Hot jobs: Sick of your 9 to 5? Here’s how to design a freelance career that works for you

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How to create your own job
WATCH ABOVE: Jobs are top of mind for many Canadians these days. But many are turning away from the traditional job search to instead become their own boss. Here’s Tomasia DaSilva on how you can make freelancing work – Nov 2, 2018

Whether you’re figuring out your first career path or looking to change directions, a new series from Global News, Hot Jobs, focuses on career strategy for a new era in work.

Tamara Elliott has backpacked through Patagonia, road-tripped through Croatia, gone spelunking in Belize — and been paid to do it.

As the Calgary-based owner of, she works as a freelance travel blogger, operating her own business and visiting various destinations, where she takes photos and writes about them.

Elliott makes money by working with brands like airlines, hotel chains and destinations in the tourism industry, helping them with things like social media and marketing campaign plans.

Before she decided to become a freelancer, Elliott had a more traditional nine-to-five job in the energy industry. Then she made the leap.

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“To be honest, it wasn’t that scary. It was actually more exciting because I had been thinking about it for a very long time,” Elliott said.

She started thinking about it five years ago, got serious two years ago and dived in this summer.

Not everyone sets up their freelance career quite so freely, though. David Hicks, a 44-year-old software developer and marketing consultant from Ottawa, came to the freelance life a different way: he was laid off.

“I had been through that cycle a couple of times, and that time, I said: ‘You know, I always had this vision of working for myself,’” said Hicks.

“At least that way if there’s a problem in my business, I take care of it. I can control my fate.”

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So he gave it a shot.

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“Here I am, 10 years later,” Hicks said.

Now, Hicks and Elliott count themselves among the 14 per cent of full-time Canadian workers who are self-employed, according to Statistics Canada — a number that has stayed fairly steady over the last 30 years.

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Ready to launch

So how do you get from idea to actually launching your business? Planning helps.

Ryan Ounjian of Futurpreneur, an organization dedicated to helping entrepreneurs develop their ideas, says that setting out a business plan is a must. Some idea of what you’re going to do and what kind of time and money it takes to do it are also key to starting your business.

Ounjian finds that a lot of budding entrepreneurs quickly become discouraged by all the work that’s involved: getting a business licence, finding financing if necessary, working out the accounting and so on.

But there are lots of tools and organizations that can help you with that as well as other people who have already done it. He strongly advises that freelancers and entrepreneurs attend lots of networking events.

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“You’re going to meet people,” Ounjian said. “You’re going to talk to people that have maybe been where you are three months ago, six months ago, a year ago and could offer up some great resources as well.”

Start small

You also need to find customers and figure out what they want.

“Ultimately, if you can’t convince somebody to take money out of their pocket and give you money for your service or business, what you really have is a hobby,” said Christopher Doré, a professor of business management at Algonquin College.

Even the best product or service isn’t worth much if you can’t sell it, he said. So how do you do that?

Freelance web developer and marketer David Hicks, working at a co-working space in Ottawa. Global News

“It’s just making connections with people, getting your name out there, following up on things. I find that over time, as you get more clients, it tends to bring in more clients because it spreads through word of mouth,” Hicks said.

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You also don’t need to do everything at once.

“What people need to know is that starting a business doesn’t need to be something that you plan behind closed doors until you’re ready to bring it out into the open,” said Ounjian.

Working on your business for just 30 minutes a day will generate results over the course of a year, Doré adds. And by starting small, you can adjust your product or service based on feedback from customers before plunging in.

Elliott’s experience was along these lines. Her business began as a side project then turned into a part-time job then, finally, after years, a full-time job.

“Make sure that you have things happening already before you make that leap,” she said. “Make sure that you’ve got clients already signing you up for work.”

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Know your limits

Elliott said she loves being her own boss.

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“It’s very rewarding to work for yourself and to be able to spend 90 per cent of your time on your passion project,” she said.

Though, a second later, she admitted that that 90 per cent estimate was a bit high.

“I am a writer and photographer, but I probably spend a lot more of my time doing the admin and accounting and marketing and things,” Elliott added.

When you work for a corporation, there are marketing and IT departments, she said.

“But when you work for yourself, you’re sort of the one-man show.”

Tamara Elliott at work. Courtesy, Tamara Elliott

Over his freelance career, Hicks has learned that he can’t spend all of his time on the parts of his business he likes.

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“You start a business and you pick your area of expertise but you have to run your entire business,” he said.

“I’m not an accountant, I’m not a business lawyer, and so there’s a lot things that I’m not familiar with that I don’t like to do.”

This initially got him into trouble with his taxes — he simply didn’t know what needed to be done, he said. He’s since learned to get outside help with those parts of his business. That means things like hiring an accountant, and adjusting the rates he charges his clients to account for those extra expenses.

“The reality is that 30 to 50 per cent of your business is not something that you can directly bill for. And you have to keep that in mind when you’re trying to figure out what rates you’re going to charge, how to structure your time.”

Time management

Managing your time is important, as your job can quickly take over your life.

“I tell people that as a freelancer, you work half of the time, all of the time,” Hicks said. “Even if you’re not directly working on a client project, you’re thinking about it. It’s in the back of your head.”

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To avoid that and make sure that he actually makes time to see his two sons, he’s started working out of a co-working space — where freelancers rent a desk or office in which to work — rather than spending all of his time at home, where he’s tempted to work even on his downtime.

“That helps because I can sort of go to work, and I have set hours, and I go home,” Hicks said.

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Knowing your skill set and “what you can take on, knowing what you can do successfully and how long it’s going to take you,” is key, Elliott said.

And if you don’t want to work 24 hours a day at your business, you don’t necessarily have to, said Doré.

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“Not everybody needs to make a billion dollars. There are businesses that you can create that you can work part-time and still generate a decent living from and still be able to balance life,” he added.

Dealing with uncertainty

Managing time is one thing. Managing the lack of a steady paycheque is another.

“One month can be really great with tons of work and then maybe it goes quieter for a couple more months. There’s a lot of ebb and flow when you work for yourself so managing that is very important,” Elliott said.

“I would say the most important thing is making sure you have a very healthy bank balance going into it. Because it’s pretty crazy how long it can take sometimes to follow up on these invoices that are missed.”

Hicks finds that he still has months with not enough work and then months where he takes on too much. Making sure you still have some way to pay the rent is important.

So is preparing for retirement, since you don’t have a company pension. Setting aside money for that takes “discipline,” he said.

Even with all these challenges, Elliott isn’t sure she would go back to the nine-to-five life.

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“I would never say never. I always am looking for great opportunities but I’m very happy with the path that I’ve chosen,” she said.

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