So You're Thinking About Quitting Your Job
5 questions to help you figure out when to hold 'em and when to fold 'em.
Quick context: my clients are mostly high achievers and high earners in sales and marketing roles. I'm aware that the luxury of deliberating about fulfillment and “cutting back on expenses” is not available to everyone, and it feels gross and weird to jump right in without acknowledging that.
Someone reading this right now is thinking about quitting their job. Probably MANY someones are thinking about it.
Maybe you’ve outgrown it.
Maybe you’re bored out of your skull.
Maybe the company or its values changed around you, and you stayed the same.
Maybe you’re in a different season, and you want different things now.
Maybe your new CEO was a contestant on The Apprentice and rides a Segway around the office with a helmet that Legal forces him to wear. Only me? Too specific? (IYKYK)
Maybe you’re tired of making rich assholes richer, dealing with corporate politics, talking about AI in every meeting, or getting a stomach ache every Sunday night.
Is it bad to admit that I have thought about quitting every job I have ever had?Sometimes I’ve been able to rein it in and reinvigorate my work life, and sometimes not. Sometimes that feeling was a deeper sign that my life needed realignment, and sometimes it was a passing frustration.
And, look, I do like my current job (I work for myself, which helps). I’m good at what I do. I get fulfillment out of my work. I love my clients. I get excited by the problems I get to solve.
If I won the lottery, I would still want to do some kind of “work.” But it would not be what I do now. It’s more likely that I’d be doing teaching arts and crafts or volunteering with cheetahs.
There was a period when my kids were little, and I was the sole income earner for my family. My husband at the time was a stay-at-home dad, and I was deeply unfulfilled with my job. I wasn’t miserable exactly, but flat. I take that back. I was miserable sometimes.
I was starving for something more meaningful, and did all sorts of volunteer work in my free time to scratch that itch. After a few years doing birth doula work on the side, I considered making it my full-time job. I ran the numbers over and over and couldn’t figure out a best-case scenario that allowed me to earn even one-half of what my corporate job paid.
I was surrounded by friends who kept telling me to jump.
“Leap, and the net will appear!”
“Trust yourself, mama!”
“The universe wants you to succeed.”
I heard their words and gritted my teeth and felt like a coward, because I couldn’t bring myself to do it. And I also rolled my eyes a little internally because almost every single person encouraging me had a partner bringing in the bulk of the income, or parents who could help, or some other floor underneath them that they took for granted.
They weren’t wrong that the leap had worked for them. They just had a financial safety net that I didn’t have.
(I didn’t leave that job, btw. I stayed until we were acquired, made a little money, got laid off when new management came in, and used my severance to take my family to Costa Rica for two weeks).
There’s a story we tell about smart, ambitious people: we’re supposed to feel called by our work. I have believed for years that fulfillment in my job is my baseline expectation, rather than an amazing bonus. I have thought that if I were not lit up by what I do, then I am either in the wrong job or I’m doing it wrong. This is a beautiful story for people with options. It is a more complicated story for the rest of us.
The Mary Oliver poem comes up a lot in these conversations. The one about your “one wild and precious life.” (I posted the whole poem at the end of the post. It’s worth a read.
I love this poem. And I think I have also internalized it as a guilt-delivery mechanism. How fucked up is it to use a Mary Oliver poem to beat yourself up? If I’m not contemplating a snail’s slime trail and looking up at the moon, or at least saving orphans and making clean drinking water, am I even living?
What I want to say is this: your one wild and precious life might include a job you like fine. A job that pays for the things you actually love doing when you’re not working. That is not a failure of imagination. It is a choice. It may or may not be the right one.
There’s a version of this I see constantly with my coaching clients who have built large incomes. Two earners often around half a million dollars combined, and they feel like they have no options.
Sometimes they really don’t. The lifestyle has expanded to meet the income, and now the income is load-bearing in ways that feel impossible to move around (almost never actually true).
More often, what’s happening is subtler than that. More often, the options exist, and what’s missing is permission to want what they actually want. If you want to earn significant money so you can take good vacations, send your kids to the schools you want, and feel financially secure, that is a completely legitimate thing to want. It just requires you to say it plainly, to yourself, and make peace with the trade.
You may have to work a job that isn’t fulfilling in order to have those things. There is tremendous power in admitting that to yourself and in making your “meh” job a conscious choice instead of something that is happening to you.
It is ok to say, “I would rather dislike my job and take a trip every year and have a nice car, than do work I love and have to downsize my life.”
Ambitious, thoughtful, progressive people aren’t supposed to admit that a nice lifestyle might be worth doing work that is occasionally soul-sucking.
So before you decide anything, here are the things to think about:
How bad is it, really?
Boredom is not the same as dread. Restlessness is not the same as misery. They feel bad in different ways, and they call for different responses.
If you are white-knuckling Sunday nights, your body is telling you something your brain is working hard to override. If the anxiety has become physical and consistent, that is not boredom. That is your system saying something is wrong, and it deserves to be heard on its own terms.
I worked with someone who was staring down the barrel of a future IPO that could mean life-changing money. Generational wealth. Tens of millions of dollars. But she had an autoimmune condition likely brought on by work stress. She was traveling all the time and missing her family. She lived at the whim of a toxic CEO. She had been telling herself for two years to just hold on, that the payoff would be worth it. She eventually left that job after coming to terms with the fact that if she HAD $20M, she would likely spend it in order to feel better and have time with her kids. We still don’t know if that IPO will happen. Whether or not it does will likely influence how happy she is with her decision.
Another client was flat, understimulated, and itching for something new. That is survivable. We worked on what she could do to make her current job work better for her while she waited for better conditions to leave.
Is this the job, or is this you right now?
Some restlessness is portable. You’ll take it with you into the next thing. If you’re burned out, grieving, going through something, or just in a hard season, the job is probably the nearest available target.
It’s worth asking whether a different situation would feel different, or whether you’d find something to be restless about there too.
What are you actually walking toward?
Not what are you walking away from, but what are you headed for? The fantasy of the “dream” (the art classes, the cheetahs, the bakery, the nonprofit) is real and worth honoring. But is there a concrete version of it, or is it still a feeling? There’s a difference between “I want to leave this job” and “I want to build something specific.”
Are you performing dissatisfaction?
This is the uncomfortable one. If you’ve built a life that requires your income, and you actually don’t mind the work, it’s worth asking whether you’ve been telling yourself a story about being unfulfilled because that story feels more acceptable than admitting you want the money and the security. There’s no shame in that want. But own it. Find some things to do in your spare time that scratch the “meaningful” itch. Giving money to charities is great, but you’ll feel more fulfilled if you give them your time.
What is the cost of staying for one defined period?
Not forever. Not with the door locked. Six months. One year. One funding round. One kid through a grade. Does that reframe feel like relief? Does it feel like permission to stop deciding for a while? Or does it feel like a prison sentence? The answer tells you something.
We are pretty good at evaluating the risk and cost of leaving something, but sometimes we fail to evaluate the risk and cost of staying.
The question of whether to stay or go is rarely as simple as whether you’re happy.
It’s about what you’re trading, what you’re funding, what you actually want the other side to look like. The people who told me to jump weren’t wrong. They just had safety nets I didn’t have, and they didn’t even realize it.
Your one wild and precious life is still yours to design. Sometimes that design includes a job that isn’t your calling. Sometimes it means staying longer than feels romantic so you can leave on your own terms. Sometimes it means getting honest about what you actually want and stopping the performance of wanting something different.
None of those is a small thing. All of them are worth the work to figure out.
If you're sitting with a decision like this or something else and want a thinking partner, I work one-on-one with founders, senior leaders, and executives in GTM roles to help them get clear on what they actually want and what to do about it.
If that sounds useful, schedule some time to talk and we'll figure out if we're a fit.
The Summer Day
by Mary Oliver
Who made the world?
Who made the swan, and the black bear?
Who made the grasshopper?
This grasshopper, I mean —
the one who has flung herself out of the grass,
the one who is eating sugar out of my hand,
who is moving her jaws back and forth instead of up and down —
who is gazing around with her enormous and complicated eyes.
Now she lifts her pale forearms and thoroughly washes her face.
Now she snaps her wings open, and floats away.
I don’t know exactly what a prayer is.
I do know how to pay attention, how to fall down
into the grass, how to kneel down in the grass,
how to be idle and blessed, how to stroll through the fields,
which is what I have been doing all day.
Tell me, what else should I have done?
Doesn’t everything die at last, and too soon?
Tell me, what is it you plan to do
with your one wild and precious life?
I'm writing this from the position of someone who has made both choices.
When my kids were little and I was dreaming about leaving to become a full-time doula, I ran the numbers and stayed. We couldn't afford it, and that was the right call.
But I also struck out on my own, twice, both times as the sole income earner for my family. The most recent was two years ago, when I went out on my own as a fractional go-to-market leader and executive coach, work I still do. Although I did not have a safety net of another income-earning person in my house, I did have 6 months of savings, which a lot of people don’t have.
That was also the right call. It worked out, and I‘ve never been happier.
I have no judgment about which choice you make! The point is that we’re all dealing with a lot of different circumstances and levels of safety nets when we are making these decisions.