What’s the lamest thing you ever did for money?

sandwich board
Wearing a sandwich board of any sort qualifies.

Our morals are relative, our bank statements, piddling, and our shame, even less. From moving in with mom and dad to to freelancing for porn spammers to dubious Couponzi schemes (disclaimer: we at Brokelyn do not endorse the puns from that show, but might borrow one if it’s right there for the taking), there’s nothing our generation hasn’t tried in the name of saving or making a buck. Some say it’s the root of all evil, but money is also the genesis of some pretty priceless stories. We asked our friends and other assorted seedy characters what they’ve done for money, and here are their confessions. What’s the most questionable thing you ever did for dough?

• “My roommate and I once stole a light bulb from a coffee house table lamp because we were too cheap and lazy to go buy one.  It wasn’t even the right voltage.”

• “I started visiting a dying relative in hopes I’d get a little something extra when he eventually passed.”

• “I moved back in with my parents.”

• “My high school friend and his frat brothers stole people’s textbooks from the library (during finals week!) and sold them.”

• “Once I bought a ticket to a Girl Talk concert I couldn’t go to, then sold it to a friend of a friend for triple face value when the concert sold out.  Then I felt like shit and made him rainbow chip cupcakes.”

• “Last summer I collected sunglasses from the lost and found at work and sold them at Beacon’s Closet.”

• “I wake up every day and go to a job that I hate.”

• “To monitor our gambling habit in college, my friend and I made a rule:  we wouldn’t gamble our own money.  We decided to recycle cans and use the money we made from it as our gambling allowance. One day, we had a Eureka moment:  the campus Eco-house had to recycle cans as a policy, and used the revenue to fund their projects. An entire dorm of cans!  We drove over and found three giant, heaping plastic bags of cans outside—the mother lode. A girl called the campus cops on us and we had to do 20 hours of community service. When the guy running the community service found out what we were in for, he’d send people over to ask us what we’d done just to embarrass us.”

• “I’m a drug dealer.”

• “In college when I went out to eat with friends I would only order an appetizer and then finish everybody else’s plates. It worked because they were all trying to lose weight.”

• “The summer after I came back from being abroad I was super broke and my friends and I started a little business detailing cars. Our first client was a blind man with an SUV (he had a personal driver). My friend filched an electric buffer from the guy’s garage, and we started using it for all of the jobs we got. We ended up tripling our production and income, as we’d been doing everything by hand up until then. At the end of the summer we made him sneak back and return it.”

• “One summer when we were living in New Haven, my friend and I answered a Craigslist ad from a Yale MFA student from Russia who needed models for a photo shoot. It paid $50 for two hours. When we arrived, ‘Olga’ asked us to pick out an item to wear from a suitcase of clothes. But it was filled only with XXL, brightly-colored, Bill Cosby-style sweaters circa 1987.  She then instructed us to dance in the sweaters, to no music, among the backdrop of a gothic Yale dining hall.”

• “I freelanced a bit and made a list of hundreds of alternatives for spam words. My best one was ‘nude man’s own dressing.’ “


  1. At some point in high school, I punched myself in the junk 20 times in a row for $80. 

    Now ladies, you might not know this, but after getting hit in the pills, there’s about a 5 second gap between the impact and you feeling the pain that brings you to the fetal position. As it turns out, those five seconds will actually postpone until you’re done wailing on your nads before the combined agony of 20 nut punches ruins your day (and probably your ability to father kids.)
    Don’t judge me.

  2. I don’t remember where I read this, but some guy claimed to have been employed as a “drink finisher” in a Catskill hotel. When people got up to dance, he’d sidle past their table and “finish” their drinks for them. The party-goers would usually just order more rounds.

  3. Contacted a woman on craigslist selling bags of used clothes.  Went to her apartment, told her they were for a class (which I made up), and I would get extra credit.  Asked her to let me take the clothes to the professor, see if he liked them, and then come back and pay her.  She agreed.  Instead, I went to Beacon’s and Buffalo Exchange and sold some shoes.  Returned, told her that my professor only took the shoes, asked what I owed her.  She shrugged and said it was fine.  Altogether I made $8, after two subway trips.

  4. Bonni

    As a cocktail waitress on a college campus I used to confiscate people’s fake I.d.’s then offer to sell them back for $50. Sometimes I would do the same with real I.D.’s. It always worked.

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