October 8, 2021

What I’ve Learned After 5 Years as a Small Business Owner in Canada

I’m Jessica and I’m a money expert, speaker, Accredited Financial Counsellor Canada®, host of the More Money Podcast, and am currently writing my first book with HarperCollins Canada (2025).
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This post is sponsored by Quickbooks Canada. All views and opinions expressed represent my own.

This coming January will be the 5-year anniversary of my leaving my 9-to-5 job to run my own company. What makes this even more unbelievable is that this was never my plan! Growing up, I never had any role models who were freelancers or small business owners. Everyone in my family worked at a company as an employee and naturally, I thought that would be my path too. So much so that when I graduated from film school in 2009 and realized the only way to make a living as a filmmaker was to be self-employed, I immediately ditched my filmmaker dreams and got myself an office job.

Jessica Moorhouse QuickbooksFast-forward 12 years and no one is more surprised at where I ended up than me. Maybe the reason I never stayed with a company longer than 2-3 years was that I was meant to be an entrepreneur all along.

Still, I’ll fully admit that being self-employed is not for the faint of heart. When I scroll through Instagram and see all these people talking about how awesome it is to work for themselves, I think to myself “They’re only sharing half the story.” Because it’s not easy. Nor should it be. You’re running your own business and that’s a big deal! It means marketing, selling, invoicing, accounting, taxes, insurance, and working well beyond 9-to-5.

This isn’t to scare you off. I just want to keep it real because I’ve been through a lot of ups and downs over the past few years. What started as a side hustle (this blog actually) back in 2011, turned into a full-time sole proprietorship in 2017, which then evolved into me incorporating my business this past June 2021. I’ve gone from doing every role in my business to hiring sometimes 4-6 contractors to support in different areas. What started as a cool idea I had one day has somehow turned into my livelihood.

With all that said, and because I recently participated in QuickBooks’ #AskTheExpert Series (make sure to watch my full video on IGTV), I want to share some of the most important things I learned as a small business owner that I wish I knew earlier. And if you have any questions for me, please comment below and I’ll answer them!

1.   Start with a side hustle

One of the best things I ever did before going full-time self-employed was starting my business on the side (on top of my day job). It wasn’t easy and it was tiring working nights and weekends, but it helped me research and develop my business with far less financial risk than if I had quit my job and then tried to work on my business.

As I mentioned, my business started with this blog in 2011. Then I added my More Money Podcast in 2015. And in 2017, I officially started my YouTube channel. In the early years, I didn’t earn a dime. But beginning in 2013, that’s when I started earning a little money from doing sponsored blog posts and freelance writing for other websites. As my audience grew and I started getting more media attention for my expertise, I started exploring other ways to make money like getting sponsors for my podcast, launching a live event series called the Millennial Money Meetup®, doing public speaking, and selling digital budget spreadsheets, merch, and online courses.

Eventually, I started earning enough money with my side hustle that I felt comfortable leaving my day job. I also saved up about $30,000 as an emergency fund, so no matter what happened in that first year of business, I would still have enough savings to live on for the year before I needed to start applying for jobs again.

2.   Diversify your business

I talk a lot about the importance of diversification when it comes to your investments, but the same should be said for your business. Diversification is an investment strategy to mitigate financial risk, and it can be applied to your business too.

In my second year of business in 2018, I was invited to a retreat with some other women content creators in the financial space who I’ve known for years. It was a retreat so we could all discuss what we were struggling with in our own businesses and help each other find solutions. One thing that almost all of us were worried about was recession-proofing our businesses. As millennials, we’d all experienced some form of financial hardship because of the Great Recession, and we all knew something big was going to happen again (we just didn’t know it would be in 2020!).

In our discussions, we realized the best way to protect your business against another economic downturn (or pandemic apparently) was to diversify your business offerings. Don’t just focus on one thing or one platform, because that may limit you. For instance, there were a few freelance journalists at the retreat and they were concerned that all of their income was dependent on their next pitch getting accepted. This made for a very feast or famine career path, which wasn’t an easy road to go down. So instead, they resolved to expand their services to offering coaching for writers and selling online courses to teach others. They both also got their own books published (no surprise there are amazing writers), which in the long term can be a nice way to earn passive income.

Hearing more about service expansion prompted me to expand my offerings too. At the time, all of my income was dependent on brand sponsorships with the blog and podcast, and some freelance writing. That’s what inspired me to study to become an Accredited Financial Counsellor Canada® and offer one-on-one financial coaching. I also later developed my Wealth Building Blueprint for Canadians course (and soon another course that’s still in development). This in turn motivated me to expand my offerigns even further to include making YouTube videos, hosting my own events, and doing more public speaking.

Let me tell you, I am so glad I diversified my business because when April 2020 hit, I was scared. All of my speaking work dried up and no brands were interested in sponsorships. But that was ok. I could pivot quickly and start offering one-on-one coaching again and sell more of my online courses. Because I didn’t put all of my eggs in one basket, I was able to recover what could have been a very financially stressful time.

3.   Invest in your business

I see a lot of people online, especially business coaches, talk about the importance of investing in your business. Here’s the thing…I agree, but only to an extent. I see too many people pour all their profits right back into their business, instead of paying themselves a salary and taking care of their personal needs. For that, I recommend everyone read the book Profit First.

Otherwise, I say invest in your business wisely. Be methodical about it. First, consider the return on your investment, whether that be saving you time or providing for increased business revenue in the future.

Besides hiring contractors as a way to invest in your business, the software has been the biggest investment for me. I run my business completely online, so having the right digital tools is essential. I use them to build my email list, schedule social media posts, design graphics, record my podcast, edit videos, and of course, use QuickBooks for all of my bookkeeping and accounting needs. The platform saves me both time and money so I can feel confident in making decisions for my business and keep planning for the future.

I should also mention that another big benefit of investing in your business is the tax deductions! Hiring contractors and spending money on business expenses like software are tax-deductible.

4.   Outsource to grow

I remember reading the 4-Hour Work Week years ago and coming away from it thinking I did not want to run my business like that. It’s not that I didn’t like the concept of outsourcing work to free up more of your time. My biggest issue was the practice of hiring contractors internationally and paying them very low wages in order to preserve more of your business profits. I believe we need to support independent workers – no matter where they live – by paying them fairly.

With this mindset, I did everything myself at the start of my business. To no one’s surprise, I burned out very quickly. Just because you can do everything yourself, doesn’t mean you should. After that experience, I learned my lesson and slowly started outsourcing my work to contractors in Canada and the U.S. so I could take back more of my time and actually enjoy my business.

Although I don’t have any full-time staff for my business, I do have a number of contractors I hire on rotation for specific tasks and projects. It makes more sense for my business this way because sometimes what I need is very specialized, and it’s not easy finding one individual who can do everything you need.

Here’s what my team looks like:

  • Podcast editor
  • Video editor
  • Virtual Assistant
  • Bookkeeper
  • Accountant
  • Agent

The first contractor I hired was my virtual assistant, who also happens to be my sister. She’s the one who helps me with a variety of things like preparing my podcast episodes to be published, some social media management and analytics, researching potential podcast guests and YouTube topics, designing and setting up my merch, managing my contest giveaways, and so much more.

My podcast editor, Matt Rideout, edits and mixes my podcast episodes so they sound super professional, and so I could finally release my sound engineer husband from doing it for free for me for almost 5 years!

My video editor, Rheanna Toy, edits almost all my videos for my YouTube channel (some I still do myself like sponsored videos or my investment account tutorials) and she’s amazing. She also went to the same film school as me.

My bookkeeper is a recent hire who I found on Upwork and she’s also been a huge asset to my business. I use QuickBooks for my business and she is a QuickBooks master! She’s able to save me so much time by organizing all of my income and expenses in QuickBooks, so I can focus more of my energy on increasing my business’ revenue.

My accountant, Lisa Zamparo of The Wellth Co, has been there since the beginning. She’s helped me stay on top of my personal and business taxes and advised me on making the big leap from sole proprietor to the corporation this summer.

And my most recent hire was my agent at the Talent Bureau. I honestly thought it was a long shot to get an agent (who do I think I am, some celebrity?), but in the past few months I started realizing I needed someone to help me with booking speaking engagements and brand partnerships. So, I sent out an email fully expecting a rejection…but got an agent instead. You never know until you ask!

5.   Never stop trying new things

The last piece of advice I’d like to share is this…never stop trying new things. As someone who started this venture at 24, but is now 35, sometimes I worry that I’m too old for certain things. I thought I was too old for YouTube, yet it has turned out to be a great way to build my audience and promote my online course. I thought I was too old for Instagram Reels, and yet it’s helped me grow my following substantially over the past few months and I actually really enjoy doing it!

You are never too old to try new things. As cheesy as it sounds, age is just a number. And on that note too, imposter syndrome is real and everyone experiences it. Every single business owner I know has experienced it. Heck, I still do! But don’t let that stop you from doing something you love like running your own business, experimenting, or tackling a new challenge to help you grow.

I’m sure glad I didn’t, and I can now look back on the past 5 years and reflect on how far I’ve come.

Disclosure: Nothing on my website or affiliated channels should be considered advice or an endorsement, and some content may include affiliate links in which I may earn a commission at no extra cost to you. Please read my disclaimer to learn more.

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  1. NZ Muse says:

    Awww congrats on this big milestone! It’s been awesome to witness your journey.

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