She’s Back! Miss Jobless Returns With ‘Mister Sadistic’

Editor’s Note: Regular readers of this blog may remember Caitlin O’Toole‘s stint with us as “Miss Jobless,” the talented but unlucky-in-employment writer who blessed us with a column every week—always entertaining, and almost always way, way too close to home.

Caitlin is back for an occasional look at the life of an underemployed writer in New York. If you like reading her, give her a job. If you don’t like reading her, give her a job anyway so she won’t have time to write for us. You win either way.

With that, we turn the floor over to Caitlin……

Welcome to another delicious chapter of the Miss Jobless Chronicles — also known as Caitlin’s tales of unemployment and underemployment woes. I just couldn't stay away.

I'd like to tell you that a lot has changed in this country since the last time I wrote. Unemployment is at 9.2 percent. It's nearly impossible to get even an unpaid internship. (Last night I yelled out in my sleep, "I refuse to be an intern at age 41!") I exhausted the intern in me at age 23.

Other things also haven't changed. I still frequent my local bodegas, where Saleem and Daman still compete over my business. I'm still a craigslist addict; my apartment is a monument to the free section. And I still hang out as much as possible with June, my 83-year-old neighbor. She’s a constant source of support.

Now, I'm writing for Snapshot magazine — again. It's strange to be back, especially since I never thought I would be. I've been going out on interviews anyway, to fill in the gaps in my schedule and bring in more flow.

The thing is, my interviewing skills are quite lacking. I look great on paper, but when it comes down to it, my nerves get the best of me in person.

I recently interviewed for a gig as a copywriter for one of those "Buy 10 CDs for One Cent" companies. I was a shoe-in for sure; my portfolio is rich in material and I have a music background. (I played recorder and clarinet before I realized that I was the geek of the school and would never get a date, ever.)

I hadn't interviewed in a while since I've mostly been telecommuting —and I didn't need to interview at Snapshot since I had worked there before. So I was extra nervous for the interview at the "One Cent" place.

I took some Xanax before the 8:00am interview. It didn't really do anything.

The waiting room of the midtown office was grungy and the chairs had brown, amoeba-shaped stains on them. It was early (early enough that the interview seemed extra shady) and there wasn't a soul in sight. I looked around the corners — no one, and the lights were off — and sat down anyway.

In comes this guy in a cheap suit, his eyes crusty with sleep. He hugs me hello, though we had never met.

"I'm Paul, yo," he goes.

"Caitlin. Pleasure."

He asks for a minute and disappears into the darkness. The lights go on — florescent, greenish tubes.

"Come in, and let me see your passport."

Since the last time I was asked for my passport was when I worked at McDonald’s, I was empty-handed. Was he sending me on a business trip so soon?

"I'm sorry, I —" My hand starts to shake. Really? I've been on a million interviews at media powerhouses and I'm shaking in this dungeon?

"It's fine. Do you have a portfolio?"

"Well, I do, but it's probably easier if you just Google me."

"Google you? No. No. No. I don't Google, yo. Let me see your clips."

I show him my book — outdated, but semi-impressive clips from Snapshot, the Enquirer,, Huffington.

"Okay, let's talk."

Pause. I'm so nervous, like never before in an interview and I don't know why. He’s not even intimidating. But my nervousness is transparent. I’m looking down, not smiling, and trembling.

"Do you know who Robert Longo is?" he goes, trying to catch my eye.

And with that, he crumples up a wad of paper and hurls it at my head. It hits me in the forehead. Can anyone really be this sadistic?

"No." I'm flustered, confused, mad at myself for not picking up the wad and hurling it back.

"Robert Longo is an artist,” Mister Sadistic informed me. “You should know that, considering your background, yo. He used to throw shit at businessmen to get them to sort of loosen up, then he’d draw and photograph them. That's what you need to do — loosen up. Your nerves aren’t serving you."

I usually bat my lashes and work my baby blues — today, my eyes were fixated on the grubby carpet.

"Why do you want this job, yo?”

"Well, I — I have a music background and I can write. I can write anything. Plus, I’m familiar with your company — I ordered the entire Pat Benatar catalog when I was 12 and only paid for shipping.”

"Really. Okay, we'll see. You were a shoe-in for this job, you know. I'll be in touch." Like, never.

I never heard from Mister Sadistic. Fuck him and his crusty eyes.

I did, however, get a gig following around famous British couple during their recent New York jaunts. Rumor had it he was being unsupportive and mean to her while his wife was pregnant, and I needed hard evidence. At least evidence enough for a tabloid.

One night, I got a tip that they were dining at the Minnetta Tavern on MacDougal, so I jumped on my bike and went down. I was not prepared for the velvet rope and the bouncer, but weasled my way in when the reservationist wasn’t looking — even though I was wearing ripped jeans and a white button down with bicycle grease on it. I spot the pair in a back corner, just sitting down. Luckily, their table is near the bathroom — so I’m able to walk past them. I not-so-subtly drop my wallet on purpose, look up, say “excuse me” to them and smile. I slowly pick up the contents of my wallet, paying special attention to their body language and expressions.

No smiles. He’s sitting back in his chair and she’s got her elbows on the table, leaning towards him. I’m no body language expert, but it seems to me there’s tension between them, I decide, and scribble a note on my pad. “He’s distant, she’s still very much in love.” Excellent hard evidence. I can’t guess what’s in their glasses, but his drink looks like a martini overflowing with olives, and hers looks like soda water. “He’s being rude for drinking when she can’t because she’s pregnant,” I jot down. Another piece of evidence that the marriage is on the rocks — so to speak,” I jot down. I made a funny.

I rush home and write the story before I forget it and send it to my editor, proud of my conclusions and insights into human behavior. The story didn’t run, but I got a $100 “kill fee,” meaning I got paid for my time and the drink I bought at the bar, trying to get info about the couple from the surly bartender.

That same week, I answer an ad on craigslist to be an apprentice to a “multi-media wizard.” I got a response right away, beckoning me in for an interview. The person who wrote the email was evasive about who exactly the wizard was and what I’d be doing for him. She only said his name was “Bob.”

The interview was in a loft on the top floor of an East 10th St. townhouse. A person buzzes me in and comes down to greet me; she’s about 23, I guess. I figure she is the apprentice whom I would be replacing.

“Who am I interviewing with?” I ask.

“Bob,” she tells me. “I can’t tell you anything else about him.”

Her evasiveness was enticing but borderline annoying.

Bob. Bob Costas? Bob DeNiro? Bob Downey, Jr.? Bob Newhart? Bob from Sesame Street? It could be any old dickhead named Bob.

When the elevator reaches the top floor, I am instructed to sit outside a door on a rickety chair and wait for the person before me to finish their interview. It’s hot as shit and I am overdressed in a too-big jacket and mid-calf black boots.

Finally the door opens, a kid leaves, and a wrinkly man peers out the door, beckoning me in.

“I’m Bob Schmidt,” he says, inviting me to sit.

“Caitlin,” I go. Pause. He looks at me and smiles — as if to say, “Aren’t you excited you’re in the company of Bob Schmidt?” I wasn’t, nor did I know who the fuck he was.

“I’m sure you’ve heard of me,” he says, looking proud. He’s sweating and so am I; he undoes the top button of his shirt.

“Yes, of course, Bob. I admire your work.”

“What about it do you admire?” he asks.

Fuck. I grapple for a safe answer.

“It’s original, yet universally appealing.”

“Do you have any questions for me?” he interrupts.

“Yes — what projects are you working on at the moment?”

“We’re making a documentary about actors who have been in prison,” he tells me. How retarded, I’m thinking through my cheesy grin. “One in particular, who shall be nameless. It’s gonna be big. Like, BIG big. What are you looking for in terms of compensation?”

It would be easier if I knew what the fuck I’d be doing for this proverbial man behind the curtain — the Wizard.

“Um, $600 a week,” I say.

An overweight cat waddles by and he picks it up by the tail. “By the way,” he goes, “totally unrelated, but do you want a cat?”

“I have two. Sorry.”

And with that he tells me he’ll be in touch. I still don’t know what the job is. But it’s too humid to ask; I want to go home and watch Keeping Up With the Kardashians on my DVR.

Never heard from Bob the Wizard.

Recently, an entertainment Web site gave me a writing test for a part-time gig. The assignment was to pick a recent celebrity news story and write 200 snarky, bratty words about it. Easy enough. I picked Hugh Hefner. His girlfriend has recently left him at the altar.

“The Hef,” I write, “is known to be a lecherous leather-faced Lothario.” I smile at my brilliance. “But he’s not necessarily lucky in love. He’s just been stood up by his fiance…”

I email it and wait for the green light. Surely I’ll get an interview!

Still waiting. It’s been two weeks.


Next up: my stint as a Kardashians reporter.

Caitlin O'Toole is a New York City-based writer and editor and the creator of "The Miss Jobless Chronicles". A native of Washington, D.C., she began her illustrious journalism career as a Washington Post paper girl and won the 1982 carrier of the year award — a plaque she still proudly displays in her teensy weensy Chelsea apartment. Caitlin's career has been punctuated by bouts of unemployment, under-employment, and run-ins with neighborhood misfits, local bodega owners and an 85-year-old technophile neighbor named June. She's written for Star, Parade, Sesame Workshop,, VH1, and Fox News, and has been a guest blogger for the Huffington Post. She's also a Kardashians know-it-all, thanks to a recent freelance stint. Please send all six-figure job offers and fanmail to