How to Quit Your Job in the Worst Way Possible

If you’ve followed this blog for any amount of time, you know that I have a tendency to make big, impulsive decisions without always stopping to think of the possible consequences. The benefit of this is that when I let my passion lead without pausing to let my fear stop me, more often than not, good things happen.

But it also means that when bad things happen, they can be disastrous.

I don’t always talk about the truly hard to swallow stuff.

For instance, you probably know all the things I loved about quitting my 9-5, but you don’t know about all the stuff that made the transition harder.

So I thought I would spend this week discussing everything I did wrong on the road to becoming a full-time freelancer.

But don’t worry, if you also want to learn how to do things right, you will be treated to a fantastic guest post next week written by my friend Robin. She’ll explain everything she did to turn quitting her job – without knowing exactly what to do next – into a positive experience.

But for now, let’s talk about what not to do.


Stop Caring

When I started working at my 9-5, it was clear almost immediately that all of my coworkers had already collectively decided that the job was only a paycheck.

In fact, one coworker even told me that the managers seem to purposely hire people who aren’t go-getters, because they don’t want to have to change anything or work harder. He also mentioned that anyone with lofty aspirations decides to leave pretty quickly.

Can confirm.

But I shouldn’t have let the toxic attitude of the place bring me down.

Sure, I only got a few hours of real work per week, but I should have spent those hours doing the absolute best work I could produce. Instead, I started phoning it in.

This got even worse when I realized that not even the clients respected the work we were doing. All they wanted was for us to twist the truth on our reports to make them look as good as possible.

And if they just wanted a document with a gold star affixed to the corner, why should I break my back doing immaculate work?

The Consequence: I brought this negative attitude with me into my new work. It wasn’t that I didn’t try my best on every job, it was that I was used to doing so little work each day that I didn’t completely fill my schedule.

And the thing about freelancing is that any hours you don’t have client work booked are hours you’re not getting paid. It’s been a year, and I’m still trying to figure out the exact right balance.

It doesn’t help that I have other businesses that I’m building at the same time, but that’s another story.



I recently listened to an episode of the Ask a Manager Podcast that Gretchen Rubin guest co-hosted. Gretchen was talking about how she divides people into 4 categories based on how they respond to expectations: Upholder, a Questioner, a Rebel, or Obliger.

I didn’t need to take her quiz, I am undoubtedly a Questioner.

I have never been able to do something just because someone in authority said so (sorry mum and dad). Well I might do it, but I will explain every reason that it’s the most inefficient, nonsensical way to do it the whole time.

Don’t get me wrong, I’m not about to fall on my sword for this. I love my ability to stand up for logic in the face of bureaucracy! But that part of me has a time and place.

I shouldn’t have let the nonsense get so far under my skin that I couldn’t stop from complaining about it to anyone who would listen, including a watered down version of the rant for my coworkers. It’s just not appropriate.

At that point, I stopped being a bastion of efficiency and started actively participating in the toxic work environment.

The Consequence: I not only added to the toxic environment of my workplace, I made every second outside of work more miserable by harping on what I couldn’t control. While I acknowledge how awful it feels to hate such a big chunk of your life, complaining is wasted energy.

It doesn’t really matter how right I was or how wrong they were, complaining just makes everything worse. All of that energy should have been put into coming up with a step-by-step plan to get the most out of work and leave as soon as possible.


Use Work as a Scapegoat

I have a nasty habit of finding external reasons for my problems. And sure, if you’re in a miserable situation, it’s no surprise that you end up feeling miserable.

But when I started getting anxiety symptoms and almost daily panic attacks, blaming it on work was a bit of a cop out. There was a ton of internal work that I just hadn’t done, and I’d been pushing down negativity for years at that point.

Hell, it’s been a year and a half since I quit my job, and I’m only just now starting to sort out what I should have dealt with then.

Unfortunately, that means I put all of my hopes and dreams into working for myself. And in a cruel twist of events that surprised no one but me, I realized that nothing had really changed.

I created myself a new hamster wheel of misery to take up the day, but now with no one else to blame but myself. Thankfully, I’m putting actual work into my mental health now.

The Consequence: again, hating such a big part of your life sucks, but believing that any one thing is the sole source of your misery is dangerous. It diminishes the agency and power we all have over our own lives.

So instead of recognizing what I could do to change things, I stayed stuck for far too long. No, I couldn’t have changed how that place operated, and I tried. I could only change my responses, and that was enough.

How you spend every waking moment is a choice. I’m just starting to really believe this.

Quit Mostly from Desperation

I’ve mentioned this before, but by the time I actually quit my 9-5, I was in a horrible place. Sure, I wasn’t giving up 100% of my income, because I was already freelancing at that point, and I had also saved a huge chunk of money to keep me afloat, but I wasn’t thinking straight.

I believed that I could replace my income within 3-6 months just because I wanted to and had done the research. I didn’t acknowledge what a bad state I was in mentally or how severely it would impact the amount of work I felt like I could take on.

I knew what to do, but I wasn’t applying it properly.

Instead of making money, I spent a lot of my time in a near catatonic state, counting down the hours until I could sleep again. Sleep was all I wanted for a long time.

Making any decision out of desperation is not advisable. When you’re grasping at straws, you’re almost guaranteed to hate the result.

The Consequence: decisions made out of desperation make everything that follows feel like a scramble. Instead of feeling happy and confident in my new role as full-time freelancer, I just felt scared out of my mind every second.

I don’t know if you’ve tried to work a full day when you’re trying not to vomit out of panic, but it’s not pleasant. It just makes you want to avoid everything.

If I thought things through a little more, I would have had a plan for dealing with my mental health first and what my post 9-5 days would look like. Instead, I tried to figure everything out on the go, which only served to make it take soooooo muuuuuuch longer.

Well, I’m guilty of quite a bit of negativity, but I don’t regret it. Making mistakes is how you learn. And I’ve learned a hell of a lot over the last year, and I’m sure I’ll learn just as much over the next year.

Now it’s your turn to fess up. Are you guilty of any of these things? Something else? Let’s discuss in the comments!

P.s. remember that I won’t see you next week, but you will be in Robin’s capable hands!

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