Hi there Mint! Margot here again with Howdy Do It and I’m really excited this week because I got a bit of an unconventional post for a design blog. I asked buddy of mine, a writer, who’s only seconds ago joined our freelance ranks. Steve’s recently been published on the AV Club (both nationally as well as for Chicago) Variety, and works with the Just For Laughs festival. He’s also former comedy editor at Time Out Chicago & has long been enmeshed in the legendary Chicago improv scene. So, he’s penned a funny piece on his first week solo so far. I’m sure guys can relate and I hope you enjoy his wit. Also, he is almost entirely responsible for getting me hooked on Arrested Development way back when, so that’s pretty awesome too.

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FREELANCING WEEK 1: I AM A TERRIBLE BOSS
By Steve Heisler

It’s 5am Saturday night, and I just got home from a night of old person bingo, $2 Old Style, Ides Of March’s “Vehicle”, and a guy with fake braces, a fake mullet, and a very real fanny pack. My head is throbbing; every muscle in my body is in pain; I barely have enough energy to hold up my toothbrush, let alone squeeze toothpaste on it and, unrelated, later change my pants. Every fiber of my being is shutting down, but I can’t turn off my brain. I haven’t been able to all night, actually. I have a flash of an iota of a thought: “I should probably transcribe that Nick Offerman interview at some point over the next few days.” Oh shit. I freak out. There’s just so much to doooooooo! Fuck. Work. God, if I could just finish that one thing, then I’d be able to relax. Ugh, it’s 5am. I open my computer, compromise with myself and make a to-do list for today, a Sunday, that’s five items long. I go to bed feeling like a failure for the eighth night in a row.

Welcome to freelance writing, I tell myself.

About a month ago, I made an important decision. After three-plus years of working as a part time writer/editor for various local publications, supplementing my income with part-time freelance work, it was time to take the full-time plunge. I was toying with the idea of a move to New York after next summer, so I needed to spend some time pursuing what I’ve only recently realized is my passion: national pop-culture journalism. I’ve done a fair amount, mostly for my wonderful friends at The A.V. Club; I needed to do more. So I gave my notice, and as of November 13, I was no longer working for “The Man,” but rather “the man,” and that man is me.

Problem is, I’m not a very good “man” (nor am I “the man,” as in “You’re the man now, dog”), and after only one week of freelancing, I’m getting scared that working for me isn’t going to be all it’s cracked up to be. Observe the many examples of my shortcomings as the boss of me:

1) Clocking in
To celebrate my newfound freedom, the first thing I did was turn off my alarm. I realized I’ve got all day to work on things, and I was willing to cut into evening hours if it meant waking up at whatever time nature intended. My usual office wake-up time of 9am immediately became 10am, then 10:15, followed by, oh, noon. There’s nothing like waking up in a panic with only roughly four hours of daylight left to really motivate a person to calmly work through his day.

So the goal for week 2: Try to, I don’t know, go to bed at a decent hour. I love the silent time when everyone else is asleep and I’m being productive, but I’d hate to turn into my weird cousin who sleeps all day and is up all night alone. He also has a scary beard.

Tax Day: Bend Over and Take It

2) Time management
When I started, my biggest fear was that I’d be too distracted by my DVR and strikingly specific video game selection to get much work done. Turns out, it’s surprising how easy it is to push bigger, deliberate distractions out of my mind. It’s the little things that are getting to me, like compulsively refreshing my email when awaiting a response to a question about a pitch, or refusing to write another word of a story until I think of the perfect opening sentence—a one-hour process that mostly includes compulsively refreshing my email. Also, I’ve found pacing around my apartment and/or changing seats every five minutes to be an addictive alternative to working.

Goal for week 2: If I’m not getting something, I need to give up after 10 minutes or so and move on. Ideally various projects will inspire one another. Even more ideally, someone else will just do the work for me in my absence. Even more ideally, it’s suddenly Halloween and only adults are allowed to trick-or-treat.

3) Leaving it in the “office”
At least when I went into an actual, physical building for work, I could convince myself that, at the end of the day, I would be leaving and whatever got done would be what I got done, and leave it at that. Simple. This isn’t just about me needing to get out of the house, because I do; almost every day last week I forced myself to go to a different coffee shop or friends’ workspace to preemptively relieve cabin fever. But I found that no matter where I go, the work follows. The simple act of me having a thought is enough to get me wondering about the status of my many little assignments, and begin freaking out. It’s like spending a day off with your scatterbrained boss, who every once in a while shares a random work thought or task he or she’d like you to do once you’re back in the office. And without that mental wall of where the “office” ends and my life begins, those little reminders force me to forget everything else. Three days ago, I made myself coffee at home and drank it at my desk. The mug is still there. Will I put it in the dishwasher? Maybe once I finish this blog. Probably not until I get that other draft out of a piece I’m performing live, send an email to a client about a time estimate, research story ideas for early 2010 for a national magazine I’m close to getting an assignment from, do that TV review from last night, and finish watching The Prisoner—yep, I’ve gotten to the point where I have convinced myself that pleasure is a part of work, just so I know it will get done. Meanwhile, that coffee cup sits there, my jacket is on the floor of my living room, and I still don’t know what time I’m meeting a friend of mine tomorrow. There’s just so much to doooooooo, I wish I hadn’t woken up so late.

Goal for week 2: Set a time to stop working, and stick to it. Even if I’m in the middle of a sente

Love it Steve! Thankssss! You’re a real Mensch. Also, this is the last Howdy Do It post until January, sorry guys! Ellie & I are both feeling a wee bit crazed trying to wrap up projects during the madness of the holidays. But I’m really excited to come back and write for you then; I’m already planning some really neat things to post! So until then, friends. Good luck everyone and I’ll miss you!

Image credits: All from Jessica Hagy’s wonderfully hilarious site, thisisindexed.com.

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Howdy Do It came from “how do you do It,” the question Ellie & Margot found themselves asking about their freelance lifestyles, and so Howdy Do It was born, a weekly column about the things we do to keep ourselves organized, inspired and on track. Margot will be here on Mint each Monday, and Ellie will be over on Pitch Design Union at the same time.