The Biggest Challenges Facing Independent Designers

June 6, 2006

Starting Up is Hard to Do

Newly-independent designers often worry about finding clients and work. It’s scary. The cost of health insurance and the ability to generate work are the two things that keep normally creative, defiant thinkers working for the man. If you’re dreaming of the independent life—your own hours, no commute, working in your underpants—the most common advice is not to jump ship until you’ve got a couple of solid gigs lined up. Make a master list of all your business contacts and get busy. While you’re planning your bust out of Alcatraz, stash away enough loot to keep you afloat for at least three months. More often than you think, those promised, guaranteed, definitely-green-light projects will be postponed at the last second, or fail to materialize at all.

The Bills Your Boss Used to Pay

Having to pay for your own health insurance and fund your retirement really sucks. I have an HMO through my local Chamber of Commerce. It’s restrictive but it covers our family. In 1996 a spider bit my ankle. Nothing bad happened. But between the grime of New York Sticky and scratching that delicious itch, the bite swelled up so much I couldn’t bend my ankle. What with doctor visits and meds, I spent about $900 in two weeks. I hate my health insurance premium (especially when I feel healthy, young, eat well, etc.) but you just can’t do without it in this country. If you can’t afford an HMO, a Health Savings Accounts in conjunction with Catastrophic might be your next best bet.

Too Much to Chew

In the past, I’ve had periods where I’ve taken on too much work. It was never worth it. Even when I was in my twenties and made of rubber, staying up half the night (or all night) drained my life’s energy. Every time I did it, it crushed a little piece of my soul. There’s nothing worse than that burned-out feeling, where you’re dragging your increasingly chubby ass to work only to climb a mountain—all the while worrying about your other clients looking for an update on their project. I’ve learned to pace myself and say “no” when necessary. I’ve learned not to work with jerks. I’ve learned not to work on projects I’ll hate.

Shark-Infested Waters

It took me five years to realize that whenever a potential client said, “If you do this one cheap, there’s a lot more work down the line,” it was, in each and every case, a load of number two. It wasn’t around when I was a tender wee lad but No!Spec is a great resource for independent designers.

Losing Your Way

One of the slipperiest slopes is trying to be all things to all clients. I started in print design, did that for a number of years, then the Web came along. For a long time, I tried to do both. Last year, however, I decided I was kidding myself if I thought I could be the greatest pixel pusher known to man and Milton Glaser’s print nemesis. It’s an easy mistake to make. When you’re running the shop, you need to pay the bills. So when a client says, “Can you turn that brochure you did into a Web site for us?” you say, “Sure!” and off you go. I’ve learned a lot doing things that way. The problem is that developing real expertise in a field means you can’t spend half your time fiddling around with something else. For me, being a full-time Web head means constantly reading, constantly learning, constantly keeping up with new Web technologies. It is a full-time job. At least now I can snort at designers who “specialize” in print, photography and Web design.

Losing Your Way, Again

Unless you take steps to maintain your perspective, tunnel vision will happen to you. Life can become a blur of work, work, work, work, work. For designers based at home, say, it’s a real struggle to maintain a solid work/life split; when my office was in the house, I never really managed it. With the computer calling out to you morning, noon and night, “I’ll just check my e-mail,” inevitably turns into an hour’s work, or more. This is a bad way to live. Your work-life is supposed to feed your home-life, and vice versa. Your home-life shouldn’t have a stapler and pile of invoices in it. I now have a separate building for the office. It’s on our property, but at the end of the day I can leave all my work paraphernalia where it belongs. I work strictly 9-5 and almost never on weekends. I know designers who seem to be able to keep their work and home lives separate, even when their office is part of their living room, but if you’re not that disciplined, and you don’t have a separate space for your studio, renting space may be something to think about.


Tied with work/life is every designer’s favorite guilty pleasure: procrastination. Some swear by it: they say the last minute pressure fuels their best creativity. Maybe so. If we’re honest, though, most of us probably swear at it, and ourselves. Procrastination cheats both designer and client. By 2005 I was so sick of my ways I read six or seven books on the topic. The best by far was Neil Fiore’s compact classic The Now Habit. I keep it with Getting Things Done in my office. Both have key-for-me passages highlighted. They’ve saved my bacon many a day.

Staying Organized

I don’t have a problem keeping track of multiple jobs. I’m well organized and have a system in place (taken from David Allen’s Getting Things Done) that does 90% of the work for me. But I sometimes find that switching from one project to the next can be quite tricky. When I’m on a roll, I’d rather spend 3-4 hours working on a project. It bugs me to have to stop and start. But keeping multiple clients happy means I’m often forced to work in 30, 60, and 90 minute project-chunks. Clients need to see a little progress every day or two. When you have 15 or more active projects running, it’s challenging.


You have to be your own bean counter. Keeping track of expenses, paying quarterly taxes, typing up invoices. Is that vomit in your mouth? I’ve got it down to about seven hours a week. Two hours for billing, the rest for planning, office work and publicity.


Not the least of the independent designer’s problems, working alone can be a serious stress on your well-being. No matter how wacky your workspace, you just get sick of being in the same environment every day. An on-line design community like HOW or Creative Ireland can take the edge off, but nattering with peers, especially when there’s an argument brewing, can become a major time-suck.

Once or twice a week, a change of scenery works wonders; WiFi is now so widespread you can easily work from multiple locations, cappuccino in hand. My local library and nearby cafés all offer free WiFi. Noice.

I read somewhere that you need 12 social interactions with different people every day—or you’ll go mad. Mad! Thankfully, they don’t have to be deep: a quick chat with the post office clerk counts. Doesn’t matter. Seeing familiar faces and dealing with your larger community just keeps you feeling topped up.

Once a day, I walk the dog and check in with the neighbors. They keep chickens, make hunting bows from scratch, distill things they shouldn’t. There’s always something going on. One guy is an expert balaphone player. Another is missing half his nose and lets his poodle shit inside the house; not, I imagine, the best of combinations. That guy annoys his closest neighbor, a crusty old geezer who fought the Commies in the Korean War, hates his brother’s dog and likes to shop at Target. That’s what’s goin’ down in my ‘hood.

In 2010, still struggling with this issue , I joined a coworking space. Many large cities have several coworking spaces, and even some smaller cities. It’s been a huge help seeing familiar faces several times a week.


12 Responses to “The Biggest Challenges Facing Independent Designers”

  1. Vonster Says:

    FYI: Avoid MEGA Health for insurance. They suck eggs.

  2. Sean Says:

    Thanks Von! GHI HMO too, they suck like an Electrolux.

  3. Good points, all.

    My situation: My kid’s on child health plus (a step above medicare), I rely on my knowledge of herbalism for my own healthcare. There’s absolutely NO way to afford rent, bills and healthcare. Not happening. Not even if I feed the family ramen noodles.

    I work out of the house. I can’t WAIT to afford an office, but for now it has to work. Again, no choice. As soon as possible, the spare money may go into afterschool for my son, because he’s the most disruptive thing about me working from home.

    As for “overspecializing” I definitely agree — to a point. I’m not the world’s greatest anything. My selling point is that I’m the world’s greatest everything 😉 I learn, I teach, I advise, and I do. I don’t procrastinate, but I don’t hesitate to overquote how long something will take so that I have the leeway for emergencies or juggling an extra project or four. Most often, though, I’m fast, efficient, finished ahead of schedule, and while I’m not the best woman for any one job, in any case where a client really really wants only one person to handle *insert 5-10 things here* I’m definitely the right woman — and if I can’t do something, or haven’t done it YET — I say so. Period.

    Some people like that. Even if I ended up outsourcing, not that I have yet but I certainly wouldn’t mind, everything passes through my hands and my breadth of knowledge means I know when I am looking at something of quality. I have HTML designers who come to me for back-end coding, but my knowledge of web design means I know how to keep my code out of the web designer’s hair.

    Even if I’m a jane of all trades, master of none, it puts me in a terrific position for team management. I can cover for many positions on the team, give suggestions, show people a new trick or three, and learn something from them. It also means I’m not in the dark on any aspect of a project, bowing to my subcontractor’s superior knowledge and being blind to errors. I’ll know if a coder is slacking on documenting their code, for example; if I can’t read it, they’d better clean it up.

    It’s not for everyone, but concentrating on one thing is not for me.

  4. […] Sean, over at Position:Relative has written a very practical and readable article about the challenges faced by independent designers. […]

  5. This was a great article! As a freelance illustrator I could totally relate. I plugged it on my blog,

  6. Sean Says:

    I didn’t realize there was such a huge on-line cult based around Getting Things Done. If you’re into GTD, you’ll find the following sites reeeeeeel interesting…

  7. Geoff Says:

    Excellent post.
    I’m a part-time freelance and I can feel the work/life split getting tiner and tiner.
    It’s good to be reminded of it from time to time.

  8. […] The Biggest Challenges Facing Independent Designers (I) By Sean […]

  9. RanMan Says:

    Great article. I can relate to every last word.

  10. Stephanie F. Says:

    This is what ALL designers should know before they start as freelancer.

  11. […] The Biggest Challenges Facing Independent Designers […]

  12. […] over at Position:Relative has written a very practical and readable article about the challenges faced by independent […]

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