It all started with a quiz — several of them. Week after week, I’d hop on Google and search “how to know it’s time to quit your job.” I’d write it just like that, a complete sentence, wanting to do full justice to my question. The first results were always quizzes:
- Is your boss a horrible person?
- Would you hate to have your boss’s job?
- Are you woefully underpaid?
- Do you wake up each morning dreading going into the office?
I did them all. I never scored 10 out of 10. No, I didn’t totally hate my job. No, I didn’t dread going into the office each morning. My boss wasn’t a horrible person. And, as head of PR for all of Google, I would say I was over- not under-paid.
But I was unhappy. I had gotten to the top of my profession, but the truth was that I was increasingly having doubts about the content of this supposed dream job. And after all those years of wondering what it would be like to run things, I realized that having the big office meant you were on one side of the glass while all the people who had once been your friends were on the other side of it. It was more lonely than fun.
And so, I found myself with the ridiculous practice of asking Google whether I should quit Google. Every few weeks, I’d try a different quiz, thinking it would yield some new insight or that my score would gradually tick upward. It took several months before I hit on the real takeaway: It didn’t matter what my score was. The motivation for taking these quizzes was itself the answer. It was time to quit my job.
Take walks in the morning. Eat more sugar. Eat less sugar. Use those free massage credits (did I mention I worked in tech?). Avoid the executive you thought was a bully. Stand up to the executive you thought was a bully. Spend more time meeting with reporters — horrible idea — spend less time meeting with reporters. Delegate more. Try to care less. Try to care more.
None of this worked for me. But it might for you.
I am generally not one for spells, incantations, or the thought that there are job fairies lining one’s career path, ready to lend a hand. But when it came to quitting my job, it seemed totally reasonable to somehow expect that the universe would rally on my behalf to figure out my next step.
If I just waited, surely my life’s purpose would reveal itself to me. I’d wake up one morning and realize that my true calling was to make flower arrangements, start a company, or become a park ranger. Or if not any of those, at least the universe would listen to me and put an exciting job opportunity in front of me. After all, I had random headhunter and LinkedIn job offers each week; it seemed very plausible that something awesome would appear one day in my inbox. Maybe some publisher would come out of the woodwork and buy the book I had written years earlier, or maybe my next opportunity would materialize when I was at the local coffee shop, where The Youth are often talking loudly about their vegan crypto projects.
I was open to anything. I just wanted a sign, flashing bright and neon, before me. Guess what? The universe was silent. Because, obviously, whether in the work world or in the fledgling vegan crypto industry, if you want to make something happen, you often have to do it yourself.
I finally came around to the fact that it was on me to figure out my next steps. I needed some inspiration, so I grabbed a bunch of magazines targeted at women of a certain age — More, Women’s Day, Real Simple. These are the magazines that spend little time telling you about the current hot lipstick color and instead assume you are a sexless void who lives to tend to your children and organize your spice rack. They were also filled with stories of women who have quit their jobs and gone on to do great things.
The narrative arc was pretty similar from one story to the next:
Leslie had gotten to a point in her career as an account executive/mid-level banker/small business marketer when she realized that she needed to make a change. The next day, as she was sucking in her gut to fit into her skirt, she had an idea — why can’t women wear even tighter-fitting underclothes to make them slimmer? Why can’t they get salon-quality waxing at the fraction of the price? What is stopping them from having better organized closets? So Leslie took a leap of faith. It was hard and she almost gave up, but today Leslie has a successful closet organization business.
I just couldn’t relate. I didn’t have a brilliant idea. My closet was a mess and always will be. The only thing I knew was that I no longer wanted to do what I was doing.
Thinking I was taking the bull by the horns, I agreed to go on a job interview for a hot car company.
“Why do you like [Car Company]”?
“To be honest, I hate cars. I find them really boring.”
“Uh, so… why would you be interested in this job?”
“Well, I think if anyone was going to make me like cars a bit more, it might be your company.”
“We should probably hire someone who likes cars.”
Next, I turned to a life coach. (Yes, once again I was trying to get someone else to figure this out for me.)
“I’m scared to quit,” I told her. “What am I without my job? All I do is work. That is all I am. What if I quit and my life is empty?”
The coach told me to write down what it would look like if I quit my job. What was the worst thing that could happen? What was the most likely thing to happen?
So I wrote it down. Lo and behold, despite how I felt inside, there was no apocalypse. Even in the worst-case scenario, the Earth remained spinning. I could always get another job; I had been working a long time and had skills that were in demand.
I decided to tell a few people I was going to quit — the idea being to make myself more accountable to my decision, like one would with a diet or New Year’s resolution.
Inspired by my coach, I decided to tell a few people I was going to quit — the idea being to make myself more accountable to my decision, like one would with a diet or New Year’s resolution. I did not typically do this in a very crisp way:
“I’m quitting,” I told a co-worker. “I don’t know when, but by the time I’m 40 for sure.” My co-worker’s jaw dropped. He didn’t say anything, so I kept talking. “By the way, I’m pregnant. Also, did you finish your headcount projections for next year?”
That was a bit awkward, so the next time I tried a more concrete approach.
“I am going to quit,” I told a friend.
“What will you do?”
“I don’t know. Maybe open an Etsy store to sell small knitted animals?”
“Do you know how to knit?”
“That’s not the point!”
When I was a manager, employees would often come to my office and spend 25 minutes dancing around all kinds of issues related to their promotion or career. For most of us, it’s not easy to talk to our managers about what we really want. At some point, I would stop them and ask what was most important to them: Money? Promotion and recognition? The content of the job?
People aren’t driven by the same things, and many of us have a particularly hard time being honest with ourselves or others when our priorities are more materialistic or ego-driven. But for the purpose of this 837-step plan, you have to put aside the little voice that’s criticizing or second-guessing what you want. (Later, after you’ve quit your job, you can go do the meditation retreat that will make you less of an egomaniac or materialist. That’s like a 2,000-step plan, and it’s not what we’re here to solve right now.)
Once you can clearly identify what matters to you, it’s a lot easier to solve your problem. At the end of the day, it’s not that different from writing a business plan at work. I need x and so I will do y to get there.
For all of my supposed management prowess, it took me a long time to follow the advice I had been giving to my own employees for years. In my case, I wanted to reduce my 90-minute commute and not have to clean up other people’s messes (a big part of any PR job). I only wanted to deal with messes that I myself had created.
That’s when it all fell into place: I needed to solve for having more control.
If I had identified money or prestige as my key driver, I might have explored options at other tech companies or a similar position in a new industry. But that would have just been taking my existing problem to a new job. I had figured out I wanted to be a one-woman show of something. I didn’t know what that was, which was probably part of the reason why I had been paralyzed for so long. So what I needed wasn’t necessarily a new job; it was something that would help me figure out what I was interested in.
So I applied to grad school, and when I got in, paid the $100 deposit. Did I know if I would finish grad school or what would come of it? No. But it allowed me to jump right into something else — something totally different that would allow little comparison with my previous life and also give me total control over my day-to-day goals.
I did all of this at 39. I couldn’t have afforded myself that opportunity in my 20s — and of course, many people my age can’t afford to take time off to figure out their next steps. The point of my advice is not to say you should take a year off and go to grad school or decamp to an ashram in India (though if that works for you, great).
After the deposit was paid, it was easy to give my notice.
Rather, it’s to say that if you’re hanging on a bit too long, afraid of what will happen next, find something that forces you into your next step. Sign up for something that you will have a hard time wiggling out of. That could be taking a night class, conducting informational interviews to learn more about a particular field, or doing some volunteer work in an area that interests you. Make a small commitment that feels easy to do at the time but later may feel hard to reverse.
After the deposit was paid, it was easy to give my notice. I knew what I was doing next, and I knew what I was solving for. I wasn’t fixing all of my job existential woes — I was getting myself on a path toward figuring out what I wanted to do.
(Side note for those interested: During the year following my departure from Google, I went back to school, ended up starting a company, had a third child, paused school to zombie-walk my way through the newborn stage, and published a book. Only the school part was in motion when I left, but none of the other four things would have likely happened if I had stayed at my job. Also, that was a crazy year; I am not normally so productive.)
Reading magazine profiles or listening to cocktail party versions of people’s quitting stories, it’s easy to think you should only quit your job if you have a super clear vision of your future or are blessed with a million-dollar idea. Because our own narrative doesn’t feel so simple, we second-guess our instincts, allowing fear of the unknown to push us toward putting off the things we know we want to do.
Instead, we’d do well to embrace the messiness of our process and dispassionately figure out what’s important to us on the most fundamental level, building a business plan for our life that gradually gets us from point A to point B.
There are some people who are born knowing exactly what they want to do or who are super relaxed about riding the seas of change from one wave to the next. But those people never clicked on this article. But you did. And you read all the way to this sentence. The question is, why? And what are you waiting for?