This as-told-to essay is based on a conversation with 41-year-old Jay Gengelbach, a software engineer from Boulder, Colorado, who lives in Canada. The following has been edited for length and clarity.
I joined Google as a software engineer straight out of college in 2006.
I loved telling people I worked at Google; it was a badge of honor that made me interesting.
After roughly 12 years there, I joined Verily, another Alphabet-owned company, in 2018, for six years.
At Verily, I earned up to $700,000, but in mid-2024, after growing unhappy in my job, I decided to resign, even if it meant a smaller salary. Making the jump was scary, but more than a year after quitting, the financial and emotional risk is starting to pay off.
This time of year can inspire people to reflect on their lives and careers and whether they’re fulfilled, challenged, or ready for change.
Business Insider spoke with people who quit great jobs to chase something new, from starting businesses to switching industries.
They shared what pushed them to act, how they managed doubt, and what they learned about risk and reward — showing that while quitting isn’t easy, it can lead to a more intentional and meaningful career.
I quit Google after 18 years on the job. It was scary but I did it well — here’s how.
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Working at Google was fun, but I got bored in the same role for too long
Google was a great place to work. We had wild benefits, nap pods, and free food. It was extravagant. Once, I saw employees having a luau-themed lunch, and it wasn‘t even a special holiday. On at least a couple of occasions, the company handed out $1,000 holiday bonuses to staff in cash.
Initially, I worked on software that helped keep the site up. After working in California for two years, I relocated to Colorado and stayed in that role for another two years. Even though I loved Google as a company, I became burned out and unsatisfied in my role.
I moved onto the payments team for four years before spending another four on the Google Now team, where I became a manager. I’ve learned I tend to get bored after doing the same thing after about four years.
Being a manager was very isolating
In 2018, I got the opportunity to work at Verily, an Alphabet company focused on improving people’s health with tech. I eventually became an engineering director there.
After six years, I became unhappy in my job. The pandemic and a period of layoffs were stressful. As a manager, I had to motivate my people, which I found challenging.
Somewhere along the way, I realized I didn’t have work friends anymore. People used to have lunch with me for fun, but after I became a manager, eating with me was seen as networking. Not having peer relationships was very isolating.
I thought about going back to Google, but I realized it wasn’t where I wanted to be. From what I saw and heard, layoffs in 2023 created a tangible shift in tone among employees. Layoffs were also happening at other Big Tech companies, and I was suspicious of working for them.
It was a fork in the road. For a long time, I didn’t have to choose between what made me happy and what paid well, but I wasn’t happy in my well-paid job, and I had to work out what I was going to do about it.
I worried I’d be miserable in a new job — and making less money
With support from my wife and therapist, I resigned from Verily in mid-2024. The tech market wasn’t looking amazing, but I had enough savings to feel like I’d be OK if I were unemployed for one year.
Toward the end of my time at Verily, I was earning a total of around $700,000. I knew that matching that compensation would be really difficult outside Big Tech.
I feared I’d still be miserable in my next job, while making half the money.
When I started job hunting, I made a list describing my dream role, including compensation, location, and title. Ideally, I wanted an individual contributor position, instead of a manager role, and to be in an industry focused on making the world a better place.
In October 2024, I took up a remote position as a distinguished engineer for an insurance company. But in January, I moved to a software engineering job at a company called Vercel, which would allow me to relocate my family to Canada. I’d wanted to leave the US, so we moved to Canada in July 2025.
Vercel helps build hosting infrastructure for websites, which is a mission I feel good about, since excellent infrastructure helps businesses move faster.
After a long stint of feeling like I wasn’t doing what I really wanted, I now feel like I’m solving hard problems again. Having an individual contributor role, instead of being a manager, means I get to flex muscles I hadn’t used in a while. I’m also enjoying the quicker pace of delivering things at a smaller company.
Leaving Big Tech taught me money can’t buy happiness
My Big Tech salary allowed me to save a lot for my retirement, but it also meant my lifestyle inflated over time.
When I moved jobs, I knew that smaller companies often have smaller bonuses and equity than larger companies, so I’d have to make some lifestyle changes. We had a pool in our house, and it was expensive to maintain the property, so we had to get that albatross off our necks. When we moved to Canada, we downsized and scaled back on vacations.
Vercel recently announced a new funding round, which roughly tripled its valuation to $9 billion. This substantially impacts the value of my equity compensation. Although my equity is currently unvested and non-liquid, the decision I made to leave Big Tech has now started to feel less financially crazy than before.
At the same time, I’ve realized money doesn’t buy happiness. I’m in a more fulfilling job and happier than I was when I was earning $700,000.
It wasn’t that I needed that much money — there were points where I stuck to an annual budget and still had $100,000 left over — but I was afraid to discover what things were like without it. It was like breaking out of golden handcuffs.
Do you have a story to share about quitting your Big Tech job? Contact this reporter at [email protected]
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