Back in 2011, still reveling in the glow of my wholly-unexpected appearance in the “Best Food Writing” anthology and the success of writing comedy for “The Roe Report,” I decided to ride the overwhelming wave of public encouragement and make a go of it as a professional writer. The result of this was that something that had been a source of joy and pleasure, writing what I wanted to write for a small audience of people I knew and loved, became a tiresome chore that was mostly about mastering the stress of constantly rallying from rejection and “keeping my chin up.” I wrote some things I liked a lot, but I also spent a lot of time unsuccessfully pleading with people who didn’t know me to give me a chance. Mostly, they did not. (Missouri Life is a welcome counterexample, but also the only one.) I have sent out hundreds of pitches to magazines, and sent book proposals to scores of agents, and the result was…nothing. A couple of kind e-mails and one condescending phone conversation.
And yet I tried. I wrote a dozen magazine articles, six plays, and eighty percent of a non-fiction book no one is willing to publish. I was and am happy with all of them, but the only proof of talent the world accepts is in how much money one is paid, and that proof is, in my case, nowhere to be found. I tried my ass off to sell them all, and to turn them into money and a career. But despite what is indoctrinated into all of us by books and television and school, not everyone who perseveres wins. Perseverance isn’t enough to turn talent into money and success in publishing. You also need luck, and of that I have had none.
In May, when I found out about my likely second appearance in “Best Food Writing,” I started to think about going out the way I came in. When Perseus Books, publisher of this most prestigious food-writing anthology, paid me the astonishing sum of $150 for the right to reprint the piece, I let go of the remaining doubts I had. I don’t need to tilt at this particular windmill anymore. I have proven to myself that I am good enough. I am as good or better than the (rapidly dwindling number of) people who do make a living as entertainment/pop-culture writers. I am not quitting because I failed; I am quitting because I am trying, at this point, to accomplish a goal I don’t even want, just to live up to some idiot schoolchild platitudes and the hopes of everyone I know who always wished they could be writers. Winners do quit. Quitters do win. They don’t always win at the first thing they try, or the second. Nor, it should be noted, do winners go on winning forever.
So on I go to the next challenge. After having spent the last year-plus also being rejected for full-time employment — most hilariously by both Ameriprise and WLS — I have finally convinced someone to let me have a chance as an independently-contracted Product Designer. I don’t know exactly what the job is, though it has something to do with apps, and I believe it is to what I did ten years ago as the Internet Director at WLS as birds are to dinosaurs: the same thing, a million generations later. I do know that the five people with whom I have interviewed all think I’ll be really good at it.
I’m of deeply mixed feelings about this shift. I never wanted to go back to a cubicle, because my experience with that environment was so awful. Perhaps things will be different this time. I will also be giving up the hope of returning to Florida more than once a year. Life is often sad that way. This is a large and unhappy sacrifice of something I had hoped to accomplish, the ability to split time between Chicago and Florida. It sucks, and I am angry. But it is time to give in to how the world works, and the way the world works right now is that companies prefer constant physical monitoring of employees. I’ll survive. I might even thrive, but that it yet to be seen.
The appeal of the job is easy to categorize: I get to return to the cutting edge of technology and represent users, something I liked a lot the first time around. Someone has to look out for the end-user, and that is something I am very good at doing. I enjoy trying to see the world through other people’s eyes and communicating how it looks from in there to those who aren’t as good at it as I am. It’s not terribly unlike theater in that way — comedy is mostly about empathy and commonality, at the end of it, and so is this. So perhaps some inadvertent good has come of the Miscreants after all.
I came in with a publishing triumph, and I go out with a publishing triumph. I start the new gig Tuesday. Wish me luck.