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Summary
What happens when the career you worked hard to build no longer fits the life you’re living? In this session, Ashley Sewall shares her decision to step away from senior UX leadership and the questions that followed. She reflects on burnout, identity, ambition, and the often-unspoken pressures of staying in tech—and explores what it looks like to apply design thinking to your own career. This is not a story about quitting, but about redesigning work to better align with values, health, family, and curiosity.
Key Insights
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Ashley experienced a gradual disconnection from her UX leadership role due to bureaucracy and politics, leading to exhaustion and a shift in career priorities.
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She used a highly systematic, research-driven approach—including AI tools and extensive data mapping—to explore over 60 career options.
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Transferable skills from UX research, like pattern recognition and customer experience design, apply strongly to real estate and other new ventures.
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Real estate, despite being a mature field, feels less structured and more entrepreneurial than UX, offering a 'choose-your-own-adventure' career experience.
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Ashley emphasizes the difficulty of unlearning productivity- and identity-driven mindsets from high-pressure tech environments.
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Her pivot focuses on tangible, human-centered work that feels more directly impactful and aligns better with evolving personal values and family life.
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Flexibility and multiple income streams are critical to modern career stability, rather than strict adherence to a linear path.
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Significant health improvements, including normalized blood pressure and better sleep, followed Ashley's departure from her high-stress tech role.
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Stepping sideways or away from a leadership track is valid and can be necessary to rediscover purpose and align with life changes.
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Ashley advises tuning into internal signals of misalignment early to avoid exhaustion and encourages small, low-risk experiments to explore new paths.
Notable Quotes
"On paper, everything looked great, but day to day I felt increasingly disconnected from the parts of work that energized me."
"I was so desensitized to the stress and urgency that it just became my baseline for living life."
"I gathered information and ran little experiments on myself across dozens of jobs to see what might fit."
"Real estate is like the Wild West. It’s very mature but also very unstructured and full of freedom."
"I’m trying to separate who I am from what I produce and the roles I hold."
"Stability today is more complicated than staying on a fixed path; adaptability and diverse skills bring security."
"I didn’t realize how much cognitive load I was carrying until I stepped away."
"Teaching yoga and working in real estate brings me tangible connection to people that I missed in tech."
"Transitions can be long. I wished I had known that the identity shift is harder than the skill shift."
"If you are questioning your path, that’s data. It’s a sign something needs to evolve and that’s okay."
Or choose a question:
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