So You Want to Be a Freelancer?


So, you're a creative professional who thinks you might also have what it takes to become an entrepreneur. You've heard of freelance writers, designers, and photographers and perhaps it's something you're considering, but what is it really like to be a freelancer in a creative industry in Winnipeg?

Robin Hamilton is a freelance motion graphics designer/animator in Winnipeg and knows first-hand about the challenges and advantages of working for yourself. He just finished wrapping up a promotional video for RVSN Media Group's launch of the first ever 46 inch Android OS touchscreen device, and although quite sleep deprived, he was happy to weigh in on some of the good, and the not so good parts of freelancing.

Check out his demo reel below and online portfolio at:

The Good

1. You Are Your Own Boss

"When you first start out as a freelancer it’s a good idea to take almost every job that comes your way, but once you’ve made a name for yourself you can be more selective with the work you accept. Having the freedom to pick and choose projects that interest me is why I love freelancing.”

“Working out of your own home is a big perk to being a freelancer. There’s no need to rent an expensive space because the internet is primarily where communication with existing and potential clients happen. I will meet with clients in person during the initial stages of a project and at the end, but as I work on a project I will send stills and clips for clients to view via email, Vimeo, and even text message.”

“Being a freelancer means there is no layer of bureaucracy separating you and the client. This is different from working for a company in that there is often an account manager handling most communication with the client and a producer overseeing the job. I prefer to ask my client directly what they are looking to achieve with a video or animation and to be the one working out the kinks with them as the job progresses so there is no miscommunication. It also doesn’t hurt that they get to know me throughout the process and then there’s always the possibility they will hire me again in the future.”

2. Flexible Hours

"I've always had trouble doing the nine to five thing because creativity doesn't work on a nine to five schedule. Plus, I happen to be a night hawk. Freelancing allows me the freedom to complete my work when I feel inspired, even if it happens to be in the middle of the night."

3. Creative Freedom

"As a freelancer, I have considerable control over the type and scope of my work. There's nobody telling me to take certain jobs and not others or looking over my shoulder at my work. I have complete creative control and this allows me to take risks, which is often how I am able to design something great.

4. Variety

"Freelancing works especially well for me because I don't have a structured personality. I dislike routine and I thrive on not knowing what's going to come next. I really enjoy the extreme diversity of handling multiple projects at once and learning as I go."

5. Recognition/Achievement

"There's no better feeling then when I've poured everything I’ve got into a project and when it's finally done, the client is ecstatic about it. I recently did a video for two Winnipeg police officers who invented a device for stress-innoculation police training. I spent many sleepless nights working on the video but it was a lot of fun. When the clients viewed the video for the first time I was really surprised, they were literally jumping up and down they were so happy with it. That made all the work worth it to me.”

The Not-So-Good

1. You Are Your Own Boss - and also the Marketing Manager, HR personnel, Bookkeeper, Receptionist, Administrative Assistant, and Creative Talent

“You don't have a boss telling you what to do but you also don't have a boss that is going to protect you when the going gets tough. If you don’t have any work lined up, you're not making any money whereas at most regular jobs, you are paid for the hours you spend at work while the marketing and sales departments worry about how to get more business.”

“Similarly, if a client isn’t happy, you better be prepared to answer to them because nobody else is going to answer for you. In fact, while you may not have a boss in the traditional sense, clients are like bosses in a way and every client will have a unique set of needs and expectations. In the end you actually have several bosses at any given time, all wanting different things from you.”

2. Staying Motivated

“For me, freelancing is a lifestyle. I’ve had to teach myself a lot of discipline and force myself into good habits such as getting down to work, even when I don’t feel like it. I think everyone procrastinates to a certain degree in their daily life and it’s very easy to put off working on a job, but procrastination only leads to falling behind on your work. I think the worst thing you can do as a freelancer is fail to deliver on time or up to the standard you promised a client. That client will simply never hire you again.”

"In the back of my mind is always the fact that as a freelancer, time is currency. If I take a few days off, I am not making any money. I've spent the last three Christmas's working fourteen hour days and even lugged a 17 inch laptop, 24 inch monitor, and external 4 bay RAID with me on the plane to Toronto so I could work while visiting family for a week."

3. Drumming up Business

“Unfortunately, you can be the most talented person in your field and unless people know about you and what you can do for them, you’ll never get work. I am still working on this one but having a presence on social media is key to landing new business.”

“If your not a people person, it’s a good idea to try and become one. Clients won’t come knocking at your door with fantastic job offers without you doing a lot of leg work. I’m constantly stepping outside my comfort zone, trying to network with other professionals and promote my services.”

"I don't actually sell a tangible product, so it's sometimes difficult to demonstrate to a potential client what I can do for them. My service is creative and customized to the specific needs of every single client I meet with."

4. Budgeting

“The costs associated with running a business are higher than most people realize. Having to replace hardware, upgrade software, pay business registration fees and for an accountant and a lawyer, costs a lot of money. Budgeting your resources and charging high enough prices for your services ensures you can cover these costs.”

“Some people choose to pay their taxes in a lump sum at the end of the year rather than throughout the year. If you choose not to pay taxes throughout the year and fail to budget enough each month for taxes, YOU WILL GET DINGED COME TAX TIME. It’s an incredibly sobering experience to think you've saved enough to cover taxes and then to find out you owe the government "X" amount of money. Take it from me, pay taxes throughout the year.”

5. Free Time

"If you're a freelancer, you are IT. You're running the show and nothing can get done without you. That means that if you’ve got a deadline first thing Monday morning and the work isn’t finished, you are not going to your Grandmother’s 88th birthday Sunday night even though your entire extended family will be there and you missed her birthday last year because you were working.”

Robin's Tips

1. Know the Industry

“It’s probably not the best idea to base your sole income on freelancing right out of school. My advice would be to gain some experience working in your field and network with as many people as you can before setting out on your own.”

“Research, research, research. Know what other local freelancers are doing. The software they use, the fees they charge, and the kind of work they go after. This information will help you make business decisions that ensure you remain competitive.”

2. Don't Sell Yourself Short

"It is my opinion that a lot of new freelancers breaking into the industry undercut their prices in order to get work. While I realize the need to land jobs, many people fall into the trap of charging low prices in the beginning and then find it difficult to increase their prices later on. It’s easier said then done, but try to trust that if you are a hard working and talented individual that clients will pay for timely and quality work.”

3. Take Advantage of What is Available to You

“New Media Manitoba is just one organization that has been a support network for me throughout my career. They offer free workshops and advice for those working in media related industries and I would highly suggest checking out their website for upcoming events and information.”

New Media Manitoba website

"There are tons of government grants available to people working in the arts and it doesn't hurt to apply for them. It is also true that you can write off a portion of your bills if you work from home.”

4. Put Yourself Out There

“Again, social media is a great way to market your business. Being active on Facebook, Twitter, LinkedIn, and other social networking sites only increases the chance that people and businesses in need of your services will come across your information. Having a polished website up and running and business cards handy at events is also important.”

5. Have a Solid Portfolio

“Your work should speak for itself. Include in your portfolio the work you are most proud of and that show your versatility as a writer, designer, photographer, or artist. From my experience, impressing clients with quality work is the best way to get hired. ”

What are your thoughts on the life of a freelancer? Do you think freelancing would be a good fit for you? Are you able to manage stress fairly well? Are you ambitious enough to motivate yourself or do you need external motivation? Tell me your thoughts, I'd love to hear them!


  1. Great info Meghan & Robin!

    1. Thanks Angie! I can always count on you to read my blog haha!

  2. Excellent post - and great tips. The worst part of freelancing: collecting the money.

    1. Thanks Kenton! And good point, I imagine collecting money would fall under the not-so-good part of freelancing!

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  4. I really enjoyed reading this post, Meghan! Some well-told insight!

    1. I'm glad you liked it! Thanks for stopping by!

  5. I really enjoyed this. I feel the same way that I can't always work on a 9-5 schedule. However, I also suffer from something called procrastination, which unfortunately is not a sought-after skill.

    1. I have a problem with procrastination as well. It's a bad habit we'll probably both need to overcome being in CreComm! Thanks for reading Rebecca :)


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