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From Bartender to CPA: Jessica Simmons’ Inspiring, Nontraditional CPA Journey

Interview Highlights & Key Takeaways

  • A nontraditional path can still lead to CPA success
  • Strong support systems make demanding goals achievable
  • CPA exams reward persistence—not perfection
  • Remote work can transform career sustainability
  • Knowing your limits is a strength, not a weakness

Before diving into the details, this conversation was a powerful reminder that there is no single “right” way to become a CPA. In Episode #113 of the CPA Career Paths Podcast, I had the pleasure of speaking with Jessica Simmons, CPA, whose journey proves that resilience, adaptability, and support can redefine what’s possible in the accounting profession.

Meet Jessica Simmons, CPA

I hosted Jessica after first meeting her at the AICPA Global Women’s Leadership Summit, and her story immediately stood out. Jessica is a CPA and relationship manager at LLI Advisory Group, currently transitioning into tax. She’s also a wife and mother of two—balancing family life while building a successful accounting career.

Jessica didn’t follow a traditional college-to-public-accounting path. Instead, she returned to school years later after starting a family—and completed her associate’s, bachelor’s, and master’s degrees while raising two kids.

Choosing the CPA Path Later in Life

Jessica shared how a moment of curiosity sparked her CPA journey. After attending a family wedding and learning her uncle was a CPA, she asked herself, “What is a CPA?” That question led her to research the profession mid-flight home—and ultimately back to school.

Her husband’s support was critical. As Jessica put it, “We looked over the numbers… and he said, ‘Yes, we can make it happen.’” That decision changed everything.

Balancing School, Family, and Boundaries

One of the most honest moments of the episode was when Jessica discussed stepping away from an internship during COVID. Managing her own coursework while overseeing two kids’ virtual schooling pushed her to reassess her limits.

“I had to be true and honest with myself about what I could handle,” she said. “At the end of the day, my kids’ education was more important than anything else.”

Her takeaway was clear: boundaries aren’t failures—they’re leadership decisions.

CPA Exam Strategy: Progress Over Perfection

Jessica passed three CPA exam sections before graduation and earned her license in December 2022. Audit, however, wasn’t easy.

“I failed the audit twice,” she shared. “I had to train myself to slow down and read every word.”

Her most powerful advice came from her uncle:

“It doesn’t matter how many times you take the exam. Employers only care that you passed.”

She also emphasized studying smarter, not longer—especially for FAR. Instead of treating it like a class, she focused only on weak areas to avoid burnout.

Finding Flexibility Through Remote Work

Jessica initially resisted remote work but quickly realized it was a game-changer. Flexibility allowed her to manage family needs without sacrificing performance.

“You can’t convince me to go back to the office now,” she said. “I can step away when needed and still give 100% when I’m working.”

Final Thoughts

Jessica’s journey is proof that persistence, honesty, and flexibility can lead to extraordinary outcomes—no matter where you start.

👉 If this story resonated with you, join my monthly newsletter for practical insights, real CPA journeys, and strategies to help you confidently master your CPA path—on your terms.

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