Blogging has always been in my bones. Back before I was Toronto Shay, I founded a company called What Women Want; a network and lifestyle blog that created community and comradery for girls like me: smart, fashion and beauty obsessed women with big ambitions.

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My first foray into entrepreneurship was initially successful but it wasn’t long before my shopping obsession caught up with me. So, once the bills piled up and I started worrying about how I was going to pay rent, back to the traditional workforce I went. I actually wasn’t upset about going back to work, while blogging was a passion, there was an undeniable allure to the 9-to-5 life; the stability and benefits of a full-time job were hard to overlook. Plus, luckily for me, I found a job that I really loved! I returned to work in media sales for one of Canada’s largest media conglomerates and worked there for nearly a decade. I took charge of multi million-dollar portfolios, worked with top-level brands, and regularly brushed shoulders with TV personalities and magazine editors. I had everything!

Or so it seemed.

In March of this year I left my job that paid six figures to return to blogging. It’s a move that surprised many, including myself!

For so long, that job had represented an idea of success that I wasn’t ready to part with.

My job in media helped me build a reputation; it helped me pull myself out of crippling debt. It had given me the means to save towards my first home. Still, the more I blogged and shared socially, the more I bonded with women whose stories reminded me that life is about more than stability. It’s about self-exploration, breaking comfort zones, and taking risks. And so, at the risk of sounding like one of those corny Instagram quotes, I decided to “go after what sets my soul on fire”. Only this wasn’t an instagram post —this was real life, and in real life you don’t leap without a safety net!

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Yes, I followed my heart, but I took my brain with me.

I could never recommend that anyone leave their job with nothing but a hope and a prayer. You have to plan for it and, you have to also realize that it is not all fun and games and sleeping in and going for lunches all day, everyday. Truthfully, making the switch from my 9-to-5 to full-time content creation has taken its toll. There have been demands on my bank account, my routine, my mental health and my marriage that didn’t exist before. Entrepreneurship is no joke but working for yourself is possible. A large part of my success since leaving my job has been luck and having great relationships —half the battle is timing, alignment and who you know. The other half? That’s all you.

Check out the four steps I took to quit my day job and become my own boss.


My job in media sales gave me skills that were directly transferable to my work as an influencer. Working in media taught me how to negotiate brand deals, so when it came time to pitch and present my own rates, I knew exactly what to do.  I was prepared for the demands of my industry.

If your 9-to-5 is completely unrelated to your entrepreneurial goals, don’t sweat it. Regardless of industry there are always basic skills that can be applied to future endeavors.

Think of your job as a corporate classroom. The trick is to be a student—observe everything.

What can the marketing department teach you about branding? What can you learn from HR about building a team? What has your boss shown you about effective or ineffective leadership? Your job is an opportunity to study the habits of successful business operation. When you leave, leverage and hone those skills for your own agenda.

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If you’re married, it’s crucial to remember that your decisions don’t exist in a vacuum. What might be exciting for you could be terrifying for your partner. It’s easy to get defensive when these disconnects arise, but know that they don’t necessarily mean that your partner is unsupportive. You’ve likely been playing out this dream for years; your man just needs a minute to catch up.

My constant traveling as a full-time influencer was new for my husband and truthfully, it took a toll on our relationship. My husband has always held senior positions that demanded a lot of him and my jobs were always less senior and had less responsibility. So now that I had to work weekends and late nights it shifted the dynamic in our relationship. Especially with a little one at home. I had to tune into his perspective and recognize that his frustration was really just concern for our family and him adjusting to our new normal. I also recognized that he was and still is my number one fan! I knew that any dreams I had for myself would not be sustainable without a healthy relationship with my husband, so I owed it to him and myself to invest in help for our marriage. Seeking help improved our communication, strengthened our bond, and fortified my resolve to move forward with the support of my best friend. Now if you aren’t married, make sure you continue to nurture the friendships and relationships that are important to you when you work for yourself you will need to depend on your inner circle for moral support and advice. And when you’re leaving work, try not to burn any bridges as this may come back to haunt you.

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A.K.A.: Get your money right! It was very important for me to be financially sound before quitting my job. Actually it was a MUST. I knew first hand that most things aren’t possible (or they are 100X harder) if you are broke. So before resigning, I saved over $30,000 from investments in stocks through my company’s investment contribution plan and I saved another $30,000 from the influencer work that I had done to date. This represented close to 1 year in after tax income. While I was working, I started off making $3000-$5000 a month as an influencer, but by the time that I was ready to quit I started asking for longer term contracts and increased my rates as my following continued to grow and was able to  quadruple my monthly earnings. Between savings and joint income, I knew I could leave my job and actually bring home more money than before.

It’s also important to note that I had paid off all my debt. That was a whole entire challenge that you can read about at your own leisure, but it was critical to me to go into business with a clean slate, and more importantly, FINANCIAL FREEDOM. All of this provided me with a cushy exit plan to leave my job with full confidence of staying afloat.

4 . JUMP!

Finally, I jumped! Once you square everything away, there’s nothing to it but to do it. Create a 6 – 12 month plan to keep yourself on track but if you know what you want and you’ve prepared for the shift, make your move. You will thank yourself later for it. And remember, if it doesn’t work out, that’s ok too. If you end up giving it your all you will not have any regrets and “failing” the first time may actually set you up for success the second time around. That is what happened with me.

I hope that my story has helped in some way. If you have questions for me, don’t ever hesitate to ask. The best way to reach me is on Instagram. Just send me a DM. I respond to all of them ❤️.


  1. Errol
    July 5, 2019 / 5:21 am

    Great blog, thanks for sharing.

  2. Kay
    July 6, 2019 / 11:03 pm

    I appreciate your honesty in all your posts. Am rooting for you!

  3. July 7, 2019 / 9:18 am

    As always this is soooooooo inspiring. I truly admire how transparent you are with numbers. I’m currently in a six figure salary and I couldn’t imagine leaving. I also tell my husband i wish i had became interested in blogging prior to making such a substantial salary and perhaps the thought of leaving wouldn’t be so scary. I’m NOWHERE near that phase in the blogging journey, just thoughts. Thank you again for sharing and congrats to you and your family.

  4. Danielle Beckford
    July 7, 2019 / 10:20 am

    This was a necessary read. Thank you for sharing.

  5. July 7, 2019 / 12:15 pm

    I always wonder how its done, thanks for sharing! I also love that you mention having a plan and being financially set.

  6. July 7, 2019 / 8:07 pm

    Great post, Shannae. I think I’m there, but I’ve worked hard to get to where I am in my current job. Leaving the guys & glory that I’ve achieved in the govt world actually makes my stomach churn, which I suppose tells me I’m not quite ready to leave yet. Sigh. Your post inches me closer though!

    • torontoshay
      July 7, 2019 / 9:21 pm

      I totally understand – it’s totally possible to do both and as long as you’re good with both, don’t let anyone convince you to do otherwise. Here’s the link to another blog posts that I wrote about bloggers with impressive day jobs. It may also inspire you ❤️

  7. July 11, 2019 / 1:00 pm

    Shay, I use to attend your events when you were doing What Women Want, and then I stopped hearing about them. The last one was in the Distillery District that I had attended.
    Happy to see you are living out your passion.

  8. July 13, 2019 / 12:11 am

    Nice read..thanks for your insights🤩

  9. July 24, 2019 / 10:48 am

    This was amazing!! I’m a influencer straight out of college!! I’ve known I always wanted to be an influencer having graduated with my Bachelors in Art, but school was always in the way, until I graduated my aunt took a chance on me!! She wanted me to be an influencer more than I did! So helped me financially and business wise and here I am six months in and doing well! I’m not where I want to be, but I’m grateful for where I am!! Thanks for sharing this!!

  10. August 16, 2019 / 5:42 pm

    Well done! This is how you quit your 9-5 right! I left my old corporate job too, way sooner than I expected. (My intuition bells were going off!) Luckily I was debt free at the time too. It does make things much easier. No regrets. While I wear multiple hats, and have less time, I’m still happy I made the move to take a risk too.

  11. Oyindamola Kolawole
    October 20, 2019 / 5:30 pm

    So inspiring..thanks for sharing

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