Child Cigarette Hawker to Semi-Professional Cinnamon Eater: 99 Hustles I’ve Tried (+ 24 I’m Still Doing Now.
Yesterday evening, I had to come up with a 95-word byline to publish alongside one of my recent articles.
Among the quirky facts I strung together (i.e., I like eating donuts and still can’t bond with my step-cat — IYKYK), I mentioned I had tried more than 100 side hustles. Upon further reflection (late-night panic), I’m reasonably sure I have. But just for fun here’s a list (wildly lacking in chronological order) of all the side gigs I have ever done.
By side hustle, I mean an online gig, cash app, freelance work (not W-2), or other miscellaneous activities. Hustles with an asterix (*) I am still doing now.
1. English tutor in France. I tutored a 15-year-old boy once a week.
2. Small Child Cigarette Hawker.
I sold packs of cigarettes and pull tabs at the church’s bingo hall — as a small child too young to read or count money or make change. Once a week I pushed a rusty cart of tobacco and gambling contraband though the church’s gymnasium, occasionally ramming into bingo chips and ashtrays and old walkers with tennis ball stoppers. For my efforts, I was paid in concession stand candy bars.
3. Apple vendor.
As in picking apples off the tree — that may have belonged to my neighbor — and selling them door-to-door to every house but theirs.
4. Korean Black Sheep — a now defunct blog.
5. InboxDollars (gig economy survey app).
6. Swagbucks (see no. 5).
7. **Upromise (see no. 6).
8. Selling on eBay.
9. **BST groups on Facebook.
Selling my kids’ used children’s clothing to the pre-selected masses who will pay $20 for used 2T pajamas.
10. **Freelance writing on Fiverr.
11. **Dear John letter writer.
This is an especially invaluable service during the Golden Age of Internet Dating. If you’re not feeling it anymore, talk to me. You know it and I know it: ghosting someone is just a dick move.
12. **Byline writer, as in writing other people’s bios for art displays or dating profiles.
13. Nanny (three different families) during college years.
14. Semi-Professional Dress Wearer.
I wore the same dress 100 days straight for a sustainability challenge to stretch my creativity and get $100.
15. Failed freelance e-commerce copywriter.
I was inexperienced and in over my head, freshly out of college. I didn’t outright fail so much as run away. In your early 20’s, most of us are far too afraid of failure.
16. **Rakuten (formerly eBates) for cash back shopping rebates.
17. **Honey. (It functions like no. 16).
18. **Capital One Shopping extension. (See no. 17.)
19. Poshmark.
20. **Kidizen.
21. Mercari.
22. Diet Coke Thief.
Not really a gig but that vocation seemed meritorious of a place on the list. I had a high school mall job where I’d make my soggy Burger King cup last for weeks as I’d return every few hours for a refill, smiling brightly at the cashiers.
23. Illegal denim counter.
A sustainable, anti-racist store who I will not malign paid me (eons ago) for coming in for a few hours one Sunday night to help inventory their denim goods
24. Tada for cash for receipts.
25. Ysense for surveys.
26. Survey Junkie for surveys.
27. Pinecone Research for surveys.
28. Harris Poll for surveys.
29. Nielsen for Internet market research.
30. Ipsos for surveys.
31. Thumbtack (but no one hired me).
32. Acorns investment app. (I thought it would be a good passive income side hustle.)
33. Concordia Language Villages.
34. **Write One True Sentence (digital dumping ground for my brain).
35. **House of Henmar (slightly less un-focused than no. 35).
36. Crayon maker (using silicone dinosaur molds).
37. Fetch Rewards (receipt app).
38. Shopkick (see no. 37).
39. **Ibotta (see no. 38).
40. Checkout 51 (see no. 39).
41. Au pair in Switzerland (part I).
42. Au pair in Switzerland (part 2).
43. Door-to-door bookseller. I sold my old books for money. I don’t recall my age, only that I was too young to read.
44. **Flightmonger. As in being amenable to giving up your seat on crowded flights in order to reap the benefits of free airplane tickets and free meal vouchers for airport hamburgers.
45. FarmVille 3. I played it to get the cash reward.
46. Bingo Blitz.
47. Solitaire Smash. (I haven’t added descriptions for other games but don’t be lazy. Read no. 45 and make some inferences.)
48. Rover (the dog walking app).
49. Some casino style app game. (I forget the name.)
50. Hair model (for beauticians in training).
51. **Foap (no cheddar yet for selling sell my iPhone photos).
52. **Robinhood investment app.
53. Sweatcoin work out app that pays rewards.
54. Accidental drug mule.
It’s not an impressive or illegal story by any stretch. On less creative days, I’ll cop to being a prescription drug courier.
55. Medical lab rat.
I underwent medical tests with lots of needles and blood draws to make extra cash in college.
56. Plasma donor.
Ok, I didn’t quite complete this one. I showed up at the lab but didn’t then meet the requirements.
57. Amazon Marketplace to sell old DVDs.
58. **Freelance article writer.
59. **Freelance blogger.
60. Ticket scalper (twice only and it was a wholly accidental endeavor).
61. Receipt Hog.
62. Extreme couponing.
It’s been a minute. But I was in super deep.
I somehow got escorted out of Target for trying to redeem too many print coupons, a feat that baffles me to this day.
The cashier (team member) flashed the checkout light when a coupon didn’t work (100% her idea) and a store manager WITH a damn security guard (slightly smaller than a woman deemed too petite to donate plasma) came over just itching to bust a coupon fraudster.
I said nothing and he (the guard — I’m working in gratuitous pronouns to let you know that the guard was a man smaller than an at-the-time very small woman) boldly insisted I had too many coupons relative to goods — without counting the actual items in my cart.
The manager (ETL) backed him, saying, “Ma’am! Ma’am! We can EVEN void this transaction now and step into my office and count EVERY item and EVERY coupon. One. By. One.”
Or I could just stop using coupons, pay for my goods, and take my (smirk) so-called savings and go.
I added a third option: just leave empty-handed. I mean I had just stood there silent and crimson-faced at their very loud and very public rebuke. Just leaving seemed the quickest way to go sit in my car and die of shame.
So yeah. I just abandoned my cart at checkout. Although I reckon cart abandons happen an awful lot (more) these days IRL, I had never before seen that particular conversion goal unravel offline before. But, I am extremely good at making digital-only things happen in the real world.
And with that harrowing incident, I just abandoned couponing for good. Target’s aggressive, proactive, vigilante coupon justice was just too much. But. I’m glad it soured (cured) me off couponing madness.
63. Uber Eats for an afternoon.
I made one delivery to get a $200 bonus for a new driver promotion that was running at the time.
64. One-time book editor for a man who on purpose did not write in lucid sentences and trolled his much-deserved hater-critics on Amazon.
65. OneOpinion surveys.
66. American Consumer Opinion surveys.
67. PrizeRebel surveys.
68. Day laborer.
I showed up at a colleague’s home (being built) and hauled trash and construction debris for several hours. I hauled it specifically “to” the dumper, as in right in front of it because I was physically incapable of actually lifting the trash over my shoulders and into the bin.
My services were not re-engaged.
69. Toluna surveys.
70. YouGov surveys.
71. Yogurt eater. I sampled myriad forms of Dannon yogurt for $5 at the Har-Mar Mall.
72. Semi-Influencer with pitiful product photos.
I got $1,000 in free clothes from a children’s brand on Instagram and a pair of free Mizuno shoes from back when I used to be on Twitter.
73. Landscaping — in the form of picking up sticks and lawn mower hazards. I think I was seven.
74. **Freelance SEO content planner and writer.
75. Babysitter.
From back in the day when people would hire 11-year-olds to watch small babies, and instead of ordering you DoorDash they’d let you help yourself to their stash of Diet Caffeine Free Coca-Cola.
76. CoinOut receipt app.
77. **Hostage negotiator for hire. This means I can write life’s un-fun letters for you.
78. Gift card arbitrage. Check out gift card resale sites and you’ll get “it.”
79. Thrift market vendor.
80. **Target Circle.
81. **Website tester.
82. App tester.
83. Professional coffee drinker. I got paid $159 and lunch for a coffee focus group.
84. Odyssey of the Mind coach.
85. French conversationalist.
I had a gig where I showed up on Saturdays to speak exclusively in French to twin toddlers for 5-hour stretches. The gig lasted until I accidentally broke the baby gate — and possibly the Nespresso machine too.
86. Accidental international purveyor of counterfeit goods.
I resold some name brand bloomers that turned out to be ersatz. The mom-buyer was very sweet and knew it was unintentional; she just had a super deep, down-the-rabbit-hole understanding of the black market for children’s luxury wear. I think I just offered to refund all her money but she paid me $5?
87. Flu-shot-taker. I did it at Target when their CVS Pharmacy was offering a $5 gift card.
88. MTurk. I did random miscellaneous tasks on Amazon Mechanical Turk.
89. **KashKick. I just signed up to try this rewards app.
90. Bubble Cash (see nos. 45 and 47).
91. Stash (see no. 32).
92. **Cover letter writer.
93. In-home bartender. A one-time gig for a Polynesisan festival.
94. Banquet bartender. A one-time gig for a quinceanera at the Ramada Inn.
95. Entering and winning Ugly Sweater contests. $35 in total lifetime prize winnings.
96. Entering essay contests, I’ve won a D.A.R.E. tee, free iPad, and free miniature family portrait.
97. Seller of cookies made from frozen logs of dough.
In college, I baked chocolate chip cookies and sold them in the boys’ dorms. I dealt strictly with the boys because the girls were underwhelmed by my efforts. Many of them likened my venture to selling snake oil and suggested I stop, or lower my per unit price down to $0.001.
98. Over-the-phone hotel rates negotiator (trumping OTA sites).
99. **Selling old clothes at Once Upon A Child.
+1. Cinnamon Eater!
I did the Cinnamon Challenge! That’s the humanly impossible feat of eating a large quantity (huge spoonful) of cinnamon, unaided by water or other food, in fewer than 60 seconds.
I pulled off this feat at Brit’s Pub in Minneapolis, winning $20 bills and dumbfounded gazes from our three Google reps (visiting us from New York) and my colleagues. I think I racked in $120 total, which is like $7,200 per hour. That’s commensurate with an annual salary of $14.98 million.
So — I clearly have marketable, millionaire moneymaking skills.
While this prolific outpouring of sidelines may paint the portrait of an unfocused (possibly insane) woman, I think I just look like a tough old bird.
I mean I do have a stable, permanent employment record of “real work” jobs, I’ve never been to jail, and I don’t eat universally disgusting condiments — although I once passed around dead crickets covered in cheese powder at my office. (Three of us were brave enough to chow down.)
I’m just a baller.
Since pre-school, I’ve always had a side hustle going.
With all these gig economy apps, most of you have probably tried at least a few dozen.
And if you have ever been in your 20s in a perpetual state of no-money, you’ve probably tried around 100 of them too.
While I’m not a broke twenty-something anymore, I do have a husband, two very small children, and a dog to support. And a step-cat. So I will hustle til the day I die.
PS: I might add my affiliate links, or someone else’s (hint: yours!) later.