6 Questions To Ask Yourself Before Quitting Your Job

May 21, 2020 · 4 min read

“The only Zen you can find on the tops of mountains is the Zen you bring up there.”

-Robert M. Pirsig

We’re ready for something new.

New lives. New health. New times.

And new jobs.

The social changes, the normalization of remote work, the restructuring — a new life feels more possible than ever.

Opportunities that arrive during the stress of a pandemic are especially seductive. But the stress is temporary and the decision to quit may not be.

Use these six questions to put your decision to quit in perspective.

On the interview trail, you hear the question: What attracted you to our company?

This question is elegantly misleading.

But by answering it before you start looking at other jobs, you gain insight into why you’re thinking about leaving. What you’re really being asked is:

Are you being pushed from your position?


Are you being pulled toward a new one?

Are you trying to avoid something bad or is there something specific you’re moving toward? Your answer clues you in to what and where the issues are, but also what your motivation is for leaving.

There are good and bad reasons for wanting to quit your job. But if you figure out that the issue is with you, quitting won’t fix anything.

If the issue is the workplace, it may be time to find a better fit.

No job is perfect.

They share the same problems, just in different proportions. Everyone has a culture problem. Broken processes abound. Toxic people infiltrate the best jobs. Communication will never be perfect.

Quitting could mean replacing your terrible boss with an awesome one. But you may gain a new broken system or a hierarchy that stifles your growth.

Which set of problems would you prefer?

Take an honest inventory of the new position. Social media and the litany of job sites make inside information easy to obtain. Take advantage and network to learn what you need to. Check online sources. Get an insider’s perspective.

The grass, as they say, may not be greener for great reasons.

A toxic co-worker who has been fired from their last four jobs is probably temporary.

An organization that waits for one person to die so they can promote someone else is a permanent problem.

Start by defining the problem with your current position. Once you understand that, you can envision the end-point. The more permanent (or farther away the end-point), the more urgent is your decision to leave. The more temporary the problem, the less urgent.

Quitting can be a permanent solution — make sure that your reasons for doing it aren’t temporary.

If you are fantasizing about the splendor of your new life, you’re not being objective.

Quitting will have consequences too.

You could lose money or benefits. You could burn bridges. You could get locked into a restrictive contract that limits your time or freedom in some way.

Take inventory of all aspects of work; not just the bad ones that seem like priorities. Pay, culture, schedule, friends, time off, benefits, opportunities for growth — all aspects of your job.

By taking an inventory of all aspects of your job, you will not only put your current problem in perspective, you’ll also realize what you could lose by quitting.

“Better to light a candle than to curse the darkness”

-William L. Watkinson

You have control over yourself and many parts of your job. Are you exercising that control or are you cursing the darkness?

Did you seek out new responsibilities or did you avoid them and that’s why you were passed over for a promotion? Did you join the committee that could fix the problem or did you join the peanut gallery?

Organizations generally have avenues to fix problems and if you learn the lingo and who the players are, you can change things. And, if you’re unwilling to put your skin in that game, why would you be any different across the street?

Personal development follows the same logic — it’s not our employer’s responsibility. Having a sense of purpose, building character or seeking new challenges are choices that lead to development. These are internal processes and decisions. They are things we can control.

If you are not willing to accept responsibility at Organization A, you won’t do it at Organization B either.

“If you don’t know where you are going, any road will get you there.”

-Lewis Carroll

If you have a life plan, this question is easy.

If you do not have a plan, a new job will feel like a square peg in a round hole. If you’re quitting because you “just want to quit” or because of a temporary reason, you’ll find yourself trying to make a new job fit.

When you have no plan, you’ll find yourself forcing a new job into your life. You’ll do this to “prove” how right your decision to leave is. The new position won’t flow and you’ll start making excuses for it before the job even begins.

If this is your dilemma, then stop — you aren’t ready to quit.

Stop lamenting your job, work on crafting a plan instead. Let your current job go on auto-pilot while you’re figuring out what you want. Your plan doesn’t have to be perfect, it just has to have a direction.

And once you know where you’re headed, the road will become much clearer.

The Helm

Today’s top business leaders, in their own words.


Written by


I get stuff out of my brain by writing about it.

The Helm

The Helm

Business leadership advice, from real business leaders. The Helm is a carefully curated collection of insightful content from the business frontlines.


Written by


I get stuff out of my brain by writing about it.

The Helm

The Helm

Business leadership advice, from real business leaders. The Helm is a carefully curated collection of insightful content from the business frontlines.

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