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, and a basket full of headlines and obituaries appealed to a kid like me. Also, it was the 80s, and having a paper route seemed as wholesome and American as one could hope for.

Until I realized my job involved dumping coupons and advertisements— junk nobody asked for. My route lasted two weeks. I didn’t quit; I just stopped doing it.

I remember my parents handing me the phone and 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 the right way instead of waiting to be fired. Import lesson learned.

I chalk it up to being nine 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 on joining or accumulating things at the expense of considering how we quit or leave something 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. Remove future promises of what it might 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 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.[^5]
  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 and 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 during this conversation, you’ll never know what their response would have been.
  3. It won’t cost you anything to find out. You might as well see.

I promise, even if you have no interest in staying, it’s in your best interest to hear them out.[^6]

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; 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 with 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 leaving and taking yourself out of an environment often has better odds of aligning your environment with who you’ve become or how your skills have grown.

Quitting a job can introduce some uncertainty into your life, but it can also be transformational. Ultimately, even if you decide to stay, how you go about the process can make you sure of 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, assuming you have done everyone’s homework is easy. 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. ↩︎

  4. Be selfish at this step if you have imposter syndrome. For everyone else, be normal. ↩︎

  5. This question is essential 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. [5]: You don’t know how your employer will take the news, so don’t try to predict what will happen. This isn’t a chess match. [6]: It should go without saying that if your manager accepts your intent to quit at face value, it means your leaving might solve a different problem of theirs (Hey! New information!), and you should feel more confident you’re making the right move. ↩︎