How to turn your side gig into a career

As the saying goes, everything you desire resides on the other side of fear. If you’ve ever dreamed of being your own boss, maybe even building an empire, you can start by exploring a side gig before leaning into it to as a possible full-time pursuit. 

Many of us already have. A recent survey revealed that 42% of Canadians sought a side gig last year to boost their income, while an estimated two out of three Canadians are interested in pursuing opportunities to earn additional income. 

Tara McEwen, founder of McEwen Media, never thought she’d become an entrepreneur and a business owner. 

“I was a senior producer with the Marilyn Denis Show for 10 years,” she says. “If it hadn’t been for getting packaged out [a severance package] during the pandemic, I never would have taken the leap to start my own company. It was a blessing in hindsight. But I was still terrified.”  

Using the career coaching services that Bell Media set her up with, she learned that many of her skills that were not always well received in her TV job were ideal for a consultant offering media services. 

“It was such an eye opener,” McEwen says. “To realize that you have these talents and skills that don’t have to be changed or altered. Sometimes you just have to find the right career outlet for them. That’s when I registered McEwen Media and got my first client.” 

As a busy mom of three young boys, Andryanna Gonko, educator, on-air lifestyle expert, and host of The Juggle is Real podcast, had a feeling that her trials as a parent could turn into a full-time job one day. 

“I know what it’s like to feel chronic stress and experience burnout,” says Gonko. “So I started my side gig with the mission to help busy moms find better balance with simple tools, activities and mind shifts. I knew that this was becoming a full-time career when I started booking national segments on television and building partnerships with large brands. Brands like Maple Leaf Foods, Sally Hansen and President’s Choice, just to name a few.” 

Thinking of turning your own side gig into a “front gig?” McEwen and Gonko offer some advice for taking the leap.

1. Get your finances in order  

You shouldn’t expect to be an instant success with your new line of work, so make sure you have some financial runway that can act as a buffer while you build up your flow of earnings. 

“The first thing I did was refinance my mortgage,” says McEwen. “I was going to put that towards another debt to pay off, but thank god I had the extra money kicking around. The stars were aligned for me because the refinance funds came in a week after I got laid off.” 

The next thing she did was lean on the expertise and guidance of her bank. “When I went to my bank, I had an idea of how much I would be getting in a lump sum payment for my severance. But wrapping my head around what I should do next was overwhelming on my own. My dad told me to put half of the refinance and severance money into my RRSP [called an RSP at Tangerine] and save the rest. But my banker wisely advised that I didn’t know how long I would be unemployed. She gave me the really great guidance that I should just park my money and that I could always put it in an RRSP later and just let it live in my business bank account until I had a clear idea of my future. She reassured me that we could adjust as I went along.” 

2. Start slow before you go full time  

The next best advice McEwen received was from a colleague who told her to find a freelance gig while she was building her business. “She told me to find something below my skill set so I wouldn’t be stressed, but would also provide enough cash flow that I didn’t have to worry about my base monthly expenses until my business took off,” she says.

“That was critical to the success of going from side gig to full-time business owner. I worked for CBC for about 10 months and finally felt confident to let it go when I had three paying clients. It was another massive leap of faith to leave that job, but I had enough saved and interest in my services to jump fully in.” 

3. Cash is king

Business financing can be tough to get and, unlike McEwen, Gonko didn’t have the cash reserves ready, so she had to find other sources of funding.  

“When I started, I struggled with the financial aspects of growing my business,” she says. “I needed outside support in order to grow, but I also needed more revenue in order to sustain it. It was really a catch 22 situation. I really wish I would have known sooner how difficult it can be, especially for a service-based entrepreneur, to obtain a loan. My business was not financially stable and all funds that I had saved for a rainy day quickly evaporated. 

“Thankfully was I able to get [a grant from the Northern Ontario Women (NOW) program] that really helped me start my business, especially in those early days.”  

4. Set up your business bank accounts

One of the best pieces of advice McEwen received was to set up separate bank accounts for her business. “When you go from a typical job where your employer takes your taxes off your pay cheque to then receiving money as an entrepreneur and charging GST or HST, it’s really hard to separate out the dollars,” McEwen says.  

“When I set up my company, my banker immediately helped me set up three accounts. One for money coming in, one to set aside the expected taxes I’ll have to pay, and one for the HST. It’s a simple process but if she didn’t encourage me from the get-go, I could see how many newbies might get into trouble spending every dollar that comes in.”

If you’re thinking about turning your side gig into a full-time pursuit, McEwen and Gonko would be the first to encourage you — but also caution you about getting your finances right before you start. Waking up every day living your passion is a worthy pursuit, and getting there is possible with a solid long-term plan and vision.