I’ve been finding unique ways to hustle for cash since I was a young kid. The first side hustle that I can remember was collecting balls from the city softball fields near my home. That complex had four fields and there seemed to be games each night during the summer.
On game nights, each filed was used for several hours so there were a lot of home runs and foul balls hit. I could collect $0.10 for every ball that I chased down and returned to the scorekeeper’s table. I’d leave the fields each night with $10 to $20 bucks – more than enough to make me feel rich!
Hustle. Make money. Lesson learned!
MY SIDE HUSTLE JOBS
Here’s a list of all of the side hustle jobs I’ve ever done in my life, in chronological order:
My Pre-Teen Side Hustle Jobs
BASEBALL & SOFTBALL CHASER
Between the ages of 8-10 I could make 10 cents for every ball I’d chase down and return to the scorekeeper’s table at our city’s softball complex. The complex had four fields with three games per field each game night. Between those 12 games that were played each night, there were probably 200-300 balls leaving the fields. I was a fast, scrappy kid and would chase down a ton of them, making anywhere from $10 to $20 per night.
CONSTRUCTION JOB SITE RUNNER
From about the time I was 10 years old until I turned 18 and moved out of my parent’s house, I went to work for my dad at his drywall business after school and on the weekends. During the summers I probably put in at least 20 hours a week. While I never once earned an hourly wage working for dad, I usually didn’t have a hard time getting enough money to buy a back of baseball cards when I was young, and as a teenager I always had spending money on the weekends.
If you asked my dad about compensation, he’ll tell you I was paid in the form of new clothes to wear to school, dinner every night, and a roof over my head. Not bad, but the real benefit here was spending some quality time with dad and my brothers, plus I learned the value of hard work.
LITTLE LEAGUE UMPIRE
Baseball was always my sport. I loved everything about it, especially practice! I spent so much time at the fields (chasing foul balls, playing, practicing) that one day I was asked to be an umpire in a pinch when the regular ump didn’t show up for some reason. From then on I was the ‘alternate ump’ and I’d keep my fingers crossed that someone would no-show. I made $10 per game as the filed ump, and $15 for being behind the plate. Being behind the plate was my favorite, not because I got paid more (I would have done it for free, no question!), but because I got to put on all the gear and call the balls and strikes!
My Side Hustle Jobs During The Teenage Years
DIVING FOR GOLF BALLS
As a young teenager during summertime sleepovers at a friend’s house, we’d sneak out at night, ride our bikes to a nearby golf course, hop the fence, and dive into the ponds looking for golf balls. We’d collect as many as would could, then sell them by the dozen on the side of the road that lead to the golf course. In the interest of CYA, I’m going to point out that you probably shouldn’t try this one out unless you get permission from the course to do so. 🙂
K-MART SHELF STOCKER & CASHIER
My first “real” job was stocking shelves for minimum wage ($4.25 per hour) at K-Mart when I was 16. It started off as a weekend night job stocking shelves and evolved into a part-time cashier position. My favorite part of the job was when the manager would let me call out the once-famous Blue Light Special. A joke for you: What are three words a rich man will never hear? “Attention K-Mart Shoppers” #rimshot!
LANDSCAPER (A.K.A. MOWER OF LAWNS)
During my mid-teen years I worked for my older brother doing landscaping. I think he paid me about $50 for 8-10 hours of work every Saturday during the lawn mowing months. The cash was just icing on the cake because the real benefit for me was the ability to work on my tan and listen to some CDs in my killer new Discman!
ELEMENTARY SCHOOL NIGHT JANITOR
Same story as above, again working for my older brother (now that I think about it, he’s always been a major hustler). Twice per week we’d deep clean different sections of a local elementary school. I think he paid me $10 an hour and we’d spend about 3 hours per work night cleaning up.
FLOUR MILL BAGGER GUY
I don’t know what to call this job, but it is without question the hardest, worst job I’ve ever had. At the flour mill, silos were constantly being filled and it was my job to empty them. The contents of the silos went into 10, 25, and 50 pound bags. The process of filling an empty flour sack, sewing it shut, then stacking the sacks six feet high onto a nearby pallet lasted just a few seconds, but the pace was brutal and unending.
You had to fill, sew, and stack those bags quickly to drain the silo faster than it was being filled. Grabbing, lifting, and stacking flour bags over and over would quickly shred the skin from your knuckles, and made your lower back and legs ache. On top of it all, the mill was incredibly hot and all of the flour and grain dust in the air made it difficult to breathe. I think I lasted about full two weeks before I quit. Mammas, don’t let your babies grow up to be flour mill bagger guys!
Side Hustle Jobs I Did During My College Years
CONCESSION STAND WORKER
During my freshman year of college I took a part time job in the Food Services department on campus. I mostly worked the concession stands at baseball, football, and basketball games, but I also ended up working as a server at a few catered events. I earned $8 per hour, but as a poor college student I was pretty much guaranteed free food whenever I wanted or needed it – that was the real benefit of this job.
In my late teens and I worked for a company that put on a 4th of July fireworks show. In the months leading up to the 4th I built the scaffold sets that would hold the pyrotechnic displays. During the actual show, the displays were ignited and became pictures of the Statue of Liberty, or a bald eagle, or whatever else the script called for. It was a pretty fun job that I did with a couple of high school buddies. To this day when we all get together, we still talk about this job. I made $10-12 per hour, which was pretty solid money at the time.
NIGHT SECURITY GUARD
The fireworks job eventually led to this night security job. Once the firework displays were assembled, somebody needed to watch them 24/7. They were a target of both thieves and vandals. I can’t remember exactly what this paid, probably $15/hr because it was a crappy night shift that nobody else would do. I took it because I was engaged to be married and needed all the extra cash I could get my hands on.
Side Hustle Jobs I’ve Had As A Married Man
LOADER AT A HARDWARE STORE
If you’ve ever gone into a big box hardware store and bought something that was too big or heavy for you to carry around the store by yourself, I was the guy that would go get it for you then load it into your truck, van, or car. Low pressure job that let me hang out behind the scenes with some pretty cool guys. I made $12 an hour part time while going to school full time.
NEW & USED CAR SALESMAN
For about 4 years or so I sold new and used cars, both full and part time. This is one of those things that I have a love/hate relationship with. I hated the job almost the entire time I was doing it,! But I loved the money I was able to make from it. I’m a people person and it bothered me that people would come in with their guard up and treat me as their enemy. I get it, I just didn’t like it. But looking back I’m glad for the experience.
I feel like I learned a ton of skills that still help me today (like dealing with confrontation, and how to negotiate). Here’s my blog post where I shared 5 tips on how to not get screwed on your next car purchase. This job was 100% commission. I’d make 25% of the profit on each car I sold. There were also cash bonuses for hitting certain numbers each month. For example, the first cash bonus of $1,000 came for selling 7 cars in the month. The bonuses got bigger the more cars you sold.
FITNESS EQUIPMENT SALESMAN
As a part-time gig during college I sold high-end fitness and sports equipment. I learned how to grip skateboard decks, wax skis and snowboards, string tennis racquets and put together a half cage. More importantly, I perfected my golf swing (not really) and learned how to chip like a champ using our golf simulator. Looking back now I can’t believe that someone actually paid me to do this job. I made $10 per hour + a commission on whatever I sold.
Side Hustle Jobs I’ve Done As A Dad
MERCHANT ACCOUNT SALESMAN
Tough job. A merchant account is what you needed if you wanted to accept credit card payments at your store or business. My job was to cold call businesses and sell physical credit card terminals. We were also selling a new (at the time) technology that allowed you to accept credit card payments online. However, not too long into this job some guy named Elon Musk created PayPal. That service was a lot better and cheaper than the stuff I was selling, and that was the end of this job.
NIGHT SECURITY GUARD, ROUND 2
At the college I attended I saw a job posting for a night security guard: $12 an hour to walk around the campus at night, making sure all the doors were locked and the lights were turned off. To me that sounded a lot like “get paid $12/hour to do your homework.” I took this job shortly after my first son was born. With the lack of sleep that comes with a newborn, working a graveyard shift probably wasn’t the best idea ever. I don’t think I made it a full semester before the lack of sleep forced me to quit.
AFTER HOURS OFFICE CLEANER
One night per week my wife and I would clean her dad’s office building. This started off as a hustle that my wife was doing with her sister, but I ended up doing it for a while when her sister couldn’t. I was able to draw upon my experience from side job #7 Elementary School Night Janitor to knock this job out of the park! I made $50 per cleaning, which usually took about 2 hours. Between my wife and I, we were making $100 for a couple hours of work – not too bad.
VENDING MACHINE OWNER
For about two years I serviced a candy machine and a soda machine in a local office building. The building owner was also the owner of the vending machines, but he didn’t want to deal with them so I did the leg work and we split the profits. About once per week, or as needed, I’d go to Costco to buy my inventory. The shopping trip and subsequent restocking of both vending machines probably took two hours per week and made me $80 per week (in change!).
At the same time I had the vending machines, I’d also partnered with a buddy to service three ATMs that he owned. Once per week I’d go the bank, pull out a couple thousand bucks in $10 bills. Then we’d make the rounds to the three different bars where we’d placed the ATMs. Besides the cost of the machines, we had about $2,000 in physical cash tied up in the machines. Each ATM required a phone line and we also paid a percentage of our take to the bar owners. We made our money from the $3.00 transaction fee that we charged. This wasn’t a great hustle. Lots of work and fees for very little return on our time and investment.
REAL ESTATE PHOTOGRAPHER
OK, so I wasn’t the photographer, but I did co-own a franchise of sorts and had six photographers working for me. This was a real estate marketing business and our product was real estate photography and virtual tours. Real estate agents and brokers would order photography services for their listings through a parent company. That company would then route the orders to my photography team, who would fulfill the orders. Of all my side hustles, this was far and away the most lucrative. My partner and I were each pulling in about $25,000 per year for less than 2 hours worth of work per month. Then the real estate market went and crashed and that was the end of this little cash cow. 🙁
STORAGE LOCKER AUCTION BUYER GUY
Yuuuuup! I got caught up in all of the excitement that was ‘Storage Wars‘ a few years ago and ended up buying abandoned storage units. Over the course of a year I went to several auctions and bought just six storage units. I nabbed them with dreams of finding jewelry, antiques, or gold coins! But mostly I just found old clothes, unpaid bill notices, and crappy furniture. I never lost money, but my hourly rate had to be in the $1.00/hour range. This was the most interesting side hustle I’ve done, even if it didn’t make a lot of money. You can learn all the dirty details in my post, Buying & Selling Abandoned Storage Units as a Side Hustle.
A few years ago when I was unemployed, an old high school buddy put me to work running a crew for his company that specialized in renovating hotels. Swinging a hammer is a tough way to make a living and for several months I was working with guys that were mostly ex-convicts. Almost all of the guys that had done time in prison were sent there for some pretty serious crimes. But they’d paid their dues to society and were now doing their best to try and make an honest living. The education I got about life, people and second chances was worth far more that however much money I made.
PERSONAL FINANCE BLOGGER?
Do I get to include blogger on here? My blogs don’t make enough money to brag about, but the pennies are starting to add up! However, like a few of the other gigs on my list, the true hourly rate I make from blogging is awful. Good thing ‘making ‘money’ isn’t the main reason I blog or I’d be in trouble. I’ll have to update this hustle at a later date, but for now I can easily say that the best thing about this blog are the few connections I’ve been able to make with my fellow bloggers. Interested in starting your own blog? Check this out.
SIDE HUSTLE IDEAS
So that’s my list! 23 part-time jobs and side hustle jobs that I’ve done throughout my life (I feel like I’m forgetting a few things?). This list does not include any of my full-time jobs. And now that I’m thinking about this, most of my side hustles have been a helluva a lot more fun and rewarding that almost all of my full time jobs. Hmmmmm – I need to think about that for a while? What side hustle ideas have you got?
Any of this look interesting enough for you to try? What cool side hustle jobs have you done? Let us know in the comments.