — completing readings, preparing for discussions, and thinking critically about how ideas translate into action.

More importantly, she found herself drawing on lessons from Wharton almost immediately. “I definitely look back at my time in EDP and pull from the skills I learned there to work with my MBA cohort,” she says.

One lesson continues to shape how she approaches leadership: meeting people where they are. Whether she’s helping clients plan meaningful travel experiences, supporting military veterans as they transition into civilian careers, or collaborating with classmates, she now thinks more intentionally about understanding different perspectives before trying to influence decisions. “I’ve learned that the best solutions start with understanding the other person's perspective,” she says. “Once you do that, you can better help them move forward.”

The relationships she built have proven equally enduring. She remains in regular contact with members of both program cohorts, exchanging ideas, seeking advice, and celebrating one another’s successes. Some have become trusted mentors; others have become close friends.

“One of the biggest surprises was realizing the learning didn't stop when we left campus," she says. "I came away with a network of people I still turn to for advice, ideas, and honest feedback.”

The experience didn't mark the end of Eberly’s learning journey — it accelerated it. In fact, she’s already thinking about returning to Wharton once she completes her MBA. Her bookshelf is filled with recommendations from faculty, her notebook is packed with ideas she continues to revisit, and she already has a list of future programs she’d like to attend.

Asked what she would say to someone considering executive education, she doesn’t hesitate. “Just do it,” she says. “Business is moving fast and things change. You can’t keep doing what worked five years ago. At Wharton, you learn what is at the cutting-edge from the people who are doing the research and working with business leaders. Both the quality of the education and the quality of your peers is exceptional.”

For Eberly, executive education wasn’t simply another item to check off her professional to-do list. It became a catalyst — one that deepened her understanding of business, expanded her professional network, and, perhaps most importantly, gave her the confidence to trust her own voice.

That confidence was on full display during the business simulation, when she persuaded a room full of experienced professionals to take a chance on an unconventional idea. But the real lesson wasn’t about whether to sell a fictional company. It was about learning that sometimes the most important leadership decision is finding the confidence to speak up in the first place.

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