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Lighting The Way
To Better Work 

Dive In
  • Writer's picturePeter Harris

Updated: Mar 25

Are you thinking of making a move from full-time or in-office work to freelance? You’re in good company. A survey conducted by Freshbooks in the fall of 2020 found that 30% of traditionally-employed Canadian professionals were expecting to transition to self-employment over the next two years. That’s an estimated 7 million Canadians planning to start their own business, freelance, or become otherwise self-employed.

The gig economy has grown considerably over the past few years. According to, gig workers now represent more than one in 10 Canadian adults (13%), and more than one in three Canadian businesses (37%) employ gig workers. 

There are several reasons for this. The rising cost of living means many people need more than one job to make ends meet, and people are also tired of the lack of job security they’re currently facing. “First in, first out” policies – which state that the last person to be hired is the first to be fired – mean that, even if you land a job, you’re still vulnerable to losing it, and workers in many sectors are facing an uncertain future. 

Hayden Brown, the CEO of freelancing marketplace Upwork, recently told Fortune in an interview, “I think this is really the story of early innings in a much bigger game. We’re going after a trillion-dollar market opportunity. We are in the early stages, even though you know we’ve been at this game, we’re a 20 year old company, and we went public in 2018. But I think the bigger potential here is actually what lies ahead of us versus what happened the last two years.” 

Brown noted that a third of Americans are participating in the freelance market. “What we’re seeing is a huge shift where in the past I think a lot of workers thought freelancing was not that safe, not that stable, something of a last resort type of career choice,” she said.

But that has changed, she said. “The narrative is now the opposite. Especially among younger Generation Z workers. They saw the 2008 recession. They’ve seen their parents go through rounds of layoffs and hardship. The work of an individual employer keeps proving to be very unstable, and people say wait a minute, if I’m going to be at the behest of the single employer, that’s actually very risky for me.” There is more security with more than one income stream, and freelancing provides that.


What is freelance work?

Let’s break down what freelance work entails. A freelancer is a self-employed individual who offers services and earns money on a per-job or per-task basis for short-term, contract, or ongoing work. A freelancer is not an employee of a company and is usually free to work on different jobs for multiple clients unless under contract to work exclusively for one client, for example, until a particular project is completed. 

Common types of freelance jobs.

Freelancers may work in many professions because these days, the technologies are available for people to do almost any job from anywhere. Various examples of freelance careers include, but are not limited to:

  1. Writer/Copywriter/Content Provider/Content Strategist

  2. Social Media Strategist

  3. Developer/Coder/Programmer

  4. Designer

  5. Videographer

  6. Translator

  7. Recruiter/HR Manager

  8. Accountant

  9. SEO Consultant

  10. PR Professional

The reality (pros and cons) of freelancing. 

Freelancers can make an excellent living, often even better than those working traditional jobs. So, if you’re wondering whether freelancing is the right career choice, explore these pros and cons before leaping. They will help you decide if it’s the right path for you. In addition to exploring these pros and cons, you should get out there and network early on, especially before you take the leap. Talk to others you know around you who have taken a similar path and ask them questions about what it was like for them and what lessons they learned along the way. 

If you’re unsure who to talk to, dive into listening to podcast interviews with freelancers. There are plenty of them, but we recommend The Marketing Millenials podcast interview with e-commerce freelance copywriter Kaleigh Moore. She started small, has skyrocketed to monumental success, and is now offering advice and support to new freelancer writers. Even if freelance writing isn’t your path, this podcast takes you on her journey, which has many parallels with multiple industries.  

The pros of freelancing. 

1. You can make your own hours.

Freelancers can have a nice work-life balance because they can set their own hours, which can be a desirable benefit for people with families, young children, or elderly parents to care for. You can work at 5:00 am, 3:00 pm, or 2:00 am. As long as you get the work done, nobody is going to bother you about it. 

2. You have flexibility.

In addition to setting your own hours, freelancers can work from anywhere they wish  – from home, while travelling, from a coffee shop. You also get to choose who you work for and who you don’t work for. Once you have established a client base and a positive reputation, you can say no to people you don’t want to work for and yes to those you do.

3. You have a diversified revenue stream.

It’s a good idea not to keep all your eggs in one basket these days. As we mentioned above, the precarious nature of the job market means a lack of job security for people across sectors, even those with higher degrees and management positions. The COVID-19 pandemic has taught us that disruption happens randomly and without warning. Businesses have had to pivot in the last few years, and people have learned that we can only try to be prepared. Having more than one income stream can help protect you against losing everything. 

4. You have the opportunity to make a lot of money.

In a traditional job, you usually have a salary, a commission, and any additional income from annual raises and bonuses. Unless you leave one job for another or manage to get a significant salary increase, it’s outside of your control. With a freelance career, as long as clients are willing to pay, you can charge whatever you want and work for as many people as you wish. Successful freelance workers who manage their careers well can easily make upwards of six figures in annual income. When deciding what to charge, research what others are doing in your line of work to know if you’re going in with a fair rate. 

5. You have variety in your work.

Some people enjoy doing the same thing and only working on one type of job. Others like variety, and freelancers often have variety in their work. You can work with different types of clients on different types of projects. For example, a freelance graphic designer might work on books, infographics, flyers, and Facebook ads all on the same day. Or a PR professional might work to promote a T-Shirt band, a software company, and a skincare line at the same time. This variety can make life exciting and keep you from getting bored doing the same thing daily. 

The cons of freelancing.  

1. Doing your taxes can be complicated.

In a traditional job, your taxes are usually deducted from your paycheque, and you get whatever extra you paid back at the end of the year in the form of a tax return. Freelancers have a more complex tax picture, and you must be vigilant about putting money away and declaring your income and expenses, lest you wind up with a hefty bill you can’t pay. Many freelancers, both inexperienced and experienced, have fallen into this trap. 

To avoid this trap, set up a My Business Account with the CRA, get your GST/HST number so you can remit your taxes regularly, and head to your local bank to create a new business account. Your bank can set you up with the appropriate accounts (i.e., Business Income Account, Tax Account, and Income Tax Savings Account) so you stay organized and on top of your taxes while you grow. 

2. You have to market yourself.

Whatever job you’re doing as a freelancer, you don’t usually get to do just that job. You also have to be in charge of marketing your personal and professional brand and be your own sales team. As this Muse article points out, you’ll have to build your online presence, among other things. This doesn’t come naturally to a lot of people. 

We will share that you do not need to have a full-blown website or portfolio when you start out. That comes with time as you build your business and reputation. Once you have completed projects and happy clients, ask for a testimonial, a Google Review, or a LinkedIn Recommendation. And even ask if you can showcase your work on your website portfolio. 

When it comes to freelancing, you will notice that much of your work will come from word-of-mouth and recommendations from your network. If you find that is not the case for you, we recommend setting up your profile with sites such as Upwork so you can start to build your client base from there.  

3. Your income can be sporadic.

While there are opportunities to make a significant income as a freelancer, it can be feast or famine. You might have trouble getting started and getting clients, and sometimes you might have a huge, well-paying project for three months and then nothing for the next three months. Those hard times can be very stressful when you have to intensify your efforts to get new clients. It is recommended that you establish relationships with your clients early on and look for opportunities to support them on a regular, long-term basis. Monthly retainer agreements can provide a level of stability for you as you grow your freelance business. 

4. Your time management skills must be top-notch.

When freelancing, nobody is breathing down your neck, watching your every move, and demanding you get your work done. You and your clients agree on a delivery date for the work you’re contracted to do, and it’s your responsibility to get it done on time. This means doing the work, anticipating problems, and gathering the needed resources. Juggling multiple jobs means you need excellent time management skills, or you will have trouble. You will have to manage your schedule because time will slip away. That’s one of the helpful tips you’ll find in this Ladders article.

5. You have no paid time off or set vacation times.

While you get to work from anywhere and at any time, for some people, that means you’re always working. When juggling multiple jobs and clients, sometimes there are no breaks. This can take its toll if you’re not mindful of your work-life balance and if you don’t schedule your downtime. 

It can certainly be difficult to take time off while a freelancer. Be sure to be mindful of downtimes in your line of work and scale back your days during those periods (i.e., December Holidays or Summer Months). This ensures you don’t burn out and miss out on life. You may still have work to do on your “vacation” but try to schedule your days around the work (i.e., early morning wake-ups) so you can enjoy your time with family and friends. 

Should you take the freelance leap?

Only you know if a fully freelance career will work for you. Take the time to plan, research your market, talk to others, and gather the resources you’ll need before making any big steps. When you do take the leap, you may never look back. Or you may decide while in it that it’s not right for you. Just like any career, freelancing is a journey. It has its ups and downs, but it’s also very enriching. You will establish many connections along the way, and you will grow as a person as well. Just be sure it’s right for you first, and we hope this article helps you make this important life decision.

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