I quit Google after 18 years on the job. It was scary but I did it well — here’s how.

This as-told-to essay is based on a conversation with Jenny Wood, a 45-year-old former Google executive who lives in Boulder, Colorado. She left Google in August 2024 and is now a keynote speaker, coach, and author. The following has been edited for length and clarity.

It seemed preposterous for me to ever think about leaving Google.

I started there in November 2006, when there were only around 10,000 employees, and became an executive — the director of American media relations — in 2022.

Google's amazing; I bleed Google colors. I loved the impact I was having, the future of opportunities I saw for myself, and the feedback I was getting as a leader. I'm also the breadwinner for my family.

I'd always thought I'd be at Google for another 15 years and would retire there.

I realized I couldn't sustain my life anymore

The moment that started the agony was when I was driving my son, who was 7 at the time, home from choir rehearsal in the dark, a 45-minute drive on winding roads.

Because of everything on my plate at the time — my role at Google, leading the Own Your Career program, navigating my book opportunities, and being a wife and mom — I was suffering from so much anxiety that it kept me up at night, feeling like I was letting everybody down and not doing anything well.

Mostly, I was incredibly sleep-deprived.

As I was driving, I was like, Oh my gosh. Did my eyes just flutter closed? I didn't actually fall asleep at the wheel, but it was a terrifying moment.

During my next session with my executive coach, I told her I couldn't sustain this anymore. I had taken on so many things in the name of success. She said, "Jenny, circumstances change."

Her words stopped me in my tracks and opened me up to the possibility of leaving — leaving well and quitting thoughtfully.

Thus ensued 18 months of back-and-forth about whether I should stay or go.

I used a spreadsheet to help me weigh the risks

I'm a left-brain thinker and approach the world in a very analytical way, so it was hard to feel in my gut that it was time to leave.

One thing that really helped was a spreadsheet I made, weighing actual risk against perceived risk. I broke it down into four components: physical risk, cognitive risk, emotional risk, and financial risk.

Physical risk included things like not sleeping at night, pain, and weight loss (which I gave a 1). Cognitive risk was mental stress, distraction, and mental drain (a 2). Emotional risk included potential for rejection, loss of connection with loved ones, negative self-talk, and fear (a 2). And the financial risk was things like paying my future mortgage statement and future earnings potential (a 2).

Breaking things down helped me get out of a catastrophizing mindset of thinking, This is a ridiculous idea, and made me think much more practically about how this might be possible.

I had to change my mindset to escape the golden handcuffs

The golden handcuffs are very real.

It wasn't just my salary, bonus, and equity; it was all of that future income as well. I would log in to my Google stock portfolio system — which tells you what you've earned and what you'll earn when your stock vests — and my palms would sweat. It was really hard to walk away from that number.

But ultimately, if you're in an executive role at any Fortune 500 company, you're probably making more than you need to live on. I guess it depends on your lifestyle; I live pretty frugally. Even so, I still couldn't imagine my income and net assets not continuing to go up and to the right every single year until I retired.

That was a mindset I had to move past.

It took my husband and me having seven conversations with our financial advisor — which ended up being more like therapy — for me to feel comfortable and confident that I could do this.

My advice on quitting well

I ended up leaving Google in August 2024. I cried after I turned in my badge and computer and as I drove away — happy, sad, and bittersweet tears. It was 18 years of my life!

When I came home, my husband and kids had written all these phrases that I'd said before through my leadership and coaching work, and arranged them in a heart shape on the window in the kitchen.

The heart is still up, 14 months later.

Quitting Google has been a massive change. I don't want to make it sound like it was easy; it was the scariest and hardest thing I've ever gone through in my professional life.

But I'd say I quit extraordinarily well. Here's my advice for others.

1. Mind your truths and tales

A truth is a verifiable fact, while a tale is a story you create to make sense around the facts. We often tell ourselves negative tales, and they don't serve us well because we believe what we think.

To get past my fears, I had to separate the truths from the tales, and then rewrite those tales to be more empowering.

For example:

Tale: I will lose my entire identity if I leave Google.

Truth: I'll no longer be employed by Google.

A more empowering tale: Part of the reason I'm leaving is because I want to have a huge book launch and possibly be a bestselling author. That's an incredible new identity to adopt!

Or, tale: We will run out of money and have to move to a smaller house, away from the gorgeous hiking trails that are behind our current house.

Truth: I will not get a paycheck with the Google logo on it every two weeks.

A more empowering tale: I've worked really hard to put myself in the best financial position possible to make this a reality.

One tale I told myself was that my kids would never forgive me for leaving Google because they love the secret game room, the climbing wall, and the free snacks and candy — Google's a really cool place for a parent to work. But I know they're really proud of what I'm doing.

What matters more to them is that now I'm done with work every day at 2:40 p.m., I drop them off and pick them up from school almost every day, and they're probably going to start traveling to places like Disney World and Vegas with me for keynotes now.

There's no question this was the right decision for my family.

2. Prioritize your dynamic dozen

Before I quit, I made a spreadsheet on my personal computer of people I wanted to stay in touch with and their email addresses. I was also posting on LinkedIn frequently and building an audience.

I set up what I call the "dynamic dozen" — 12 people you want to meet with in the next 12 weeks. This is great if you're trying to switch roles within your company, if you're looking for a new job, and also if you want to quit. It could be 12 people in 12 weeks, or 30 people in 30 days.

Mine was probably closer to around 60 people in 60 days, because I wanted to leverage all of the relationships I had: people who might want to bring me as a keynote speaker in the future, or people who might want to buy a hundred bulk copies of my book two years from then.

When you leave a company, your network always remains, so double down on that before you peace out. Have honest, intentional conversations, put time on someone's calendar, and reach out to people, even if it's been years since you had a working relationship.

I had to push past the fear that no one at Google would want to work with me once I was on the outside, that I'd be irrelevant. My work is a lot about how to thrive in a corporate environment, so I wondered, If I'm no longer in one, will any of my content still be valid?

Now, my number one client is Google. The vast majority of my coaching clients are Google employees, and a huge chunk of my speaking revenue is from Google speaking engagements or consulting.

3. Move, then map

Once, I was hiking in Montana with two friends, and the trail diverged into two paths. I'm always trying to optimize, so I started peppering the park ranger with all of these questions: "What is the perfect path? Which one will be more cardio? Which one is a lake view and which is a mountain view? Which trail is muddy?"

And from 50 feet ahead, my friend yelled, "Jenny, it's all beautiful! Just start walking!"

I'm always trying to map out everything perfectly — how much income I'd make, how quickly I could build a business, what I'd be if not a Googler.

You can't do that. Fear adds friction, which slows you down without actually minimizing risk.

Trying to map every little possible component also takes the joy out of the process. Action makes progress; thinking provides clarity. When you move and then map —or at least move and map in tandem — you're going to be set up for so much more success.

If you quit your job for an unconventional path and want to share your story, please reach out to this reporter at janezhang@businessinsider.com.