Millennials are accused of being many things. We’re avocado-toast-eating, diamond-industry-killing, increasingly childfree pet parents who are utterly fixated on our side hustles. Fellow millennials, you can decide how much these labels apply to you, but I am guilty as charged. Especially on the side hustle front.

Generation Side Gig

The hope of striking it rich through fortuitous application of creative talent has been part of my life since childhood. Everything I did well, I was told, was a potential source of riches. I showed an early aptitude for creative writing, so naturally I should write a book at 14 and become the next Christopher Paolini. (No offense to him, but I’ve never quite gotten over the comparison, and as a result still can’t bring myself to read his work.) I was good at horseback riding, so if I played my cards right, perhaps I could go to the Olympics as an equestrian athlete. Coding HTML and CSS websites in the heyday of Geocities, Tripod, and Angelfire? Clearly, I needed to start a website design business and get rich through entrepreneurship. Every hobby was a potential chance to make money. The only trouble was figuring out how not to fail.

I’m certainly not the only one who got this message of constant self-monetization. Between encouragement from our parents, the advent of social media influencers and content creation, and the rise of e-commerce and gig economy platforms like Etsy and Uber, millennials have been perfectly positioned (and conditioned) to pursue the rise-and-grind life. As of 2023, 50 percent of us have a side hustle, making my generation second only to gen Z in that regard. All told, side hustles represent $50 billion in extra monthly earnings for Americans — a whopping $600 billion per year, or more than the 2022 GDPs for more than a couple European Union countries.

A Feast of Failure

So, as a self-proclaimed side hustle addict, how much of that $50 billion pie have I personally scored?

Basically nothing.

As inspired as I am by each and every one of my business ideas, and as good as I honestly am at my hobbies and interests, I’m hilariously bad at side hustle follow through. To date, I have tried:

• Website design. I had 0 customers. Granted, I was a teenager, but I think it still counts.
• Music. I was once in a band. Actually, that was fun; I’d do it again, given the chance.
• Selling short stories. This was during that brief time when I was educated enough to produce decent stories but hadn’t yet lost the desire to write. After a full year, I had sold one story. I don’t remember how much I got paid, but it was definitely less than $50.
• Freelance copyediting. A thoroughly confusing and discouraging experience. I don’t remember what site I tried to get work through, but I gave up after being constantly undercut by people whose profiles were riddled with egregious grammatical mistakes.
• Amazon Mechanical Turk. So much effort. So little gain!
• Photography. I took pictures at horse shows and then offered them for sale to riders and their families. My website hosting fees outweighed my sales, and I had to shut everything down when I stopped riding and lost my contacts in the “scene.”
• Streaming on Twitch. I have actually made money from this. No, I’m not famous. I’ve probably done better than many other small streamers, but from a business standpoint, it’s really not a success. Let’s just say I still couldn’t buy anything more than a mediocre guitar with my total earnings so far, and I started in 2019.
• Daytrading. This one will definitely warrant its own post in future. Fun? Yes. Profitable? So far: emphatically, no.
• Print on demand. This started as merch for my Twitch and spiraled into another offshoot business. I spent a lot of time creating original vector art, and I promoted the designs on Pinterest and Instagram. After a year and a grand total of two sales that probably netted me $3, I was unceremoniously banned from Redbubble. I still have no idea why. (I’m only a little salty. Okay, a lotta salty.)
• YouTube. For a brief chunk of 2023 (just a few months, really), I decided to go all-in on creating a YouTube channel to complement my Twitch. Eight or so videos later, I burned out so spectacularly that I haven’t so much as peeked at my dashboard in at least six months.
• Game development. Maybe this one doesn’t count, since it’s pending until all my other stuff isn’t so overwhelming. (Ha!) But anyway, for some reason I decided I needed to write a visual novel. And do the art. And code the game. Easy, peasy.
• This blog? No point being disingenuous here. Whatever this might be, I promise never to stoop to that entrepreneurship guru crap. (Buy my course and I’ll tell you the secret of success! Which is to build a course and sell it to other people who … also want to know the secret to success. Ugh.)

I’ll leave theories about why all my side hustles fail to another post. At the end of the day, I have to acknowledge that a track record of 0 for 11 is admittedly abysmal. I’m not ready to give up, though! For all the struggle, I feel like there’s something out there for me if I just keep trying.

Scratching for Scraps

I can be somewhat comforted that statistics show that my low side hustle earnings put me in good company. While the grand total of side hustle earnings isn’t anything to sneeze at, how much all this extra work benefits most individuals is up for debate. While a recent Bankrate survey did find that side hustle earnings average $810 monthly, I would argue this figure is skewed by upper limit outliers. The same survey provided earnings brackets indicating that 42 percent of side hustlers earn less than $100 per month. Add in another 11 percent making between $101 and $200 a month, and we see that the majority (53 percent) of people with side hustles aren’t exactly making the big bucks.

Whether or not a side hustle is successful, the endeavor can come with downsides like burnout. If you’re like me, and your side hustles revolve around cherished hobbies, turning these into a side gig also runs the risk of ruining things you once loved by turning them into work, something I know all too well. I made it all the way through grad school before the weight of a formal creative writing education and attempting to make my writing into A Business drove me to drop writing altogether. This proved especially awkward because I had presented fiction writing as an integral part of my personality. Cue 10 years of embarrassing questions: “How’s the writing going? When can I expect to read a published book?” Gee, thanks. What a lovely, painful reminder to bring to an otherwise pleasant social gathering.

Why Even Bother Hustling?

You may be familiar with a famous saying that goes: “Insanity is doing the same thing over and over again, but expecting different results.” (Incidentally, not an Albert Einstein quote, but rather, possibly attributable to mystery writer Rita May Brown. But, I digress.) If we — myself and so many others, maybe even you — are so aware of all the bad parts of side hustling, why on earth do we keep coming back?

Speaking for myself: it’s complicated. For one, it’s probably the neurodivergence. People with ADHD are (famously) attracted to a host of different hobbies. And what’s shinier than a new hobby? Turning that hobby into a potential source of wealth, of course! However they’re inspired, these new ventures are exciting and invigorating. (And yes, I’ve totally been guilty of watching those sensational youtubers who promise millions in a snap.) You would be right to suggest this is a dysregulated approach to ADHD, but whatever. As long as I’m not pouring money into MLMs or paying hundreds for dubious success courses, I think I’m owed some fun.

Perhaps a more nuanced reason is that side hustles represent a freedom that I won’t get through traditional work. I’ve written about my difficult relationship with employment and the tempting solution I see in the FIRE movement. Through those lenses, a side hustle could be a double whammy of wish fulfillment. Self-actualization through pursuit of my passions plus the income I need to reach financial independence! All this for the price of … well, possible burnout and recurring failure.

The Plan (Or, Why I Even Started This Blog)

If I can’t beat my compulsion to jump into a myriad of ill-fated side hustles, perhaps I can turn it to my advantage. Through the flurries of research required for each of these start-ups, I’ve become frustrated by how internet advice about side hustles seems like a minefield of unreliable information (and sometimes outright lies). I know I can’t be the only one who feels this way. Some of the advice seems like blatant, paid advertisement. Other sources just seem to be unwilling to admit they were early entrants to a now-oversaturated market. Many may actually be good advice for everyone except my very busy, burnout-prone, neurodivergent self. Perhaps if I can explore different options and document their pros and cons from my perspective, I’ll find my unicorn side hustle. And if some of that no-bullshit information helps someone else? Even better. 

Whatever I do, I need to learn some balance, because apparently, I’m not as invincible as I thought …