To quit, or not to quit your job?

3 questions to ask yourself, to help parse if it's the right time to quit

I’m currently a third-wheel on a trip with my parents to celebrate their 35th anniversary. And during this time, I’ve been the beneficiary of those uniquely “parental” travel comforts.

A spare charger in my dad’s suitcase. An extra toothpaste in my mom’s toiletries. And a ziplock snack tucked into one of their fanny packs.

Which, I readily scavenge for — after insisting at breakfast that I would make it pedaling 50 kilometers on a bike, powered by only one slice of toast.

While this rare time with my folks has come with the delight of many comforts, it has also come with the obligatory parental discomforts. Perhaps you know the type?

You arrive at your accommodation, and your parents march back to the front desk to request a room with a better view. You follow the restaurant host towards a table, but your parents firmly point to a more preferred perch. To be clear, my parents are never rude, and always reasonable. But if it’s not up to par or wrong, they will make it right.

And while I know these are all fair requests on their part, I get inexplicably flustered. Maybe it’s the unavoidable nature of all grown children — to bristle at parental ruffling of feathers?

But, in my case, what I do next is even more odd. A curious sort of thing:

I do the opposite of whatever’s making me uncomfortable — and veer towards another extreme.

We enter our hotel room overlooking a slab of parked vehicles, and I spring — How convenient! We can keep an eye on the car! We find ourselves seated at a table wedged beside the kitchen, and I shout over a deafening percussion of clanging pots — This is great! A front row seat in the bustling atmosphere!

But I wonder sometimes if this odd inclination of mine, is not merely mine alone. In fact, I wonder if we all have some of this tendency to grasp for opposite extremes, when we’re bristling most in our discomfort zone.

Maybe when we’re most distraught, it feels easier to overcorrect. Too tired, or too scared, to navigate towards a better outcome tucked somewhere in the middle.

It’s just a theory, but one that I’ve seen play out before in my career.

I stewed on what I wanted to do about my job, but never actually problem solved. Instead, I salivated for 5 years straight — for a drastic, but easy cure.

I longed desperately, and I longed daily — to rage quit my job.

When the “optics” of quitting, cloud vision on the decision

There was a period of my life where I fantasized about quitting my job on a daily basis — hitting send on some poignant farewell email, slamming my laptop closed, twirling some gaudy baton in the air, and sashaying my way through the office lobby before prancing out the front door.

I quite liked the optics of it. Leaving while I’m ahead.

So intrepid! So brave! So bold! — surely what my co-workers would have said.

But on the inside, I felt a deeper truth, tapping ever so lightly on the glass of this fragile story. I couldn’t help but wonder if the sheer emphaticness of my desire to quit, was incriminating in and of itself.

Beating the drum so loudly to leave, to bury the truth of my greatest fear: the work required to stay. And the conflict it might take, with others and myself, to break free of my broken ways.

And so, I craved drastic action, not because I felt like it was the strong route forward, but rather, because I felt scared — it was the only way out.

Maybe the more emotional we are in our desire to quit our job, the more we need to pressure test the integrity of that impulse.

Which makes a worthy question for all of us to ask ourselves:

Do we want to quit because it’s truly wrong, or because staying and fixing it feels hard?

When we feel the desire to rage quit, perhaps we should pause and hunker down. Asking ourselves the difficult question — is it frustration with our bosses, our co-workers, our scope, our company, or the “culture?”

Or, in fact, the fault of something within ourselves — impressively adept at scapegoating everything else.

3 questions to ask yourself, to ensure you’re not quitting out of fear

To be clear: this is not a blog post encouraging you to stay in some soulless, suffering career. But, it’s also not a rally cry to join me in ditching the corporate world. If I had quit any earlier, I would have been a rebel without a cause — which is still a slave to fear.

For most of us, quitting our job is not an uncertain event. In fact, it’s nearly guaranteed. Unless you have your heart set on parking for three decades at the same company, nearly all of us will eventually leave.

So that means, we need questions that help parse the “when” part of quitting:

How do we know if we’re stalling, and staying too long — or fleeing, and leaving too soon?

And we won’t answer that by stewing on the diametric ends of the option space — to maintain status quo, or ditch it all and quit. Rather, we need to hone in on the messy middle ground, and ask if we’ve taken the most uncomfortable approach of all: radically overhauling ourselves first.

To stay a bit longer, but not stay the same way.

Questions to ask yourself before quitting your job

1. Is there something or someone that, if removed, would dramatically change how you feel about your job?

Consider this: if a particularly distressing project on your plate was magically plucked off, or a particularly frustrating person (co-worker, boss, client) playing a role in your duress suddenly disappeared — would you still feel an equally strong urge to quit?

There’s nothing wrong with quitting to protect your peace against a bad situation that can’t be changed. But if you can pinpoint a single factor or two that shapes your sentiment dramatically, that’s probably not the case.

And that’s the only wrong reason to quit: quitting before you’ve even tried to address the source, and spur meaningful change.

That could mean finding a way to shift your scope, testing out a different part of the org, or having a frank conversation with someone face-to-face to let them know that their working style, ain’t gonna work for you.

If something localized is sitting at the base of your desire to quit, be wary of any impulse.

Sometimes our self-doubt makes us long to overhaul everything, just to avoid conflict with a surprisingly narrow piece.

Conversely, if this isn’t the case — and you can readily say that the issue you have with your job is ubiquitous, that’s a different story. Maybe your company is small to begin with and there are few adjacent areas to explore. Or maybe the place really is over-saturated with the wrong types of folks.

Either way — be honest with yourself: is the discomfort relatively self-contained with a clear “source”, or indeed, pervasive in the setting and inherent to the work? Then, you can have clarity on the cause and make a cleaner decision based on that. Either stay and really seek out levers to address that small problem zone, or go, knowing it isn’t the right space.

2. Do you fundamentally dislike the nature of the job or do you dislike the way you make yourself feel doing the job?

Even in my darkest stints of burnout despair, I still liked many core features of my job — writing product proposals for new features, strategizing on pitches to win customers, and debugging breakages with engineers.

I just didn’t like the stress that came with it — the high stakes nature of the business, and the self-induced pressure to uphold an “A+ pupil” persona that I couldn’t bare to lose.

In fact, I wanted to quit most, when I felt the most tired of keeping that secret from my higher-ups:

I didn’t actually have the maturity as a leader to know how to handle high stakes tasks, without doing it by overworking and destroying my health.

The strife of my job was wholly self-induced. But in cases such as these, it can be all too alluring to assign the blame to something else.

The volume of the workload! The toxicity of the culture! The unreasonable expectations of the C-suite!

And while some environments may certainly stoke feelings of stress more than others, the foundation of it will always be based in ourselves. Something we know, but hate to hear:

No one else can single-handedly “create” your stress. Our choices — our daily actions, or in some cases, inactions — always run point on shaping the feelings that we feel.

So before quitting a job, those feelings need to be parsed.

Our feelings about the what of our work, shouldn't be mistook for the feelings bleeding out of our bad habits in how we work ourselves. I liked the shape of tasks that my job entailed, but I did not like living in a perpetual state of hyper-productivity to soothe an acute “under-performance” fear.

The good news is, it’s the simple stuff that can still be tremendously powerful in fixing that. And there’s no secret sauce to the “how” that you haven’t already heard: prioritize your time, communicate directly about what you won’t do, and do your best while practicing caring less about how the quality of your work is perceived.

3. Does the prospect of leaving feel more like excitement or relief?

Before I found writing, I told myself that I needed to quit because I had no time outside of work to solve my greatest frustration: there was nothing — no pursuit, no craft, no calling — that I felt genuinely ambitious about.

My job became a wonderful fall guy for the problem that I hadn’t yet been able to solve. But while more free time is nice, it won’t make existential relief spontaneously appear.

In fact, parachuting out of your job prematurely may only constrain your ability to explore.

Your job, if nothing else, is a financial tool that lets you cast a wider net in the areas you can explore.

So use that flexibility to re-invest in yourself — cleave off time in your daily routine to cultivate curiosity, and make micro investments in things that interest you.

That way, once you find some clues, quitting won’t feel like a corner that you were backed into, or a shoddy leap of faith — a blind trust that you’ll suddenly build discipline to try new things.

Take steps to find at least a few clues towards what excites you, first. And then leave your job to continue it — leaning into the insights and momentum that you already have.

Conclusion

What surprised me most when I finally quit my job, was that it did not feel like jubilant elation. Instead, it felt peaceful.

A calm, quiet sort of readiness.

And once I’d stayed long enough to prove to myself that conflict aversion wasn’t calling the shots, quitting no longer felt like the easy escape hatch.

Rather, it felt hard.

So, yes — do quit. Absolutely, when the time is right.

Quit when you know in the deepest parts of yourself that the work you had to do at your job and on yourself, is indeed, done. And quit, when quitting no longer feels easy — but rather like a new opportunity.

A new showdown with fear, and a new mission to conquer self-doubt.

---

If you found something here that speaks to you, leave a comment :)

Your support is greatly appreciated, and indeed helps this writer feed her soul 💛