The Side Hustle That Cost Me $2,000

papers on desk with hustle pen

I walked up the path, double-checking I had the right address on my phone. A dog on the other side of the front door barked madly as it hurled itself against the glass.

The hound gnashed and growled, as the app on my phone had warned me he might. The notes told me he only sounded terrifying, but he wouldn’t attack once I got inside.

A barking dog baring his fangs
He snarled and growled and gnashed his teeth; he was vicious I tell you, beyond belief!

My Side-Hustle: Wag!

I was using the dog-walking app Wag! as a side-hustle. This was my very first walk, so I diligently read through each instruction and struggled to get the lockbox open. The impatient pup threw its staunch body against the glass, which shuddered on impact. I was sure a neighbor would call the cops on me as the booming barks echoed down the street. Finally I got the key, slid it into the lock, and opened the door a fraction to avoid letting the dog out.

Just as the notes had promised, the dog did not viciously rip my arm off as I wedged myself into the small entryway. However, with a stranger in its house and the promise of an imminent walk, the creature was in a full-blown frenzy. I tried to calm him with a soothing voice as I reached for the leash, petting his head.

When I bent down to clip it to its collar, the dog launched itself upwards to lick my face. Its thick skull whacked my jaw, the type of impact that brought tears to my eyes immediately. I reeled back against the wall, eyes shut, holding my mouth as the pup wiggled in pure excitement, apparently unaffected.

Happy dog smiling
He did not seem very concerned for my well-being, to be frank.

I collected myself after a minute, carefully clipping the leash and shutting the door behind me before the dog yanked me up the sidewalk. Little did I know that this little experience would come back to haunt me half a year later.

The Rise of the Side-Hustle

From driving for Uber, delivering food via DoorDash, or hosting people through Airbnb, the side-hustle can be a fantastic way to make some additional income. In fact, 4 in 10 Americans have a job on the side. If you have the time and the resources, it can be a no-brainer way to rake in a little extra dough.

However, opponents of the side-hustle gig economy pose an important counterpoint: the cost of a side hustle may outweigh the income deposited in your bank account.

My Side-Hustle Compensation vs. Cost

Wag! was a phenomenal way to make money on the side. I go for daily walks anyway, and I love dogs, so an app that pairs people with dogs that need a walk was a perfect match. Overall, I made $315 by putting in a little effort of downloading and setting up my profile in the app. Not too shabby for time I would have spent walking anyway.

Screenshot of my walks from last year

Yet even that simple side-hustle had a significant cost.

Remember the dog-skull vs. human-mouth face-off of 2018? Apparently, trauma to the face can kill the nerves in your teeth, resulting in damage that requires a small surgery. For me, it meant an endodontic appointment for TWO root canals.

Given the fact that one tooth runs anywhere from $900-$1,100, I was looking at a bill of $1,800 to $2,200 as a direct result of dog walking on the side.

The Costs to Consider

Of course, it was an unlucky circumstance that is (hopefully) unlikely to be repeated. It was my very first time walking an unfamiliar dog, and being new to any side hustle introduces a bit more risk. With more experience and more time, the dividends might begin to outweigh start-up costs (or surprise medical bills, in my case).

However, the shock of the bill is a good reminder to keep costs in mind when starting up a side-hustle. Don’t forget to consider:

  • Maintenance costs (think of the wear and tear on a vehicle while driving for Uber).
  • Damage to the residence (Airbnb).
  • Burn out.
  • The opportunity cost of working on a side hustle compared to your full-time job.
  • Dogs that use their heads as battering ramsdog nuzzles man in the cheek

To be quite honest, that bill would not be enough to stop me from continuing to walk dogs in my spare time. (I did stop using Wag!, but only because the app didn’t switch over properly to my new phone).  However, the bill was a wake-up call to remember that sometimes extra income has its own cost.

The Cost To Your Main Hustle

The main argument against a side-hustle is that the energy you put there might be put to better use at your main job. As Maurie Backman writes in the Motley Fool:

“If you’re so focused on your side hustle that your performance slips, you might lose out on raises or promotions that boost your primary income stream.”

If your performance doesn’t slip, then keep on keepin’ on! But that time might be better spent focusing on your main job. Better performance at work might mean a large raise worth more than the extra few hundred you might have made otherwise.

The Costs We Forget

There are often obvious upfront costs to a side-hustle, like setting up a website or, in the case of Wag!, paying $20 for a background check. However, there are other costs that are easy to miss.  For example, Uber drivers ostensibly earn $24.77 per hour on average, but that is far from the amount that actually ends up in their bank account.

The total is cut in half to $11.77 after factoring in commissions, gas, and car maintenance. If we take into account the cost of health insurance for a full-time driver, the take-home pay drops to just $9.21 per hour.

Someone might enjoy driving for Uber to meet new people, explore their city, and earn a little supplemental income, but it is important to remember that the income we see is not always the total we reap.

Does the Benefit Outweigh The Cost?

Some side-hustles make sense. If you want to explore your city by bike, try delivering for Postmates. If you are passionate about statistics, tutor on the side and fulfill that itch. Plenty of people find fun and engaging ways to stash away some pocket money.

It is perfectly viable to monetize the time you spend away from your day job. So embrace a side-hustle, but be cautious about hidden costs. It is possible that your side hustle could be at the expense of your time, your energy, or more drastically, your dental health. Much like a dog, a side-hustle may seem fun and easy to care for, but if you are not prepared, the reality may come back to bite you.

Get Posts Delivered Straight To Your Inbox!


  1. Ouch, that doesn’t sound too good! I love dogs too, but some of them are very clumsy and don’t know their own strength. Dog walking would be me ideal side hustle though, when I come to work in a city-center I would love to to that!

    1. Yes, I still recommend it! I’m sad to be leaving a city-center so I will have less chance to side-hustle, but it means I can make big plans for when I move back to a big city!

  2. Oh no! I’d never have imagined that the physical trauma from being bumped in the face by an excitable dog could have resulted in two root canals. Though I’ve also had the unfortunate experience of a freak accident resulting in thousands in dental bills somewhat recently. (I had a bit more outwardly visible physical trauma at the time, from tripping on the sidewalk, and my root canal needs were more immediate.) It’s pretty awful! I didn’t comparison shop for dentists/endodontists that much, but I still found that there could be dramatic price differences. I’m actually surprised at the $900 to $1100 average price for a root canal, because in downtown-ish Manhattan (more expensive neighborhoods), I was quoted either $650 before insurance at my neighborhood dentist (though their equipment is much less advanced and it take them nearly a half hour longer, I think I’d rather pay more to do it elsewhere) or $1200 at a fancy endodontist that didn’t take mine (or most other) insurance plans. I guess that makes me feel a little better about what I paid.

    Anyway, my industry doesn’t really lend itself to side gigs. Biglaw firms, in particular, expect attorneys to be potentially on call at basically all times. There’s a few people in the industry who have lucrative blogs or similar flexible online “businesses”, but that’s about it for side gigs I know of.

    1. Oh no that sounds awful! I’m sorry about your trip. I wrote this article based on that average, but my actual payment ended up being a bit less after insurance and some help from a dentist in the family. The bill definitely added up quickly though, with each x-ray, the anesthesia, and the follow-ups as well.

      I know of Financial Panther, who is an attorney and a huge side-hustler, but I can imagine that being on call doesn’t make you particularly excited to use your free time to do other things.

  3. I’m grateful that Uber exists, but it makes me wince to think about all of the miles these people are putting on their cars, wearing them down more quickly. But I never thought about dental costs, that’s for sure! So sorry you had to deal with that bill. I’ve had a root canal before. Have you already had it done? If not, check out discount dental plans in your area. I think mine cost closer to $600 to $800 because I had one.

    1. I’m grateful it exists too! Those costs are easy to forget though, the extra maintenance would bother me. Thanks for the idea! I have already settled the bill, it turned out to be less than the quoted amount in the end thankfully. Good job thinking about discount dental plans!

  4. Yes side hustles don’t pay very well once you factor in maintenance, healthcare, etc. It’s important to focus first and foremost on your main hustle then find something enjoyable to do in your free time as a side hustle.

    1. Yes, I think it’s definitely important to enjoy what you do on the side, otherwise it’s just another thing to burn out with! I’m glad I have the blog to be my side-hustle.

  5. It’s good to see a warning of the potential pitfalls of side hustles. Unfortunately, I think many of the “gig economy” jobs are not very lucrative for the giggers, like the Uber example you gave. It’s often hard for people to quantify things like maintenance, and even to properly value their time. At least with Wag you can get some exercise!

    1. You make a good point about learning to value our time. That is definitely its own learning curve as well! It’s great if you can benefit more than just monetarily, like exercise or community building (our blogs!) 🙂

  6. Thanks for sharing this story. So sorry that happened to you! My husband volunteered with Austin Pets alive when we lived in Austin, TX. He was bit by a dog. This required medical attention – and he still went back to be with the dogs over and over again!!! He still walks dogs all of the time for free. He even has a dog walking business in mind as our sons first business. I’m going to show him this article for an alternative perspective a little closer to mine…

    1. If you can “vet” the dogs beforehand (see what I did there!) then it could be a fun little business idea. I at least had some warning that this dog would sound scary and also that it could not be walked anywhere near other dogs. Definitely not kid-walking friendly! But MOST of the dogs I’ve walked have been super sweet. I wrote another post with my Wag! review a few months ago (before the dental fiasco) that shows pics of all the sweet doggos. I’m glad your husband enjoys what he does despite the one bad experience 🙂

  7. I know that you were trying to tell a salutary tale, but it is wrong that it made me laugh? I’m going to put it down to your skill as a writer.

    On a more relevant note, the opportunity cost point from both my main job and my life is what holds me back with side hustles. I’ve started a few but always stopped as I realised that there were other things that I would rather do with my time. Yes I would have less money but I would be happier…and that’s what it’s all about for me.

    1. I’m glad it made you laugh! Now that the procedure is over, I can laugh too 🙂

      I completely agree that opportunity cost is a huge one. If someone can pick up side hustles that are in-line with something they were going to do anyway, it makes sense to do it. But if working a side-hustle takes up more of your time and energy that you want to spend elsewhere, it makes perfect sense to quit!

  8. Side hustles always seem to be a love/hate relationship for me. I think the sweet spot has to be something you would do even if it didn’t bring in money. Then the use of your extra free time on the side-hustle doesn’t feel so much like a second job, it can have the wonderful feeling of spending time on a hobby.

    1. Yes, that seems like a good way to frame it. You get to spend time on a hobby with the added benefit of some extra $$$!

  9. Really great post. We’ve signed up for Wag in 2017 but made non negligible money through online referral that we didn’t even bother look for dogs.

    We basically entered our referral code on a few coupon/promo site at the right time and then let the SEO do its magic to have a LOT of ppl use our code.

    As all things always come to an end this « passive income » stream has dried up but in 2018 alone that was a gross revenu of about $2,500, which was a pretty good ROI on our time invested.

    Have you consider side gig income through referral only?

    1. Wow! That is an amazing story, I haven’t heard of someone doing that before. The only thing that came close like that for me was Imperfect Produce. I signed up for the first round of free groceries, then friends kept using my referral code which meant I could keep buying groceries for 4-6 more months. Then no one signed up and I didn’t bother to push the referral link out so I cancelled my subscription. That is a fascinating idea though, and a great ROI for you!

      1. I thought about this when you mentioned “The (hidden) Costs to Consider” in your article. Iff you manage to get on the top 3 results of these promo/coupon website (as we did by accident) you might be able to generate some very passive income. I am actually wondering if people are making a nice living out of that. We definitely got lucky on that one!

Leave a Reply

Your email address will not be published. Required fields are marked *