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Should I Quit My Job? Take This Quiz to–Just Kidding

Should I quit my job?

This is a question people ask me with a frequency that surprises me and in a variety of contexts.  I could answer as one of my reader question Monday posts, I suppose, but I’ll just answer straight out.

If you’re a regular reader or someone who came here via share, and you’re asking yourself, “should I quit my job,” the answer is yes.

And if you wound up here from a Google search for “should I quit my job” then the answer becomes “Dear God, yes.”


Well, before I get to that, just look at the results of that Google search.  You’ll see why I had a little fun in the title of this post.  Each site that addresses this topic goes something like this.

Should I quit my job?  Answer the following 25 questions on a scale of 1 to 5, with 1 being strongly disagree and 5 being strongly agree.

  1. Does coming to work each day make me want to drink bleach?
  2. Does my boss actually, literally make me drink bleach?
  3. …………………
  4. Meta question: if I were taking a quiz about should I quit my job and it asked me if I should quit my job, would I say yes?

Now, tabulate your score.  If you got more than a 50, you should quit your job, mister, yah, you betcha!

So let’s just skip the quizzes and head games and get straight to why you should quit your job.  I’m just dispensing with the busy work and telling you what you came looking to hear.

Understanding Your Motivation

Do a thought exercise with me, if you’re one of those wondering, “should I quit my job?”  (Or, go ahead even if you love your job, but the effect will be understandably muted.)

Say you do this internet search, land on one of those silly quizzes and take it, giving your career the same treatment as a Buzzfeed quiz about finding out which character from Game of Thrones you are.

Don't sacrifice your positioning strategy to code-jousting sites, as illustrated by this joust-ready knight.

Let’s then say that the answer comes in.  You should, most decidedly, NOT quit your job.

What’s your next move?

Do you shrug and say, “welp, that settles that.  Back to the grind, never to contemplate this again!”

Or do you keep taking quizzes and reading articles about quitting?

I bet it’s the latter.  And you do something like this because you’re shopping for an answer.  You’re not looking for the internet to answer your question as much as you’re looking for it to supply you with ammunition.

So roll with it.  Accept that you should quit, gather your ammunition, and start planning when and how you’ll quit.

I’ll offer more on when and how momentarily, but with a quick spoiler.  I’m going to counsel patience and a long game.  If you’re looking for someone to validate your plan to march in like a moron and let your boss have it, I’d suggest looking for apocryphal Facebook posts.

Quitting is a Matter of When

Staying out of the realm of the macabre or the weird, there are only three basic modes of employee termination.  You resign, retire (a specialized resignation) or walk out following involuntary termination (terminated for cause or laid off).

Given this limited set of end states, on the very first day that you start work at a place, surrounded by onboarding protocols, smiling coworkers and a fruit basket, you face three prospects.

  1. I work here until I’m tired of working in a very permanent way.
  2. I work here until they decide they’ve had enough of me.
  3. Or, I quit at some point.

Nobody plans on (2) when they start, and, if you’re close enough to retirement for (1) to matter, congratulations.  But few plan on that.

So, by default, your outlook from day one is already to plan to quit at some point.  The question, then, just becomes when you should quit.  I’ve written about the dynamic before in a post called “Always Be Leaving.

So there you sit, googling around for “should I quit my job” when the answer is, and always has been, “yes.”

The Standard Algorithm for Quitting

So far, all of this might sound both a little bleak and a little facile.  Yes, eventually you’re going to quit your job, but why not enjoy the ride until the magic runs out?

Well, first, you’re fighting knowledge worker trends with this one.

We’re seeing the rise of the so-called gig economy and the marriage duration between employers and employees hitting an all time low.  A majority of people feel disengaged at their jobs, so staying put is largely a matter of inertia in many cases.

So yeah, you can hope that you’ve finally found the right job to settle down with, but recent history works against you.

But even beyond that, I’d advise a cynical, calculated outlook for another reason.  Consider the de facto algorithm for deciding that it’s time to move on.

  1. Work at the same place until you start feeling miserable.
  2. Then keeping working there, while going home at night to google “should I quit my job.”
  3. Then keep at it, just a little longer.
  4. Just a little longer.  Until you ABSOLUTELY CAN’T TAKE IT.
  5. Then you furiously interview for a few weeks and quickly take another gig.

Does that really seem somehow more noble than assuming an exit from day one?

Understanding the Corporate Hierarchy

I’ve written about the value-destroying proposition of pyramid shaped corporations managing knowledge work plenty of times on this blog (and also a book on the subject).  You can find an introductory primer here, about the corporate hierarchy.

What I’ve described here is the quitting and (lack of) leverage game of the corporate pragmatist.  Pragmatists are people who put in enough work at the company to avoid getting fired and to secure run of the mill raises and advancements.

But they don’t sacrifice their lives at the altar of over-performance for the love of the company (and ostensible, but not accurate investment in one’s career).

Those are idealists.

Idealists tend to have weird, messy divorces with the company, and idealists probably don’t ever google “should I quit my job” (or read my blog for that matter).  So, odds are, you’re a corporate pragmatist.

The corporate pragmatist strikes an inherently unfavorable but stable arrangement with the pyramid shaped employer.

I’ll always give you a game, if sometimes half-hearted effort, and you pay my mortgage and shield me from the vagaries of the market.  

For the pragmatist, a career is defined as the stable periods between “I’m excited about this new job” and “I sort of hate all of you and am excited for my next new job.”

But for the people at the top that I have yet to mention — the opportunists — a career is defined as an ascendant, planned march up the pyramid that never stops.

So who do you want to be?

Each Job is a Mission

The opportunist’s outlook treats each job and each project as a mission.  You take it for some purpose, plan success (and failure) scenarios, and have exit criteria.

For instance, consider some of the following.

  • I’ve wanted to go into management consulting, so I’m going to take a job with a software consulting firm, work there for two years, and then look to jump to management consulting.
  • I want to work as a designer at a major player Silicon Valley outfit, so I’m going to first take a job as a designer anywhere to get some experience, then take my next job in the valley, then plan my big break within five years.
  • This company is offering me a promotion to management with a big payday.  I’ll try it here for six months, then evaluate my options.
  • I’ve been waiting for a year here with no advancement.  I’m going to give it another year max and then hit the market.

Notice that, in all cases, there’s nothing much about feels.

The people saying these things are treating their own careers as projects on which they work.  They understand their long term goals, and they work backward from those goals to figure out how long they should spend in a role and what they should accomplish.

If you’re a pragmatist, you let your employer do “career planning” for you in the form of performance review theater.  If you’re an idealist, you gleefully participate.

But if you’re an opportunist, your real career planning mostly happens quietly, off the record, and in your head.

Should I Quit My Job?  Only With a Mission Accomplished

If you’re googling or idly daydreaming about quitting, table flips, and “dramatic quitting stories” then you’ve inhabited the land of pragmatists for far too long.  You’re fantasizing about taking the one little moment of career leverage that you might have and cashing it all in for basically no reason.

Don’t do that.

I get it.

  • The senior architect in the group is making you miserable.
  • Management is filled with idiots.
  • You’re in a death march.
  • There are enumerable scenarios that have you going home in frustration, dusting off your resume, and firing up the spiteful job searching apparatus.

I’ve been there myself.

Yes, you should quit your job when those things are true.

But you should also quit your job long before those things are true, when life seems great.  That ship sailed, and now your hand is being forced?  Only if you let it.


If life is great at work, do some reflection, set an expiration timer and some goals to get out of your job.  Plan your next step.

Do this if you think it might be time to move on.  Do it if you’re angrily googling epic ways to quit.  If the day to day is too much for you, check out, stop fighting, under-perform.

Whatever — get your sanity back and plan your exit.

Most importantly, learn from your experience of angst and frustration or from boredom and resignation.  Create a mission for yourself, gamify your career, and make sure that you approach each job like a project — with an end state in mind from the beginning.  You’ll never again wonder if you should quit your job because that makes no sense.

There is no quitting — just successful completion and moving on.

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[…] though, I’ve got some pointers for how to handle this.  I’ve given general advice on whether to quit a job and how to quit a job before, but this will be specific to the exit interview portion of […]