Betting on herself: How UK Alum Sydney Fessler Turned Curiosity and Connection into a Career at Fidelity Investments

When Sydney Fessler arrived at the University of Kentucky, a career in finance wasn’t part of the plan.

Originally set on healthcare, Fessler changed her major to finance just before freshman orientation, a decision that ultimately led her to Fidelity Investments and a career helping people through financial planning.

Through two internships with Fidelity, countless networking conversations and a lot of hard work, Fessler is now a full-time Financial Services Representative at OneUK collaborator, Fidelity Investments, one of the world’s leading financial services firms. Founded in 1946, Fidelity serves more than 40 million investors and manages trillions in customer assets through services including retirement planning, wealth management, brokerage accounts and financial advising.

Although finance was not originally on her radar, Fessler always knew she wanted a career centered around helping people.

“I grew up always wanting to go into healthcare because I really wanted to help people,” Fessler said. “But I was always pretty good at math and liked numbers, so I picked finance on a whim.”

During her time at UK, Fessler immersed herself in campus involvement through organizations like Women in Finance Society, the Lewis Honors College and Greek life during her first few years on campus. Looking back, she credits much of her growth to the people she surrounded herself with.

“I think being surrounded by motivated people really helps a lot,” she said. “A lot of my friends were the same major as me, so we would go to study sessions together and bounce ideas off each other. It really pushed me.”

Fessler landed her first internship with Fidelity Investments in the summer following her sophomore year through networking and connecting with people within the company. She worked as a Financial Operations intern, gaining experience with the behind-the-scenes and accounting side of the business. While the internship gave her valuable experience, she quickly realized she wanted something more people-focused.

“I thought ‘Look, this isn’t really for me,’” Fessler said. “It was great experience, but I started creating meetings with people across the company. I think I talked to around 50 different people just asking, ‘What do you do every day?’ and trying to figure out what really interested me.”

That initiative ended up shaping the rest of her career path.

Through those conversations, Fessler connected with Fidelity Investments leader Chris Tischner, who later invited her to shadow at an investor center. That experience introduced her to financial planning and reignited the passion for helping people that originally drew her toward healthcare.

“I really liked the idea of financial planning because it still involved helping people,” she said. “It just ended up not being through healthcare. I also realized I love talking to people. I didn’t think I could sit behind a desk typing all day.”

After staying connected with Tischner through LinkedIn and networking opportunities, Fessler attended a UK Gatton College of Business and Economics career fair the following year, where she reconnected with him at the Fidelity Investments booth. Soon after, she applied for another internship opportunity and earned a position as an Investor Center intern during the summer following her junior year.

The internship gave Fessler hands-on experience with the company’s client-facing side of the business. She shadowed multiple roles within the branch, greeted clients, observed appointments, and learned how different positions worked together to support investors and clients.

“I was one of the first faces clients saw when they walked in,” she said. “I loved interacting with people and creating a welcoming environment. I also got to shadow different roles and see what career growth could look like long term.”

Alongside her internship responsibilities, Fessler was also completing UK’s capstone course for the university’s Financial Planning Certificate program. Balancing both experiences required discipline and organization, something she says became one of her biggest strengths.

“I’m a huge schedule person,” she said. “My planner, my calendar, everything has to be organized. Staying on a routine really helped me balance everything.”

Throughout the internship, Fessler continuously pushed herself to go above and beyond. She often aimed to be one of the first people in the office and one of the last to leave, always looking for opportunities to learn more and improve.

“I wanted to show that I was capable,” she said. “I tried to go the extra mile every single day.”

That dedication eventually led to a full-time offer following graduation, but the process was not without moments of uncertainty.

Like many young professionals entering competitive industries, Fessler experienced imposter syndrome throughout parts of her journey, especially at just 21 years old.

“I feel like everyone struggles with imposter syndrome at some point,” she said. “I’m 21 years old, and sometimes I’m like, ‘How am I doing all of this?’”

Over time, she learned to give herself grace and trust the work she had already put in.

“You worked hard, and your work speaks for itself a lot of the time,” she said.

Now working full time as a Financial Services Representative, Fessler says one of the most rewarding parts of her role is the opportunity to connect with people and problem-solve in an environment where no two days look the same.

“You never know what you’re going to get,” she said. “Every day is different, and that keeps it exciting.”

She also emphasized the supportive culture she experienced throughout both internships and now as a full-time employee. From intern mentorship programs to opportunities for growth and licensing support, Fessler says Fidelity invested heavily in helping her succeed from the beginning.

“They really take care of people,” she said. “Not just interns, but employees too. That support system is something that really stood out to me.”

Fessler also hopes students understand that Fidelity offers opportunities far beyond finance alone. While the company is widely recognized for financial planning, retirement services and investment management, she says there are opportunities for students from many different majors and backgrounds.

“There are so many different roles at Fidelity,” she said. “You don’t have to just be a finance major to work here.”

Looking back on her journey, Fessler encourages UK students to stay curious, build meaningful relationships and trust themselves, even when opportunities feel intimidating.

“Network, ask questions, and maintain those relationships,” she said. “And honestly, bet on yourself. As long as you believe in yourself and put in the work, you’ll go far.”

From changing her major just weeks before starting college to building a full-time career at Fidelity through determination, networking and initiative, Fessler’s story is a reminder that sometimes the best opportunities come from simply being willing to start the conversation

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Fidelity is a OneUK collaborator of the University of Kentucky. To learn more about OneUK and the companies engaged with UK's campus community, visit businessengagement.uky.edu/oneuk.