The Rise of the Freelancer: How to be your Own Boss

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Thinking about making the jump to freelancing? Vv Magazine’s Ama Scriver interviewed 5 successful Canadian freelancers to find out the highs and lows of being your own boss.  

Just a few months ago, I decided to leave my high paying full-time job and go freelance. It was one of the scariest decisions I ever made in my life but also one of the most exhilarating. Apparently, I’m not alone in these feels. According to Forbes, there are 53 million freelancers in America today. By 2020, 50% of the U.S. workforce will be freelancers. While that article largely refers to the U.S. – I would hazard a guess to say, the Canadian workforce is much of the same. 

It seems like there are a lot of misconceptions out there about who freelancers are and what they do. You see, not all freelancers are millennials that are sick and tired of their jobs. Some are people who have wanted to carve out something for themselves and make a new career path. For many, it can be inspiring and hard work. But most of all, it’s rewarding when done right.  So I decided to talk to some people who have made the jump from full-time to freelance to find out why and how they did it and what they advise.

Erin-McPhee

Erin M., freelance illustrator

Q: When did you decide to leave the 9-5 life and what made you decide to leave?

I think there were a few things that contributed to me making the leap to freelancing full-time; firstly, before graduating from college I’d already imagined that working freelance/on a contract basis would be something I’d do in my field (illustration and design). And by the time I made the jump to full-time freelance, I’d already been working on freelance projects (outside of full-time work) for a year or so. Secondly, I grew up with a parent whose entire career was contract work, working in theatre and film as a scenic artist. So, when I was young, this kind of work was modelled to me as a feasible way to support oneself (although definitely not without its own challenges). A 9-5 job was always a possibility in my future, but it didn’t feel probable for me.

In a more straight-forward way, my path to freelance was this; I left a contract position as a contributing designer at a magazine (where I was still doing freelance projects on the side), to pursue a 9-5 in-house print/packaging designer job at a large company (for the stability/salary/health benefits!) However, the corporate work environment was so alienating and disempowering, and that negative experience finally gave me the confidence to save up some money, quit, and freelance full-time.

Q: How do you make or obtain clients and/or how do you deal with slow months.  Have you ever had to take on other part-time jobs to make ends meet?

I’m a huge advocate of folks being open about the conditions in their lives that allow them to freelance. I know some freelancers who are in supportive partnerships, and that’s something that is beneficial during the slow months. When they are not making as much money, they have someone there to help out. That definitely isn’t the case for everyone. Personally, when I’m experiencing slow months – I’ve either had support from a partner, or I’ve had to pull money from savings to keep all my expenses covered.

I’ve known plenty of freelancers who have had to take on part-time jobs to make ends meet. I don’t want to assume, but I think there’s some stigma/guilt around this. Like, if you can’t support yourself doing freelance 100% of the time, you’re failing at this thing, which is definitely not the case. It takes time to build your business, to save a small amount of money/savings to float you when cash flow is an issue, and even then it’s not always a straight-forward path from point A. (freelancing/building your business while working another full-time or part-time job) to point B. (freelancing full-time).

“I’ve known plenty of freelancers who have had to take on part-time jobs to make ends meet. […] I think there’s some stigma/guilt around this. Like, if you can’t support yourself doing freelance 100% of the time, you’re failing at this thing, which is definitely not the case.”


 

Michelle, freelance producer/host

Q: When did you decide to leave the 9-5 life and what made you decide to leave?

I decided to leave the “9-5” life in March. There were many things behind this, but most importantly I have had an unshakable feeling over the last couple of years that I want to be my own boss. I am surrounded by entrepreneurs – some family members and several close friends. For the most part, they work a lot of hours and they work hard, but they are more satisfied with what they do for a living than most people that have a “job”. I found that incredibly inspiring. I wanted to have something that was my own.

Q: Could you tell me a bit about what you’re doing now and what you love most about freelance life?

I do a lot of things at this point. I am a freelance producer/host, writer, media consultant and coach. What I love about it is that I don’t sit in a desk all day. I just can’t sit for 8 or 9 (or 10 or 11) hours a day. I’ve been there at certain intervals in my life and it drove me nuts. It’s incredibly unhealthy, and I just can’t think clearly if I am desk bound for that long. I’m not nearly as productive when I can’t move around. Also, I love the autonomy.

“For the most part, [the people I know that freelance] work a lot of hours and they work hard, but they are more satisfied with what they do for a living than most people that have a ‘job’.”


Sam-Brooks

Sam B., freelance video production

Q: Could you tell me a bit about what you’re doing now and what you love most about freelance life?

Everything. My day-to-day can be anything from writing proposals and budgets, accounting, wiring cameras in garage or out in the field shooting. The flexible hours are kind of a blessing and a curse. Having a 9-5 routine is predictable and comfortable, but gets really dry really fast. This job is much more unpredictable but generally affords a better work-life balance too. There will definitely be days when I’m working 12+ hours a day straight for a week because we have a pressing project, but there’s also times where it’s more relaxing and I can enjoy a slower week and get some personal chores done. I also really love the challenge of building something totally new.

Q: What has been one of the most interesting things about transitioning from traditional 9-5 life to freelancing/being your boss life.

Taking time to learn things. When you work for a big corporation, taking a day or even a few hours to study something and devote time to learning really feels like “time wasting” (or at least it did to me). There’s so much to learn in this new place that if I take a full day to research something, there’s space to allow me to do that. It’s really strange to get used to doing something as passive as research and yet not having that weight of “wasting time” on your shoulders.

“The flexible hours are kind of a blessing and a curse. […] This job is much more unpredictable but generally affords a better work-life balance too.”


 

Chris-Stevenson

Chris S., founder and CEO of Ripple Creative Strategy

Q: What has been one of the most interesting things about transitioning from traditional 9-5 life to freelancing/being your boss life?

It’s like you are living in an alternate universe that only other entrepreneurs can understand. Weekends don’t mean anything to me. Most of the time I don’t know what day of the week it is. One time this summer I wondered if my email had gone out before I realized it was a long weekend and none of my clients were working. You also start to think of your whole life as a big ongoing project, with your business as part of that. That’s pretty cool actually because you are now thinking on a higher level of self-betterment and growth. On the downside, you are never really not working. Even when you are out with friends or sleeping or doing anything else, there is always a little part of your brain thinking about the business 24/7. If I had to work this hard for another employer, I would probably resent it, but when it is “your baby”, you don’t mind. I haven’t had a vacation in four years. I’m hoping to change that soonish. Then again, that cliche about building a life you don’t need to take a vacation from might have some truth to it.

Q: How do you make or obtain clients and/or how do you deal with slow months.  Have you ever had to take on other part-time jobs to make ends meet?

In the early years, things could get really scary. A few times I even went and did some job interviews just to have a backup plan because things were getting so tight. I never rule out the idea that I might need to go back to a regular job at some point, and I know I can do that if I have to. Now things are more steady, but there are still patches where it feels like you might never work again. These are usually followed by patches where you have more work than you can handle – it’s always feast or famine.

Cash flow is a hugely important area that all entrepreneurs need to learn and understand. When people ask me about starting a new business I always advise that they have at least 6 months of living expenses in the bank. When you can get it, have some credit available to you, but be VERY careful about how you use it. I keep my options open for other opportunities that are extensions of what Ripple does, too. This Fall I will be teaching Multimedia Storytelling at the University of Toronto School of Continuing Studies, for example, which I am really excited about. In addition of being another source of revenue for me, it will help to ensure I stay sharp and on top of trends in my field and introduce me to people that I may be able to hire or work with in the future – all good stuff.

“I haven’t had a vacation in four years. I’m hoping to change that soonish. Then again, that cliche about building a life you don’t need to take a vacation from might have some truth to it.”


 

Amanda-Lynne-Ballard

Amanda Lynne B., freelance integrated producer and project manager

Q: What has been one of the most interesting things about transitioning from traditional 9-5 life to freelancing/being your boss life.

No matter what, you’ll always have a boss as you’ll always have to report in to someone. But this means you don’t have people actively and constructively critiquing your work. You need to find your own mentors, you own support system and continually challenge yourself to do better – this is a big learning lesson, as you will immediately need to become self-sufficient and self-critical of your own success and career path.

Q: What is some advice you would give to someone new to freelancing or interested in becoming their very own boss.

Know what you are getting in to and do it right; make sure you have the resources and some money saved up. I think one of the biggest misconceptions is around how much free time you’ll have. You can’t always grab a coffee or head out to the island on a nice day. Remember, you’ll be doing your own bookkeeping, invoicing, taxes (x2 if you incorporate your business), business development on top of actually doing your job. Time management skills and self-discipline are your keys to success. Also, know what the going rate for a freelancer in your job, with your years of experience is – don’t over or under value yourself – the trick is finding the sweet spot.

“I think one of the biggest misconceptions is around how much free time you’ll have. You can’t always grab a coffee or head out to the island on a nice day.”

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Are you a freelancer? What are some of the biggest challenges you’ve faced? What do you love about freelancing? Let Vv Magazine know in the comments below or tweet us @ViewTheVibe.

Ama Scriver

Ama Scriver

Amanda (Ama) Scriver is a passionate storyteller, community builder and a loud and proud feminist and body image activist. She freelances for several publications including Foodism, Paste Magazine and BizBash. In her off time, she lives for coffee, trashy reality television, hip hop and all things drag. Follow her on Twitter and Instagram via @amascriver on at her website AmaScriver.com
Ama Scriver