1993: Starting a Baby-sitter’s Club*
Over the summer of 1993, I decided to start a baby-sitter’s club, despite not having any friends, let alone enough friends to form a crude “club” of any sort.
The club was the lynchpin in my three-part plan to dramatically launch myself into the social orbit of middle school: first, I’d get some money; with this money, I would then acquire the hallucination-inducing early ‘90s clothing item of my choice (probably a windbreaker that changed color when you touched it); then, after I strutted around in my windbreaker for a bit, all sorts of first kisses and emotionally abusive friendships with popular girls would be mine for the taking!
Only after assembling some “kid kits” (king-size Snickers bars + broken Jenga game) and signing up for a Red Cross first aid seminar did I realize that I didn’t even know any babies, and also that I disliked responsibility. I gave up on starting the club, and by the end of sixth grade, was just really into grunge and only cared about babies when they were used in eerie and/or culturally incisive album art.
Expenses: $13 to assemble “kid kits”
*Any resemblance to a certain series of books about a group of clever tweens and their adventures with rudimentary capitalism is purely coincidental.
1996: Selling Magazines, Wrapping Paper, and Cassette Tapes
Perhaps you experienced this, too: you and your friends were pulled out of math class, herded into an auditorium, and encouraged to reach for the stars and achieve your destiny by selling magazines, wrapping paper, and cassette tapes. You received a certain amount of points for every item sold, and if you earned enough points, you would eventually be rewarded for your trouble with the grandest prize of all: a “sunburst” wall clock, presented to you on stage at an all-school assembly.
Everybody lost their shit over the prospect of becoming an independent adult via selling off-brand greeting cards for about 15 minutes, and then everyone forgot about it—everyone except those who were exceedingly cocky, exceedingly desperate, or exceedingly in need of a large wall clock.
What did a 13-year-old need with a large wall clock? Well, I was going to hang it in my old playroom, and then slowly convert the room (which was at the time just a shallow mass grave for perversely mutilated She-Ra dolls) into my own swinging bachelorette pad, complete with water bed, bead-curtain thingies, and cable. This foray into adult sophistication and worldly elegance hinged entirely on the acquisition of a large clock.
Also, being presented with something on stage at an all-school assembly seemed like the middle school equivalent of eating the still-beating hearts of your enemies as they looked on, and that appealed to me.
I did not sell enough magazine subscriptions, wrapping paper, or cassettes to get the “sunburst” clock. I sold an Esquire subscription to my dad, a cassette of Sting’s “Ten Summoner’s Tales” to my mom, and then I was all out of ideas. I accumulated enough “points” to get a single fuzzy pom-pom with eyes glued to it. The eyes fell off almost immediately. My mother also didn’t let me move into the playroom, but she eventually let me get cable in my bedroom because she felt guilty about getting divorced.
Profits: That Esquire subscription proved itself weirdly useful in decoding the way of men, once I hit puberty.
1998: Selling Beanie Babies on eBay
This was mostly my mom’s failed scam, but I feel that I was complicit, because I didn’t stop her—in fact, I egged her on, because I also believed in the Beanie-based economy of the future.
My mother, like everyone else’s mother at the time, got confused by how people sold old toys for tons of money on eBay, and thought that you could sell literally anything for tons of money on eBay, for reasons that weren’t entirely clear (possibly “the millennium” or “Y2K”).
With this knowledge in hand, my mom drove all over the state of Connecticut every day after work in the spring of 1998, engaging in furtive Beanie swaps with other Beanie-crazed moms and swooping down on small-town hobby shops that didn’t even realize that they were in possession of a Punchers the Lobsters, for god’s sake!
This wasn’t all complete insanity—some people actually did make a lot of money selling Beanie Babies. But by the time word had gotten out about it, the boom times were over. My mother never made any money off Beanie Babies, and, when you add up the money she spent on the Babies themselves, gas used for her Bean-ing excursions, and all those meals at McDonald’s to get the Teenie Beanies Happy Meals, I had an early lesson in the prices we all pay for chasing our dreams.
Expenses: I will probably die prematurely from having eaten 5 “Teenie Beanie” Happy Meals per week during the spring of 1998
Profits: Something interesting to talk about in therapy!
1999: Flipping Star Wars: Episode I Action Figures
This was like Beanie Babies, but for greedy nerds, and sadly, this one is all on me.
The logic here was obvious: if people wanted one Boba Fett action figure, because it reminded them of their childhood and innocence and hope, and they were willing to pay top dollar to get it– wouldn’t it stand to reason that they’d want 19 brand-new action figures of Qui-Gon Jinn, a new character that they had never heard of before, 19 times as badly?
I stockpiled Episode I action figures in the weeks leading up to the movie’s release, and if I’d managed to sell them before the movie actually came out, I might have been fine. But I held on to them.
By the time that I got up during the pod race scene to pee, got locked inside the single-occupancy bathroom at the movie theater, banged on the door until an assistant manager unjammed the door for me, came back into the theater, and saw that it was still the pod race scene, I knew I was royally fucked. The action figures are still all at my mom’s house, but I’ve been too ashamed to look at them since 2001.
Profits: Learning to never trust anyone (especially George Lucas)
2002: Getting Hit By a Bus
One of the first people I met in New York City told me that you could make a ton of money if you got hit by a city bus (non-fatally, of course). He knew, because he’d made $100,000 suing the city after getting slightly run over by the M20. Of course, he’d spent it on hookers and drugs in the interim, but it definitely happened, and it was a super-easy way to get cash. Way easier than going to a job that’s not getting hit by a bus, because most of those expect you to show up, like, every single day! This, like electro-clash and fashion-mullet haircuts, seemed like a decent idea to me at the time.
I had forgotten about this whole thing until this past year, when a friend of mine–through no fault of her own–was non-fatally hit by a city bus. Wow, it turns out that guy’s story was not true at all!
Profits: Learned to never take life advice from someone whose story ends “…and then I spent all that money on hookers and drugs, and that’s why I’m living at my ex-girlfriend’s mom’s house right now.”
image – Shutterstock