Side hustling is terrific. It’s a way to pick up some extra dough to make lean times a little less difficult, to bulk up your savings, to pay down your debt or even to dip your toes into the self-employed world while still holding onto all the perks of your day job.

I’m a big advocate for side hustling and I really think it’s terrific. I would highly encourage anyone to do it (and if you need an idea, I’ve got 114 of them here).

…BUT

Sometimes things don’t go as planned.

I present to you: Side Hustle Fails

The Story of the Sad and Soapy Rabbit

 

TaskRabbit is a great place to pick up a huge variety of side hustles. Seriously, if you think you don’t have a marketable skill but can coherently put together IKEA furniture or do laundry, you can probably pick up some cash there.

I have personally used TaskRabbit to have some poor soul drag 20 pounds of sugar and corn syrup through NYC to the theater I was working at when I needed to build prop windows. Best $15 I ever spent to make my own life much easier.

Melanie, a TaskRabbit regular, picked up a gig to tidy some gentleman’s kitchen and run a load of dishes in the dishwasher for him. Easy peasy, lemon squeezy, right?

Some things just aren’t meant to be though. Melanie doesn’t have a dishwasher and didn’t have much of a background with them and mixed up regular dishwashing soap and dish washer soap – resulting in a petty epic and soggy fail.

To make it even better, instead of a calm reaction, she had one of these:

You can read Melanie’s full story here on her website Dear Debt.

Moral of the Story: Accidents happen. If it’s so bad you can’t hide your dismay, always roll with the PG version of frustration in front of a client. And read the labels on everything before you use it.

The Big, Bad Bank Bust 

In my opinion, one of the best kinds of side hustles is when you see a need for something and can fill it with ease.

Tahnya started out freelance writing and was successful enough to get more gigs than she could handle. She realized that this put her in a great position to act as a sort of middle-man for freelance writers and started her own little gig contracting out freelance writing opportunities.

Tahnya’s day job was as a certified financial planner at the Big, Bad Bank, where plenty of her other coworkers were also working second jobs to get by and so she shared her new idea with them.

Turns out the Big, Bad Bank was not a fan of Tahnya’s idea and she wound up getting fired. Since she had already shelled out $1,000 to start up her company, Tahnya was now out a hefty chunk of money, folded her freelancer middle-man gig and lost her day job.

This side hustles attack story has a happy ending though, since Tahnya went on to find a job in a company that actually supports her and continues freelance writing. She just keeps all the gigs for herself now. J/K. She skips the commission and passes them on to friends.

You can read some of Tahnya’s excellent articles on her website The Me Project.

Moral of the Story: It never hurts to check in with your company’s HR policies before starting a gig that is in any way related to your day job.

The Very Hungry Little Show in a Church

I wouldn’t just rat out these other ladies if the entire idea for this series hadn’t come from an experience of my own.

So another terrific side hustle is taking something like a hobby you know how to do well and finding a way to get paid for it. Even though I work in theater, I’m a production manager these days and do exciting things like schedules and budgets. Back in the day though, I was a lot more hands on and I’m actually a passable electrician and props mistress.

My main side hustle is building and shopping props. While my day job is at a pretty high level in the NYC theater circuit, for my props gigs I look roughly a step above community theater. I want to get paid, but I also want a lot of freedom. And generally it works out great. I attend roughly 1-2 production meetings and then I just check in through email or phone calls and start buying or making stuff and dropping it off.

A show I worked on over the winter though just grew and grew and grew and grew, until for about $250 it tried to eat my entire life. At some point during this process, I even became the set designer – for no additional pay.

By tech week I was totally swamped, in so far over my head, completely overworked and extremely angry about everything that was happening. The show wound up being one of the worst I’d ever worked on because A.) I am a really bad set designer, so I was trying to do something that I don’t know how to do well anyway – which they knew. B.) I didn’t have a high enough budget for things they wanted me to do, so everything looked messy and unfinished and partially thought out. C.) My attitude was terrible.

That last one still haunts me because as everything was getting worse and worse, instead of stepping back and speaking up about their demands going so far beyond our initial agreement, I just started getting angry, short and nasty with them.

Honestly, I really should’ve quit about midway through the process, but it felt wrong quitting something. In reality, the whole production would’ve benefited from me walking away… which is a sad and horrible thing to realize about yourself, but sometimes, there it is.

Moral of the Story: Always speak up when you’re not happy about how things are going or you think you’re being taken advantage of. Don’t agree to things that are beyond your skill level. Also, sometimes it is better to quit.

Still ready to get your side hustle on? You should be! For every fail there are dozens of successes! So learn from our mistakes and get going!