Writers fed up with run-of-the-mill freelance work should check out the travel writing program at MatadorU.

I AM what people might refer to as a “workaholic.” I am also a freelancer. I enjoy the feeling of completion that comes with clearing my work queue. I’m a devout list-crosser; there is nothing better for me than compiling a to-do list and ticking the items off one-by-one.

Do I particularly like writing copy for real estate courses and IT websites? Hell no, but I like finishing things, and finishing things means doing things, constantly, while looking for more work to add to my list of things to do, thus perpetuating a cycle of unachievable completion.

Sisyphus did (does?) something like this, and had this cycle named after him. He’d be a great freelancer.

Confession: People shouldn’t be jealous of me.

A friend of mine recently expressed some jealousy in regard to my freelancing schedule. “It’s not fair,” she lamented. “You get to wake up whenever you feel like it and take days off whenever you want.”

What my friend didn’t see was someone who is never really not working, who has chosen to forgo the simple joy of an empty weekend with nothing better to do than simply be. I can’t sit around the house watching TV all day, fueled on a steady intake of corn-based snack foods — I have successfully conditioned myself to eschew non-productivity. It makes me anxious, much the way work probably makes lazier people anxious.

Confession: I binge on productivity.

During one of my more desolate freelance work famines, I went on a semi-crazed binge of completing skill certifications on Elance in hopes of bolstering my profile. These are essentially arbitrary 40-question quizzes on things like the Chicago Manual of Style, SEO, UK English mastery, web design, financial prudence, etc., and are designed to show prospective clients things you are good at.

Rather than going to the movies with my fiancée on her days off, as I should have done, I would spend hours a day poring over these quizzes and applying for freelancing jobs I would never get, propelled by some disturbing, inexplicable compulsion to do something “productive.”

Confession: Family doesn’t always come first.

Once, a good client came to me with an urgent editing job while I was with my extended family in Amish country in Pennsylvania. The nearest computer with internet (dialup) was miles away, so I had him email it to me. I edited an entire document in the body of an email on my phone while I pretended to participate in discussion with my seldom-seen family as they rocked away on a swing, watching kittens play-fight in the grass.

You try ignoring your grandma and play-fighting kittens while you edit a construction contract.

Confession: I’m addicted to over-delivering.

One night I took on a client who had a short but urgent job. He didn’t like my drafts, so we cancelled the contract. Agitated more by the audacity of someone knocking my work than by the wasted effort, I proceeded to engage him in an email discussion. I advised this veteran marketing exec about his approaches to the content, offered criticism, and generally shot the shit about marketing. My rice pasta turned to mush in the kitchen as I pushed dinner back by “just one more email.”

He used half of my work and all of my advice. I didn’t get paid.

If I get a freelancing job with a three-day deadline, I have to assume something might prevent me from working two of those days, or that if I work quickly I’ll impress the client into working with me again. I once took a multi-day job, had friends ask me to go sledding, and turned them down to finish the work that day. I could have been fucking sledding, but I chose to work, then didn’t have anything to do the next day when no one was sledding.

Confession: I’ve made stupid mistakes.

My back went out a few months ago and I had to employ a broomstick as a staff just to walk around my apartment. I looked like a 20-something urbanite Gandalf.

I forced myself to pound out an entire website of content in a single day, even though it made me yelp just to move enough to scratch my leg. That freelance work is still pending payment, as the web developer dropped out, but God only knows how it actually turned out. Similarly, I was in such a hurry to finish another client’s ad copy early that I misspelled the company name (I’ve done this several times).

Confession: I’ve alienated myself from people.

When you’re freelancing from home, people tell you how “awesome” it must be to only work whenever you feel like working. For me, the problem is I always feel like working.

While visiting my fiancée’s family this spring, I locked myself in her little brother’s room to edit articles, then stayed up until 3am writing new ones when everyone was asleep. When we went with friends to see a concert in Phoenix, at dinner I typed emails on my phone while they ate dim sum, then stood quietly between songs thinking about the freelance work that was waiting for me on my laptop at our hostel. The night before moving 2,000 miles away from my family last year, every time my awesome nephew with spina bifida would ask me how much longer until I could play with him, I would say “a few more minutes” into my computer screen until it was his bedtime. That client never paid me.

I have worked daily for weeks straight. I have worked on Thanksgiving. I have worked during a creative writing conference. I have worked impromptu emergency jobs while already drunk. I have worked on vacation in New Orleans. I am technically on vacation as I write these words. I have three other open freelancing jobs I will think about when I finish writing this. Ad nauseum.

I’m never really 100% “in” any moment, but that’s a cost of having a career I enjoy.