How To Be A Happy And Successful Creative Freelancer (Or Work With One)

Freelancers share their best practices for being their own boss, and why you should so totally just do it.

When talking to creative freelancers, there’s one phrase that’s often repeated: “I don’t mean to sound cheesy or cliché but…” What follows that “but” ranges from waxing lyrical about the ability to control the professional and personal work they do, to an appreciation of work-life balance, to a full-on embrace of occupational joy and diversity. “It sounds cheesy, but if I’m not having fun, I’m not happy.”


That many freelancers sound like they have to defend their chosen career path says something about the state of the work world. It’s as if being satisfied in your work and how you go about it is something to feel guilty about; like somehow being your own boss is equated with not having a real job and faffing about in your jammies; as if in order to do real work you have toil away at a “stable” job with an office and its attendant politics. But, really, it’s the full-timers who should be defending the act of working at a desk inside a big office. Because, as we know, the state of work is changing.

As Fast Company has documented at length in its Generation Flux series, work can’t be defined in the old ways.

The pace of change in business and culture is breakneck, and predicting what that job at that big company is going to look like next year, or what creative opportunities are going to present themselves to you, more difficult. As noted in Generation Flux: “what defines GenFlux is a mind-set that embraces instability, that tolerates–and even enjoys–recalibrating careers, business models, and assumptions.” It’s a mind-set that’s shared by people who choose to pursue a self-driven creative career.


But what advice do successful freelancers give in terms of actually living and working this way? Mainly: get over it and just do it. While working independently is not all lollipops and rainbows, what with the added responsibilities of business finances, the stress of erratic income, and the unpleasant prospects of hustling for work, freelancers will tell you that the benefits far outweigh the drawbacks.

We solicited the opinions of nearly a dozen creative freelancers, from the established to the newly independent, to get the skinny on being your own boss. They shared candid insights on everything from building their own personal brand, to the ways in which they choose and create their work; from the sharing tips on navigating the annoying bits like finances (spoiler alert: get a great accountant), to the lifestyle perks that seem to trump the pain of going it alone. Here are their insights.


Since the purpose of this exploration was to gain insight on how to be a happy and successful creative freelancer, we surveyed a range of creative people, including agency writers and art directors, developers, designers and digital creative directors. Known for a specific expertise, their freelance work has followed the path they forged while working full-time. In fact, that’s the biggest piece of advice for those looking to take the leap: work in your chosen industry for long enough to establish contacts and gain experience. Then, follow the work you want.


“I’d say don’t start freelancing until you’ve done at least five years in the business you’re freelancing in,” says Tom Christmann, a longtime agency executive creative director who struck out on his own two years ago and balances his time between ad work and creating comic books, graphic novels and designing games.

Tim Geoghegan

Tim Geoghegan, also a former agency creative exec and now a global nomad who’s been known to work from a hut in Bali, agrees: “Build a strong reputation first. Don’t destroy that reputation while freelancing. Try not to burn bridges. Know your strengths and weaknesses. They’ll become very clear and exponentially stronger and weaker while freelancing.”

But experience alone won’t necessarily cut it, says Kerem Suer, an independent UX/IA designer who started freelancing so he could “work hard and play harder.” He recommends some serious research before setting out on your own. “Freelancing is not that fun little side thing you do, it’s a job and it comes with responsibilities. So a little market research wouldn’t hurt.”


Being as prepared as possible will help when that panic of the unknown strikes. And it will. But, according to art director Daniel Shapiro, who initially started freelancing as a way to look for a solid full-time job he could settle into, “The unknown is what makes it both challenging and enjoyable. It will be slow at first and it will terrify you but try and relax and enjoy the time because once you’re busy you probably will be for a long time.”

Building Your Own Brand

Let’s face it, talking about yourself in “brand” terms can be a bit unsavory. Yet, it’s a necessary evil, particularly when striking out on your own. Whether creating a corporate entity under which to operate, or rocking it as a sole proprietor, freelancers need to ensure they’re consistently in front of prospective clients.

“I always felt weird networking and selling myself, but I’ve found it’s a necessity,” says Geoghegan. “When I first started in this business, the rule was ‘let your work speak for itself.’ To a point, it’s still true. But the chances are, even if you think you’re top of people’s mind, you’re not. You just have to promote yourself and point to your track record.”


The most important reason to spend some time being fully employed in your field of choice is to build such a network of friends in hiring positions so work can come from word of mouth and referrals. Because the alternatives can be a bit dicey.

“Online freelancing services are a last resort to me for finding work, mostly because they come across as cut-and-dry projects thrown out to the masses for the lowest bidder,” offers developer Nick Jonas. “While I’m sure one can find some great opportunities on sites like Krop or AuthenticJobs, they are like the E-Harmony of the creative professional world. I’m more keen on working with someone I’ve established a sense of trust with, whether it’s a 1st, 2nd or 3rd degree connection.”

But that doesn’t mean all online networks deserve the same dismissal. New breed services like Working Not Working (with its simple mechanism for letting ad creatives broadcast their availability status), The Supply (which specializes in representing and placing highly specialized digital talent), and The Idealists (a tightly curated community of talent and clients that allows for creative matchmaking), as well as sites like Dribbble and Scoutzie, all provide more connections-based ways for freelancers to find the right work.


While on the topic, don’t even get freelancers, particularly designers, started on the topic of crowdsourcing. Quickly hailed as a new way for clients to tap (exploit?) the power of the masses, crowdsourcing is generally seen as a scourge by many of those who are paid for their ideas.

Adam Tompkins

“I don’t, and would never, use a crowdsourcing platform or site,” says Justin Gignac, who, along with fellow art director Adam Tompkins founded the aforementioned Working Not Working and who also made art out of New York garbage. “Creatives should get paid for the work they do and not be throwing work into the mix in hopes of ‘winning’ and getting paid.”

Still, no matter how work is scored, the biggest boost to a freelancer’s personal brand is the most basic. “Work hard and be nice,” says Shapiro. “The more people you work with the more chances you have to make a positive impression. People who do a good job are talked about, and so are the people who don’t.”


“Networking is very important, but being a good human is number one. No one wants to work with an asshole,” offers digital art director Katie Meza, and Gignac adds: “Don’t be an asshole. It’s not just about being talented anymore. People will only call back freelancers they actually want to work with.”

We’re sensing a theme here.


So what does the work life of a freelancer look like? It entirely depends. Some choose to work in-house at various agencies, taking one gig at a time, while others insist on working from their own space and handling multiple projects at a time. No matter the chosen path or clients, freelancers say be sure set limits on your work–a difficult thing for creatives accustomed to high-demand work environments.


“I would say one of the biggest challenges with freelancing at an agency is setting and maintaining limits,” says creative director and art director Kim Haxton. “You are getting paid for something that you agreed to in advance, and of course because of the nature of advertising, something will inevitably change, you’ll be asked to work longer hours, you’ll be asked to take on more than was initially explained to you. If you’re not tough, it’s easy to get taken advantage of.”

The best agencies to work with, she says, are the ones that realize the situation they are putting you into. “They take the time to brief you properly. They give you access to all of the shop’s resources, and they are realistic with their expectations. That is the best way to set up a freelancer to succeed.”

The in-house or in-your-own-house question is dependent on both the freelancer’s preference and the client’s needs.


“I won’t work on-site. I’ve lost some opportunities because of this, but really people want you to be within their sight because they want to babysit you,” says says front-end developer and creative technologist Mike Bodge, who started his career as the “first digital guy at JWT.” “These are the clients that suck. I will go in for meetings and reviews and stuff, but any real work I will do in my own office. I have my setup all perfect, and the best environment for me to work.”

“Everyone in this business knows the real thinking happens away from the desk and out of the meeting rooms. The best creative resource managers understand this,” offers Geoghegan. “There’s a very real, professional way to manage a ‘loose’ creative process by using check-ins and strict deadlines. Then again, face-to-face and spontaneous interactions are often essential as well. That’s why I like new workspace situations like Co Collective’s Grind or Wework. I think that’s closer to the future of how we’ll all work.”

If the choice is to work from home, limits need to be set there, as well. “It’s really important to have a separate office area,” says Haxton. “You can’t work from your bedroom, or your living room. You have to be able to feel like you’re not at home. Otherwise, you’ll just get distracted, and end up vacuuming or something. You really have to pretend that you are away from home, at work.”


For Christmann, “a comfortable chair, Spotify, Black Sabbath and a pair of noise-canceling headphones” turns any physical space into the perfect workspace.

Tom Christmann

That decision, whether to step into an office culture or work alongside it, can have an impact the level of collaboration on a project, though most freelancers say they feel a part of whatever creative process they’re working in (with the occasional comment about being a hired hand for certain jobs). But for Geoghegan, being slightly detached has its privileges. “I’ve learned to just let go more. To present ideas I love, to fight for them of course, but to know when to let go. It’s like a breath of fresh air when you’re actually paid to… let go.”

Tompkins agrees: “I value the constant change. I never liked getting too involved with one client or another. The longer you work on a project, the more politics you are exposed to. At a certain point, it’s hard to not get involved and it’s never good for the finished product. As a freelancer, it’s easier to float above that stuff, seemingly ignorant to its existence.”



Image: Flickr user John Wright

Unlike other professions, being creative for a living is a nuanced alchemy of working to a creative brief, inspiration, talent, and perhaps a bit of eye of newt. Which is to say, it’s impossible to define how exactly to be creative. That said, the freelancers we spoke with have all devised a custom-fit routine that allows them to work at full capacity, whether it’s the ability to take a walk outside, as valued by Haxton, or the ability to work in your unmentionables (“Someone is paying you to click around on your computer while you’re in your underwear. Never forget that privilege,” says Bodge.)

“It’s important to have a routine rather than simply work when the mood strikes–sometimes the mood may never strike and work just won’t get done,” offers Jonas. “Remaining focused is always challenging, and I think highly depends on the work environment you put yourself in and staying healthy and active outside of work. It’s hard to stay focused in a noisy and distracting work environment, and equally hard with little sleep and exercise.”


Bodge divides his time up between “concentration days,” where he follows a strict schedule to allow for uninterrupted thought and doesn’t talk to anyone, and “random stuff days,” which involve calls, writing proposals and client revisions. “I hate these days the most,” he says. Regardless, he tries not to work past 6p.m. “I don’t believe working later makes me more productive. If you have to work long hours it’s because you have unreasonable deadlines or you’re not working efficiently.”

Christmann says he’s a big believer in quantity over quality when it comes to idea generating. “I try to get four ideas in the morning and four in the afternoon. It makes it a game. So after three days, I’ll have 24 ideas that are all on brief and pretty good. Once I’m in crafting mode, when I can see an idea becoming real, a great idea is inspiring.”

It’d be near unfathomable to talk about setting your own work schedule without meeting a few night owls. Suer is one such, and he takes this idea to the extreme. “My creative process is not really that different than when I worked full-time, but timing is almost opposite. I now work night shifts where there are no email or phone distractions. But my wife’s schedule is also helping the situation, as she’s a night shift nurse.”

“I’m more productive at night when there are less distractions and my brain has slowed down a bit. Between emails and iChat and the Internet it’s more of a challenge to be efficient during the day,” says Gignac, adding that for him, motivation and productivity are sometimes at odds. “I’m motivated by all of the amazing, inspiring and envy inducing things I see on the Internet all day. Which are the same amazing, inspiring things that make it so difficult to stay focused during the day.”

And what of that all-important motivation? It seems that when the choice of work is theirs, freelancers find motivation comes a little more readily.

“Motivation is easy. I’m always motivated to do a good job, no matter what I do, because I don’t consider what I do separate from who I am. It reflects on how I feel about ideas, people, and life itself,” says digital creative director Sheena Matheiken, who is behind the popular Uniform Project. “Inspiration, on the other hand, is a tougher beast. It has to be nurtured, molded, left alone, brought back to life, wrestled with, caressed, fussed over… all of that and more.”

Tompkins, who describes himself as a binge and purge freelancer, says success is his motivator. “Every creative wants to win. If you solve a problem for a client and it’s your work that gets produced, and that work helps them (or wins an award for being especially creative), that is success. Success is the same for everyone. More work, better work, more money, personal satisfaction and growth. Happy parents that brag about you. It’s all good.”

Building Your Office

There is one very distinct pleasure that freelancers find when they first establish themselves: the ability to go tech-toy shopping and write the spree off at tax time.

Says Bodge, “Having a great setup at home was always important to me even before I was a freelancer but now buying toys is fun because I can just tell my wife it’s for work and it’s a tax write-off.”

Shock of shocks, the freelance contingent we spoke to are doing their part to keep Apple stocks nice and high. MacBook pros are the central nervous system of choice, though whether or not a dual-screen 27” cinema display is part of the packaged depends largely on the creative focus. “My Mac Pro with dual 27” screens and Aeron chair is my cockpit and I see these screens more than I see the back of my own eyelids,” says developer Bodge. “It’s a seriously pimped out machine that can handle anything I throw at it. Never be cheap with your computer or chair if that’s your job.” Some creatives, on the other hand, prefer smaller gear for those days when working in the garden at MoMA is a must.

Adobe also fares well at the hands of creative freelancers (“I would have no possible way to make money in this world if it wasn’t for Adobe. I can’t build anything with my hands, I’m a horrible rapper. Trading .PSD files for money is the only way I can keep my lights on,” adds Bodge.)

Other common indispensables include Basecamp for project management, Harvest for time-tracking and invoicing, Wallet for password management, Actionmethod or Evernote for note keeping, Google apps for remote collaboration, and Spotify or Rdio for tunes, of course. And calendars, says Suer, who admits that his super-specific planning has resulted in friends calling him a “schedule Nazi”.

Getting Paid

The love-hate relationship of working as a creative freelancer can be broken down simply: art vs. math.

No surprise, but some creative people don’t much like math; they prefer creative variety, meeting new people, being stimulated by environments, a lack of office politics, having ownership of their own success, free time in between jobs and the ability to work on personal projects. Things become a drag when billing, IT, accounting, health insurance and other logistical matters enter the picture.

“There’s a reason we became creatives and not business people, because we’d be terrible business people,” says Gignac.

“There are so many formalities, paperwork, technicalities and math. This is not why I went to art school,” echoes Suer.

But according to our freelancers, it’s worth sucking up as a tradeoff for the freedom and flexibility of freelancing, though not without a word of caution: have about six months cash in hand before making the jump.

“Overextending yourself can have real implications, and not having a certain amount of liquid cash on hand can mean you miss a deal to invest in one of your own projects,” cautions Geoghegan, who also recommends invoicing quickly, clarifying details up front and staying up to date on COBRA payments. Freelancers Union is also valued by freelancers when it comes to insurance.

And then there’s the question of setting your rate. Like the noxious Honey Boo Boo, freelancers gots to get paid, the difference being, of course, that creative professionals tend to shy away from the topic.

“Set your rate competitively, with a lot of consideration. Then, never go down on that rate. Your rate is how you value yourself and that is how others will value you,” says Geoghegan. “And a day rate might seem like a lot, but when you factor in taxes, expenses, chances of not getting the next gig quickly, it evens out. The only time I’d go down on rate is if I’m invested financially in a project, or it’s an opportunity outside of advertising that will benefit me more in experience more than financially.”

Bodge insists that freelancers should never work for free. Ever. “Once someone knows they can get free work from you, they will expect it in the future. Make sure you have a simple but beautiful portfolio that shows off your work. This is what will get people to call you.”

Matheiken views her rate strategically. “Always say yes to gigs you feel excited about, even if they can’t meet your standard rate. If you choose those gigs wisely, working for less money can actually put you in a position of power. I make it a point to negotiate this by buying myself more flexibility and time in return for a lower rate. It almost always works. The clients are appreciative of the deal you are cutting them because you are excited about their business, product or whatever it may be. And that eventually leads to more work, at your standard rate.”

The final bit of logistical advice is rather simple, according to Meza: “Get a bomb-ass tax ninja!” Taxes will often come as a shock to first-year freelancers, but saving money for the tax man and working with someone who’s skilled at eking out the best deductions for creative professionals is simply a no-brainer. “Work with them to figure out how to pay your quarterly taxes. And also start to save your receipts for everything,” adds Haxton. “As a freelancer, you have a much higher percentage of getting audited.”


Image: Flickr user Thomas Milne

The dream of freelance is sold on the promise of work-life balance. Take a month off after a tough gig! Spend more time with the kids! Finally work on that backlog of personal projects!! All noble aims and the best reasons for anyone to take a less defined career path. So what of the infamous freedom of freelance? Living the dream takes work and a large dose of discipline.

“I just worked through my second vacation in a row, so I may be a workaholic,” says Christmann. “But having breakfast with the family every day and making my own schedule has been amazing. And yes, I still get nervous when the work dries up. But then it comes again and I’m like “why didn’t I enjoy the down time?” Maybe someday I’ll learn.”

Yes, time management is a perennial bugbear when it comes to striking the balance between professional and personal work. No one wants to say no to interesting work, and the fear of not making enough money can lead to less than ideal gigs.

“I still tend to take on too much work at a time. Even though I’ve been saying no to a lot of agency work, I’ve said yes to a lot of independent projects–mostly because it’s stuff I actually want to work on. But now that I’ve got so many projects, each one is probably going to be a little less good, and therefore satisfying to work on because I have to divide my time,” confesses Haxton, sharing the creative risk of over-booking.

“When you’re freelance, you take on 2 or 3 projects and you get 2 or 3 times the money. But you have to be sure you have the bandwidth. Sometimes you bite off more than you can chew. I’ve learned to say no. But it still burns,” says Christmann.

It seems the key to successfully balancing interesting work with a better quality of life comes in not worrying about money, counterintuitive as it might be.

“I don’t freelance for the money right now,” says Geoghegan. “Downtime is so important. It’s a necessity to refuel and recharge. The amount of time between projects can revitalize you, de-stress you, fill you with new ideas and expose you to a lot more stimuli than if you were stuck in an office on 5 projects at a time, every single day. That’s what breaks people, burns them out, and causes most full-time positions to average about 2 years. That’s the antithesis of what a creative industry needs.”

Matheiken says it’s been really important to not stress about money. “When I decided to go independent, I made a very strict rule about only working 50% for money and dedicating the other 50% to personal projects and other collaborations that I truly cared about. I can honestly say I’ve stuck to this plan so far, except that instead of 50/50 it’s been more like 80/80. And yet, there is no stress. I quite enjoy everything I’m doing right now. Of course, when I’m done with current projects I’ll take a month off. Knowing that you can do that is in itself half the reward, and the main reason to be freelancing after all.”

“You’ve got to learn to relax in the downtime or it will drive you mad,” says Shapiro. “After a few months of freelancing you begin to see how the industry cycles. The sooner you realize this the sooner you can relax.”

“In the end you have to do what makes you happy. Life’s too short, and if you’re not happy at your current situation, know that you have the power to change it into whatever you want. You just have to be brave,” adds Meza.

Gignac puts the question of balance in plainer terms. “Remember you can say no. You don’t have to take a job you don’t think is right for you and don’t want to do. You don’t have to work weekends. You don’t have to cancel family vacations or birthday dinners or plans with friends. You’re in control of your life and your schedule.”


For this group of creative freelancers, the overriding sentiment is one of satisfaction. Sure there are annoying bits, but with curiosity, a good work ethic and the commitment to consistently producing good work, freelancing can be extremely fulfilling.

“I seriously don’t know why more people aren’t doing this,” says Matheiken. “I know too many talented people stuck at unhappy full-time gigs under the false pretext of security or comfort or whatever they rationalize it to be. Being independent brings a new sense of openness, which is incredibly nourishing for creativity. I am suddenly open to the world, to new ideas, to new friends, to new opportunities; everything has an enriching possibility.”

And that, says Geoghegan is exactly what the creative world needs more of. “We need that to be the driving feeling for everyone in a creative business. Freedom. The freedom to break out of every boundary including our antiquated working model. It would make the business much more creative, and contrary to perception, much more productive.”

And happy. As if providing the perfect endnote, Gignac recounts a story about Australian nurse Bronnie Ware who had spent several years caring for patients in the last 12 weeks of their lives. “She recorded their epiphanies in a book called The Top Five Regrets of the Dying,” he says. “Number one on the list: I wish I’d had the courage to live a life true to myself, not the life others expected of me. And number two: I wish I hadn’t worked so hard. These people know what they’re talking about. We should listen.”


About the author

Rae Ann Fera is a writer with Co.Create whose specialty is covering the media, marketing, creative advertising, digital technology and design fields. She was formerly the editor of ad industry publication Boards and has written for Huffington Post and Marketing Magazine