It was New Year’s Eve 2013, when Amanda, then an employee of a loyalty rewards company, was sitting in her family room, discussing her goals for the upcoming year with her best friend. They both had the same resolution: make more money. Their 9-to-5 jobs were great, but their wages hadn’t kept up with their increasing costs of living. Both were working moms trying hard to make ends meet.

“We started to talk about business ideas we’d always thought about but never had the guts to follow through on,” Amanda says. “My friend recently had an abdominal surgery and was left with a long scar across her stomach. I had also had two surgeries that left me with tummy scars. We came up with the idea of trendy temporary tattoos that could cover the scars as needed, like at the beach.”

And so TuckTats, was born. It’s been time-consuming, sometimes exhausting and friendship-testing, and they’ve had to use their income and vacation days to build their company. But five years later, sales are steadily growing, and they’re finally profitable. The pair intend to take a paycheque from the company for the first time since they started. Both are ecstatic about the extra infusion to their budgets.

Every day, more and more Canadians are considering taking on extra work or turning to self-employment to earn extra money. According to a 2018 study, the number of workers in Canada who hold multiple jobs has increased by 30% over the last 30 years.1

“We are certainly seeing more clients with secondary income” says Elena Rizzuto, Regional Vice President of Financial Planning at TD Wealth. “In major cities in Canada, the cost of housing and rent has exploded, and wages are not keeping up. It’s a new reality for the average person living in these areas.”

With the rise of the “gig economy” there is no shortage of work to undertake: You might drive for a ride-sharing service, make and sell crafts on online marketplaces, pet-sit, or even perform in a band at your local pub. If there’s something that interests you enough to spend your free time doing it, you can bet there may be a way to make money at it.

If you are thinking of making some secondary income or are starting to hustle already, here are some things you may want to consider, from some folks who would know.

Side hustler: Charlotte

Day job: Food services manager

Sideline: Business professor

Years hustling: 5

Why did you start?

"With increasing pressures on the family budget as my kids got older, I needed to supplement my income. We know how teenagers spend money. My first paycheque went to buy three laptops."

Key lesson:

"Ensure you can handle it with your current workload, book time in your schedule. Plan a trip or budget for something you want, so then it’s more enjoyable."

Ask yourself: Why are you hustling?

While starting a new business might be a fun way to earn extra cash and make life a little more interesting, for some it might make financial sense, particularly if you have a lot of debt, or if your expenses are higher than the money you are bringing in. In cities where housing and rent are expensive, you may find yourself needing to work overtime to make ends meet.

Extra money aside, deciding to take on another gig can be a big decision, especially if there are other people that need to be considered since any secondary employment may take time away from your family. And in the case of starting up a side-business, it may also initially take money out of the family budget as you pay for your start-up costs and supplies. Also, if you work an already strenuous job or long-hours, a second job may lead to burnout and exhaustion, even if it’s something you love doing.

“My friend and I have tried hard to ensure that business doesn’t impede on family time,” says Amanda. “But inevitably, Saturdays and after our day jobs is when we need to talk, plan, and run the business. In an effort to preserve family time, we’ve even had our kids help us with little tasks related to the business where possible.”

Side hustler: Rachel

Day job: Medical receptionist

Sideline: Crochet artist

Years hustling: 7

Why did you start?

"Because my youngest child needed a costume for a school play, I crocheted her a hat. People gave her huge compliments on it, and I realized that not many people crochet anymore. So, I started with hats, then did stuffed toys and crocheted movie characters. A comic book store order helped it take off."

Key lesson:

"Research the audience you're targeting and whether there is a demand for the business. If it is a niche market, you may struggle to build a customer base. It is not impossible though, just definitely not easy."

Make a plan

Some people may fall into their second job through a hobby that unexpectedly takes off. For Nikki, who works for a television news program, she calls her business “an accident” that came from her passion for sculpting. While working on a model of an anatomical heart, she learned from friends and others on social media that there might be a market for it. She soon opened Little Shop of Hearts, selling hand-made resin anatomical heart sculptures and pendants.

“The idea that anyone would want to own something I have made with my hands still fills me with extreme gratitude and joy,” Nikki says. “It genuinely blows my mind whenever I get an order. It never gets old.”

But for most of us, a little thinking and planning will be in order.

Identify your talents and marketable skills, create a goal-based schedule for finding work or opening up shop, and find dedicated time to work towards getting there.

If the perfect side hustle doesn’t come to mind immediately, ask yourself some questions: What do you know? Do you have any hobbies or interests? Is your idea for a side hustle viable and marketable? How much money, if any, would you need to start up? How much time do I need and when do I have time to do this?

“Even for a small business or part-time work, it’s a useful exercise to create a business plan that sets out your mission, your target market, a simple wealth plan, and roles and responsibilities for each player,” says Rizzuto. “A business advisor can help, or there are many resources online that you can use.”

Side hustler: Andrea

Day job: Barista

Sideline: Eyelash technician

Years hustling: 1

Why did you start?

"I longed to make a job out of doing something I’d enjoy from the comfort and coziness of my home. I’ve always loved making things pretty and I wanted to be able to connect with women, make new friends and give them a little pep in their step when they leave my studio."

Key lesson:

"Work hard to promote yourself. Social media can be your best friend. It’s always good to ask questions and seek help in areas you aren’t too familiar with as well. I’m so thankful for those who’ve guided me through the process of having a small business!"

Get organized

You’ll have some decisions to make in order to address the legal components of operating a business — namely whether you intend to be self-employed as a sole proprietor or incorporate as a business. Incorporating your business will cost money but may offer some financial protection in case of any legal action brought against the company. Alternatively, it’s relatively easy to work as a sole proprietor, but your personal assets may be at stake if your business encounters any legal problems.

Either way, you’ll be able to write-off some expenses come tax-time. On that note, yes, you absolutely must pay taxes on your second income. The Canada Revenue Agency expects you to report your additional income on your tax return if you are a sole proprietor and file a corporate tax return if you are incorporated. Also, if you think you’ll make more than $30,000 in a year, you may wish to consider registering to collect and remit any sales or services taxes. Your tax preparation will become much more complicated with self-employment income, so it’s worth considering the services of a business advisor, financial professional or accountant.

“Even if you don’t make that amount, it can make financial sense to collect it anyway, as you can recoup the GST or HST on your purchases,” says Rizzuto. “Not having an HST or GST number can make your business look small and identify it as a side job. A financial professional or accountant can help you to make those decisions.”

Know when to grow it

Eric is a television producer and freelance writer who saw the need for language translation services for video and TV shows. In 2013, he and his business partner started Power of Babel to dub and subtitle audiovisual content for businesses. It’s now growing into his full-time job.

“We were almost ready to fold up shop,” Eric remembers. “But then a curious thing happened: A major client walked in the door and decided they liked our work. Suddenly we had a steady stream of projects, were profitable, and it felt like a real business.”

Other clients started calling. “Now it feels like if we can get this much work without trying too hard, imagine what we could do if we did some sales and marketing.” Eric is currently working to turn Power of Babel into something close to a full-time business.

“There is no perfect time to quit your day job, but you’ll have to decide when you’ve reached a critical mass with your business,” says Rizzuto. “When doing both jobs is becoming unsustainable, and the more lucrative work is your side-job, you may consider doing it full-time.”

Plan for the growth. Building a business doesn’t just happen; it takes purpose and intention. Marketing is key, and you should learn from others in the same business.

Of course, some businesses will always be destined to remain side hustles, and that’s OK too. “It is important to me that all my items are always made by hand and not mass manufactured,” says Nikki of her resin hearts. “I can only make so many at a time, so I do not see myself expanding this into a full-time gig. In a perfect world, if I could hire other makers, I would certainly consider teaching them my techniques and standards and offering them a fair wage in an effort to expand, but there’s something really genuine about it all truly just coming from me.”

DENISE O'CONNELL

MONEYTALK LIFE