One really fun thing about side hustling is the variety of opportunities you have to choose from. For those who have done multiple side hustles, this also makes for some great stories to share about what worked… and what didn’t.

In this article, I’ll turn the spotlight on myself and share with you both of those things: the cornucopia of side hustles that I have done in my life, as well as a few tips about what (or what didn’t) make them successful.

I began to list them all out, and I came up with a tidy sum of thirty-one! (This number also has the added benefit of nostalgia, reminding me of childhood summer days in Baskin Robbins 31 Flavors munching away on a sugar cone topped with my favorite ice cream, Jamoca Almond Fudge.)

I like my tales of failure served ice cold… with a cherry on top!

A word of warning, though: this isn’t going to be a manicured list of successful business ventures. On the contrary, my past history with side hustles has left mostly a trail of halfhearted attempts, semi-successes, and outright failures. There may be some overlap, but generally I tried to lump together the hustles that made the most sense to put together.

So, why would I share this? It certainly won’t win me any “entrepreneur of the year” awards. For those of you who have had more success than I have, it may read like a cliched horror story, with you saying “don’t open that door….!”

I guess it’s my hope that you’re partially entertained and partially inspired. Maybe it will even spark some ideas. As I share each one, I’ll list what I learned the most as well as what I’d do differently next time. I’ll also share the ones that I’m currently doing.

So, without further ado, I present to you: My 31 Side Hustles!

1. Manual Labor

Many an hour of my youth was spent doing unskilled labor… whether it was an odd lawn mowing job here and there or helping a friend move, I’ve done my fair share. I will summarize the manual labor side hustle this way: there are certainly a lot of easier ways to make money.

The worst day of labor I remember was the time my friend invited me to take part in tossing hay bales into a trailer. It was a sweltering summer Texas day around 100 degrees Fahrenheit, and I found out I was allergic to hay. By the end of the day I was exhausted, hot, and my skin was red and itchy from the hay inside my clothes. But hey… I was $47 richer!

My favorite gig was getting paid to harvest olives in Italy. At the time I was studying in a villa outside Florence during college. I was basically being paid to climb trees and hang out with friends as we shook the olive branches into a parachute. The days were beautiful and the weather was perfect, and at the end of the day we watched the sun set in the Tuscan countryside. It was like living in a Federico Fellini movie.

“… you missed one over here, Jerry.”

Other manual labor hustles I’ve done were framing carpentry, staining crafts, working in a warehouse, and cleaning a college stadium after football games.

What I like about manual hustles is that you certainly get a good night’s sleep after doing them (providing you didn’t injure yourself). Another good thing about them is that you can pretty much always find them.

What I don’t like about them is pretty obvious: you have to trade your time (and, in some cases, health) for dollars, which isn’t a very good trade. It also doesn’t scale, unless you hire people to do the jobs for you… in which case they can be pretty good. I know someone whose side hustle is lawn care… he doesn’t lift a finger to mow a lawn, he hires people to do the mowing, and he makes the calls and does the administrative work from his laptop.

2. Sales (Including Multi Level Marketing)

Many of us have had childhood experiences selling magazines or candy bars to raise money for stuff. I’ve done it, too, and I was never very good at it. I also hated the idea of selling, and everything about it.

While in college, I let a friend talk me into buying into a multilevel marketing franchise selling a phone service called Excel. As with all those things, the real money is made in the “downline”, getting other people in your sales team. I failed to get a single person signed up!

I’ve learned that sales and multilevel marketing is not for everybody. If you’re a natural people person with the gift of gab and truly believe in what you’re selling, I’d say go for it. My mistake was in trying to force myself to do something I didn’t believe in or believe I would be successful at… it just resulted in misery for me and awkwardness for the poor people I tried to sell to.

A footnote about this is that I’ve since learned that “selling” doesn’t have to be an end unto itself… it can be an effective skill that’s part of your overall business. I sell now all the time, and since I’m passionate about helping people, and put them first, it’s just a natural part of what I do.

3. Modeling

I’m a little embarrassed about this one. I got a offered to model for a brochure for my dad’s company. I was about 16, and there I was, braces and goofy smile and all, holding up a leather belt.

I did get paid $150 to just stand around for an hour, which wasn’t bad. (Maybe if I get enough requests, I’ll share the picture…. )

4. Selling Goods

I didn’t know how to phrase this other than “selling goods”, which also includes “selling stuff I happened to have lying around and didn’t want to just trash it”.

Contrary to the “sales” item in #2, I have had a lot of success selling various things. I’ve sold stuff both online and offline. I’ve sold art supplies, stereo equipment, toys, collectibles, video games, movies, cars, and even a deer mount.

… anybody wanna buy some cheetos?

The key to selling stuff, I’ve learned, is being able to take decent pictures and to describe things in a comprehensive way. It helps to know generally what sells and what doesn’t on various platforms, including Ebay, Amazon, and Craigslist. I still do this all the time and I probably always will, because it’s a great way to get rid of stuff I don’t want and generate quick cash in the process!

5. Performing Music

While in high school, I was in a garage band. We weren’t very good, and we didn’t really get paid, but it’s nice to think that if we had continued to improve and get gigs we could have made some money (and had fun while doing it).

Lenny and the Liquid Thunderpants… coming soon to a high school auditorium near you!

I’ve also performed with various vocal groups and while I didn’t really make money there either, it’s given me a lot of great experiences and opportunities. I got to travel to Scotland with a singing group. A choral group my dad sings with got an opportunity to sing onstage with Andreas Bocelli, and they needed forty singers to fill out the group so I was asked to join.

I really like music as a casual side gig, and money is a nice side bonus when it happens. Even as a side gig, though, you have to have some talent, and you have to love it enough to spend time practicing your craft.

6. Graphic Design

As a full-time artist, I’ve had frequent opportunities to design the odd logo or brochure from time to time. While I don’t seek these gigs out, I don’t necessarily turn them down either… I charge a couple of hundred dollars for a logo design and it’s a good way to get a little cash for a few hours’ work.

Some sage advice: when you design a logo, one way to make sure it gets attention is by making it really creepy.

If people don’t have that much to spend then I refer them to Fiverr.com. When I don’t have the time to do it (or just plain don’t feel like doing it), I’ve subcontracted design work to overseas virtual assistants, which is a great way to collect a bit of money for basically being a middleman.

7. Fine Art

I’ve always had some natural talent for drawing, and from as early as I can remember I’ve taken people up on opportunities to do art of various kinds.

It’s also been a great way to give gifts. The value of the time I spend making art as a gift is usually more than the money I would’ve spent buying a gift, so it’s always appreciated.

My first art show I made over $1000 selling various paintings, so that always remained in the back of my head as a possible side hustle (or maybe even a full-time hustle, If I treated it like a proper business.)

The controversial, recently discovered masterpiece “Mona Lisa As A Sloth” is slowly taking the art world by storm.

8. Selling Ideas / Royalty Income

One of the coolest ways to make money is by selling your ideas. Ideas that are more fully fleshed out and that make money are called intellectual property, and they can generate royalty income for years afterward.

My first experience with this was when I interned at a T-shirt company one summer designing shirts. Once a week the art team met and shared ideas for future shirts, accompanied by quick sketches. If our ideas got chosen, we would get a $50 bonus and got first pick to be the one to design the shirt. I won a handful of these, and it was really fun to come up with the designs and equally exciting to have a design be chosen.

After I left this internship, they asked me to continue to submit ideas. A few of these got chosen and I got to do the designs on the side, and got royalties for each shirt sold. I remember the feeling when I got my first royalty check in the mail… it wasn’t huge, but month after month for about half a year I would get paid for work I already did! It was a pretty cool experience, and it was my first brush with passive income.

9. Building (And Hosting) Websites

When I graduated from college, the world wide web was just starting to proliferate. I decided to learn how this new invention worked, and taught myself how to build websites. Pretty quickly I started building sites for various people and businesses on the side. Over the years I kind of became the “go to” person in the family for this, and got a few referrals.

AAaahh, HTML without CSS, circa 1995. Now that was the wild west.

Eventually I realized that for many people and small business the whole hassle of domain names and domain hosting vs. web hosting was way more confusing for them than it was to just offer to do it all for them. So I invested in a good web host and tools and began to offer my web services as an all-in-one package and charge a monthly fee to host the site and do maintenance and updates. I’ve enjoyed regular income over the years that’s mostly passive as a result.

10. Nonprofits

I’ve done a lot of work for nonprofit organizations over the years. While much of this has been volunteering, some of it’s been paid as ministry internships for churches back when I was in college.

The great thing about working with nonprofit organizations is that you can choose one that resonates with your beliefs and that helps a lot of people. This can give you a tremendous amount of satisfaction and fulfillment that monetary rewards never can touch.

A myth about nonprofits, though, is the idea that working for one won’t generate much income. Nonprofits still have to pay staff and other people to do various things, and some of them pay very handsomely… especially if you work in development or grant writing and get a cut of the funds. I know people who make a very good living doing this… and they have the satisfaction of knowing they’re working for a good cause, too!

11. Voiceover Work

If you have a set of pipes that sound good enough, and you can speak clearly, you may find a good side hustle in occasional voiceover work.

I haven’t made a lot of money with this, but working in the commercial industry I’ve occasionally had an opportunity to do voiceovers for commercials, movies, and other media. I’ve also auditioned to read audiobooks on ACX, Amazon’s audiobook self-publishing arm.

I highly recommend it, it’s not much work for the financial return you get. For many commercials, you can get residual income well after the initial voice work is done. In many cases you don’t have to have an agent or talent agency to get started, but it can help tremendously to have representation if  it’s something you continue doing.

12. Video Shooting / Editing / Finishing

There’s a lot to doing video… I’ve done various video projects over the years from shooting interviews and “b-roll” to editing it on my laptop and finishing it. While finishing commercials has been a main job for me, a lot of side opportunities have come up in this area and I usually take them because they’re so easy for me to do, and I have much of the equipment (or know people who do!)

Since smartphones have become so good at shooting video, for many low end projects (and most of the side gigs are) I just use my iPhone. I’ve even shot and edited a music video on nothing but my iPhone! The key to getting smartphone video to look good is decent lighting (outdoors is easiest) and having a tripod or mount to get rid of “shaky cam”. It also helps to do decent color correction.

Yes… it really is that easy.

13. Visual Effects

Visual effects work also has been part of my regular day job for years, and has led to some side gigs, too. There will always be low-budget indie films and music videos that need some kind of visual effects work, and it can be fun, rewarding, and possibly lucrative if you do it right.

Much of the visual effects work that pays well is the garden-variety “fix it in post” type work… things like taking out power lines or rigging from the background. This is the easiest and most plentiful work to do. The next-level type stuff is doing things like more extensive background replacement, greenscreen compositing, and adding basic environmental visual effects like adding pre-shot footage of rain. Higher than that requires realistic CG, rendering and advanced compositing, which can get really expensive and is out of the reach of the casual vfx side-hustler.

One of the more embarrassing moments in visual effects history.

14. Animation and Motion Graphics

This is also something I do in my day job from time to time and has resulted in side gigs. Usually the kind of animation I do isn’t character animation like what you’d see in a Pixar movie, but animating type or graphics.

An animated logo like what you’d see at the beginning of a YouTube video or sales presentation is an example of this.

One form of animation that’s rather popular is the “whiteboard animation” you may have seen used for explainer videos. There are a number of online tools available that can create these kinds of videos, and if you like to teach and tell stories then this can be a great side gig for you. (And you don’t even have to learn how to draw!)

15. Surveillance Camera Installation and Maintenance

One capacity that I help with in the family oil change business is maintaining our security camera system. I also designed and installed this system and it’s been invaluable in various ways to the business.

It consists of a custom built pc with surveillance software and hard drive storage, power and surge suppression equipment, and 32 cameras that point to different areas of the facility. Though it was built using all off-the-shelf components, there was a lot to doing this that I didn’t realize… but now that it’s in place it’s been working for many years with little upkeep.

For someone who wants to make this a side hustle it could definitely be a good niche. You could charge a fee for the initial installation and then subcontract the camera installation work to people like stereo system installers. You could then charge a monthly fee to maintain the system remotely. The business could enjoy a hands-off system that works and they don’t have to worry about it.

… if you’re gonna go to the trouble to install it, just be sure it points in the right direction, ok?

16. Bartering

This is an ancient practice that still works very well today! I’ve gotten either free (usually discounted) services in exchange for using my own talents in service of a business, usually web design.

One example of this is when I needed a new HVAC system. I looked for a small “mom and pop” business that had good ratings but a bad website and offered to to redesign and host the site. I treated them like I would any other paying client, and invoiced them so they would know the value of my services. In return, I got an installed system for about two-thirds of the price.

I’ve also bartered services for other kinds of work, like concrete refinishing and landscaping. As you can imagine, it really dovetails nicely with a real estate side hustle.

I don’t, however, advise bartering with these guys.

17. Credit Card Hacks

The word “hacking” may not be a very good term to use, so maybe a better term would be “taking advantage of credit card promotions.” I’ve gotten free airfare for my whole family to Disney doing this, gift cards, and even a Taylor acoustic guitar! You can often get cash back, too.

This works really well if you have a side hustle where you have to buy a lot of materials or things to sell… just put it on a card and accumulate the bonus points, then cash in on the points.

It goes without saying that to do this you need to maintain a good credit score so you can get the best offers. You also need to exercise good organization and financial discipline to pay off the cards and not carry balances that can eat into your profits.

18. Real Estate

There are lots of great ways to make money in real estate, and without a doubt it’s been the most profitable side hustle I’ve done so far.

I’ve done what I call “slow flipping”, which is to buy a distressed single family house, fix it up, and then rent it out for four to five years. After that, I sell it and put the money into another property. This method allows you the advantages of immediate passive income as well as longer-term income.

It can be very time consuming to get set up and find good properties, and it might not be possible in all markets… but if you do it right, it’s a fantastic way to earn money.

 19. Affiliate Marketing

Affiliate marketing is basically referring people to a product or service on behalf of an affiliate partner. Affiliate partners can be single individuals who sell stuff online, or they can be large companies like Amazon.

It’s actually very easy to find and become an affiliate partner… the difficult thing is amassing enough people (referrals) to get a substantial income from it. Bloggers and internet marketers who have large (and engaged) email lists can be very successful at affiliate marketing, because all they have to do is send a single email referring a product and it can result in thousands of dollars of affiliate income. They can also have a lot of traffic to a website and refer people that way using affiliate links on their site.

I’ve had some moderate success from sharing affiliate links to things that dovetail with what I’m sharing or teaching to my audiences. While I haven’t focused a lot on this, it’s been a nice bonus.

The best affiliate relationship I’ve had has been referring people to Bluehost, an internet web host. To generate traffic for this I created a free video course here that shares the exact steps to create a self-hosted artist website, with the affiliate link scattered throughout the page.

A real, live example of affiliate marketing at work! Not saying you have to click the link or anything… (but hey, if you do and sign up for a Bluehost account, I do get a nice cut! Just sayin’…)

20. Blogging

I started blogging way back around 2004 when I started to share our journey with my son who was diagnosed with autism. I started a few other blogs since then, including a tutorial site called smoketutorials.com (no longer around) that taught how to use smoke, a video production software. I also started a blog for artists called ArtistMyth, and it’s generated the most organic traffic and email signups.

Blogs are a great platform for a business, especially if you’re a solo entrepreneur. They act as a great home base where you can share info, useful articles, host online courses, build your email list, sell information products… the list goes on and on! That’s what this very blog you’re reading is… my home base for anything relating to my self-branded businesses like GenX Side Hustle.

Building websites has helped me with a lot of the tasks of building a blog, but you don’t have to be a web expert to build one for yourself. I love how you can have your very own piece of virtual real estate for a mere fraction of the cost of a real piece of real estate. And with super-easy technology like WordPress, as well as the generous offering of plugins available, anybody can build a blog.

And if you DO need a blog host… why not Bluehost!?!? (I know, I should be ashamed of myself…)

21. Small Business Marketing

Being in the graphic design and commercial advertising industry, as well as dabbling in web design and writing, has qualified me to do a little marketing side hustling now and then for local small businesses. I’ve helped my dad’s Oil Change family business for years, and a few other family members as well with theirs.

Online-only businesses are great, but I’ve found that the combination of a local business presence plus little web savvy can be doubly effective in getting customers and clients. Small brick and mortar businesses can reach out to local customers in ways that online-only business can’t… but few of them know how, or have the time and resources to do it effectively. That offers great opportunities to the savvy side hustler who does!

Yes, they misspelled ‘stressful’, but I decided to use this meme anyway.

22. App Development

A few years ago, I got bit by the app bug and learned how to create and publish iPhone apps. I’m not much of a coder but I found out about templates that you can buy and then “reskin” them to create a new, unique-looking app. You’re restricted to the base functionality the template provides, but for many apps a fresh coat of paint (a.k.a. new graphics and media) is all you need.

I bought several templates, and chose one that was a photo booth type app to start. I “reskinned” and published one called Candy Cane Camera, and then another called Classmates Photo Booth. I didn’t make much money from them, but I did learn a lot… and since I used templates, I didn’t lose much money since I didn’t have to pay a bunch of developers.

In retrospect, I’m glad I did it but I found it was just too technical to my liking… and too much was beyond my control. I would be willing to make another one, though, should the situation present itself.

23. Self Publishing

In 2014 I started a company called Color Serenity and published a couple of coloring books, titled Sacred Geometry and Decorative Dogs, using Amazon’s Createspace platform. Createspace allows you to make physical books “print on demand“, which means they only create them when they’re bought, and it ties directly into Amazon. My books have earned a modest amount of money and continue to generate completely passive income.

But Amazon isn’t the only online retail outlet Createspace publishes to… if you have your own ISBN codes (which you need to purchase separately) then you can open your books up to being sold on many other outlets too, even to libraries. Much of my income has come from these other venues.

Kind of like blogging, I also regard self-publishing as a means to an end…  if you make a little money, then that’s great. Publishing your own books and ebooks (and audiobooks) is a great way to build an audience and build qualified leads to your business. I plan on releasing a number of books in the coming years to further my brand and build my audience.

My self-designed cover for “Decorative Dogs”, the second coloring book I published. I used Fiverr to find an artist and commissioned him to create 25 images for it. You can see the Amazon listing here. (Or, you could just grow up and stop using coloring books.)

24. Retail Arbitrage

Retail Arbitrage is the practice of buying items at retail stores and then selling them elsewhere for a higher price. An example of this is when you might find an item at a local Wal-Mart or Target that may be discounted for whatever reason, buying it, and then selling it on Amazon for more money.

As you can imagine, this has little margin upside, it’s unpredictable what you’ll be able to find for a low enough price to sell, and it can be time-intensive. On the upside, if you live near a lot of stores (say, a suburban area) and enjoy the scavenger hunt of finding deals, then this may be a good side hustle for you.

I really only did this for awhile as an experiment, and to ease myself into the Amazon game. It was pretty easy; the very first time doing it, I downloaded a price comparison app to my smartphone, did some scanning, spent about $100 on some products, and listed them on Amazon. Within a few weeks I had nearly doubled my money. Not bad for a few hours’ work.

When your garage starts to look like this, your retail arbitrage side hustle needs to get a storage unit.

25. Private Labeling

Private labeling is the practice of buying a manufactured item at wholesale and putting your own branding on it. To the end buyer, (and really, in reality) you have your very own product. You decide on all the customer support, selling, anything related to the product after it’s manufactured.

I researched what I wanted to sell and decided on a colored pencil set that comes with a case. I sourced my own product from China, finding a factory through Alibaba, and ordered up a small batch to test selling it through Amazon’s FBA (Fulfilled By Amazon) program. When that was successful, I ordered a larger batch and during the Christmas season I was able to get it ranked number 126 in the Arts & Crafts category.

The rise and fall of this little business was kind of epic for me, and I’ll probably share the whole story pretty soon… suffice to say I learned a great deal from doing it, and it’s definitely a fantastic business model for a lot of side hustlers out there who are willing to learn how to do it and have some monetary capital (at least $2000) to start with.

When you have your own product, you can use your family members as models for product shots! This is my daughter happily coloring with the colored pencil set that I sold on Amazon.

26. Selling At Shows, Fairs, and Festivals

After my Amazon experiences with my colored pencil set, I decided to try selling at a local fair this past year and had some great success… I sold completely out of product within four hours!

The model with these venues it that they’re seasonal. Wherever you live, there’s probably an online directory of the fairs that are coming near you along with info on how to contact the organizers. You purchase a booth or table at the fair and then you can sell your wares. Especially if the venue is outside, there’s a number of other things to consider such as a tent or tarp, chairs, signage, a credit card chip reader, and things like that. If you sell food or need electricity to your booth/table, there are additional but modest costs involved.

While it was a physically tiring experience, and I had to commit a Saturday to do it, I would definitely do it again. I really enjoyed meeting customers face to face. The fair atmosphere is very friendly and the people are fun to be around.

To level up and gain experience points, sell your wares at a renaissance faire! Dilly, Dilly!

27. Creating and Running A Kids’ Summer Camp

You don’t have to buy a bunch of acres of land or sacrifice an entire summer to create a summer camp! While there’s a lot of organization to it, you can do a thematic camp very economically and in just a week’s time.

I worked with a couple of other parents at my kids’ school to do a Kid’s Animation Camp. It ran for four days and cost each kid $200, which paid for food and supplies. Most of the supplies I was able to get donated, and the rest were supplied by the school or from stuff we were able to borrow (or had ourselves).

It was a great success, and the kids (and parents!) still talk about how fun it was… and when we’re doing another one.

This stop motion animation was created by our youngest teams, and features a heroic cheetah who saves a prehistoric planet of animals from an asteroid attack. The story and animation were all created by the kids, and I put it together in Adobe Premiere and added some sound effects.

28. Designing And Selling T-Shirts

To an artist / designer like me, the whole print on demand revolution is a fantastic opportunity. Ever since I worked at a T-shirt company in college, I wanted to try my hand at creating my own T-shirts and selling them on my own.

To try it out, I started an account at the print-on-demand site Gearbubble and bought the domain ShirtDroid.com, then pointed my new domain to my Gearbubble page. In minutes I was uploading my own shirt designs. Like other print on demand sites, they will print stuff on a lot of other products, too, like mugs, pendants, and pillows.

This is my most popular shirt, which uses a Saul Bass-inspired design to poke fun at a certain aspect of Star Trek lore.

29. Online Courses

Building and selling online courses have been a fantastic way to use many of my talents and experiences to create truly passive income products. I’m able to incorporate my love of teaching, video, graphics, and technical knowledge and have lots of fun while doing it.

I’ve experimented with a number of niches and platforms for hosting online courses. I tried selling on Udemy, Skillshare, Teachable, and after that I decided to invest in the Rainmaker platform, created by the folks at Copyblogger and Rainmaker Digital, so that I can host my very own courses on my own site.

Here’s a handy infographic that shows the major differences between Teachable vs Udemy, two different kids of ways to host your course online.

30. Public Speaking

Never in a million years did I think that I would enjoy (or be good at) public speaking. I did speeches and spoke before various groups back in college, and I didn’t enjoy it at all. How things change!

A few years ago I was asked to give a software demo using some of the virtual reality techniques that I’d developed using the video finishing and visual effects software Flame. It was very well received, and that led to other speaking opportunities in New York in Las Vegas. I’ve since joined Toastmasters International to continue developing my speaking skills, and I continue to use speaking as an income source as well as a way to develop my clients and audience.

31. Coaching

Last (and definitely not least) we come to what is one of my favorite parts of my business: coaching.

A part of me has always loved counseling people one-on-one, but I didn’t want to undergo all the schooling and hours necessary for a therapy degree. Years later, I discovered the practice of coaching (specifically, business coaching) as a way to do the same kinds of things, but in a format that’s much more targeted to the specific needs that people have.

I invested in a coaching training program and did around 100 hours of actual coaching, learning all kinds of techniques on how to help people overcome various aspects of building and growing a business, in addition to helping them overcome whatever other challenges are in their life. Coaching will probably always be a centerpiece of any business that I do, because I love doing it and it’s amazingly effective at helping people achieve what they want in life.


31 Side Hustles… And Counting

Whew! That was a much larger post that I had anticipated. It turns out that I had done more side hustling than I had thought.

But guess what? I wouldn’t trade the experience I gained for anything. Even if it was a side hustle I didn’t really like, or didn’t earn much (or any) income while doing it, I still gained a tremendous amount of knowledge and self-confidence from doing it.

And since I really enjoy being a micro-entrepreneur, a side hustle here and there will probably always be something I do.

What’s YOUR Side Hustle History?

Now, dear reader and fellow hustler, it’s your turn.

  • What have you done as a side hustle?
  • Any funny or interesting stories?
  • What’s worked well for you, and what side hustle business ventures are you still pursuing?

Please feel free to share in the comments below this article. I’d love to hear from you!

Keep hustling,

Mike