How to Know When It’s Time to Quit Your Job


I’ve never said this out loud, although, I’ve often fantasized about setting my computer on fire and walking away from my desk with a six-pack of “I don’t give a fuck” apple cider. It’s over the top, I know, but in the nine-to-five agency setting, quitting and changing careers is something I’ve always debated. That’s not to say the nine-to-five life is all tears, passive aggressive frustration and head slaps. It’s secure and above all, it pays for my bright red nail polish, highlights and Kensington rent. But is this what a career is really all about? Daydreaming about high-kicking my senior leads with a high heel on and scavenging leftover muffins from the president’s morning meeting? IS THIS IT?

I always knew I wanted a 9-5 career because it provided me with the freedom of stability, a solid pay cheque and pride of having the word “Executive” in my title. Which leads me to a simple question: how do you know when you’re ready to leave the 9-5 job? Answer these questions and find out.

Do you want your boss’s job?

Look ahead at the person you want to be in this agency. Are they cool? Do they have nice hair? Do they have a cat named “Gilbert”? These questions will vary, but it’s important to ask them to find out if this is the position you want to have in a few years. Truth being, I care about the type of things my superiors are doing at work, but I also judge them by their Instagram feed and general “coolness” factor as a human being. If my boss is the first to try the new Fried Tongue Sandwich at People’s Eatery or has time to enjoy interesting hobbies like knitting outside of work, then yes, I want that job!

Are you happy?

I recently had a conversation with a pal about happiness. We talked about our earlier dreams of travelling the world as a freelancer, owning a coffee shop in Roncesvalles or becoming a worldly food blogger tweeting about the latest dessert that everyone’s whispering about. All of these career paths are fearless and demand dedication, passion and everything that’s worth anything. Now that I’m in the nine to five, and I’m watching others leave to start new careers, I can’t help but think, can I still become the indie coffee shop owner? The answer to this question is yes, but not right at this moment. If the career change is in the horizon, a little planning and saving will take you a LONG way. Point being, if you’re jumping into the ocean, make sure you’re wearing a life jacket. Because god knows, you may not like owning a coffee shop in the end (although, I still think this is the best job in the world).

Dollar Dollar Billz Y’all: How much money do you need? 

As much as we would like to believe that money is a secondary consideration to the dream job, it’s usually the first, because money lets you enjoy the finer things in life, like Russian Red lipstick from Mac or an un-cracked iPhone screen. Money matters, and wherever your career takes you, remember that the 9-5 will always guarantee a bi-weekly pay cheque with benefits that protect you against the injuries you never planned for, like a sprained ankle from pool hopping at Dundas and Bathurst (ouch!). Don’t forget about the role of money, but don’t settle for it either. Money is what you make it, and if your passion is outside of the 9-5 safety, be fearless and find alternative methods of income.

The Worst Case Scenario

Doesn’t matter how old or senior you are in your position, it’s never too late to make a change and don’t ever forget that. Worst case scenario, the new career path isn’t what you thought it would be and you can likely get your old job back. Which is why you shouldn’t burn bridges when making the transition from a 9-5’er to a Trampoline Artist, because who knows, right? Maybe Trampoline Artists have a lot of back problems and you’re not into that.

Now that we’ve evaluated the pros and cons, you’ve got two options and both are equally cool and admirable. On the one side, you’re about to leave the safety of your desk job to explore a new and exciting career path as a purple-haired entrepreneur. On the other side, you understand the downsides of 9-5, but are willing to work hard to become the boss you’ve always wanted to become. In short, follow your heart ladies. You only live once, right?

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