The Careful Guide to Quitting

I was a delivery boy until they fired me.

The idea of delivering newspapers, riding my bike in the morning air, a basket full of headlines and obituaries, appealed to a kid like me. Also, it was the 80’s, and having a paper route seemed as wholesome and American as one could hope for.

Until that is, I realized my job involved dumping coupons & advertisements— junk nobody asked for. My route lasted two weeks. I didn’t quit. I just.. sort of.. stopped doing it.

I remember my parents handing me the phone, a man’s voice saying I did a bad thing and that I was a bad kid for doing what I did.1 I also remember tossing a stack of undelivered papers in a dumpster behind a truck lot.

If I could do it over again, I would have quit instead of waiting to be fired. Import lesson learned.

I chalk it up to being ten years old.

How to quit your job

Unless you’re leaving your paper route, quitting involves three steps:

  1. Plan to quit.
  2. Tell people you will quit. 2
  3. Quit.

The topic of quitting has always interested me. As a society, we focus attention on joining or accumulating things at the expense of considering how we quit or leave things behind. I believe both areas are equal opportunities for learning and personal transformation.

Yes, quitting can be good for you.

Even before The Great Resignation, I’ve wanted to write a guide on ‘careful quitting’. It seems to be in the air lately. I’m sorry to say this article isn’t the guide I originally had in mind. It’s more like a pamphlet.3

So you’ve decided to quit your job. Let’s quit it together.

First, we plan…

Take a deep breath. You haven’t quit yet, and nobody knows you’re considering it. Ask yourself a few questions:

“Where is this job going?"

It’s time to be critical of where you work. Take away any future promises of what it might turn out to be someday and focus on the here and now.4 Are you happy if nothing changes in this job for the next six months?5

“What’s the worst that could happen without this job?"

It’s important to talk to someone else at this point to pressure-test the areas where you’re being too hard on yourself. For example, most people assume their current job is the only thing keeping them from complete financial ruin. Unfortunately, that may be true for many folks, but how true is that for you? How much control do you have over the time between “my current job” and “my next job”?6

Copenhagen’s Happiness Research Institute surveyed 2,600 Danish workers, from every sector and type of job, about the sources of professional contentment. The winner, by a sizable margin, was a sense of purpose, which contributed twice as much to an individual’s job satisfaction as did the runner-up, having a high-quality manager.

Quit Your Job(2016)

Ready set.. wait?

Phew. Prep work over. Now pause a bit. When it comes to quitting your job, it’s a two-step process:

  1. Tell your boss what’s going to happen.7
  2. Do what you said would happen.

In other words, before you quit, tell your manager that you intend to quit– but don’t pull the trigger (save that for the inevitable follow-up). Consider something like the following:

  • “I’m not happy here. I’m planning on quitting.”
  • “I don’t see progress here for me, and I plan to quit.”
  • “It’s time for me to leave, and I wanted you to know first.”

Regardless of how you say it, your manager should hear (a) you are making a decision and (b) there is nothing you are hinging this decision on.

This should be a ten-minute conversation but if your manager asks for some more time to respond, give them a chance and hear them out for a few reasons:

  1. You’ve just given your boss a lot of new information. You don’t fully know how this messes up their plans.
  2. It works in your favor. You don’t have all the information on how the company will respond to the news. If you quit in this conversation, you’ll never know what their response would have been.
  3. It won’t cost you anything to find out. Might as well see.

I promise, even if you have no interest in staying, it’s in your best interest to hear them out.8

Go! Go! Go!

Your second conversation is where you formally quit and wrap things up. If you talked to your manager on Friday, make this follow-up a Monday or Tuesday. Don’t wait a week. You want to signal urgency, and not doing so suggests you weren’t that serious about your decision to quit.

On this second conversation, sit down with your manager and if they have new information, they’ll share it. If your decision stands, expect to fill the next eight minutes of this ten-minute meeting what your remaining time will look like, and you will leave on good terms.


It can be hard to recognize how we as individuals change over time, and this is especially true at work.

But it’s often the case that leaving, and taking yourself out of an environment, has better odds on aligning your environment with whom you’ve become or how your skills have grown.

Quitting a job can introduce some uncertainty in your life, but it can also be transformational. Ultimately even if you end up deciding to stay how you go about the process can make you certain in your reasons for doing so.

  1. As much as I hated the job, at least my job didn’t involve calling kids on the phone to fire them from their paper routes. ↩︎

  2. People seem to mess up at this stage. Once you settle on a course of action, it’s easy to assume you have done everyone’s homework. Recognize that you’ve done your side of the work, but quitting is fundamentally about handling a relationship. There are two parties here. ↩︎

  3. ”The Careful Pamphlet to Quitting” doesn’t have the same ring to it. ↩︎

  4. For those with imposter syndrome: be selfish at this step. For everyone else, be normal. ↩︎

  5. Asking this question is important for later conversations with your boss. ↩︎

  6. Don’t let “my manager will be disappointed in me” creep into your worst-case scenario. Good managers will not be upset if you put thought into it. They’ll respect you for being deliberate about quitting. If your manager reacts poorly, they weren’t a good manager. ↩︎

  7. How your employer takes the news is unknowable to you, so don’t try and predict what will happen. This isn’t a chess match. ↩︎

  8. It should go without saying if your manager accepts your intent to quit at face value, it means you leaving might be solving a different problem of theirs (hey! new information!) and you should feel more confident you’re making the right move. ↩︎