I quit Google after 23 years of watching it go from scrappy startup to global power. 4 questions helped me decide it was time to go.

Ex-Googler Alana Karen bounced around many roles at Google before finally deciding it was time to leave.

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.