When To Leave A Job

Unfortunately, I have had to make the decision to leave a job more times than I would have cared to. I’ve even had to switch career paths.

Thankfully, through adversity grows wisdom. I’ve developed an easy three-part system (currently in desperate need of a catchy title) to decide whether or not the time has come to hang up your gloves and move on.
You need to ask yourself three questions:

1. Does my job comfortably pay the bills?
2. Am I happy and enthusiastic to go to work in the morning?
3. Am I making a positive difference in the world?

Let’s talk about each question and really get to the heart of things here:

1) Does my job comfortably pay the bills?

There’s a difference between making a base salary that needs to be supplemented by three other time-consuming, mentally draining jobs. What I mean by “comfortably” is your job is taking care of the basic necessities and generally removing financial concerns from the problems that may fill your life.

If you are making 3 million dollars a year from one job, even if it’s eroding away at your life and it’s consuming a huge portion of your day, you can most certainly answer an enthusiastic “yes” to this first question (unless you are insanely bad at handling your finances).

However, life is complicated. And for many people, this question cannot be the only one that matters. Most of us don’t want to dread our days, we don’t want to live for retirement, and we don’t want to go to our graves knowing our sole contribution to the world was having amassed a well-stuffed bank account.

(For the record, I can honestly say that I’ve never really felt the sweet taste of saying “yes” to this first question.)

2) Am I happy and enthusiastic to go to work in the morning?

I gather most of the world doesn’t love getting up in the morning, throwing on their suffocating suits and ties, and driving through sluggish traffic, in order to stare at cubicle walls in between bursts of getting chewed out by overbearing bosses.

If only one’s morning coffee could go on forever!

I enjoy my current job. I’m not saying that I’m pushing over people to make sure I get to my desk on time each and every morning (partially because I work from home), but I do enjoy getting started. And I remember a good, solid 3-4 year period in which I was absolutely ecstatic to get to work every day. However, that leaves a whole lot of time in which getting to work was an abysmal chore.

If you are itching to get to work in the morning, and you’re doing so not because you’re escaping loud children and a nagging wife, but because you legitimately enjoy what you do, you can answer “yes” to this question.

3) Am I making a positive difference in the world?

This one could be complicated. And we could of course fool ourselves into coming up with a positive answer. For example, if you’re selling shoes, and someone walked out of your store with a pair they really liked thanks to your skillful salesmanship, are you making a difference in the world? Maybe.

But maybe not.

Some things are a little more clear cut.

A surgeon who routinely saves the lives of patients. A fundraiser for an organization that helps starving people. A company that manufactures products to assist the blind. You know you’re making the world a better place, and you should sleep soundly at night for doing so. And that’s even if you hate your job!

Selling fake online degrees. Selling overpriced, low-quality t-shirts produced in an overseas sweatshop. Cameraman for low-budget pornography. They might pay the bills, but I think those with these jobs can safely answer a hefty “no” to this question.

Most of us find ourselves somewhere in between these examples, and need to do some serious contemplation to give an honest assessment. But there is an answer to the question

Putting Everything Together

First, let’s look at the easy cases. If you answered a solid “no” to all three questions, get out. Get out now. Run. You’re in a dead-end situation and even in a lousy economy, there’s little to no reason to stick around.

If you answered “yes” to all three questions, your life is a miraculous dream, and barring serious complications, you should probably hold on to that job until the day you die.

However, for most people it’s not that simple. If you answered a completely honest “yes” to even one of these questions, I wouldn’t start overturning desks and telling your boss to “shove it” just yet. In a lot of ways, you’re still ahead of the curve. It’s worthwhile to keep your eyes open for something better, but in this economy, just to have a steady job is already a blessing.

What about a positive answer to two questions?

In one of my earlier teaching jobs, I recall multiple former attorneys who left their field to become teachers. They abandoned a life of financial security for a life where they enjoyed what they did on a daily basis and truly felt like they brought meaning and inspiration to others.

It might not feel like all three questions are of equal value, but I assure you, they most certainly are. Just to have cash in your pocket is worth very little if you don’t make a positive impact and dread your every working minute.

Just to have cash in your pocket is worth very little if you don't make a positive impact and dread your every working minute. Share on X

In summary:

If you answer “no” to all  of these questions, run. Run far and fast. You really can do better.

If you answered “yes” to one question, start asking around. Spruce up your resume. Update your LinkedIn profile. Do it all subtly, because you might just need to stay where you are.

If you answered “yes” to two of these questions, life is really good. You’re way ahead of most people. You should cling to your job with all of your might, and you shouldn’t even consider leaving unless some ridiculously amazing, once-in-a-lifetime opportunity comes around. Even then, be careful and methodical about the decision.

And if you answered “yes” to all three questions, do not go anywhere! You’re among the extraordinarily lucky few of this world. Wrap your arms around the job with all of your strength, and never let go.