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Miss Jobless

The Miss Jobless Chronicles: Damned If I Do

The Miss Jobless Chronicles is written, on a (semi) regular basis, by Caitlin O’Toole.
I know, I know, it’s been a long time since the last column. I apologize — but I do have an excuse. I have been working! Yeah, you heard me right. Granted, I am still under-employed — but at least I’m not at the bodega scratching off lotto tickets with the local hoodlums.

It’s funny about work — actually, it’s not really funny at all. I feel damned if I do and damned if I don’t. My stupid insurance company (which shall be nameless) won’t allow me to work over a certain amount or they’ll drop me. (Sound familiar to any of you?) I got this very cool freelance offer to to work for a company that’s sort of like “Pop-Up Video”. It’s great money, and it will allow me to be the bratty, snarky, irreverent bitch that I am! Yay!

But I can only work for them a certain amount or I will lose my benefits. How dumb is that? I won’t go on about it because I am bitter and slightly disheartened. But who the fuck wants to pay an $1100 a month premium just to be able to make at least $1100 a month to PAY the premium? Retarded, right? I’m curious to know what people do about this, and how I can work as much as I need/want to and still be covered if I get hit by a speeding Vespa, say.

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The Miss Jobless Chronicles: Insurance Dilemma!

The Miss Jobless Chronicles is written by Caitlin O’Toole.

It’s been kind of a sad time. I lost my 16-year-old cat, Lucy, very suddenly to what I think was kidney failure. I don’t think she suffered, but I am still plagued by guilt that I could have done something to keep her alive or minimize her suffering (though I believe it was rather minimal).

I buried her ashes under a tree outside my building and planted some Pansy seeds so her sister Ethel could look out the window and see Lucy blossom into flowers in the spring.

I was walking past the tree the next day in the Indian Summer rain, kind of at peace at my decision to place my cat there, and this fucker flicked a cigarette butt that landed on Lucy’s fresh grave.

I held my tongue, but picked up the butt and threw it into the street. Lucy always hated smoke.

Then, a woman let her two Chihuahuas underneath the railing and into the flower bed to pee.

“Would you mind not letting your dogs in there?” I said.

She said nothing, but coaxed her dogs back onto the sidewalk.

The following day, she was back with her fucking dogs — again, they were peeing in the flower bed.

“If you don’t stop letting them relieve themselves in there I’m reporting you,” I go.

“I’m sorry,” she said. “We’re from California and they’re just not used to cement.”

Only in New York.

As I told you, I’ve been working some, which is such a relief. A total self esteem booster. However, because I am now in a different income bracket, I won’t be eligible for my Healthy New York insurance policy come the end of the year. Ah, the joys of freelance!

Healthy New York kind of sucks, by the way. It’s relatively cheap (about $350 a month) but that only covers very specific medical care and doesn’t cover certain prescriptions (like Xanax, which is so key!) Most important thing, of course, is that if anything — god forbid — happens to me, like I get hit in the head by a falling satellite, I have catastrophic coverage. It’s not really the everyday things that insurance is most important for, like sore throats. It’s really for the things you don’t see coming. (Like falling satellites.)

The company I work for isn’t taking taxes out of my check, which means I will be royally screwed in April. I’m saving up to buy a laptop before the end of the year so I can write it off. I make donations (however small) to good causes for the tax-deductible receipts. If I go out for a drink for a work-related chat, I save the “evidence.” I’m getting pretty anal retentive about bookkeeping.

I fantasize about going back to school sometimes. I recently met two people in grad school. One of them is a “performance artist” and a pretty good painter. I thought she might be going to the School of Visual Arts or Parsons. Turns out she’s going to some school I’ve never heard of.

“What are you majoring in?” I asked her, genuinely curious.



I left it at that, wondering if there are are different levels of lactation classes. Like, in 101 you learn to maximize your milk production and in the next level you learn to pump. Wonder what happens in the advanced level.

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The Miss Jobless Chronicles: Art Attack

The Miss Jobless Chronicles is written by Caitlin O’Toole.

I’m glad fall is finally here. The New York summer was grueling and, for the most part, I found myself irritable and slightly homicidal. The height of annoyance? Standing on the subway platform in the blistering August heat while some asshole plays "Que Sera Sera" on the pan flute. It was even worse than the time I heard “Don’t Worry, Be Happy” on the steel drums.

Autumn usually means more job opportunities, so I’ve picked up a little work, which is good. Helping a friend jump-start his new political blog. And writing celeb news content for a website. It’s good to have structure. Even though I’m telecommuting (my editor is in L.A.),  I make myself get up at 6am, get showered and get dressed as if I am going into an office.

Lately , I’ve been wearing my 21 Jump Street t-shirt and a tailored black jacket.  Sometimes,  a skinny gingham tie, white button down and my blue and black checkerboard Vans. I look like a Cheap Trick groupie or an extra from “Miami Vice”. Don Johnson would be proud.

Forcing myself to sit down at my desk at 9:30am and begin working sends an affirming message to myself. It’s good for me to get out of my sweats and into the habit of looking un-grungy. Which can be a challenge when you’re not working or working very little. (I think it was Seinfeld who once said that wearing sweats is like “giving up.” It’s so true.)

Because I am bringing in more income, I’ll soon no longer eligible be for my current health insurance plan. It’s that freelancers’ insurance dilemma, which I will touch on more in my next column.

Daman and Saleem, two neighborhood bodega owners, are still fighting for my business. (See “The Bodega Wars”.) Basically, Saleem is the Pakistani man who runs the convenience store part of the Lukoil station, and Daman, a handsome Indian man with an unfortunate bad complexion, runs the bodega across from the gas station on 10th Avenue. To me, Tenth Ave. is no longer just a bustling gateway to the Lincoln Tunnel; it’s become Kashmir. If I go looking for a diet peach Snapple at Daman’s and I don’t see it, I’ll head across the street to get one at Lukoil. Daman will literally run after me.

“Wait! What are you looking for,” he’ll shout as I’m halfway across Tenth.

“Oh, you don’t have it — diet peach Snapple…“

“No, we have! We have it!”

He runs inside and runs back out to the street with my tea. Anything to keep me from going to the gas station; the enemy. I pay him right there on the street with a pocketful of lint and change. It feels like a drug deal, only we’re dealing in Splenda.

In an effort to lure in customers and compete with Daman, and in the never-ending battle to make his establishment more attractive, Saleem has purchased ten huge palm trees and put them next to the gas pumps. Because when I get gas, I like to pretend I’m in a tropical paradise, don’t you?

My neighborhood is spotted with art galleries, and for that reason, as well as the fact that the Highline just opened on 23rd and 10th, masses of New Yorkers flock to my hood, leaving trash, cigarette butts, and the occasional graffiti tag on the mailbox outside my door.

Saleem, at Lukoil, decided to jump on the bandwagon and host an art exhibit. So in between shelves of second- and third-rate snacks — like Herr’s jalapeño cheez curls and Andy Capp’s hot fries and Lady Linda honey buns — there are mixed media collages and sculptures and random scribbles with obscene price tags on them.

As I went there the other day to marvel at this new “gallery”, one of the “artists” was there — and I bumped into her horribly executed painting as I went to grab a soda.

“Mind the art, please,” she goes.

I said I was sorry, but what I wanted to say was “I do mind the art. I mind it a lot.”

Then I think, this poor girl is going to have that on her resume — that she showed at the Lukoil station in 2011. These are desperate times for sure.

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The Miss Jobless Chronicles: Desperate Measures

The Miss Jobless Chronicles is written by Caitlin O’Toole.

Arianna Huffington was on The Today Show recently discussing a HuffPo piece by Amanda M. Fairbanks. The gist of the article is that the economy is in such a horrible state that many women are relying on rich older men to pay off their college debts. (They call themselves “sugar babies”; I call them hookers.)

“Saddled with piles of student debt and a job-scarce, lackluster economy,” Fairbanks writes, “current college students and recent graduates are selling themselves to pursue a diploma or pay down their loans. An increasing number, according to the the owners of websites that broker such hook-ups, have taken to the web in search of online suitors or wealthy benefactors who, in exchange for sex, companionship, or both, might help with the bills.”

One facebook user responded almost immediately. “Thanks to the GOP and Tea Party, I'm too poor to be a sugar daddy — and thanks to Mother Nature I'm too old to be a sugar-boy. As they say, timing is everything.”

I commented on Ariana’s facebook post that this sugar parent arrangement is not exclusive to heteros — gay and lesbian sugar people are also in high demand. (No response from Arianna. Doesn’t she know who I am?)

So, given my current underemployed state, I decide I’m going to look for a sugar person, too. I know, it’s not original — but I decide to follow this rather disconcerting trend just to see what happens.

So I start doing some research. What kinds of people are looking for a sugary kind of arrangement? Are they normal people? Freaks? People like me?

I scour craigslist for other women looking for sugar mommies (I need only search for the keyword “sugar”) and find many, many far-more-serious women than I am. In every major city. (But in Allentown, Penn., there are two people in the women seeking women section who are looking for sugar babies. Should I move there?)

In New York, though, there are at least ten active “looking for a sugar momma” listings. But even the women looking for sugar mommas don’t mince their words.

“too old, wrong figure, no sugar — 30,” one ad stated. “I was way too proud, worked too hard and wasted all those years. I probably could have made a fantastic whore. Now i'm broke, unemployed, old and fat. And from actually-dating all those years, way too picky about who I sleep with.”

“Where is my sugar mama? 21,” another ad states. “Hello I'm Here looking for a companionship with a beautiful Older women that's fun caring and love to have fun. I'm 21

5'1 full of energy love to make people smile Just looking to spend sum magical days and nights wit sum 1 Interesting. i have braids and a couple of tats. Serious replies only ladies I'll be waiting. Plz no men no couples……plz send a pic an i will do da same”

The ads in all caps are placed by women who are even more desperate. Like this Los Angeles-area woman’s:


By god, I am NOT ALONE!

So I place my own fucking ad. But the difference between mine and most people’s is that I am 41; they are in their 20s. (Should I be looking for a sugar grandmommy?)

“I need a sugar momma — 41 (Brokesville),” I write. “I'm nice, cute, hardworking, nearly famous and will make you laugh in exchange for dinners out and frequent trips to the mall. I can't really cook, I clean only when I have the urge, and I rarely put out. Sound like a dream come true? Write me!”

I get two responses: “Lol” and “r u for real?”

So I amend my original post: “Sugar mommy needed — 40 (Not kidding),” I write.

My email pinged immediately!

“butch or femme?”

“I’m more like a tomboy with a nice rack,” I respond.

I feel gross for placing the ad — even in jest — and pull it down immediately.

I clearly need to find another way of supplementing my rather sad income.

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 You can also fan Miss Jobless on Facebook.

The Miss Jobless Chronicles: The Troll

The Miss Jobless Chronicles is written by Caitlin O’Toole.

A wise man once said, "Under-employment is rough — especially when it's 100 degrees out and it's the first of the month." Okay, a wise man didn't really say that — but someone should have.

The air is thick like soup, and my shifts at ‘Snapshot’ magazine are sporadic. I'm getting some other nibbles, but companies are taking total advantage of the shitty economy and hiring people for like pennies an hour. Desperate fools like me apply, then do the work while quietly resenting it.

The perk of hanging around — however involuntarily — is that you get to know your neighbors. I've told you about June, my friend down the hall. Who's kind of like the hip Betty White of the building and has achieved a weird kind of Chelsea cult status. Now I have new friends — Liam, an older gay guy with a Houdini mustache who told me the other day that he had a dream about me. Creepy. Then there's Billy G., a sort of has-been actor who never really was. He has two dachshunds that drool and lick my feet in the elevator. The other day, he invited me up to his apartment to see his renovation which I was a little freaked out by — not that I was nervous about being alone with him — he seems harmless — but New Yorkers don't like to get close to anyone or make new friends. Sort of kidding, but I think I actually fall into that category.

Then there’s the woman in the apartment below me, who I simply call bitch face, who complains that my music is too “bassy.” I swear she came up one night when I was playing Billie Holiday and complained about the bass level.

Then there's Eleanor, who I call The Troll, because she's short and has insanely matted salt and pepper hair. As if someone took her in their hands and shook her like she was a toy perched on top of a pencil. She has a slightly pock-marked complexion, like she had a shitty acne problem in high school and can't get rid of the faint craters. Her skin always looks kind of moist and she has beady troll-like eyes. She also smells like patchouli, and few people can get away with that. She's always petitioning for some cause. Like, yesterday she had me sign a list to try and get the mail person to deliver the mail earlier. Okay…. I love getting mail as much as the next person. But really, honestly, it doesn't matter when it comes unless I'm expecting a check — then if it doesn't come by 6pm it sucks because I can't cash it til the next day. (Which, on most days, matters.)

The troll is tres annoying, if you haven’t already gathered. Like, she corners you with her clipboard at the door when you’re just coming home.

“Will you sign my petition?” she’ll say in her nasaly voice.

“Well, it depends on what your petition is.”

“We’re trying to get the post office to offer a more gender-neutral selection of stamps.”

Gender neutral stamps? Who does she think she is, the Betty Friedan of the building? Who the hell does she want on the stamps — Chaz Bono?

Like, right now I have Liberty Bell stamps. Are those male or female? Read more

The Miss Jobless Chronicles: Kickin’ It With the Kardashians

The Miss Jobless Chronicles is written by Caitlin O’Toole.

They say Kim Kardashian is "famous for being famous," but I think that's not very fair. She’s famous for lots of stuff — including endorsing tons of products that we may not even know existed without her magic touch. (Like Fabio — who unapologetically endorses Old Spice deodorant.)

Recently, Kim attended the opening of a public bathroom in Times Square. She was there for a product endorsement — she was representing Charmin. And I got to attend the event with my very coveted press pass.

I  made my way to the park in my Sunday best — not only excited to see Kimmy, but hoping I would get free toilet paper. I also had to pee like hell, and the new bathroom was being touted as one of the cleanest in the city.

The first thing I noticed was velvet rope wasn't velvet — it was made of Charmin. I went to the event, tried to get close to Kimmy, but there was were white and pink ropes of toilet paper separating us. Bummer. I wanted to shake her demure, famous little hand. She looked pretty proud to be there — and why wouldn’t she be? She was all smiles as they cut the Charmin, allowing the eager public inside the bathroom for the first time. You can say what you want about Kim Kardashian, but you can no longer say that she doesn't pick important (and squeezably soft!) products to endorse.

How do I know all this, and why should I care? I went to the event. In fact, I followed the Kardashians around New York City for six months for a popular TV website. It didn’t pay that well, but I got to attend book signings, hang out at their DASH clothing store in SoHo, and the hotel Kim, Kourtney and her baby daddy Scott Disick lived in last fall while they were filming "Kourtney and Kim Take New York." I would wait outside the Smyth Tribeca hotel, trying to push my way through throngs of fans dying to catch a glimpse of the foursome, as well as Kim’s fiance, New Jersey Nets forward Kris Humphries. Sometimes, The Sisters K’s mom/manager Kris Jenner would often fly in and make an appearance. I saw the family several times. They're so gracious and untouchably pretty in person — like friends I would die to have in my real life.

I even stalked Shengo, the Australian bodyguard with whom Kim had a brief affair that was documented on the reality series. I interviewed him for OK! Australia about the tryst; he had fallen head over heels in love with the celebutante but his visa expired and he had to return Down Under. My heart bled for the couple, who clearly were made for each other.

I followed the family's tweets — as informative, poignant, and important as they were. Kimmy visited Africa to endorse a new brand of vodka. Her plane got stuck on the tarmac due to inclement weather. Luckily, she had WiFi access and was able to tweet that she was stuck and that she was "dehydrated and starving." I felt bad for her and yet curious as to why she would use such a phrase. After all, Africa is a continent with a humongous population of people who are really starving. But shit, Kim may have just forgotten her snacks or protein shakes and really was as starving as a malnourished African person. I didn't judge and you shouldn't either.

I researched all the ways that Khloe, the youngest of the brood, could more easily get pregnant. She and her hubby, L.A. Lakers power forward Lamar Odom, were having a very public struggle conceiving. Could be because Khloe admitted on the reality show that she didn't know she had to be ovulating to get pregnant. Maybe she's just been sheltered, or maybe Kris Jenner didn't do a very good job educating her about the birds and the bees. Again, I don't judge.

Here are some methods I suggested in an article that Khloe and Lamar try:

1. Belly Dance

According to some sources, dancing can actually stimulate blood rush to the reproductive organs and aide conception. In fact, belly dancing was originally a form of ancient fertility rites and men were not even allowed to watch!

2. Avoid soy products

A popular myth suggests that soy acts like estrogen in the body and makes it difficult for sperm to swim to fertilize the egg. Stay away from those soy lattes, Khloe!

3. Swim in the sea when it’s warm

One woman offered this tip on a Yahoo message board. We’re not saying it’s the most reliable of sources but it can’t hurt, right?

4. Conduct a wiccan fertility spell

One of them involves a watermelon:

1 watermelon

1 tbs. powdered Palo Dulce

1 cup mixed rice and beans

1 tbs. shredded coconut

2 tbs. fresh basil leaves

1 tbs. anil powder

1 tbs. river water

1 tbs. sea water

2 cups molasses

3 cups olive oil

7 pennies

1 wick Statue of Yemaya

5 . Have Lamar stop wearing ‘tighty whities’ and start wearing boxers! The myth that the kind of underwear a man wears can prevent pregnancy is a big one.

Meanwhile, if and when Khloe does become pregnant, there are a few old wives’ tales she should keep in mind:

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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.

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The Miss Jobless Chronicles: The End … Or Is It?

Editor’s note: and now, a very special installment of MJC, from, as always, Caitlin O’Toole..

Ev’ry time we say goodbye … I cry … a little…

After ten fun months of writing The Miss Jobless Chronicles, I am moving onto other pastures. I have landed a full-time freelance job with a major entertainment web site. I’ll be telecommuting. I already started and I love it.

The past months of unemployment have been a wild ride. From crazy bodega owners to my run-in with Nicole Kidman to hanging with my loving 82-year-old neighbor June, unemployment has been an exercise in making the dull less dull. I never encountered the kinds of characters I encountered when I was scrounging around for work. I think there’s a lesson in that. I’ll let you know when I figure out what it is.

So I am closing up shop. For now. But in this economy, you never know when I might be back. Good luck to everyone in your search for jobs and answers and whathaveyou… and thank you for reading! Happy Thanksgiving!

Love, Miss Jobless

caitlinotoole.pngAnd, well, that’s all folks, for now. If you miss Caitlin as much as we already do, find her on Twitter at @MsOToole, or just keep an eye out for her name in high places. And we’ll try to get her back to write about the world of employment every so often, so stay tuned, fellers and ladies.

The Miss Jobless Chronicles: The Rabbi

Ed. note: “The Miss Jobless Chronicles” is a weekly series written by Caitlin O’Toole. Read the rest in the series here.

I should know better by now than to respond to craigslist ‘help wanted’ ads. But, being a craigslist addict in every sense of the word, I can’t resist. (I still scour the pets ads and the free sections.)

I answered a job posting last week — this time, to be an executive assistant to someone “prominent” in the entertainment business. Sounded feasible, fun and right up my alley.

I have no personal assistant experience, but I have enough experience in the entertainment world — mostly as a writer — to be able to fudge it.

My cover letter reads as follows:

“To Whom It May Concern:

I’m interested in the Executive Assistant position and I’d love to be considered for it.

I’m a seasoned journalist with many years of experience in the business, so you can count on me understanding your busy schedule and keeping you organized. I work hard, am smart, savvy, creative and funny. I’m also extremely detail oriented.

I hope to hear from you. Resume is attached.”

I got a response the next day from the very curt assistant of a very prominent executive rabbi. He lives in Fort Lee, New Jersey. I figure I have nothing to lose — and decide to go see him.

I put on my Sunday best — a greenish tweed jacket that looks kind of like a riding jacket, black pants, and black “flats” (my mom’s favorite word). It feels weird to be out of sweats. But it feels good, too.

The interview is at 1pm, so I leave at 11am — which will leave me enough time to get to the GW bus station and catch bus number 171 to Paterson.

The bus ride is kind of fun, but I figure if I get the job, the novelty will wear off soon. I get off at the Fort Lee stop, right over the bridge. I have no idea what kind of structure I am looking for — an office building? A temple? A house? I just have an address scribbled on one of my old business cards from

I manage to get lost for about 20 minutes, walking, trying to find the address, a blister stinging my right foot. Finally I find it. It looks like OJ’s Rockingham estate. A gated mansion obscured by autumn-colored trees. There’s a Bentley in the driveway. And a lime green VW bug. I buzz the gate and a female voice answers, asking my name. I say I am here to see the rabbi. I am let in.

At the back door, there is no sign of life — not a barking dog, not a radio, not a footstep, not a sound. My ears are ringing. I knock unsurely, then twice, and finally a woman answers the door — Nadine, she says, and tells me it’s nice to meet me. She has the personality of a wall, and I imagine she’s the personal assistant I would be replacing.

She leads me down a dark corridor and apologizes — the rabbi is not “back yet” and I can have a seat at the computer and wait. The energy in the room is heavy and depressing. I try to imagine myself working every day in such a quiet, remote place. I can’t. But I am desperate.

Nadine gives me a writing assignment.

“We just want to get a sense of your writing style,” she tells me, and I’m wondering what kind of ‘style’ is needed to be an executive assistant to a rabbi. The assignment: Write a letter to him, telling him about yourself. I go to it.

“Dear Rabbi:

We haven’t met yet, but I’m definitely looking forward to meeting you soon! In the meantime, I wanted to tell you a little about myself.

I’ve had an interest in journalism since I was 12. I delivered the Washington Post for three years. I remember sitting on the stoop, folding my papers in my quiet neighborhood, imagining my very own byline. Well, years later, my dream came true…”

I went on to tell him about my published clips, TV jobs, and my blog. I tell him I’d very much like to work with him. I kiss ass as much as possible. I need this job.

Nadine comes back with a very well-dressed woman named Nancy, who is also a candidate for the position. Nadine tells me to get up from the computer so Nancy can also write a letter to the rabbi about herself. I am left standing in this dark, musty, depressing place, waiting for the mystery rabbi to come back from wherever he is. My blister stings. Nadine disappears around a spooky corner, then pops her head back out.

“Caitlin, thanks for making the ‘schlep’, as we say,” she says.

“You’re welcome.”

I stand in the corner awkwardly for about ten minutes, when I hear signs of life in the other room — the rabbi, I am told, is back. He emerges from around the corner dressed in shiny black running shorts, a turquoise ‘Just Do It’ hoodie, Nike Shox and a yarmulke. His beard is overgrown and greying and there is a sort of cunning, all-knowing twinkle in his eye.

“I’m Rabbi Michael,” he says, extending his warm, dampish hand.

“Nice to meet you, Rabbi –”

“Call me Mick,” he says, not even cracking a smile.

“OK, Mick, thank you, sir, it’s a pleasure.”

“I need five minutes to dry off,” he goes, and I’m thinking — um, gross. But completely intrigued, slightly amused, and eager to see what ‘Mick’ has in store for me.

I go stand back in my musty corner and wait for Mick to cool off. There’s no sign of Nadine or anyone else in this strange place.

Five minutes later, he beckons me into a large, bright “office” that looks more like a greenhouse full of cheap faux-leather furniture from Staples. It’s full of plants, books, and a purplish tweed couch from the ’70s. I can see the lime VW bug out the widow. I imagine him driving it and smile to myself.

“So,” he says, glancing at my writing sample and resume, “you’re a writer.” Read more

The Miss Jobless Chronicles: An Open Letter to the Department of Labor

Ed. note: “The Miss Jobless Chronicles” is a weekly series written by Caitlin O’Toole. Read the rest in the series here.

Dear Unemployment People:

How are you? I hope you’re great. Just a quick note to let you know that, with all due respect, you suck big eggs.

Thanks for the measly weekly pittance, it’s barely enough to live on — and, I must say, for an organization that supposedly aims to get unemployed people back to work, you have failed miserably. Ironically, you have totally destroyed my chances at working for my last employer. Let me explain.

In 2009, I wrote copy for a very popular web site — for the sake of anonymity, we’ll call it X. I got a flat-rate assignment from X about twice a month, for $500 a pop. The weeks that I worked, I did not collect benefits from you. I went on to your web site on the Sunday after I worked and clicked “I worked this week.” Just like you told me to.

Now, because you have absolutely no understanding of the freelance process, I confused you royally! It seems you thought the dates on the checks I received were the dates that I worked — when indeed, the dates of my invoices indicated the dates I worked. The dates on the checks were just that: Dates. Because you couldn’t figure out this simple thing, you got your panties all in a bunch and assumed that I lied and “double-dipped”, i.e., worked AND collected unemployment at the same time.

Do you get it? Should I spell it out for you? I think I need to. Let’s say I worked this week on a project for X, and the exact dates I worked were October 18, 19, and 20. I received $500 for those three days. So this Sunday, the 24th, when I logged on to the DOL web site, I indicated that I worked this week. So I would not receive benefits for the week. When I got paid for those three days, though, since payroll departments also suck, the check would be dated for the week it was cut. A week that I DID claim benefits, because I did NOT work. Are you with me? So, to you, it looked like I lied. When I did NOT. There was simply a discrepancy between the dates on my invoices and the dates on my checks.

To make things even more annoying, and embarrassing, every time there was a break in between a project for X, you would send me a notice in the mail asking why X had no more work for me. I would dutifully fill it out, and say I was no longer working for them “because of lack of work.” There was no box to check that said “because there is simply a gap between projects.” It’s called FREELANCE. Then, I would send the form to you, and you would send it on to X — asking if they had more work for me. Because I completed about 20 projects for X in 2009, they received these notices in the mail 20 times. Annoying for them, right? Do you think that this helped my case? No.

So, I get this call form one of your seedy, surly employees early in 2010. I apparently am “under investigation” for “lying” to you. Then, without warning, my benefits stop and I start borrowing money to live. The DOL tells me I have been “under investigation” for a while. I felt like a fucking criminal. Luckily, I had all of my pay stubs and invoices from when I worked. I was ready for them. I even got a letter from X stating that I worked the dates of the INVOICES, not the dates on the CHECKS. Arrrgh. Breathe.

I was “under investigation” for months, while you took your fucking sweet time arranging a hearing for me, at which I could present my case. In the meantime, I was living off hand-outs and credit cards. My finances were in the toilet. Long story short, months later, I was summoned down to the DOL and had my chance to explain and present my case. And I did. Months later, I won. Fuckers.

Now, X won’t talk to me — they won’t return emails or my calls. And who could blame them? They were harassed endlessly for my financial records, and bombarded with phone calls. They must have thought I was a first-rate LIAR. Well, I wasn’t! And X, if you’re reading this, I want more work from you! I loved working for you.

So, ironically, the organization that’s supposed to support my work efforts totally ruined my chances at ever working with X again. Thanks bunches!

Love, Miss Jobless

caitlinotoole.pngCaitlin O’Toole is a New York City-based writer and editor. A native of Washington, D.C., she began her illustrious journalism career as a Washington Post paper girl. She has since written and edited for Sesame Workshop Digital, Star Magazine, The National Enquirer, Glamour,, and Washington’s City Paper. Her work has also been featured on Fox News, ABC, MTV and VH1. She lives in Chelsea with her two cats, Lucy and Ethel. She can be reached for work at her LinkedIn page and Tweets at @MsOToole.