The Miss Jobless Chronicles: Making Money: A Desperado’s Guide

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

When I was a kid, I used to say to my dad, “If EVERYONE in the world sent me a penny, I would be rich!” And he would go, “Why would everyone in the world send you a penny?” At five, I didn’t really have an answer to that.

I’ve had cockamamie money-making ideas like that since forever. That said, I’ve never been a very shrewd businesswoman and money burns a hole in my pocket. I’m sure I’d spend the pennies as fast as they arrived.

When I used to live in the Village, stoop sales were a festive sign of spring. On any given Sunday, I could rake in upwards of $400 selling shit from my apartment laid out on an old tablecloth. Now that I’m in Chelsea, I don’t have a stoop — and I don’t exactly want strangers coming up to my apartment to rummage through my shit.

At, before Google was a household name, we used to joke that we needed a way to quickly asses whether a person was dead or not. We decided we needed a 1-800 number called 1-800-WHO-DEAD. You’d call an automated system: “Welcome to 1-800-WHO-DEAD. Please type in the first three letters of the last name of the person you think may be dead.” And you’d type… N-E… “If you mean Paul Newman, press one. If you mean Randy Newman, press two. For Willie Nelson, press three.” OK, so you press two. “Paul Newman is indeed dead. To find out if another person is dead or not, press one.” Brilliant, right?

Well, the Internet has made it easy to instantly check on this, so 1-800-WHO-DEAD doesn’t hold water in the new millennium. So I’ve come up with a few modern, money-making ideas for hard times.

Idea #1: The Pooper Scoop. Phobic people pay me to trail them while they walk their dogs. If the dog poops, I scoop and make $2. If the dog doesn’t poop, I still get $1 for showing up.

Idea #2: The Lemon Drop Stand. This is the old lemonade stand idea of yore, only the modern version — Absolut lemondrop shots on the street. The stands would be skillfully placed throughout the city on very dismal corners, like outside the unemployment office and funeral homes. Shots are $3.

Idea #3: A new restaurant called “Sides.” Haven’t you ever gone to a restaurant and just wanted a few side orders? Well, then you need to visit “Sides” — all sides, only sides, all the time. For $8 you can get a trio of sides — apple sauce, mac and cheese, fries — for dinner.

Idea #4: The Holiday Pet Pal. You pay me $9.95 and I’ll take a picture of your pet with me, dressed up in timely holiday garb (Santa Claus, the Easter Bunny, Hanukkah Harry, whomever.) See photo!

Idea #5: The Lawyer. You pay me $5 to call anyone and pretend to be your lawyer and scare the shit out of them. I’ll even create an email address to follow up the phone call with a scary mail. Perfect for landlord disputes! (I need a name for my firm. Anyone?)

Idea #6: The Umbrella Sella. Stand next to the $3 umbrella guys in a rainstorm and sell umbrellas for $2.99.

Idea #7: The Taste Tester. I hang out in restaurants and you am the one who’s there to assess if something is spoiled or not. This is kind of a play on a joke Ellen does in her stand up act. I lurk around people’s tables and wait for someone to say, “Wow. This tastes like crap. Do you think it tastes like crap?” And then I taste it and decide whether or not to send it back.

Publish date: May 3, 2010 © 2020 Adweek, LLC. - All Rights Reserved and NOT FOR REPRINT