Market Data 
This as-told-to essay is based on a conversation with Alana Karen, a 47-year-old ex-Google employee, author, tech leader, and speaker based in Palo Alto, California. It’s been edited for length and clarity.
By the end of my 23-year career at Google, the company felt like my bad ex-boyfriend. The one who didn’t give me everything I needed, but I still stayed.
I really felt like I had to keep proving myself, but after 20 years of being a solid employee, it felt demoralizing. High performers need to feel valued. I did not.
I still feel very fortunate to have worked at Google for as long as I did. I watched it transform from scrappy startup to global power, but after 20 years, four questions helped me decide it was time to quit.
My first decade at Google was a rocketship
I was hired at Google in November 2001. My job was manually reviewing and approving ads that people submitted to run on Google.
When I started, Google had only a few hundred employees, but we were constantly changing buildings and shifting desks to accommodate more people. I enjoyed the rapid pace of development because I faced a new challenge every day and never stopped learning.
It was intense, nonstop work, but I loved it. I spent most days deep in nitty gritty work, solving tough problems with many really smart, fun people. I felt excited to work for a company with a mission I supported — making information more accessible. Plus, the company was small enough that I really felt like I was contributing to it personally.
I wish I had taken advantage of the perks
There’s all this talk in tech about the perks like table tennis or bouncy balls, but in those early years, I didn’t have time for any of that. I do think other people took better advantage and took better breaks, but I remember it being rare to have a break.
Though this wasn’t necessarily a negative. I never burned out because I felt connected to Google’s vision, I saw my purpose, and I felt like I was doing good for the world.
Over time, I felt the company shifting away from its scrappy, startup feel, and I found myself sitting in lots of long meetings with charts and graphs and people myopically arguing about numbers.
I considered quitting a couple of times after working at Google for 10 years
I hit my 10-year mark while on my second maternity leave in 2011, and I considered leaving. Instead, I found a new role within Google Fiber, a fledgling startup creating high-speed internet access, which had me hopping into another fast-paced role that reignited my passion for my work.
I loved my new role, and I didn’t question my career again until 2017 when Google Fiber reversed directions, and I, alongside hundreds of people, had to find other roles in Google or get fired. It was a true heartbreak.
I created a Q&A system to help me determine if a Google role was the right fit for me
For much of 2017, I worked full-time as director of the access transition team. In this role, I helped coworkers find other roles at Google before deciding where I wanted to land next. I started to feel the stress in my body and had to question if I was truly OK to stay.
I decided I would continue with Google, but I was wiser to the fact that I can’t put all my faith into the company. I knew it was up to me to protect my health and emotions. I transitioned to the core of Google, Google Search, as a program manager, quite intentionally. I wanted to work somewhere I knew Google was concretely invested.
My new role rekindled my excitement, but I came up with four questions to ask myself at the start of every year, to make sure I was still happy at Google. Do I like what I’m doing? Am I having fun? Do I like the people I work with? Am I still learning?
By 2021, my job was getting harder and I absolutely felt at risk of being laid off
I felt my job was taking up more of my personal energy. A structural reorganization followed by a series of layoffs really took a toll on company morale.
Plus, in the race to develop AI, I felt pressure to work around the clock and crank it out, but with fewer people due to layoffs. I noticed people sending emails in the evening or on weekends more, trying their best to look indispensable.
I knew I was great at my job, but I worried the company would see me, a well-paid program manager director, as a line item they could no longer afford. But, I wanted to stay because I still loved many of my coworkers, I felt responsible for helping my team through this major adaptation, and because I was the main breadwinner for my family.
I gave myself an ultimatum. Then I quit.
I checked in with my four checkpoints, and my results were degrading. I wasn’t learning, and in the midst of tough layoffs, I wasn’t having fun.
In 2024, I applied for the next progression of my program manager job in hopes it would spark some new learning. I told myself if I didn’t get the job, I’d quit.
Well, I didn’t get the job, and I immediately went to my HR person to quit. My ending felt very complete, and I was happy to have left based on my own decision.
I miss my coworkers, but I make time to keep in touch. The biggest thing I’ve learned since leaving is that I’m a whole person without Google. It’s been nice to give myself the space to explore new avenues.
If you have worked in Big Tech for over 20 years and would like to share your story, please contact the editor, Manseen Logan, at [email protected].
