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Exit Interview #3: Same as It Ever Was: What Leaving Tech Taught Me About Change

Wednesday, December 17, 2025 • Rosenfeld Community

This video is featured in the Exit Interviews playlist.

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Exit Interview #3: Same as It Ever Was: What Leaving Tech Taught Me About Change
Speakers: Chelsey Glasson
Link:

Summary

After more than a decade of exploring the world as a user experience researcher, I found myself at a crossroads: continue in a traditional user research role or venture into something new. I chose the latter. Today I’m in the early stages of a legal career, having just wrapped up my second year of law school. Remembering how scary it initially felt to even consider a career pivot, I’m excited to share why I made a change, some of the humbling and sometimes funny moments along the way, and how the skills I developed in UX continue to set me up for success today. Whether you’re contemplating a transition of your own or just curious about what a non-traditional UX-to-something-else journey can look like, I hope my story offers insight, encouragement, and a bit of validation for wherever you are on your career path. And if you're considering a change, please know you’re not alone. There’s a whole community of us out here, cheering you on and excited to provide insight and empathy.

Key Insights

  • Many UX professionals come from diverse, tangible job backgrounds before entering tech.

  • Chelsea Glasson's transition from UX to law was inspired by her pregnancy discrimination memoir project.

  • The law school’s modern client-centered approach closely parallels the UX research and design process.

  • Tech’s performance calibration cycles promote short-term focus and gamified competition rather than long-term career vision.

  • Ageism and early exits for women (average age 35) in tech contrast with law, where experience and age are more valued.

  • Leaving tech often means rebuilding networks and confronting imposter syndrome, but framing it as a research project helps.

  • Shifting industries can feel like starting over but leveraging UX skills enables smoother transitions.

  • Financial and family pressures strongly affect decisions to stay or leave the tech industry.

  • Burnout and systemic biases in tech create openings for career pivots into adjacent fields like law or policy.

  • A career can be viewed as a marathon with scenic detours rather than a single linear sprint.

Notable Quotes

"My last job outside this field was as a furniture salesman — flipping burgers or wrangling children, many started outside tech."

"That holiday party in Medina was eye-opening—tech execs talking about vacation homes, and I thought, I want that world."

"The six-month calibration cycle in tech gamifies performance but discourages a long-term vision for career longevity."

"Legal careers value experience and credibility more as you age, unlike tech where ageism is prevalent."

"Writing my book was just another UX research project synthesizing my career and leading me toward law."

"My law professor outlined the modern legal process as UX: listening, researching, co-creating solutions with clients."

"Moving into law felt like starting over, but reframing it as a UX challenge made it manageable."

"Leaving tech meant rebuilding my social and professional networks outside the industry, which took time and courage."

"I sold my Seattle house and downsized in Spokane to manage financial pressures during this transition."

"Working in tech was a scenic detour on a long-term career marathon, with more detours ahead but now I have the tools to navigate them."

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