Bourbon Cowboy

The adventures of an urbane bar-hopping transplant to New York.

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Location: New York, New York, United States

I'm a storyteller in the New York area who is a regular on NPR's "This American Life" and at shows around the city. Moved to New York in 2006 and am working on selling a memoir of my years as a greeting card writer, and (as a personal, noncommercial obsession) a nonfiction book called "How to Love God Without Being a Jerk." My agent is Adam Chromy at Artists and Artisans. If you came here after hearing about my book on "This American Life" and Googling my name, the "How to Love God" book itself isn't in print yet, and may not even see print in its current form (I'm focusing on humorous memoir), but here's a sample I've posted in case you're curious anyway: Sample How To Love God Introduction, Pt. 1 of 3. Or just look through the archives for September 18, 2007.) The book you should be expecting is the greeting card book, about which more information is pending. Keep checking back!

Saturday, April 08, 2006

Which Pile of Shit Should I be Eating, Exactly?

I haven’t updated the site in a few days because, in the bluntest terms, writing for the site is a lot of fun, and I don’t see any reason I should be having fun right now when I still don’t have a job. However, the entire process of jobhunting, such as it is, has given me a few insights I thought it might be useful to share.

The chief thing I’ve learned is that up till now I’ve lived a pampered life. Not Paris Hilton pampered, of course. (And—side note—could there be any worse example of unearned power and prestige than Paris Hilton? She first became famous for being fabulously wealthy, ignorant of reality, and blithely uncaring about it because people think she’s fun to party with. Every move she’s made since has confirmed that her willful ignorance will never hurt her, because she’s surrounded by media people who manage a form of “reality” for her that gets spun off into every show or appearance she does. We get the celebrities we deserve, and I can’t imagine a celebrity more fitting for the Bush era. It’s so depressing, I think I need a new paragraph.)

(Pause while my dander ebbs.)

Okay. What I’m saying is, I’ve been lucky. Up until now, every job I’ve ever held was given to me. I lived at home till I was about 20, and didn’t need a job before then. I got my first job with the PREVENT program because my parents sold the house, I needed a job desperately, and I was dating the boss’s daughter. Got my job at Hallmark because they came through Tucson, saw my work, and hired me. (They even paid for my move.) Went to Florida State because the second I applied I was offered a scholarship and a teaching assistantship. Those are the only jobs I’ve ever had. My other creative work—puzzles, short stories, etc.—have never even paid the utilities. I’ve been in the Atlantic, World’s Best Fantasy and Science Fiction, and Mirth of a Nation, but after some quick math it seems the sum total of my freelance earnings comes to about $9500 since 1990.

Maybe this is how most people do it, and I’m not as pampered as I think. But I do know that starting from zero and attempting to get the attention of an entire city is completely new to me, and developing the skill to pound on doors and get a job is like learning a new language: it’s absolutely exhausting, and I can only get about half as much done every day as I expect. I’ve been sleeping a lot, and I don’t think it’s depression—it feels very much like a protection against nerve-shredding stress. Even when I’m looking at job postings, it’s very easy to psych myself out. I’ll have the skills required, but they’ll add a line like “Some knowledge of Spanish would be helpful,” and I’ll think, “Well, damn. My skills meet the minimum, but what are the odds there’s someone else in this city who meets or exceeds that minimum and also speaks Spanish?” Or I’ll see an “entry-level” position, and I’ll think, “I bet that means they’re expecting a college graduate fifteen years younger than me.” And then I can actually agonize for up to twenty minutes wondering whether it’s worth going to the trouble of applying. Multiply this by fifty, and then I only send out about five queries, none of which I'm particularly optimistic about. Then add the irony that I'm agonizing, strategizing, and using all my fighting dander to think about a series of jobs that I really don't even want.

This slowness of mine isn’t quite as stupid as it sounds, because I have some form of attention deficit disorder that makes this particular kind of work—the proper filling out of many many forms—much more stressful than it is for a normal person, like writing with my left hand. In fact, when my friend Jen recently suggested that I might get a performer’s license, I brightened, because busking sounds a little more in keeping with my tendencies. (No forms! Oh wait--except for the license.) But then there’s the additional problem: what do I actually do? I don’t play any instruments. I’m not a particularly skilled singer. I can’t break dance. I’m a friendly comedian type. If you sat and talked with me for ten minutes, you might find me charming enough to toss money my way. But comedy takes more time to present than people have when they’re moving from the A to the E train at 42nd Street. And I suddenly can’t tell: is this realistic thinking or am I psyching myself out again? I have no idea because I have nothing to compare it with.

Hey, I just thought of something: I could lead tours! I’m personable, entertaining, love to teach . . . And as soon as I thought of this, I thought, “And I’d be competing for those jobs with every goddamn actor in town.” And my next thought was, how many jobs like that are there? What’s the competition like? Am I good enough to make the effort worthwhile, or should I save my energy for something that’s less of a pipe dream? And would it pay enough to make rent? And then—you didn’t see this—I started pacing the room, thinking about it, wondering how to even get the answers to these questions. It could be half a day of research before I even figure out that it’s not worth the trouble. This paragraph has taken me fifteen minutes to write. On the plus side, it feels like I'm doing something instead of waiting around for no one to call me.

(You know what job I’d be good at? Bestselling humor author. I don’t seem cut out for much else. So where’s my agent? Aargh! )

Anyway, I just thought I’d share a little bit of what the process has been like. Those of you who read this blog and have been through it might be able to tell me what parts of my thinking are wise and which I need to learn to ignore. (P.S. Jen—your letter came yesterday. Thanks!)

While I’m at it, I have to add something else: my computer connection sucks beyond the legends of sucking. It was my roommates’ bright idea to give us a wi-fi network rather than running a splicer and sending acres of cords into every bedroom, and I guess I can see the value in that. But in practice, it has meant that my signal is so intermittent that I can literally print only five words at a time before the system pauses to think—and it pulls the same wait-twenty-seconds crap EVERY TIME I fill out a single entry in a single form. So yesterday I went on and jobs@nytimes, and although I spent all day going through their resume process, I only actually managed to apply for five jobs, and spent at least ninety minutes of that time just waiting for the damned computer to unfreeze. The rest of the time was spent clicking through to various sites, reading every job in depth, clicking to another site, etc. . . .and with my shitty connection, the whole process took about four times as long as it needed to. Very frustrating. Would it be worth it for me to go down the street to UPS and use their $3-for-ten-minutes connection instead? Again, I don’t know. Pile another quandary on the heap and watch as I circle the whole thing in helpless madness like Hobbes’ ass, unable to choose among twenty identical-seeming options. (And that’s how bad it is—I think the “Hobbes’ ass” reference is an error [I was thinking of some famous ass that died because it was given two exactly equal bowls of food and couldn’t decide which one to eat; death by abulia] but I can’t even justify spending time to double-check the reference when there’s jobs to be hunted down. How un-Davelike!)

All of you who know me know that I’m basically a sunny cheerful person, and I hate to be depressed. And I’m trying like all hell to be conscientious, send out my resumes to all and sundry, and spend hours every day hunting opportunities down. I’ve sent my applications to ten employment agencies, and in over a week none of them have even asked me to come in for a skills test. (Is that normal, or is that I sign I should stop trying that area?) And weekends are the worst, because I’ll think of someone I might want to contact and then think, “Oh, wait; they’re probably closed till Monday.” (Or do publishing houses, for example, stay open all weekend? Heap . . .) It’s not even a question of swallowing my pride. I’ve been a t.a. and a comedian; I haven’t had pride in years. The question is what to swallow it with, in a town with a million restaurants. Sigh.

P.S. I’ve checked. They don’t have any greeting card writer jobs in New York City. At least, not on the web.


Anonymous Anonymous said...

Ah, Dave, you are discovering the harsh realities if big-city job hunting. I dated a girl who worked for an employment agency and she told me how it works. First of all, I was stunned to learn that there is not really a position behind all ads posted for jobs. Sometimes companies post for a position just to see what kind of applications they receive. Sometimes they will even interview a few candidates just to see how much it is going to cost them in salary if they create the position in the future. Sometimes they have already filled the position but have to advertise to appear fair or fulfill corporate or union requirements. What that means for you is your worst possible nightmare. You can't just pick the five most promising ads and apply to those. You have to apply to every single ad you can get your hands on in a statistical shotgun approach. Even applying to ads where you are marginally qualified will increase the chances that you are at least applying for a real position.

I always assumed that the way employment agencies worked was that they take an applicant's resumé and then search for positions that fit that applicant. After all, that is how they advertise for applicants. The unspoken service you assume they provide is helping you find a job. It is actually just the opposite. Employers call up temp agencies with whatever their current demands are: wharehousemen, secretaries, accountants. Then the agency rushes to find a candidate who can fill the position. They rush because the agency who can fill it first gets the sale. And, I know this is hard to figure, the agencies are lazy. If they need an accountant, they call the first accountant they can think of. That is, someone they used before, or the first accountant in the pile of resumés who is available when they call at that moment. Managers tend to hire people they know. It's the same with temp agencies. Once they get to know you personally, they tend to call you first. So what that means is, it is not enough to send in your resumé and assume they are feverishly working day and night to find you well-paid meaningful work. You have to send in your resumé and follow-up. Call the receptionist at the agency. Be funny and remind her what your skills are. Remind her that you are available today for whatever position happened to pop up that morning. Employment agencies are really there to serve the employers because that is where their revenue comes from.

When my roommate first moved to L.A. he got a job selling wine for a few months that way. He had never sold wine before, had no wine qualificatons, and no interest in wine as a career. He just happened to physically be in the lobby of the agency when the wine job came in and they asked him if he wanted it. He was there to give them his resumé as an HTML programmer. Long story short, he sold wine until he could get a programming job he liked.

Go ahead and announce that you can speak a little spanish, you will take that entry level job, you will sell wine and busk all while expertly using Excel. If it doesn't work out, at least the agency will know your face. There is no shame in taking a job that sucks and doing it for a few days and then calling the agency and telling them the job sucks do they have anything else? At least they know you and will think of you first when the demand for a bestselling humor writer position comes in. And you can always get certified to substitute teach. Don't tell them you have a Ph.D. though. It's easy to get discouraged. Hang in there. It may take longer than you'd like but you will find work that pays a living wage while you feed your writing habit... It doesn't feel comfortable because you are new to the scene, but you are doing it right.

4/08/2006 1:24 PM  
Anonymous Anonymous said...

All that helpful advice from Jason, and my comment was simply going to be that you were probably thinking of Buridan’s ass.

Good luck with the job hunt. I did find the Museum’s job postings, but there doesn’t seem to be much there of interest, unless you’ve been hiding your knowledge of systemic herpetology…

4/08/2006 2:10 PM  
Blogger Cowboy Dave Dickerson said...

Actually, it would follow from Jason's advice (if we go ad absurdum) that I should apply for the Museum job and say, "Yes! Yes, I *do* know a little systemic herpetology. . ." After all, it worked for Leonardo DiCaprio in Catch Me If You Can.

4/08/2006 2:48 PM  
Anonymous Anonymous said...

There's gotta be free wi-fi you can use. If you don't have a laptop, there's also the public library.

I always liked the sound of the jobs on You should also try to get on focus groups. Sign up online for as many surveys as possible, though the live ones are most lucrative.

Here are a few, but searches will find more.

4/08/2006 3:23 PM  
Blogger Cowboy Dave Dickerson said...

Thanks, Ellen! Like the universe, your grooviness continues to expand without any immediate limit.

4/08/2006 6:59 PM  
Anonymous Anonymous said...

I posted my resume on and the like, to no response. Granted, Austin is no NYC, but I've heard from several people that it's tough getting a job here, given that it's one of the most educated cities in the country. (Who conducted that survey? Who cares?) Anyway, I didn't get much response until I had "business peeps" look mine over and give me work-shop-esque pointers, including "I'm bored and stopped reading after 'Qualifications'. I'd be happy to go over stuff with you (not that I'm the next Trump or anything) but I changed things up and have been getting more response. Which led to a corporate-cubicle-monkey job, which means money coming in.

Ah. money. The root of all evil.

Take it sleazy,

Message me on my space, man.

4/10/2006 1:11 AM  
Anonymous Anonymous said...

Hey Dave, great advice up here, especially from Jason.

Have you seen any freelance writing jobs you're interested in on or or other like sites?

And what does your resume look like anyway? Shoot me a copy and I'll critique it!

4/12/2006 12:51 AM  

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