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To Dance the Dance of Freelance

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In: Articles

By Matthew D. Jordan

Published on March 27, 2007

Thinking back on my transition to full-time freelance work brings a myriad of emotionally confusing scenarios to mind. I sometimes allow my brain to conduct a symphony of uneasy visions of the parts of my life that would be better had I remained under the full-time employ of The Man. There would be the certainty of my regular paycheck, and its amount. There would be a kind hand on the shoulder and a soft word in the ear from my bank. There would be other people to interact with all day. There would be a plethora of insurance benefits toppling those I have now. There would also be the strong possibility that the synapses in my brain would once again begin to misfire due to a micromanaging stereotypical corporate agency, letting my thoughts yield to the primal urge of setting the building on fire and painting a large archaic symbol on my chest using the blood of my coworkers.

This is one reason I remain a freelancer.

Several years ago, I was hired in my first agency position as a 3D animator. As a sample of my work, I shared an uncomfortably bizarre demo reel laid across obscure techno music, a piece I had put together using old 3D software called Bryce. I wasn’t applying for a job as a 3D animator mind you—I went in basically looking for them to hire me to do whatever they wanted, be it 3D work or holding my hands in a cupped shape for the CEO to discard peanut shells into. A week later I was hired, so I bought some tan slacks and colored socks, and I cut my long hippie hair into a respectable corporate haircut. I spent the next fourteen months there and—much like microwaving my own shoes—I accomplished very little, but learned a lot.

You see, due to the poor management of this company on every level, they had hired a 3D animator (me), but had never done 3D work before—and they didn’t do any active marketing for, well, anything. I wasn’t making much money, so it wasn’t a huge financial drain on them, which meant I was able to haunt the hallways for a little over a year, picking up things such as how the design process works, how to properly conduct process meetings, and that you can roll up an entire pack of Gushers Fruit Snacks into a ball and eat it like one giant Gusher. I was gradually transitioned into the Interactive Team and got really interested in web design. I created that agency’s first intranet, a massive project that they promoted internally by way of posters and even themed coffee mugs. We launched the intranet, used it like crazy, and then they canned me a few weeks later. Checking their portfolio, I see it’s the same now as it was six years ago.

After I was canned (they called it laid off) as a pseudo-web-guy, I spent about a month just sending out resumes and sleeping until about seven at night, slowly slipping into physical depression, living on chocolate-chip waffles and store-brand Fruit Loops. I finally got a phone call from an advertising agency that was looking to hire someone to replace their web intern, and when I got there I was so out of it I totally forgot what I was interviewing for. I only had a couple of websites in my portfolio, but they seemed to do the trick, because a week later they offered me a job. I spent the next four years gradually learning to hate the typical poorly paying advertising agency, its micromanagement, and its disdain for its employees. While my agency time wasn’t fun, I learned a lot about the world of web design, and went from replacing an intern to being the agency’s only web designer. I wasn’t that great, mind you, but I can make a mean pot of Joe, and I acquired a killer French toast recipe—never doubt the power of French toast. I learned about screen dimensions, color theory, the client process, and not to splice photos of my Grandma at the roller disco into a design just because it’s funny. OK, I never really did that, but it’s something I’ve often thought would provide the sweet, sweet icing on top of the “I quit” cake.

The transition from full-timer to the “oh my God, I need clients” freelancer wasn’t a smooth one—but it rarely is. This is probably the topic people ask me about most often—along with wondering why I keep sending them anonymous photos of their family eating dinner. I made the move one trepidatious step at a time.

In January 2005, despite the apparent financial success of the agency, this was another year in a row where bonuses would not be distributed, and raises would be less than two percent—that is, if you got a raise at all. Instead of doing what any rational person would do, and start threatening management by keying foreign curse words into their cars, I decided I was going to leave—to finally strike it out on my own. I knew that it seemed like everyone everywhere offered web designing services. “Need a new computer? We do websites too!” or, “Okay, that’s one large soda and extra fries. Need a website with that?”, or “My nephew does that website stuff, too. He uses Microsoft Front Expression Page Live 2.0.”

Slowly but surely, I made connections by looking online, and researching local companies that offered web design but did a poor job of actually designing anything. I offered myself up as a third party contractor, and as soon as they saw that my portfolio was, oh, a million bazillion times better than their portfolio of gothic MySpace themes, they were ready to start using me. Once I had enough of these resources on board, I gave my notice at the agency, and I was on my way.

My best recommendation is to get involved in freelancing while you’ve still got the comfort of your full-time job. Now, for many people, this causes a conflict of interest with the current company, so be sure you aren’t violating any corporate rules by moonlighting. At the very least, there’s nothing that says you can’t put up a portfolio and start making connections. I cannot stress enough that you must have a portfolio to show examples of your work. Don’t have any work? Start by thinking of projects for yourself or friends and family that you can put together. The last thing you want to do is put an ad in the Yellow Pages that links to your blog about your friends and their ironically hip clothing. Do that, and the next thing you know, you’ll be tap-dancing for nickels in a shady downtown bar called, “Uncle Nathan’s Cheese-Stick Jamboree,” counting the seconds until your day is over and you can go back to crying into your box of wine. I was constantly working on my portfolio, while also scouring the internet, reading dozens and dozens of articles about people out in the field—not to mention soaking up plenty of information about things like taxes and incorporation rules. I knew there would be a lot to consider.

My very first major client was a law firm that, like many law firms, needed a web presence. Man alive, did I learn a lot, and I learned it the hard way. Not the fun kind of hard way where there’s a montage of me doing web things over some eighties music, and at the end I nod to the camera and give it a big thumbs up—screen wipe—and I’m shaking hands with the client. No, this was a foray into the world of the picky client who never reads email. This was a magical journey that taught me I should always have a formal document that serves to outline the process from start to finish, so we always have something to refer to when questions arise. I also learned it’s important to have an inside man on every job, if you can. Sometimes, the big boss who ordered up the website has very little time to actually get you the answers you need to your questions and pay your invoices, and without a useful contact inside the company, you will only draw closer to setting up that army of frog skeletons in your basement—whom you refer to as “The Legion”—who obey your every command. My first project was a three-week website that took almost an entire year to complete. In the end, it was the sum of both of our faults, but there are just some things you learn the hard way.

From then on, it’s been a series of learning experiences that are invaluable. Okay, I’d probably trade them for a cool million—but I’m getting ahead of myself here. When I was working for the agencies full time, I always had this fantasy that when I went solo, I’d wake up at the crack of noon, throw on my sweatpants, make some coffee, then head to my desk and watch the rain fall. AHAHAAAHAHA…hahahah…haa…whooo…that was a good one. I quickly found that penciling in a trip to the movies or spending all day in a coffee shop like we see on television is a pipe dream, and nobody who makes actual money or grows a business can do things like that. I found that the biggest positive to freelancing is that I can decide what projects I work on, in what order, and when the client can expect them. Nobody tells me how long a project will take—I tell them. If I need a break, I take one—no one is scowling over my shoulder if I need some Ovaltine and a fifteen-minute dose of Keith Olbermann. All in all, freedom to schedule my work week the way I want it is my favorite part. Also, I don’t have to wear big boy pants to work.

I have ten t-shirts and four pairs of sweat pants that are my work clothes. Now, I do have to put on real clothing when I head out to a meeting, but this is increasingly rare—I’d say ninety-five percent of my work is conducted in a virtual environment. On any given day, I’m having meetings, working, or setting up projects with people in four different states. I’ve conducted entire projects, start to finish, this way—I’ve even been doing consistent work with one company over the past two years, and we’ve spoken on the phone only once. There are down sides to this, though. I spend most of the week in what I call the “Matt Cave”—it’s our finished basement, and I’ve set up camp in one of the rooms. It’s quiet, and I can listen to music all day while my bulldog Carl sleeps on the couch, but I’m actively looking into getting a laptop so I can move to and fro in the world and not slowly become one with my home. The last thing I want is for my wife to come home and find she can only communicate with me ethereally—I’d whisper to her through the duct work and use my sheer will to paint hearts in condensation on our windows. It’s very easy to let freelancing consume your life, since you’re technically always at work, so I set limits for myself. I don’t answer client emails after five p.m., I don’t work on the weekends, and I don’t sleep in a fetal position next to my computer waiting for the dee-doo chime that lets me know an email has arrived. Try these rules for yourself if you work from home—because you must set rules and act like your own boss. After all, you are.

For those whose eyes will squint, dart side to side, and ask, “Just who are you, freelancer?” I answer you this. I’m just another brave soul on this rotating ball of dirt and stone we all call home. I’m just another traveler taking in the smells and unearthing the truth that lies in the space between the light and the shadow. I’m just a man calling his lifetime an adventure—helping those in need who call out in the night, aiding the drifters with questions about the nature of things. That, and I do freelance web design.

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Related Topics: Business, Client Management, Web Design


Matthew D. Jordan is a freelance web designer (Electric Dynamic) out in beautiful Colorado, and author of the weekly web show

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