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.”

“Yes, sir. I mean, Mick.”

“So do you have any experience as a personal assistant?”

“Well, not per se,” I say. “But I have worked in the business for many years and I understand its rigors, its ups and downs. I’m also familiar with the players in the entertainment world. I’m sure I can keep you –”

“No experience?”

“Well, as I said –”

“To be honest, looking at your resume, you’d make a sucky assistant,” he says, totally straight faced.

And I’m wondering if this is the first time a rabbi has ever used the word ‘sucky’.

“Where do you live? How did you get here?” he continues.

“Bus. I live in Chelsea.”

Now, if I had balls, I might have said, “If I would make such a sucky assistant, why the fuck did you summon me here for an interview?”

Instead, I smile.

“Are you really willing to commute for four hours a day just to come here and be my assistant?”

“Yes, sir,” I say.

“Well, as I mentioned, you would suck at it. But I could use you in another capacity.”


“If I were to hire you as an assistant writer,” he said, “what’s the lowest you’d go? Level with me.”

Now I wasn’t about to tell him I used to make $75K. But I didn’t want to totally lowball myself, either. I’m really just looking for something in the $15/hr range.

“Um, thirty-five thousand,” I tell him.

“Twenty five. No, ten dollars an hour. I’ll pay you ten dollars an hour to help me write. Before we get into the nitty gritty, though, let me ask you — do you know who I am?”

I did. I had done my research. I know he has counseled many down-and-out celebrities and done a lot for charity. I’ve seen his columns and various blogs. I’ve watched his motivational videos. In short, I was a fan.

“I’m familiar with your work, Mick. Yes.”

“OK. Why don’t you come out here tomorrow and we’ll try this out? How does that sound?”

In my head, I’m figuring out the cost of transportation ($13/day) versus my $10 an hour salary. Take home pay (minus taxes) after 40 hours a week plus 20 hours of commuting: $212. Sad. But I tell him I’ll take it.

Long story short‚ next morning I dress up in corporate attire and head up to 175th St. to the GW Bridge terminal. It takes about an hour. I buy my bus ticket. Then I get a message on my voice mail.

“Hi, it’s Michael. I think I’d rather you work at home today. I can dictate some articles to you over the phone.”

WTF? This “job” has already cost me $26 and I haven’t even started yet. I head back home, deflated, pissed and tired.

I decide to cut my losses and tell him thanks but no thanks. Though I am unemployed, my time is still valuable.

Later that day, I get a promising phone call from a very big entertainment web site. They want me to possibly write for them. Could this be my big break? Tune in to next week’s MJC!

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.