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How to Quit a Perfectly Good Job

Updated: 15 hours ago

The interesting things about the trajectory of my career is that I’ve become whatever it is I’ve decided to be. But if I were to graph that trajectory it looks less like a shooting star and more like the stock market on a volatile day – up, down and then up and down again - but somehow it always works out.

Right out of college I became an account rep at two different banks, and when I couldn’t see a fast enough path to promotion, I quit and became an event planner with an on-going travel addiction, ticking off something like 15 countries while helping to build a multi-million-dollar catering business.

And when I decided to write about all of those travels, it led to freelance writing gigs that paid, and suddenly I was a writer. But when the kids came along, the deadlines were killing me so I pivoted back to events and deemed myself a wedding planner, because somehow nervous brides were more forgiving than newspaper editors when naptime went sideways or someone spiked a fever.

The wedding planner phase worked really well for so long. It was stressful but rewarding, and because the kids were young, I could compartmentalize their experience around my stress. While they slept, I was staggeringly productive, and arrived to the end of their naps feeling as though I had hung the sun and the stars while they slept. I was always exhausted, but in the cycle of 24-7 childcare, events gave me a real sense of accomplishment and a value that mothering didn’t always provide.

But a few years ago, the whole thing grew very tired. My kids were getting older, I was getting older, and the brides? They were somehow staying young, and showing up in droves with visions of wedding days filled with Pinterest and Instagram perfection. The expectations were getting harder and harder for me to manage, which is a tough one when you’re a people-pleasing perfectionist with clients that want their wedding planner on-call, and at their whim.

And I began to wonder how many more years of the kids’ memories were going to hang on the image of me at my computer, or taking frantic calls after dinner, or on Sunday, or first thing in the morning while packing their lunches. How many after-school hours and Saturdays would I give them a mom that was running off to save the day again?

So, I decided to stop booking weddings and entered a long phase of saying no to everyone and everything. I settled into the deeply uncomfortable place of waiting and listening and waiting some more until the right thing came along, which some days felt like was never going to happen.

But it did.

Yes, it was a position in events again, but at a gorgeous winery and farm only minutes from my house. In so many ways, it felt like coming home. It put all of my skills from all of my careers into play – sales, marketing, planning, strategizing. Taking care of the now, while also building a vision for the future. And they trusted me, they deferred to me and so with their blessing, I gutted the events department and together we began the long haul of building something new and truly special.

For nine glorious months it was a phase of my career that was healing me in ways I never expected. Until that spring, March 2020. Need I review that notorious moment in history where everyone and everything came to a halt?

While personally that spring brought a much-needed pause, professionally I suddenly had a fresh batch of brides that wanted answers and they wanted answers now. I was back on the hot seat. Back to being the one who had to have a plan. And a crystal ball that could tell the future. And also, fully understand the ever-changing mandates and expectation in a way that avoided lawsuits and financial peril.

If you know hospitality as an industry, you know it always takes its pound of flesh. It requires a level of professionalism and grit and self-sacrifice that few industries require. It takes a special kind of crazy to love it, and for so long I loved it. In a life where I so often felt out of control, event planning placed me squarely and officially in control, officially a fixer, a goddammed heroin that always showed up with a cape and clipboard to save the day.

I loved it. And then I didn’t. The pandemic shone a light on what might have been obvious for years – it was time for me to go. What had been true for me in this career, was no longer my truth. What had been possible, for me, was no longer possible. What had worked in 2019, no longer worked in 2020 and definitely didn’t work in 2021, and likely wouldn’t work for me ever again.

And yet knowing this, I still couldn’t figure out how to let go. What exactly was I trying to prove anymore? In the early years, I always felt my effort was digging us out of something, but it turned out that the harder I dug the deeper in I sank, and the same became true in my new position up the street. Harder, more efficient work only brought me more work. I couldn’t just get to the top of the mountain and take a moment to enjoy the view, there was always more to be done.

In that pandemic pause, I had a moment to really think about what had become most important for our family, and I realized how much of my career I had spent deferring and delaying what was important to me. How many times I said yes, thinking it was the last time, thinking something would surely change, thinking something new would miraculously come along to save me. In my mind, I was cashing in lottery tickets I never bought. I was borrowing time from my kids that none of my clients or employers could pay back. I was selling the most precious moments of my life, and all I got from it was a fleeting sense of satisfaction and another Sunday with sore feet.

So, yep, it was time. I knew it because when the pandemic began to lift, I required a good cry in the shower before getting ready for work. The time away on weekends felt like a dagger in my gut. Just the act of opening my emails produced a lump of dread in my throat.

But what to do then? What to do when one gets to midlife as a real expert in a long career, but you simply and thoroughly don’t want to do it anymore?

I didn’t know, but on a Tuesday morning last December, without a plan and without another job, I sat with my General Manager and resigned my position. I knew I had to do something radical or I would just keep saying yes, and doubling down, and sacrificing things I could no longer afford to sacrifice.

We both sat there in disbelief. I was shaking. I couldn’t steady my voice. I heard the words come out of my mouth but I felt out-of-body. It’s the feeling you might get when jumping out of an airplane without first checking if you grabbed the parachute. You know you’re supposed to jump, but you’re not really sure if you’re ready.

Not a great feeling. A feeling so strong and icky that it made me want to take it all back. It made me want to tell my aching heart to shut up, and instead re-up the affair I was having with my overly productive head.

The conversation at dinner that night didn’t go much better. I hadn’t fully vetted this decision with my husband. We had talked around it, he agreed I needed to go, but we didn’t have a plan. In my mind, this all made sense: I had resigned, but I hadn’t given my notice so there would be a long exit. I would stay to help find my replacement. I would make sure it was a smooth transition. I felt all of this would be reassuring to him, but I’m married to a practical man that can’t imagine jumping without a fully-checked parachute and a backup chute, and a life line tethered to the airplane. In his mind, there is no jumping like this version of jumping.

And I don’t blame him. It isn’t an ideal time for me to be unemployed and experimenting with a new career. We just came through a costly house remodel, we have three young kids in private school, and we don’t exactly have stacked bank accounts to furnish me a long and languid soul quest. On the heels of turning fifty, it’s a ripe age to decide a 25-year-old career needs to be tossed.

But what was done was done. I had leaped and I wasn’t looking back. My mantra through sleepless nights and uncomfortable conversations became simply: we’ll figure it out, we’ll figure it out, we’ll figure it out.

But figuring it out would prove to have an unexpected challenge. I could find another job, no problem. But as I looked around, a discouraging revelation came to me: jobs are mostly all the same. Sure, the hours and titles may differ, but pivoting to another job was going to deliver the exact same dilemma that comes with all jobs – the more you do the more is expected. The more you accomplish the more you will be required to accomplish. It’s the fabric on which our economy is built: if more is possible than more is what we should strive to do.

The very principle of being an employee at just about any American company is an assumed agreement that the job is your first priority, full stop. It gets the best of you. It gets your first thoughts of the day and doesn’t let up until it spits you out, exhausted and empty, at the end of the day. It delivers you to your family frustrated and overdone. A version that needs two drinks and moment to get right enough to struggle through the evening’s responsibilities.

I’m painting a grim picture, but this version of ourselves is everywhere. It’s in our coffee culture, our bar culture. It’s in the way we talk about being exhausted and busy like they are badges of our effort and worthiness. It’s in the way we have come to demand being entertained, numbed, always plugged in, always distracted from a life that we keep hoping will deliver something other than burn out.

So, I kept looking, and the jobs got more and more demanding. They all required their version of a pound a flesh and frontal-lobotomy in order to conform to the job descriptions that were as long and detailed as my arm. They were all safe and predictable choices, but safe and predictable didn’t fit anymore. Safe and predictable was slowly killing me. It felt like the worst thing for me.

What if the most radical thing I could do was to say no to all of it?

During the quarantine phase of the pandemic, I caught a glimpse of a woman I wanted to know better, a version of me that I want my kids and husband to know better. A woman that was getting healthy, finding rest, making herself whole. A woman who didn’t compromise or apologize. She’s slipped in and out of the mist over the last two years, but I caught a piece of her garment back then and I decided not to let go.

And finally, this month, as I complete my phase-out of this long and memorable career, I feel that version of her emerging bigger and stronger now. Unburdened by drama. Terrified but trusting. Rested and healing. Clear headed but unwilling to formulate a plan past the end of the month. I’m attempting to persuade the full version of that woman to stick around. It’s tempting to run back to what has always been known, but I can’t this time. This time, to not, feels absolutely necessary.

I’ll remain grateful for the type of professional and person that all of those years of hustle sculpted in me, but I’m fighting to set myself free from needing it. I’m finding a way to let go of that version of what gave me value. To find value instead in what brings me joy, and a sense of belonging to myself. It feels radical. It’s certainly amounting to be the hardest work of my life, but I’m here for it.

So now, I will do what I have wanted to do for so many years -- take the summer off. This month we start a new chapter where summers are on their terms. Where time expands. Where they get a mother who is present, not pressed. A mother with time to play and dream and learn right along with them.

And we’re doing what I have longed to do for so long – an extended time away. A road trip across the dessert and into the mountains. A sojourn. A hard reset. A pause to decompress and deprogram from what I think is possible to a greater scope of what I know is possible. I hope out there that my vocation as a writer, and the career that’s supposed to come next, finds me and grabs me and lifts me up, so that when I touch down again, this version of me becomes a former version of me.

To that end, I stopped waiting, and went ahead and wrote myself a permission slip. Permission to step forward in trust, without assurance. To move anyway, without a promise. To be a woman that doesn’t need a plan to know the right direction. From there, I hope to be filled to full, and become a wellspring of what’s to come.

And so, my mantra has evolved and now it goes something like this: Surrender, woman. Let yourself be free. It’s okay if you don’t have all the answers. It’s okay if you fall. Just keep turning back to your own wisdom. Just keep listening to your own voice. And be ready. You might fall, but most likely you will FLY.


One day you finally knew what you had to do,

and began,

though the voices around you kept shouting their bad advice –

though the whole house began to tremble and you felt the old tug at the ankles.

“Mend my life!” each voice cried.

But you didn’t stop. You knew what you had to do,

though the wind pried with its stiff fingers at the very foundations,

though their melancholy was terrible.

It was already late enough, and a wild night,

and the road full of fallen branches and stones.

But little by little, you left their voice behind,

the stars began to burn through the sheets of clouds,

and there was a new voice which you slowly

recognized as your own

that kept your company

as you strode deeper and deeper

into the world, determined to do

the only thing you could do –

determined to save the only life you could save.

Mary Oliver, The Journey

Photo Credit: Michael and Anna Costa, Aurelia D'Amour, Valentina Glidden, Mathew See

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