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Secrets of Successful Freelancing

Joy Deangdeelert Cho didn’t set out to be a freelancer. After moving to Philadelphia from New York with her then-boyfriend (now husband) in 2005, the designer began looking for work. Although she won interviews, she failed to find a job that fitted and which could deliver the best aspects of her previous position at a boutique advertising agency. As she continued searching, she began taking on freelance jobs. Those projects continued to pick up until Joy realized that if she put in a little more effort, she wouldn’t need to find a job at all; she could freelance full time. Now the owner of Oh Joy! a successful and growing freelance business, she has designed exclusive stationery for Anthropologie, Chronicle Books and Target. She writes a weekly column for the Philadelphia Inquirer’s Home & Design section, and she’s the author, with fellow freelancer Meg Mateo Ilasco, of Creative Inc.: The Ultimate Guide to Running a Successful Freelance Business. In a joint email interview, Meg and Joy explained what they saw as the secrets to successful freelancing and what freelancers should be doing to win work.

Surprisingly for freelancers who have been this commercially successful, a theme that runs through Meg and Joy’s advice is the importance of personal work and creativity. While Joy stumbled into freelancing, Meg has worked for herself for most of her adult life. The focus of her business has been on products: wedding invitations, stationery and home accessories, and now a magazine called Anthology.  Most of her freelance work though consists not of tasks completed for clients but self-initiated projects such as books that give her extra freedom as well as some useful revenue.

“For me, freelancing became an outlet for expression outside of my product-based businesses as well as an additional way to earn income,” she says.

Mixing Regular Work with Fresh Jobs

Maintaining that free expression can be harder than it appears for freelancers. Joy notes that while some freelancers base their businesses on one large, regular client, and others take on lots of small projects from a never-ending stream of clients, she likes to have one or two regular suppliers and another three to five occasional clients.

The total number of clients lets her feel that she has enough work but the balance between regular gigs and new challenges also ensures that she doesn’t get bored and that her work stays fresh.

“I think new work is crucial to feeling creative, energized, and excited about your work,” she says. “While reoccurring clients are great, after a while, you’re probably doing more of the same thing for them. But taking on new clients regularly gives you a chance to work on a new brand, new format, and possibly a different style.”

That new work doesn’t just provide a sense of satisfaction though. For Meg Mateo Ilasco, it’s also a vital tool for bringing in more new projects and new challenges. She recommends that freelancers put their newest work on their websites and their blogs, and suggests that they also upload their personal projects as a way of guiding their careers in the direction they want them to go.

“Those projects often resonate with people and can help steer your career. It can help you produce more of the work that you truly want to do.”

In time, she argues,  those personal projects and new work will mean that a freelancer won’t need to go out and look for clients. They’ll start to come in by themselves.

The Nine Qualities of a Successful Freelancer

That may be valuable advice, and not just a good excuse to find time for the projects you’re more likely to enjoy. But for many freelancers, the biggest source of new jobs isn’t the new, exciting and fun work on their websites (which have to be promoted) or their blogs (which have to be written) but the clients themselves. Referrals remain one of the most effective ways in which freelancers build their businesses and generate new income.

Both Meg and Joy agree that current clients are a valuable source of new clients. And winning that work, is much easier, if less enjoyable, than finding the time to finance and complete your own projects. Mostly, says Joy, it comes down to doing a good job and making sure that the client knows you’re available to take on more.

“Sometimes clients may think you’re too busy for more work or they may think you don’t need it. But if they know, they are usually happy to share you with others!”

Fresh jobs, generous clients and personal work aside, Meg and Joy identify nine qualities that all successful freelancers share: a strong business sense; a love of their art; curiosity; confidence and a strong vision; good listening and observations skills; good communication skills; the ability to handle criticism and rejection; a positive attitude and professional demeanor; and good work habits.

Those aren’t impossible qualities to obtain but it’s notable that most are related to business and professionalism rather than to talent and imagination. Creative freelancers might need to show off their personal work and their curiosity but mostly they have to be able to track down clients, work to deadline and understand what the client wants. Get all that right though, and new freelancers might be surprised to find that their search for a new job turns into a rejection of the traditional work world and an embrace of an independent working life.

“While in school, we were always told about the huge ad agencies and design firms, so I had the idea that if I wasn’t at a big company, it wasn’t seen as reputable by my peers,” recalled Joy. “But nowadays, I think that you can be super-successful on your own too.”

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