An Expert’s Guide to Quitting Your Job

By Jane Mountain | February 25, 2015

If you’re going to embark on long-term travel, or any life-changing dream-chasing scenario, there will come a time when you may need to quit your job.

It might not something to brag about, but I have quit more jobs than most people hold in a lifetime.

I am an expert quitter.

I have also quit bands, hobbies, clubs, and friendships with alarming frequency.

I have even quit entire countries, moving away from Canada in my 20s, deserting England in my 30s, and saying “see ya later” to the USA now that I am in my fabulous 40s.

Yet, with all this quitting, I am still on friendly terms with most of my former bosses, who are more than happy to provide recommendations, and would work with me again if the opportunity arose.

(Notice I say ‘most’. There are always one or two who… well, let’s not waste any more time thinking about them.)

Especially in this age of open and easy communication, keeping these relationships sweet is crucial. Everybody knows someone who knows someone else who can be linked back to you and your behaviour. People will be talking about you, no matter what you do, so you might as well do your best to ensure they’re saying good things.

So put aside your dreams of sliding down the airplane emergency chute, cussing out your employers as you go. It sounds like a lot of fun, but I don’t recommend it.

Instead, follow my 4 golden rules to quitting your job.

How to make a clean break from your job, without looking bad, losing your friends, or pissing off your boss.

Rule 1: Create A Job-Quitting Roadmap

If you’re ever going to free yourself from the tyranny of the cubicle, the first step is to establish a timeline.

First, choose the date on which you want to be completely free of your current job. This date could be tied to a plane ticket, a number in your bank account, or the end of a big project you’re working on. Or just choose your birthday to give yourself the ultimate gift.

Work backwards to mark the day you need to give notice. Most jobs require two weeks minimum, but depending on your role, a month might be wiser. Give your employer time to find someone to fill your shoes. If you leave a you-sized hole in everyone else’s workload when you go, not only will your boss resent you, but all your coworkers will as well.

An Expert's Guide to Quitting Your Job

Now make a list of all the things to do before you quit, like retrieving important files off of your work computer, clearing your internet search history, planning your leaving party, and saving enough money.

Yup, you’re going to want a little financial cushion, of course.

If you currently have zero funds in the bank, start by reading How I Saved $13,000 For A Round-The-World Trip In Seven Months.

If you have no idea how to handle money, or always seem to be broke, despite your healthy income, I also highly recommend the Mr. Money Moustache blog.

Rule 2: Keep Your Big Mouth Shut

Now that you’ve decided to go and you know when this miraculous feat will occur, it’s going to be terribly tempting to tell. You’re going to want to whisper your little secret in your best work friend’s ear or stand on your desk and yell it at the top of your lungs.

Do not do it.

I repeat, in a loud and commanding voice:

Do not tell anyone at work!!

You’ve heard of owning the news cycle, right? Well, quitting is your big story, and only you should get to decide how it plays out. Your boss should not hear rumours and whispers about your departure, and neither should any of your coworkers.

So your job, right now, is to keep your mouth shut, until the day you quit your job.

Rule 3: Quitting Day Is Boss Appreciation Day

Telling your boss you’re leaving can be downright terrifying. Before you march into their office, imagine the worst that could happen. Will there be yelling, crying, accusations, and recriminations? Quite frankly, probably not.

Let’s face it, quitting your job is nothing like breaking up with someone. Employees come and go, and no matter how close you are to your boss, their biggest problem after you quit is that they have to find someone to fill your shoes. They will not spend their evenings weeping over your absence.

So relax. But don’t just wing it. Plan exactly what you’re going to say before you go in there.

If possible, weave in a few of these key phrases:

  • So grateful for everything you’ve done for me…
  • Will really miss everyone here…
  • I just feel it’s time for a new challenge…
  • Such a hard decision…

In other words, you’re most likely going to lie your ass off.

But that’s OK, because now is the time to make your boss feel appreciated. Even if they’re a total tyrant who has made your working life miserable, don’t be tempted to let loose with your vitriol. Take this as an opportunity to spread a little love; being mean and petty accomplishes nothing.

(The last time I quit my job, I really did admire and respect my boss. That made this conversation so much easier!)

As soon as you leave your boss’s office, grab your favourite coworkers and break the news.

Do not lord it over them. Try to act a little sad, even if you’re dancing for joy inside your head. Instead, tell them how much you’ll miss them, how it’s been great working with them, and how much their friendships mean to you.

Rule 4: Be a Model Employee

The deed is done, you’ve given your notice, and everyone at work knows you’re leaving.

Now it’s party time, right?

Nope. It’ll be party time soon enough. For now, your job is to build relationships and be the best darned employee you can be.

During your last few weeks of employment, stop fooling around and put your nose to the grindstone. If anyone notices a change in you, it is that you are working harder and producing better results than ever. You should also offer to train your replacement, and leave that person with the definitive written guide on how to be the new you.

If you are in an industry that uses LinkedIn, write recommendations for the coworkers you respect and then ask them to recommend you as well. Never recommend someone you wouldn’t truly want to work with again; it will only reflect poorly on you.

With all this hard work, the final weeks of your imprisonment employment will fly by. Before you know it, it’ll be time to say goodbye to your old life and wave a big hello to whatever is just around the corner.

Bonus Rule: Quit Your Job At The Right Time

How do you know when it’s time to take that final dive out of the emergency exit?

  • Do you wake up in the morning and dream of jumping in front of a bus so you won’t have to go into work that day?
  • Do you ever hide in the bathroom stall and cry?
  • Do you have fantasies about punching your co-workers in the face?

(Trust me, I have been there.)

  • Does anyone at work ever thank you for your efforts?
  • Have you done anything at work in the last six months that you’re proud of?
  • Is there anything about your work day that you truly enjoy?

(My sympathies, I know the feeling all too well.)

If you answered yes to more than one of the first bunch, and no to more than one of the second, then it’s time to go.

Start your quitting roadmap tonight.

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