4 of My Most Interesting Side Hustles

4 of My Most Interesting Side Hustles - picture of man feeding cow

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Dudes, I have worked a lot of jobs over the years. Seriously…a lot. I thought I’d amuse myself the other day, so I decided to count them all up. I came up with a quick count of 27 different jobs that I can remember working since I was about 10 years old. From delivering newspapers to being a mortician, I’ve pretty much done it all at one point or another.

Of course, most of these jobs were part-time gigs that I worked back in my high school and college days. That being said, a bunch of them would make for a great side gig if you’re looking to make extra money. I thought you’d get a kick out of taking a stroll down memory lane with me and discussing 4 of the most interesting side hustles I’ve ever had.

Farmhand at a Pheasant Farm

When I was about 13 years-old, I spent a few weeks during my summer break working as a farmhand on a pheasant farm. The man who owned the farm happened to be my 7th grade history teacher…and the father of my aunt (by marriage). Basically, I spent 8-12 hours a day inside of a giant pole barn. My job to catch the baby pheasants running around inside the barn with a fishing net. We’d then shove a plastic “blinder” through their beak so that they didn’t peck each other to death. Good times.

While the temperature outside of the barn hovered in the mid to upper 80’s, the temps soared somewhere close to 100 degrees. Besides that, we had to wear jeans, T-shirts, and workboots. Plus, there was no breeze, so it was ridonkulously hot. The strong smell of ammonia in the barn also made the conditions a bit more brutal. I learned how to work hard and was happy to make some money, but I was glad when the summer was over. I definitely wouldn’t want to do it full-time, but it was definitely one of the most interesting side hustles I’ve ever worked.


When Holly and I decided to start a blog a few years ago, we did it mainly as a way to have fun. Of course, we always hoped that our hobby would make us a bit of extra money in the future. We quickly realized that we enjoyed blogging, but it took a lot more work than we ever imagined. We pressed on, continuing to bust our butts to grow the website, and it eventually started making money.

Starting a blog was the best thing we ever did. After putting a lot of blood sweat and tears into the project, we started to generate some actual revenue. Holly was eventually able to quit her job, and I followed in her footsteps about two years later.

Wedding DJ

One of my favorite jobs I ever held was while I was in college. Almost every weekend for about 2 years, I traveled around the state and worked as a disc jockey at wedding receptions, company parties, and special events. It paid fairly well and it was a ton of fun. I got to meet a lot of people, be a part of their special day, and MC the party at one of the most important events in many of their lives.

I got the job through a radio station in the town. Basically, they booked all the gigs and then sent me out to perform. There was a group of about 5 or 6 of us who worked there, although the shows were all solo gigs. Plus, they were very accomodating to my school schedule, so that was good. Since the shows were almost always on the weekends, this was really a perfect side gig.

Sports Official

Did you know that you can get paid to referee your favorite sport? It’s true. I used to officiate both hockey and baseball games. Not only is this a great way to make a few extra bucks, but it is also a great way to stay involved with your favorite sports long after you’ve quit playing.

The cool thing about officiating is that schools and organizations are almost always looking to hire officials. Games are typically held during the evenings and weekends, which makes this another perfect side hustle. Depending which levels you wish to officiate at, you may need to complete a 1-day training course and pass a rules test. Generally, this is required to officiate at the high school varsity level or higher. If you’re looking for some legit side income, it is almost always worth it to complete these certifications because you can make more money at the higher levels. There is no way to get there without completing the certifications.

Workin’ It

I still can’t believe how many different jobs I’ve tried over the years. Of course, I haven’t loved every job (see the pheasant farm above…), but each and every job has taught me something that I still use today. I hope you’ve enjoyed this trip down memory lane with me, and maybe you’ve even picked up an idea for an interesting side hustle or two. Until next time, Seacrest out!

What are some interesting jobs that you’ve worked? Do any of my jobs remind you of your past gigs? What kind of questions do you have about pheasant blinders? Fire away in the comments below!

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  1. I’ve always been interested in sports officiating. I love playing volleyball and could definitely ref. Issue is that I love playing it too much! Best for me was construction for a high end metal working facility. We had to install the clean room ceiling. other one would be Dunkin Donuts. Worked with friends and my future wife in high school. We worked hard and had a blast… And ate too much. I actually lost weight going to college!

    1. Officiating is great, but it can take up a lot of time. However, if you really love the sport, it can be a blast. You lost weight in college? I didn’t think that was possible 🙂

  2. I feel like I had fairly typical jobs growing up, but I always ended up having to do really weird/awkward things. For instance, I worked in a bookstore. Totally typical. But on my night to tend the restrooms, some patron decided to flush a pair of pantyhose. To this day, I still can’t board that train of logic. I imagine you’d see some reall i

      1. Yes. Yes I did 😉 I’ve seen some really interesting things in a few of my jobs…some I wish I hadn’t seen!

    1. Penny, I spent 17 years working for a used bookstore company, and I’ve decided bookstores just attract weirdness. Most of the staff I worked with were very creative, interesting, fun people, but not exactly mainstream. A lot of the customers could have been sitcom characters. There were some truly original (and sometimes disgusting) things found in the store bathrooms and in the boxes of books customers brought in to sell. Still, being a used book buyer is about the most fun thing I’ve ever done. It was like a treasure hunt every day.

      1. That actually sounds like a blast! I absolutely love bookstores. I don’t know why, but I just love going in there and browsing. I always have.

  3. I hat birds so that pheasant thing would be the worst job ever in my book. I haven’t had a crappy job in a long time but I do look back with fondness on my times and a lifeguard, garment factory worker, and seller of snow cones. I learned lots from all those jobs and for sure learned that I needed to do much better than minimum wage!

    1. Funny, I never was a lifeguard. I completed all the swim lessons I needed but never did the lifeguard training. I wish I would have. Like you, I learned a lot from all of my jobs…some of that being that I never wanted to do it again!

  4. That pheasant farm job sounds like fun. 😉 I had relatively “normal” jobs as I was growing up though my oddest one was a computer tester when I was in college. I was the final line of defense, after they had been put together on the assembly line, and had to make sure they were put together right and worked like they should. Seeing as I have no technical skills to speak of it was the perfect job for me. 😉

  5. The first thing I thought about when you said you worked as a Wedding DJ was the movie Wedding Crashers! Do you have any fun stories to share? “)

  6. Aside from the blog, no. That farm job sounds like hell, but mostly because of the heat. I can only imagine what it must be like wearing jeans in that circumstance. I would have a hard time being a ref, mainly because I don’t like to get yelled at. 🙂 But somewhat similarly I guess I coach beach volleyball…where I get to do more of the yelling. 🙂

    1. I have coached as well. Personally, I like coaching and being a ref/ump…but I haven’t done it in years. With kids, it would be hard for me to find the time.

  7. Wedding DJ is my favorite here because I never would think to try that! Pretty cool. Most recently, my aunt suggested I do taxes on the side for people. I’m thinking about that as a side business next year…

    1. Wedding DJ was one of my favorites ever. It was a lot of fun! I hate doing my own taxes, so I definitely don’t want to do others. However, that would be a great short-term side gig to make a few extra bucks.

  8. Being a wedding dj sounds like it would be one of the best side jobs ever. So much fun! Though I can’t keep a beat to save my life so probably not for me haha

    1. Eh, you’re not really spinning records. Just playing songs, so the equipment does most of that type of work for you. It was a lot of fun though!

  9. Shirria @GDTH says:

    I haven’t had any “odd” jobs really. But as I become more and more determined to get out of debt there are not too many things I wouldn’t do (temporarily) for the extra money, except maybe work on a farm or with any animals for that matter.

  10. The pheasant farm sounds interesting! 🙂 My daughter works every winter as a reindeer handler for a company up here that brings live reindeer to different events. I’m trying to talk my little brother into being a sports official – they pay a good $30 and up here.

  11. How about salmon butcher?

    I spent the summer of \’89 in Alaska. Went to do salmon fishing, but by the time I got there, the Exxon Valdez spill had closed the fishing. Spent 5 weeks up to my elbows in freezing water and fish parts until I managed to get on the oil spill cleanup crew (yet another interesting job).

    Good times. Great money.

  12. I love side hustles! My most interesting ones have been mystery shopping, tutoring, babysitting, and being a nanny.

  13. That pheasant farm sure sounds like a brutal job. When I was 14-15 I worked the concession stand at a dirt racetrack in Kentucky. It was only on the weekends, but it was in the evening and I got yelled at by a bunch of rednecks without teeth. I guess it was a good thing my first job was so awful because it was only uphill from there!

  14. Greg, you just gave me another side hustle idea. I am a fan of basketball and feel confident in being a sports official. I think I can be a referee for a basketball game, which I have done before. This is really interesting and I can’t wait for it. Thanks!

  15. Greg,

    I have a good one. While in college I worked for several police K9 academies, which is where they train dogs for police departments. Sooo…I was the guy that had to wear the suits and basically get attacked. Suits were heavy and thick and on the hot sunny So Cal days, it wasn’t fun though it was a great workout. Paying $25 an hour as a college student isn’t bad! I quit shortly after finishing up college and landing a job. Thinking back now..What was I thinking?!! Some close calls but luckily I had no “real” bites!

  16. I think mystery shopping lead to a lot of interesting experiences. I got to stay in hotels, play at arcades, go to (small) amusement parks and even gamble in (small) casinos. Plus restaurants and all that good stuff.

    Other than that, I was a monthly columnist at the Anchorage Daily News when I was 15 – 16. It only paid $50, but this was back when minimum wage was $4.75. So I was thrilled.

    Blogging is definitely a weird side hustle. I thought I’d try it for a couple of months and get bored. That was 7 years ago.

  17. I actually have a good friend who referees for high school and college basketball games and not only makes great money doing it, but he gets to enjoy the sport that he loves AND get in a great workout running up and down the courts.

  18. My manager’s husband refs high school football, honestly more for fun than for a side hustle. Poker was by far my favorite side hustle. Blogging is actually getting in the way of me doing other side hustles I want to pursue, but I can’t complain.

  19. The wedding DJ sounds like a lot of fun! My favourite job ever was waitressing at a golf club. I made good money and found it really fun. My least favourite job was being a maid in a fancy hotel…now that was super hard work!

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