How to Know When to Quit Your Job Part. II

How to Know When to Quit Your Job Part. II

WE BACK WITH PART II YOOOOOOOOOO. (You can read Part I here)

First of all, thank you everyone who has commented, messaged, or texted me to say congratulations! Your support really encourages me to believe that I can actually pay for groceries and my mortgage without a full-time salary. Unfortunately the bank does not take payment in congratulations comments, so the hustle really starts NOW.

(PS if you ever want to send me food, clothing, cat litter, toilet paper, or just MONEY, my door is always open).

Hehe. I kid.

Anyway, this post is all about: How to Know When to Quit your Job.

Is it something that slowly happens? Is it something that you think about for a long time? Does it feel RIGHT, but also scary?

To me, it was all those things.

I’ve been thinking about quitting my job ever since I got hired at my job.

It’s not even that I didn’t like my job, or I didn’t enjoy what I was doing. It was just that DEEP DOWN, I knew that I wanted to create more. I wanted to be more than an employee, executive, or CEO for someones company. And I’ve felt like this forever.

But for all those years I just pushed those feelings aside, because you know what? I’m practical.

It doesn’t make sense to quit your job if you have nothing lined up. If you have no irons in the fire, no one ready to just PAY you money to work for yourself, then it’s nonsensical.

Like most bloggers I know, I was working easily 14 hours a day. 8-4 at my regular job. Gym, dinner, then sending emails or editing photos until 10 PM, when I finally called it a night. I handled that pretty well for the past year or so.

But then something happened in the last couple months, that made me realize something needed to change: Every time my alarm rang in the morning, I was SO unhappy. I didn’t want to get up and face the day. I didn’t want to go into the kitchen and make my breakfast, put it in a container, put on my bike clothes, bike to work, go to work, eat my breakfast, work, eat lunch, work, gym, eat dinner, work and reply to emails.

I didn’t want to do any of it. I was so tired. I was so unhappy for those first 2 minutes every morning.

But being unhappy for 2 minutes every morning is NOT ENOUGH to say, “I’m ready to quit my job.” It’s the beginning of your first step, but it’s not enough.


If you don’t have a plan, then it’s not time to quit your job.

I didn’t just decide to up and leave my job and roll around in bed with Winston all day (however grand that would be!)

I decided to come out with a new program and I wanted it to be amazing. For it to be as good as I wanted, it would require a LOT of work and hours putting it together. I basically decided to make this new project my full-time job. That means getting up at the same time as I do now, doing research, creating worksheets, coming up with ideas, shooting/editing videos, etc.

You need something that will take up your time and those hours in your day. And it has to be something you’re truly excited about! My plan wasn’t to go and sell apples at Trinity Bellwoods and hope for the best – it was more concrete and forward thinking than that.

Whatever your plan is, it has to be realistic and something you are passionate about.


If you don’t have an income, then it’s not time to quit your job.

You need to have a well thought out, written down, detailed list of how you’re going to make money.

For me, it was a number of things. I’m so so lucky that I can make money through my Instagram and blog. Not only that, but I found that I had a dedicated group of people who came out to my group training sessions in Toronto. I also decided I would take on some personal training clients at the same time as a final addition to my income.

Chances are it won’t add up to what my current salary is, but that’s ok. I figured having 3 sources of income was a good place to start, and after a few months I can adjust as necessary.

If you’re thinking of quitting, look at how you can make money. Look at the best and worst scenarios and see if even at the LOWEST points, you could still pay what bills and liabilities you have. When I made my decision to quit, I wrote it down 3 separate times to make sure there was nothing I missed. Do your due diligence.


If you don’t have savings, then it’s not time to quit your job.

I would recommend at least 3 months worth of savings to pay everything you need. You would be surprised at how much it all adds up each month. Here’s a list of my top payments each month:

  • Mortgage payment
  • Maintenance fees
  • Transit
  • Insurance
  • Groceries
  • Entertainment/Meals out
  • Phone bill/Internet bill
  • Hydro

That get easily get up to $2,500 a month.

If your plan does not work out immediately, you have to be able to pay off these items. Unless you don’t want both of your knee caps. Or to be able to check Instagram every 0.05 seconds. Both scenarios sound like hell to me.


The first three were practical. This one appeals to your emotions.

I had a plan. I had more than enough savings. I had a (fairly stable) projected income.

I was also just ready. Deep down.

I just turned 26 years old. Dis bish aint getting any younger. And 5, 10 years from now, there was no way I was going to quit my job and try to make it as a fitness blogger/trainer. The chances of that happening were slim to none. Now is the time for me.

There always comes a time in my life when I KNOW that I’m ready to move on. When I was done high school, I flew to Vancouver and never looked back. When I was done University, I flew to Toronto and never looked back. And now I’m done with this part of my life, and I’m ready for something new.

If you are fully content at your job, with your life, and you enjoy things JUST the way they are – don’t fix something that’s not broken. Believe me, you are one of the lucky ones.

For those who want to make their lives a little bit more difficult, and do something different than work a 9-5, I say DO IT. But don’t do it unless you have those 3, boring, practical, issues sorted. You want to start your new adventure off on the right foot. Not the broke one.

What About You!?

Are you self-employed or work full time?

Have your left your job recently?

Other posts you might like:

  1. I love hearing about how bloggers have made it (and other side incomes) into a sustainable living. There’s so much passion and heart behind taking that kind of plunge.

  2. Dallas

    12 October

    So happy for you! I quit my job in 2015 to go back to school to become a Nutrionist, I don’t think I had planned it out in so much detail but I knew nutrition and helping people was my real passion and I could not picture myself sitting at a desk any longer. I first tried to quit and my boss talked me out of it then 6 months later I stuck to my guns and said good bye…. best decision I ever made 🙂
    So excited to see how your journey unfolds!

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