3 Side Hustles That Cost Me More Money Than I Made
Side hustles have become essential so let me save you time

Standing in a downtown alley, the frigid Canadian winter air was turning my beard into ice. I felt my phone vibrate in the pocket of my winter jacket. 9 PM the clock read as I swiped to see the text message from my partner.
“How are you making out?”
Should I tell her the truth? I’m frozen in a back alley on a Friday night. The wind is killing me tonight and I’m behind a restaurant in the name of a side hustle that I’ve made almost no money working.
The Great Pandemic
According to Forbes, there were 2 million Americans added to the side hustle lifestyle in the first few months of the pandemic in 2020.
In Canada, we are experiencing a housing crisis, unlike anything we have seen in years. Our rents are soaring since the pandemic and salaries are not catching up. It’s to the extent that university students in Victoria, British Columbia are having to sleep in camper vans.

Side hustles used to be something people did because they wanted extra cash, but now? It’s essential.
My rent has increased by almost 50 percent while my salary stays the same. I don’t work my side hustles because I want to. I do it for survival.
In order to make ends meet I’ve tried a few different side hustles that boast about their compensation. In my search for the perfect side hustle, I have come across a few duds that ended up actually costing me more money than I ever made doing them.
There may be exceptions to the rules but these have been my first-hand experiences and I wanted to share them so you don’t lose out like me.
1. Food Delivery
Doordash was my first foray into the side hustle world. I saw a job advertisement on a local job board with its promise of 25 dollars per hour. That was more than I made at my day gig, so it was a no-brainer.
Major downfalls
- Waiting. Food delivery works on the premise that you get as many orders done in as short of a period as possible. Often you will wait 20 mins or so for the food once you arrive at the restaurant. Expect the restaurant staff to treat you with a bit of disdain while you wait, sometimes relegating you to the back alleyway in the -30C Canadian winter.
- Waiting some more. The company I worked for required you to sign up for 3-hour shifts. Sometimes it just wasn’t busy so I spent many hours in between orders camping out in my car on the downtown streets. Too much time spent not earning money, not to mention wasting gas while idling your engine.
- Driving distance. The number of deliveries I would get that required me to drive 15 km’s out of town was staggering. I would get the food, drive it out, and then have to turn around and drive the 15 km’s back into town in order to get another delivery. This made round trips hardly worth it, yet they were the norm. If you don’t take them, you don’t get jobs.
Why it cost me more
- Gas used. Driving 30 km’s for an 8-dollar order while gas prices are soaring is illogical.
- Customers tips. Customers do tip, but hardly enough to make it worth long drives, and why should they? The food delivery companies are already charging them exorbitant fees. In fact, Doordash was even caught stealing tips from their drivers.
- Wear on the car. Driving all night for pennies also put serious wear and tear on my car. My brakes, tires, and struts all had untimely deaths because of running the roads for 100 to 200 km’s a night.
- Time away from family I think the part I hated the most was how it stole valuable time away from my family and me being together. You can’t just log in and work whenever you want, and it made for long 3-hour shifts where no action came in.
2. Grocery Delivery
When I came across Instacart it looked a lot like Doordash, with two major differences.
- I didn’t have to schedule my shifts and I could work whenever I wanted during the day. It also required much less driving and had decent tippers.
- It seemed easy. Get the grocery shopping list, shop the order for people, and deliver it.
Major downfalls
- Customers. This could honestly be the only downfall I need. Customers often report items missing or damaged. This leads to a bad rating and decreases your chances at better-paying batches.
- Shopping time. I have been caught at grocery stores for up to two hours when the stores are busy.
- Stores are low in stock. Stores can have little or none of the shopping list customers require.
Why it cost me more
- Time. Spending long amounts of time in the grocery store leads to fewer batches available for me to take. Batches tend to have a shop time of 30 minutes at the minimum.
- Batch pay is low. The pay per batch is low. It often wasn’t enough to make up for the extra time spent in grocery stores and driving.
- Tips. Customers will give you a large tip upfront to entice you to take a batch and then yank it away. In the biz, we call this “tip baiting.”
3. Flipping thrift store items.
There are a lot of proponents of flipping items to make a great profit. I will admit that it can be quite addicting to find an item for 3 bucks and flip it for quadruple the price.
I’ve done it successfully and know it can be done, but it isn’t the money-making machine Gary Vee would have you believe.
Major downfalls
- Profit is at the mercy of the store. I had no idea if a store was going to be a treasure trove or a bust. You are completely at the mercy of whatever stock the store has the day you are there.
- You must have a great eye. You have to be keenly aware of your local area and what items people will buy on the resale market. If I take my partner with me, she has a great eye for fashion and items that would re-sell easily and quickly. I do not have that ability.
Why it cost me more
- Items Not selling. Sometimes no matter how nice an item was that I found or how good of a deal I got, it wouldn't sell. I once bought a hoodie that I had flipped two times previously and when I tried to sell it again, it sat on the marketplace and I had to eat the cost.
- Too unpredictable. It was way too unpredictable. When I need to rely on a side-hustle income, potentially sitting on hundreds of dollars of stock and never being able to move them was detrimental. There were more than a few times I couldn’t move product and I got stuck with an item I couldn’t sell or even return back to the store.
I do have 2 side hustles that have been worth my time.
- Selling Custom Digital Prints. I make up digital prints of people's favourite songs, custom quotes, and I draw digital portraits of them. I mocked a few up to get started and listed them on Facebook Marketplace. The best part is I can create them in under 5 minutes and sell them for 20 bucks a pop with no costs to me other than time. This has been a game-changer for me.
- Making Youtube Thumbnails. I found a few mid-sized YouTubers that I work with and create their thumbnails for their videos. This is steady work and most of the YouTubers I work with need 3 to 4 thumbnails done per week. It’s steady and allows me to count on additional income.
I understand that those two side hustles might not be something you are capable of but I challenge you to think of something you could do on the side that already exists within your wheelhouse.
I am a graphic designer by trade so it made sense for me to naturally extend into those two categories. I have faith that you can think of something that is in your line of work that will help you make the side income you need.
I would love to hear from you in the comments about what side hustles you have tried. Do any cost you more than you make? Do any work better than you thought?
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