Nearly half of women in tech leave the industry by age 35. In Part One of this series, we explored how this statistic isn’t due to a lack of ambition or skill—it’s a systemic issue. The real reasons behind the exodus? Toxic workplace cultures, lack of support, and impossible expectations.
To better understand these challenges firsthand, we sat down with Chelsey Glasson, a former tech leader whose departure from the industry sparked conversations about discrimination and workplace equity. In this interview, Chelsey shares her journey in tech, the reasons behind her decision to leave, and what needs to change to create a more inclusive industry.
Where Tech Started for Chelsey
Chelsey’s path to tech was shaped by early experiences in her hometown just outside of Seattle. With Microsoft’s headquarters nearby, the tech world felt like a big presence in her life. “Microsoft was just a big deal,” she says, sparking her initial interest.
However, her first encounter with computer science at the University of Washington was challenging. “I was one of few women. I stood out, and it was uncomfortable,” Chelsey recalls. After sharing an assignment with a male classmate who copied it, she found herself in trouble. “We got pulled into the class, and the professor said we could get kicked out of the university,” she explains. This experience led her to drop the course, only taking one more CS course in her time at UW.
Despite this she didn’t give up on tech, and in fact felt a renewed sense of determination after chatting with a family friend who was a woman in tech who reminded Chelsey of herself. She went on to pursue a Master of Science in Human-Centered Design and Engineering, blending research, interaction design, and engineering. This new direction ultimately led to roles at T-Mobile and Salesforce, marking the start of her career in the tech industry.
What Led to Her Departure?
Chelsey’s 10+ year career in tech started with excitement and passion. “In the early years, I just loved it,” she says, enjoying her work as a user experience researcher. But as time went on, she encountered systemic issues she couldn’t ignore. “There was an undercurrent of inappropriate behaviors,” she reflects.
The pivotal moment came during her maternity leave when she received a poor performance review while still on leave. “They gave me a needs improvement score… it was just so cruel,” she recalls. This incident made her realize that the industry wasn’t as secure or ethical as she once believed. “It was a big crack in my loyalty as a tech worker,” she shares.
She also highlights how this issue extends beyond new mothers. “It’s not just moms on maternity leave,” she says, emphasizing that the performance review process doesn’t accommodate people stepping away for family, health, or mental health reasons.
Working in Tech: Personal Life and Mental Health
Recalling her time with one tech company, Chelsey says, “There was this mentality… you have to put in your time,” which became even more difficult as she balanced career advancement with family life. After receiving a superb performance rating, she expected a fast promotion but found herself caught in a cycle: “You need at least a year before you can get promoted.” This pattern was repeated when she had her first child and had to miss a calibration cycle, further delaying her progression. “If you have anything outside of life other than work that doesn’t fit within this narrowly defined process, it’s really hard to move up the corporate ladder. And of course, those things and dynamics start to add up over time.”
She also reflects on the advice from higher-up moms on balancing work and life, which centered around “delegating” life responsibilities to external help like nannies and cleaners. However, Chelsey quickly realized that this model relied on financial resources, which required promotions to access. “This doesn’t feel right,” she thought. “Maybe I don’t want to delegate all areas of my life outside of work.”
What to Keep in Mind
Chelsey’s advice is to be proactive in thinking about the long-term, especially when you’re deeply engaged in your work. “When I was really enjoying my work, I thought I’d be in tech forever,” she reflects. “It wasn’t until I got pushed out that I started to think about a plan B, and that added a lot of pressure.”
Her key takeaway: don’t wait until you’re in a tough situation to consider your options. Take the time to ask yourself, “Can I see myself working in tech at 50, at 60?” Even if you love your job, it’s crucial to have a backup plan. “Think about a plan B, just in case,” Chelsey advises. “You never know what might come up, and it’s better to be prepared.”
Opportunities Are Out There
Since leaving tech, Chelsey has found fulfillment in law school, where she’s discovered unexpected overlaps between her tech background and her new path. “The skills tech workers have—research, writing, advocacy, brainstorming, storytelling—are all core skills for attorneys too,” she explains. While transitioning into law school felt daunting at first, Chelsey now sees it as a natural evolution of her career rather than starting from scratch.
Her perspective is clear: “There’s a whole world out there that’s hungry for the skill sets you bring to the table.” If you’re thinking about moving beyond tech, Chelsey reassures, there are plenty of opportunities to apply your experience in new ways.
Companies that want to retain women in tech need to do more than just acknowledge the problem—they need to change the structures that create it. To help break this cycle and create lasting change, consider supporting organizations like AnitaB.org, which work tirelessly to empower women in tech. Your donation helps fund programs that give women the resources and opportunities they need to thrive and lead in the industry.
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