My List of Unique Side Hustles Over the Years

Side hustling is a great way to make extra cash and build skills. Working side gigs has been part of my lifestyle since I was a teenager. Initially side hustles were a way to make a little money for video games, baseball cards, and other fun toys. During more recent years, my side hustles have funded family vacations, kept me entertained during evening hours, and helped me develop skills that translate into many different areas of life. Keep reading to learn more about my unique list of side hustles over the years.

Lawn Mowing Service

In what may be the original side hustle, at the young age of 14, my friend and I started our own lawn mowing business. The term “business” may be a stretch as we only had three or four clients. Regardless, it was enough to make us $100 or $200 a month. That amount of money seemed like a lot as a teenager.

To start the business we printed about 200 fliers and distributed to everyone in our neighborhood. As a result we got a few calls to mow lawns for about $20 a piece. My friend and I split the income. We used our parents’ equipment so our only cost was gasoline. This is still a great way for teenagers to make money. Add to the list shoveling snow during the winter and you can make a decent amount of money.

eBay Flipping Business

As I went off to college I found myself in a situation where I needed to make some money but working a traditional job was tough. Between school, playing a sport, and homework my days were packed. We often had weightlifting at 6:30 am, followed by class from 8 am to 2 pm, with practice afterwards until about 6 pm. Factor in homework in the evenings and it wasn’t easy to find a job.

Therefore, I had to get creative. This was in the mid-2000s in an era before smartphones and before anyone talked about flipping. My main sources of inventory were dollar stores and garage sales. My best selling items were videos and computer games. I’d buy a lot of videos for $1 and then sell them for around $10 on eBay. Every once in a while I’d get lucky and find something that would sell for more.

For example, there was a computer game called Total Annihilation that was available at dollar stores yet sold on eBay for about $40. I ended up buying about 50 copies of the game and sold them all within a month. I ate really well as a college student that month!

On weekends I’d wake up early before baseball practice or games and find items at garage sales. You wouldn’t believe what people are willing to get rid of at garage sales. Video games, board games, sporting equipment, and electronics were my specialty. In this day and age, garage sale flipping is in some ways easier and other ways more difficult. It’s easier with smartphones since you can immediately find out about what you can sell an item for. It’s difficult because people can more easily sell expensive items when in the past they may not have known what it would have sold for.

Online Poker

I debated if I should include this one because online poker is gambling for some people that end up losing a lot of money. However, if you treat poker like a business it can be a profitable side hustle. Playing Texas Hold’em online was my primary side hustle for two or three years after graduating college. I deposited $40 one time and ended up turning that into thousands of dollars over the years.

So how do you turn online poker into a side hustle? The easy answer is to win more money than you lose, but it’s not that simple, of course. My approach started with studying poker. I read two or three books and immediately put what I learned into practice. After finding out which games were most profitable and the ones I was best at, I went “all in” and primarily played those games.

Managing your bankroll in poker is essential to running a profitable poker side hustle. Nobody ever wins all the time in online poker, but if you can find the games where you win more than you lose it can be profitable. When I played, it was at the height of the online poker and Texas Hold’em movement so there were a lot of inexperienced players out there. Making money really wasn’t that difficult. My assumption is that the players are much better across the board today, so it would be interesting to see how I’d fare in this day and age.

Freelance Recruiting

One of my more unique side hustles was freelance recruiting for a friend’s business. My friend had recently left working for an agency to branch out to start his own recruiting business. He needed help to fill positions so I would help him to find resumes and occasionally conduct initial interviews with potential candidates.

Recruiting can be a very lucrative business. Recruiters can make anywhere between 15% and 30% of a candidate’s first year salary. Recruiting can also be a very frustrating business. Even though you get paid very well when landing a candidate, you’ll work more overall for candidates that don’t get placed.

During my two years of recruiting, I made about $20,000 on the side. It was a lot of work though. The skills I got out of this side hustle were more important than the money I made. I had interest in getting into a management position at work during this time. While recruiting, I learned how to quickly scan resumes, spot red flags in candidates, and identify indicators for high performers. I carried these skills over into my full-time job. Hiring people is one of the most important things you can do as a manager in corporate America, so having this experience gave me a leg up over other inexperienced managers.

Blogging

That brings us to my current side hustle: blogging. I guess you can call it a side hustle as it’s by far been my least profitable one to date. Up until very recently I haven’t made a single dime from this blog. In fact, I’ve lost money paying for hosting, domain name, and a few other low cost tools. I probably spend about $500 a year total on the blog and have treated it as a hobby up until this point.

Last month I decided to experiment with putting ads on my blog using Ezoic. Ezoic is a platform designed to improve the user experience of your website while also providing a connection to Google Adsense. The customer service I’ve experienced at Ezoic has been top notch. Onboarding was simple and it’s exciting to finally start making a few dollars off of my blog.

If you’re interested in joining Ezoic click here for more information (affiliate link)

My plan is to take any money that I make and invest it back into the blog. I plan to start treating the blog more like a business with the goal of growing sustainable traffic. That may include hiring a freelancer to writing a blog post or two a month or joining a paid blogging community. This blog will still mostly be a hobby that I work on a few hours a week, but I’m also excited about treating it a bit more like a business. We’ll see where it goes after a few years!

My List of Unique Side Hustles

On their own I’m not sure if any of these side hustles are particularly unique, but I challenge you to find anyone out there that has a similar list. Even though I work a 9-5 job and have no intention of stepping away from it, side hustling has always been a fun way to make money on the side and tickle my entrepreneurial interests. If you have questions about any of these side hustles, please ask below in the comments. Thanks for reading!