“I think it’s something the legal field needs to be more transparent about,” Claire Gregory tells PEOPLE
NEED TO KNOW
- Claire Gregory earned her law degree, passed two bar exams and started her legal career expecting it would bring both stability and fulfillment
- Instead, the 28-year-old found herself making roughly “double” as a bartender and server — all while enjoying the work far more
- As a result, in 2025, Gregory left law behind and now tells PEOPLE she’s never felt happier
Most people assume that becoming a lawyer guarantees a certain level of financial stability and success. For Claire Gregory, however, that expectation never fully aligned with reality, despite earning her law degree, passing two bar exams and working across various areas of the legal field.
Over the years, even after reaching those milestones, the 28-year-old from Richmond, Va., ultimately realized that the life she had worked so hard to build wasn’t the life she actually wanted or needed. Instead, in October 2025, she made the bold decision to walk away from the profession and pivot full-time to the hospitality industry.
“It was always where I felt like myself and where I had the most fun,” Gregory tells PEOPLE exclusively. “It was never the ‘serious’ thing; it was just the thing I actually loved doing.”…