I was lucky enough to go to a Creative Mornings event last Friday and lo and behold the theme this month was money. I was so excited to hear true, personal and hilarious stories about people and money. I walked in and was given a nametag. On the nametag, it asked, “What is the strangest thing you’ve done for money?”.

The question, if nothing else, is thought provoking. I got to thinking…..and I thought some more. I’ve done some pretty strange things for money over the years.

I worked as a telemarketer for an arts organization. We used to have this game, that whoever gets hung up on the most, wins. At one point, one of my callers tried to have phone sex with me. How awkward (and creepy) is that? I started an innocent enough conversation about the theatre, his favorite shows and somehow it turned into what am I wearing, how old am I? Yuck.

I once got paid to “look busy” at an office in LA. I answered a Craigslist ad for a company whose CEO was coming to town. The company wanted the office to look more flush and busy. I could do whatever I wanted on the internet, I just had to “look busy”. It was so strange, but kind of awesome. I got paid $11/hr to surf the net and do what I would’ve done at home anyways.

I worked an all night rave from 10pm-6am as the “water girl”. Essentially, I sold water bottles to crazy, drug-induced ravers.  It was a packed event, with music that I didn’t really care for and people strung out like nobody’s business.  When that many people are dancing and doing drugs, people are dehydrated and will pay anything for water. I think I found my market there, but the rave scene really isn’t my thing.

I did a performance outside of NYU begging for tuition money. This was really interesting, and was originally a project for a class and a social experiment. Who would give money to a white, privileged student? The reactions were diverse: chuckles, sneers and surprisingly $29 in donations after 45 minutes. One guy even bought me a bagel and coffee. This piece simultaneously restored my faith in the world but also made me feel awful. Do people that really need money make that much? Do homeless beggars who need a meal get food? The answers, I still don’t know. I have a feeling that my experiment was successful because people could relate to me. I dressed the same, I looked “normal” and I could be their daughter. I was interested in highlighting the high cost of tuition and making visible the pain of student loans– but I ended up learning a lot and was ridden with more questions. I ended up giving the $29 away to others that I thought could use it more than me.

I sold books that I got from the free section of my apartment. My boyfriend really thinks this is low, so I’ve stopped. He thinks the whole point of having a ‘free section’ is to avoid monetary value and capitalist consumption. I get it.

There was also a time I sold an unused package of ProActive (yes, the acne treatment) to a thug looking dude in a parking lot at Rite Aid. (Oh, Craigslist)

While at NYU, I participated in medical research. I got hooked up to all these cords and had an electrode attached to me, while watching a screen. I had to press a button every time I felt the signal. I started feeling dizzy from the screen, so I asked them to stop. They paid me my $30 and said I was now ineligible for future research!

2 years ago, on Christmas, my boyfriend and I helped out a Woody Allen-esque Italian family for Christmas dinner. Did I have catering experience? No. Did I cook at the time? No. But I know I am super helpful and organized! I did a great job at cleaning, and organizing but my boyfriend and I burnt their green beans and the fire alarm went off. One of the mafia like Uncles proclaimed, “Who hired these guys?”. We still left making $250 on Xmas and lots of memories.

Some other questions that came up at the event were also fascinating to think about.

What have you spent too much money on? I think the obvious answer here is school. It really is the only thing I sort of regret. It’s complicated, because I went to a great school and had a great time, but I don’t know if it was worth it. I also don’t know if I would have ever lived in New York, or met the people I did. Although I spent too much on it, it felt right at the time.

What do you wish you spent more on? Art. I love the arts in all forms and want to see more plays, concerts, dances, take more workshops and classes. Sadly, because of my debt and lack of finances I’ve forgone these experiences that I cherish.

What’s the best financial investment you’ve made? Studying abroad. When I was 21, I worked all year making minimum wage to pay for myself to study abroad. At the time it seemed like a bad investment. I had student loans (that I didn’t really think of at the time) and was taking a couple months off of work to live in Spain. But I was determined to make it work and it’s been the best investment of my life. My Spanish improved dramatically in a short period of time and afterward I was able to call myself proficient. I have been hired for exactly three jobs, including my first ever career job because of this skill. I would not have my current job if I didn’t have the experience of studying abroad. Considering the skills I developed and the experience I had, this has been the best investment. I spent 5k to study abroad. I’ve made that money back in no time given what the experience has afforded me in terms of jobs.

What’s the stupidest thing you’ve spent money on? Now, this is embarrassing. When I was a teenager, I was made fun of all the time for being flat chested. When I got my first job at 17, I spent $250 on breast enlarging “vitamins”. Of course, they didn’t work. It was so stupid and such a waste of money. It’s pretty funny now, in retrospect. The other stupid thing I spent money on was a psychic. After my last breakup, I was devastated as my love at the time dumped me out of the blue and didn’t want to talk to me “so he could move on”. I was such a mess, I decided to go to a psychic. They would have the answers! I was desperate for any information or any morsel of faux truth I could cling on to.The psychic told me we would get back together, have three kids and live happily ever after. HA! Thank goodness that didn’t happen. I am now happier than ever with my love of almost 5 years!

Now that I’ve shared my crazy, personal and hopefully funny stories with you, I want to hear from you!

What’s the strangest thing you’ve done for money?
What have you spent too much money on?
What do you wish you spent more on?
What’s the best investment you’ve made?
What’s the stupidest thing you’ve spent money on?


Melanie is a freelance writer currently living in Portland, Oregon. She is passionate about education, financial literacy, and empowering people to take control of their finances. She writes about breaking up with debt, freelancing, and side hustle adventures at DearDebt.com.

Currently she puts more than 50% of her income towards debt, while living a frugal, fun life. In addition to her love of personal finance, art and music, she is also a karaoke master. Follow the adventure @DearDebtBlog.

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15 responses to “What’s the strangest thing you’ve done for money?”

  1. Wow, thanks for sharing such personal and interesting stories (especially about the psychic, I was so close to resorting to this during a break-up, too, but I think just spent it on retail therapy instead). The strangest was definitely being a bartender, which was okay save for the fact that we dressed fairly provocatively… it was great tips, at least. Great post!

    • doordebt says:

      Retail therapy would’ve been much better than going to a psychic! I always kind of wanted to be a bartender, but I think you have to have a certain personality and be able to deal with a lot of crap. Don’t know if I can do it– it would probably ruin bars for me, lol.

  2. Wow, those are some interesting stories! I can’t say I’ve done anything that strange for money…yet (maybe I should start living)! I definitely spent too much money on my education too and it was by far the stupidest thing I’ve spent money on because I know it wasn’t worth it.

  3. Wow I love that, especially how you got hired to “look busy.” Easy money huh? The strangest thing I ever did was play a car accident type victim so firemen could get their EMP certification. Not bad huh?
    I’ve spent way too much money on just about everything.
    There is probably nothing I wish I would have spent more on. Maybe a longer vacation. The best investment is my health, and my future.

    • doordebt says:

      That is interesting! I’d love to know how you got involved with that. I’d do it, haha! I think investing in your future and health are great investments and very wise on your part.

  4. So interesting the social experiment at NYU. I’d be curious about whether people were more or less likely to give you money because you didn’t look homeless. $29 in 45 minutes is a pretty good hourly rate 😉 I’ve never been in an experiment, but I’d be willing to do so as long as I didn’t have to take any medications.

  5. […] anyway, I read Do or Debt’s post and thought it was a kind of fun (hey, my favorite f word!) way to think about money and the […]

  6. […] Do or Debt-What’s the Strangest Thing You’ve Ever Done for Money? […]

  7. […] I’ve also been in situations where my class was made very apparent. In addition to my list of the strangest things I’ve done for money, I’ve also worked as a house-cleaner. In NYC, when I was getting desperate I answered an ad on […]

  8. Debby says:

    Oh wow – such great stories Mel! I once did a summer job at a pasta factory. I was hired for a month but I gave up after 3 days of seeing dried noodles flashing before my eyes for 8 hours straight.
    The stupidest thing I ever spent money on, was on a Honda CRV jeep while I was already paying big bucks on my mortgage. I did look really tough and ‘something’ in the car, though. Alas, I was not 🙂
    Debby recently posted…Day 241 – Beating jetlag.My Profile

  9. What’s the strangest thing you’ve done for money? Chaperoned an athlete and witnessed drug testing at a qualifying olympic lifting event. $55 for 40 mins of work and free admission to an event I was going to attend anyway.
    What have you spent too much money on? Jewelry when I was in my early twenties and shoes in my thirties. Luckily, I didn’t go into debt for either.
    What do you wish you spent more on? Travel, travel and travel. Did I mention travel?
    What’s the best investment you’ve made? It’s a 3-way tie: my education, home and retirement savings.
    What’s the stupidest thing you’ve spent money on? A new SUV. I’ve long-since been reformed. I now purchase vehicles for utility, not as status symbols.

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