DESIGN WAS so much easier before I had clients. I assigned myself projects with no requirements, no schedule, no budget, no constraints. By most definitions, what I did wasn’t even design—except that it ended up creating new things, some of which still exist on the web. Soon I had requirements, schedules, and constraints, but most of those were self-imposed: for instance, I designed the first A List Apart, published a fresh issue every week, and created title illustrations for every article. This was design, but self-directed. I found it easy and natural and it never felt like work at all.
But then a curious thing happened: I began to get clients. And the more clients I got, and the more complex and sophisticated the projects became, the harder design became for me. I wish I could say I approach design with fearless joy, but the truth is, the longer I do it, the harder and more unnatural it becomes. Starting new projects is easy when you have almost no clue what you’re doing—as easy as playing is for a child. With experience comes knowledge of all the depth and skill you lack. You know how great some design can sometimes be, and how unlikely you are to attain anything resembling greatness on any given project. The very idea of beginning terrifies you.
You work past that, because you’re a professional, but the ease is gone. Maybe it’s just me.
And it isn’t just design. Writing comes naturally to me when I’m expressing myself on my own site, with no outside assignment and no deadline except my own sense of urgency about an idea. It’s easy when I’m crafting a brief text message or tweet. Or a letter to a friend.
But give me a writing assignment and a deadline, and I’m stuck. Paralysis, avoidance, a dissatisfaction with myself and the assignment—all the usual hobgoblins spring immediately to life. I fulfill my assignments, because I’m a professional. Sometimes, once I’m far enough past the initial internal pleading, denial, and bargaining, and have put in the first dull miserable hours of setting one word in front of another like a soldier on a long march through waist-high, rain-drenched mud—sometimes at that dreary midpoint, everything unblocks, and I feel pleasure and clarity as flow returns. That’s what writers on assignment fight for—to reach clarity and naturalness after slogging through the hateful murk.
I also play music, and I’m good at it as long as I’m sitting in a corner at an instrument or console, making stuff up for my own pleasure. But create a commercial music product? Not so much. I once had a small recording studio. I got rid of it. Too much pressure.
You get it.
In my heart I remain an amateur. The spirit of play is where my gifts lie. After 30 years in business I can do the other thing—I can fight through the loneliness to make good product on demand. That is, after all, how I feed my family, and there are many far worse ways to earn a dollar. But it’s never easy. It’s never The Joy.