Dear Daily Jar,

I’m looking for some advice. For a friend, not for me. Over the past seven years the longest my friend has held down a job was three years subbing. My friend recently turned 33, has no real work experience to speak of, and can’t imagine a career he wouldn’t hate that wouldn’t entail grad school debt (he’s currently 20 grand in the hole). He wants to find a way to make $ writing more than anything else but is weighing that risk against the security of a professional job. What should I, er, he do?


Why Don’t You Call Me Ishmael

Dear Ishmael,

Make money from writing? You are asking the wrong guy! Seriously, in all the years I’ve been writing, I’ve gotten paid maybe ten times. I made a little money when I published the Sacramento Comment, but not enough to make a living out of it. The Comment kept me in sneakers and beer.

In order to make money writing the first thing you need to do is shake a few hands. Understand that I have no problem talking about me me me, but I am pretty shitty at selling myself. I hate cold-calling people. It is difficult for me to ask for work. I’d rather write than administrate. That, my friend, is not the path to getting paid to write. It doesn’t matter that I can write purty decent like, I am good with deadlines, I am easy to edit (as in I can write to word count with clarity and few mistakes and when I do need editing I am fairly cooperative), I can write on plenty of topics, I know how to research, I have plenty of “clips” (published items), and I (I I I I’m not your stepping stone) am much easier to work with than my literary voice sometimes suggests; if I don’t sell myself (like I just did), I am just another guy who can write…and there are plenty of us out here.

But, let’s say I do sell myself. I sit down with the editor of a local weekly paper and tell her I’d like to write for them. I have my clips, twenty years of history, a rep, a readership, and a good pitch. Of course, I am not expecting to get hired. Very few publications hire writers off the street, I know that. Fine. They’d like me to freelance. And they want me to start at the bottom. So I write bit pieces, reviews, profiles, stuff like that and get paid fifty or a hundred bucks a couple times a month. I work my way up to an essay and there’s a few hundred in my pocket. Fall turns to Winter turns to Spring and I’ve earned enough trust to snag a cover story. Great! I work on it for a couple weeks and I get paid a grand, give or take a hundred or two. In a couple months I score another cover. Perhaps after a year or two, I get offered a column or maybe a job as staff writer. Until then it is a lot of freelancing.

Don’t get me wrong, you can make a living freelancing. Many writers do, but it is a lot of work. You cannot rely on one publication. You have to develop relationships with several different publications. Too often you have to hassle them to get paid, gently though because you don’t want to screw things up for yourself. During that time, you are holding down a job because you need to pay the rent. 

Maybe I am getting a head of myself. How much writing for publication have you done? Oh, I don’t mean internet record, movie or restaurant reviews - not unless you’ve built a rep doing them. Talking shit on on web forums or blogs doesn’t count either. You gotta have published articles, stuff of substance. Ah you don’t have anything. Well, start working on it…but don’t expect to get paid. Right now you are building up your “clips.” When have a pile of clips from a handful of publications, start looking for freelance work. Freelancing isn’t the only path to a writing career, but it is the one true path that will get you paid.

Reality check: Most writers have side gigs. People at the top of their game make a few grand for a piece in the New Yorker, but they teach at a college or university as well. Or they do a little bit of radio along with writing, however that usually comes only after they’ve nailed down one or the other.  Hell, even when people bought books, the greatest writers earned their keep doing something other than their craft. Faulkner, Hammett, Fitzgerald - to name just three - went to Hollywood to earn money…and they already “had arrived” as writers.  People who make the big bucks writing are as rare as rock stars. For every Stephen King, there thousands of people writing for monkey wages or nothing at all.

If you want a short cut, the only thing I can think of is that you go out and do something daring, a grand exhibition of sorts. If Willard “Mitt” Romney comes to town, break through the crowd, drop trou and wiggle your penis at him. Sure, it is a one time event but it will be good for at least one well placed article (the size is up to you): Call it “I Wiggled My Dick at a Dick” or something like that. If you dry hump him (and I am not suggesting this), you might have a cover story. Dry hump him while on drugs and you have the makings for a book, especially if you feel bad about it, reject your drug-taking, dickhead candidate dry humping, penis wiggling ways, and turn to the Lord. Take that on Dr. Phil, tell your tale with as many tears as you can muster up, and you’ve got yourself a career.

Let’s say that the “penis-wiggling, dry humping a dick head candidate, while on drugs” idea doesn’t appeal to you. I understand we all can’t be heroes; but know that the premise behind it is still legit: Write what you know. That is where you start. At the very least, we know our own life. We have experiences. A biography. Maybe there is something there that you can sell. 

If you don’t want to get personal, if you want to write about something other than yourself, mine your interests. Is there anything that you know a lot about that you can offer up to other people? Not music or restaurants or the arts, perhaps in the future but not now. Is geology your thing? Seriously. John McPhee has written wonderful stuff on geology. How about the potato? One of my favorite books is The History and Social Influence of the Potato. Is there a historical event that you are obsessed with? The point: You start with something, some passion and you become a translator. Why read A.J. Leibling’s The Sweet Science? Because he translates the experience of a boxing match better than anyone has. Elizabeth David on food, Paul Theroux on traveling, or Lester Bangs on being a rock & roll fan. These writers are translators. Find something to translate to people. Put it out there and when you become good enough, perhaps people will pay you to do it.

Of course, there is copy writing. But I don’t think you are asking about writing advertisements, catalog entries, text book captions, etc. Copy writing pays, often very well, but that, too, takes time to get into. 

Sorry to say but there is no short cut to financial success for a writer. If you want to get paid for it, you have to work hard at getting paid. And while you are working hard, you write. Always write. Money, yes; Money, no; You write. Job security? There is no job security in writing simply because sometimes the words don’t come. When they do come you write. Write and write and write. Whatever words you have you write. Sometime it is for people to read, sometimes not. Sometimes people read what you write, sometimes not. But you write. I don’t get paid to write but I write. I don’t even like writing and I write. I write because I don’t know what else to do. I write. 

That said, if any of you chuckled at the Romney dry humping gag, you owe me five bucks (at least). There’s a paypal donation button to the right. Use it. I’d like to get paid.


The Daily Jar