Working Girl: Honesty is Not Always the Best Policy

Working Girl: Moralistic Values Gleaned from My Time in Chicago’s Seedy Underworld

Moral 110: Honesty is Not Always the Best Policy

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My boss Caroline had decided to extort one of her clients. She couldn’t decide whether $7,000 or $10,000 would be more appropriate.

“What do you think,” she asked me. “Should I go high or low?”

I was just a lowly personal assistant. I hated it when my boss the high-rolling escort asked me for advice about things like money laundering or extortion.

“Why are you extorting this guy again?” I asked, trying to put off the moment when I’d have to give her advice. Couldn’t she just send me out to buy more Reddi-Wip or condoms? Those errands were always a little uncomfortable, but at least they didn’t involve crime.

She sneered. “Because he’s a jerk! You should’ve seen the way he treated me during our session. It was really scary and weird. I deserve thousands of bucks for what he put me through.”

I winced. If Caroline said something was scary and weird, it really must’ve been. I couldn’t imagine what it was, but I could imagine that she’d felt powerless.

If there was one thing Caroline hated, it was feeling powerless. She was a mega control freak. She employed a group of younger escorts, and strictly controlled the clients they saw and the money they made. Opening her cabinets revealed row after row of identical glossy red gift bags which held all her belongings and were appropriately labeled. She had been an escort for over 20 years and never suffered the “protection” of a pimp.

“And he threatened to tell the FBI about me!” she said.

For a professional sex worker, those were three worst letters in the alphabet. So not only had this guy treated her like crap; he was still making her uncomfortable. No wonder she was going after him with her big guns.


Moral 108: When you act like a jerk, you just might be underestimating the person you’re mistreating.

So maybe the person you’re jerking around might seem powerless now, but they might try to extort you for thousands of dollars, or they might know an FBI agent, or they might become a writer and tell everyone about the way you behaved.

Just saying.


“But I’m not too worried he’ll actually tell the FBI,” Caroline said. “I mean, first of all the guy’s in California. I don’t think the California feds would go out of their way to come after me in Illinois. Second, if he tells the FBI, I’ll call his wife and kids and tell them that he saw a prostitute and what he made me do. I have the upper hand here. Do you think I have the upper hand here?”

The right answer was yes. “Yes.”

“Me too. He won’t tell the FBI. I think he’s bluffing. Do you think he’s bluffing?”

How could I gauge whether a john in California was bluffing about contacting the FBI? I shrugged and skirted giving a direct answer. “Depends on how pissed off he is.”

She folded her arms and leaned against her counter. “That’s not very helpful.”

“Sorry,” I said. “But I don’t think I have enough information”—or experience with extortion or the FBI—“to make a call here.”

Caroline closed her eyes and tipped her face toward the ceiling, as though summoning patience.

It didn’t work.

She was angry when she looked at me. She folded her arms and cocked her head to the side, narrowing her eyes. “You know Leslie, sometimes it feels like I don’t have an assistant at all! Don’t dare apologize. It doesn’t matter. I’m going to call his bluff and make him give me money. Now, should I ask for $7,000 or $10,000?”

She was already in a bad mood. It would seriously piss her off if I refused to answer. But I really, really did not want to get involved in this.

I told her I would rather not get involved.

“TOO F—–ING BAD! YOU DON’T GET TO BE A PRINCESS ANYMORE! Now tell me seven or ten or get out of here and don’t come back!”

Wow, what the hell had that guy done to her? My heart was pounding. “Okay, ten.”

“Good. Why?”

I shrugged. “Why not?”


“Okay, well, you’re already engaging in prostitution and extortion . . . so why not go all out?”

She was more satisfied with this answer. “You’re right. I’m already breaking the law. What’s a few more thousand going to do?”


Moral 109: If you don’t create strong boundaries, you’re going to get involved in stuff you don’t necessarily want to get involved with.


I cleaned her kitchen while she made several threatening phone calls demanding $10,000. There was a lot of “how dare you,” and “you won’t get away with this,” and “I’m coming after you.” When she hung up the phone for the last time, she handed it to me.

“I have a client coming,” she said. In general, I wasn’t great at talking to johns, but she couldn’t very well take calls when she was with one. That’s when it was my job. “Answer the phone if it rings, but if the guy who owes me ten grand calls, don’t talk to him. Just hang up.” She gave me a list of errands that would have me running all over Chicago, and sent me on my way.

I breathed a sigh of relief as soon as I left her apartment. She was in a bad mood today. That in itself was dangerous. Add federal crime to the mix, and I was lucky I hadn’t had some kind of anxiety attack. This job was getting way too stressful for me.

I hadn’t been gone twenty minutes when the phone rang. I had really, really been hoping this wouldn’t happen.

I took a moment to collect myself, and then answered as calmly as I could, “This is Kira’s assistant. Can I help you?” Kira was Caroline’s favorite fake name.

“Yes, I hope so,” said the voice on the other end. He sounded polite and gentlemanly. “This is federal agent Fitzgerald with the Los Angeles FBI. Who am I speaking to?”




This wasn’t happening.

What the hell should I do? Should I LIE? To the freaking FBI? I was bad at lying to my mom! How could I lie to a freaking federal agent?! My brain stopped functioning. My mouth began working all by itself.

I answered as cooly as possible, “This is Kira’s assistant.”

“Kira?” said the polite but absolutely terrifying FBI agent on the other end of the line. “Is that your boss’s real name?”

“It’s her business name,” I said.

“Mm-hmm, and what does your boss do for a living?”

“She’s an escort.” Oh crap, I’d actually said that!

“Mm-hmm, and what does that entail? Does she sleep with her clients?”

“Her clients pay for her time in 45-minute blocks, and what happens in that time is between her and the client.”

“Mm-hmm, so do you think she sleeps with them? Probably, right?”


Oh, I was totally screwing this up. This was going all wrong, wrong, wrong!

“And what is Kira’s real name?”

“Caroline Richards,” I said. I was so screwed. Deeply. Royally. But I couldn’t stop talking. It was like Professor Snape gave me veritaserum.

I proceeded to answer all of the ever-polite Agent Fitzgerald’s questions with complete and utter honesty. I told him all Caroline’s cell phone numbers. I told him her address. I told him her birthday and how long she’d been working as an escort. I told him she employed a bunch of girls who she sent clients to.

Then the questions became about me.

“And what do you do for her, again?”

“I’m her assistant. I clean, cook, shop. Shopping’s what I was doing when you called, actually.”

He didn’t believe me, of course. I could hear it in his condescendingly polite, know-it-all, FBI voice. “And what’s you’re name?”

I had just thrown Caroline under the bus. And it was a big bus. It was one of those massive mobile home tour buses that bands use when they travel across the country. If she got arrested, she would throw me under the bus too and say I was a prostitute. My Catholic mom would have some kind of siezure.

“Listen, I’m sorry, I really have to go! Nice chatting with you!”

I hung up.

I’ll tell the rest of the story next week. It does not end pretty.


Moral 110: Honesty is not always the best policy.


Working Girl is going to be a book! I’m winding down to the end of the series, and I’m collecting all the entries into a book, along with additional material and microwave instructions. 50% of the proceeds will go to sex trafficking non-profits for the entire life of the book. It will be released March 25, but you can pre-order it and get more information here! Let’s help people and convince ourselves our lives have meaning!

If I don’t make the March 25 deadline, I’ll dye my hair pink. No, really. It’ll be Jem-tastic.

I’ll also do fun and frightening milestone events. So when we sell 500 copies, I’ll sing a karaoke version of Damn, I Wish I was Your Lover and share it online. But fair warning, I can’t sing. So buy a copy and contribute to my awkward humiliation!

L. Marrick is a fiction writer and freelance copywriter. She waxes poetic about swords and the Renaissance Faire at her author blog. She looks all professional-like at her copywriting site. She eats too much chocolate and still doesn’t believe downward dog is supposed to be a restful yoga pose. You can connect with her at either of her websites, and follow her on Twitter @LMarrick.

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