I Tried 5 Side Hustles in 6 Months. Here's What Actually Made Money.
#finance #side-hustle #income #freelancing

I Tried 5 Side Hustles in 6 Months. Here's What Actually Made Money.

I kept seeing those posts online. You know the ones. "I make $3,000 a month passive income from my laptop!" "Side hustles that pay $50 an hour — you won't believe number three!" "I quit my job and now I make more money than ever!" Every time I scrolled past one, I thought the same thing: that's either a lie or they're selling a course.

But the curiosity got to me. Not the "I want to get rich" curiosity — I'm not delusional. The "is any of this actually real?" curiosity. Could a regular person with a full-time job and a limited amount of free time actually make meaningful money on the side? Not "quit your day job" money. Just "cover the car payment" money. "Take my girlfriend to a nice dinner without checking the bank balance" money.

So I decided to run an experiment. For six months, I tried five different side hustles. I tracked everything: time invested, money earned, startup costs, and whether the whole thing was worth the effort. I didn't sign up for anyone's course. I didn't buy any "secret systems." I just did the things that the internet says make money and recorded what happened.

Here's the full, honest, slightly embarrassing story.

Hustle #1: Delivering for DoorDash

DoorDash was the first thing I tried because it seemed like the lowest barrier to entry. Download the app, get approved, start driving. I figured I'd do it on weekday evenings after work, maybe Saturday mornings, and earn some extra cash while listening to podcasts.

The approval process took about a week. Background check, vehicle inspection (they check your car for basic safety — do the lights work, is the bumper attached, that sort of thing), and then you're in. I signed up in March 2026 and started delivering that same week.

My first shift was a Tuesday evening in Richmond. I logged on at 5:30 PM, got my first order at 5:45 PM, and drove to a Chipotle to pick up a burrito bowl. The customer lived 4.2 miles away. Total delivery time: about 25 minutes. I earned $7.80.

I did the math in my head. $7.80 for 25 minutes of work. That's about $18.72 an hour. Not bad. But then I subtracted gas. I was driving my Honda CR-V, which gets about 28 MPG. The round trip was about 8.5 miles. At $3.50 a gallon, that's about $1.06 in gas. So my actual earnings were $6.74. For 25 minutes. That's $16.17 an hour.

Not terrible. But not great either. And that was the best-case scenario — a short delivery to a nearby customer. The reality was more varied. Some deliveries were quick and easy. Others involved waiting 15 minutes at a restaurant for the food to be ready, then driving 7 miles to an apartment complex where the customer didn't answer the buzzer and I had to call them three times.

Over the next two months, I delivered about 4 or 5 nights a week, usually for 2 to 3 hours each shift. My total earnings over those two months were about $980. My total hours (including waiting time, driving between orders, and time sitting in parking lots waiting for pings) were about 87. My effective hourly rate: $11.27. After gas ($86), my actual hourly rate was $11.27 minus about $1 an hour in gas, so roughly $10.27.

But here's the thing nobody tells you about DoorDash: it's not consistent. Some nights I'd make $40 in 2 hours. Other nights I'd sit in a parking lot for 45 minutes without getting a single order. The algorithm decides who gets orders, and if you're in the wrong area at the wrong time, you're just sitting in your car earning nothing.

Also, the wear on your car is real. I put about 2,400 miles on my car in two months of delivering. That's oil changes, tire wear, brake wear — costs that don't show up in your DoorDash earnings report but show up when you go to the mechanic.

I stopped delivering after two months because the inconsistent income wasn't worth the stress. Some nights were great. Most nights were mediocre. And the $11 an hour I was earning (after gas) wasn't enough to justify the time away from Sarah, the wear on my car, and the mental energy of navigating apartment complexes at 9 PM.

What I'd do differently: If I did DoorDash again, I'd stick to lunch shifts on weekdays instead of dinner. The lunch crowd tips better, the restaurants are less busy, and the deliveries are shorter. But honestly, I wouldn't do DoorDash again at all. The hourly rate just isn't there once you account for the real costs.

Hustle #2: Freelancing on Fiverr

A buddy of mine — Marcus, the same one who told me about meal prepping — said he'd made $2,000 a month on Fiverr writing blog posts. "It's easy," he said. "You just sign up, create a gig, and people come to you."

Marcus was not entirely accurate.

I created a Fiverr profile in April. I wrote blog posts, website copy, and product descriptions. I set my prices low to start — $28 per 1,000-word blog post — because I figured I needed reviews before I could charge more. The first week, I sent proposals to 12 different jobs. I got one response. The client wanted a 1,200-word article about outdoor grills. I wrote it in about 3 hours, submitted it, and the client gave me a 5-star review and said, "Great work, will hire again."

One client. One article. $28. That's not a hustle. That's a hobby.

But then something happened. Fiverr's algorithm started showing my profile to more people. I got another order. Then another. By week three, I was getting 2 to 3 orders a week. By month two, I was getting 4 to 5. The clients were mostly small businesses — a lawn care company in Texas, a dental office in Ohio, a real estate agent in Florida — who needed blog posts for their websites but didn't want to pay agency rates.

I raised my prices. After 10 completed orders, I went to $50 per post. After 20, I went to $75. After 30, I was charging $100 for a 1,000-word post, and I was turning down work because I didn't have time.

The money was real. Over the six-month experiment, I earned $340 from Fiverr. But that was with only 4 months of active work (I started in April and the experiment ended in September). If I annualized it and kept going, I'd have been earning about $500 to $600 a month. For 12 to 15 hours of work a week. That's about $12 to $15 an hour. Not great, but not terrible. And it was work I could do from my couch at 10 PM while watching Netflix.

The worst part was the inconsistency. Some weeks I had 5 projects. Some weeks I had zero. You can't count on it for steady income unless you build long-term client relationships, which takes months. And the platform takes 20% of your earnings, so that $100 blog post is actually $80. After taxes, it's more like $55. That $100 blog post is suddenly a $55 blog post, and you spent 4 hours writing it. That's $13.75 an hour before you factor in the time you spent responding to messages, revising drafts, and waiting for clients to get back to you.

What I'd do differently: I'd specialize earlier. The first month, I was taking any job — blog posts, product descriptions, email newsletters, press releases. That spread me thin and kept my rates low. The money got better when I focused on one niche (finance and home improvement) and became an expert in that space. Clients pay more for expertise than for generalism.

Hustle #3: Dog Sitting for an Aggressive Chihuahua

This one started as a favor and turned into a side hustle. My neighbor, Lisa, was going on a week-long vacation to Cancun in May and needed someone to watch her dog. Her dog was a 6-pound chihuahua named Ricardo. Ricardo had one eye (the other was lost to some kind of infection years ago) and the personality of a creature that had seen things.

"He's a little aggressive," Lisa said.

"What does 'a little aggressive' mean?"

"He bites sometimes."

"He bites."

"Just when he's nervous. Which is most of the time."

Lisa was going to Cancun for 7 days. She offered me $45 a night to stay at her house and watch Ricardo. That's $315 for a week. Not bad for hanging out with a dog, right?

Wrong. So wrong.

Ricardo was not a dog. Ricardo was a tiny, one-eyed landmine with teeth. He bit me on the first night — just a small nip on my finger while I was putting food in his bowl. He bit me on the second morning when I tried to pick him up to take him outside. He bit me on the third day for reasons I still don't understand — I was sitting on the couch, minding my own business, and he walked over and bit my ankle.

I called Lisa in Cancun. "Ricardo bit me again."

"That's just how he shows affection."

"That's not affection. That's assault."

She laughed. She was on a beach. I was in her living room, bleeding from a tiny chihuahua bite, watching Netflix with a one-eyed demon on my lap.

The thing is, once Ricardo settled in — which took about three days — he was actually kind of sweet. He'd sit on my lap while I worked. He'd follow me around the house. He'd sleep at my feet at night. He was just nervous, and he expressed nervousness through his teeth. By day four, he wasn't biting me anymore. By day six, he was sleeping on my chest.

The week at Lisa's house was also when I discovered that Lisa had a very nice house. She had a Keurig, a big TV, a comfortable couch, and a shower with three different shower heads. I was living better in Lisa's house than in my own apartment. When she came back from Cancun, she said, "How was he?"

"Fine," I said. "We bonded."

"He didn't bite you?"

"Only a few times."

"See? He likes you."

Ricardo bit me one last time as I was leaving. A farewell nip. Like he was saying goodbye in the only way he knew how.

Total earnings: $315. Total time: about 168 hours (I stayed at Lisa's house for the full week, sleeping there every night). Effective hourly rate: $1.87 an hour. If I'd counted only the hours I was actively interacting with Ricardo (feeding, walking, playing), it would have been higher. But I was "on duty" 24/7 for a week.

What I'd do differently: I'd negotiate a higher rate. $45 a night is fine for a well-behaved golden retriever. For an aggressive one-eyed chihuahua, I should have asked for $75. But I was doing it as a favor, and $45 felt generous enough. Next time, the demonic chihuahua tax applies.

Hustle #4: Reselling Clearance Items on eBay

This was the hustle that made the most sense on paper and worked the least in practice. The idea: buy clearance items at Target, Walmart, or thrift stores, list them on eBay, and sell them for a profit. The internet is full of people who claim to make thousands a month doing this. "I bought this DVD player for $5 at Goodwill and sold it on eBay for $150!" they say, and you think, "Why am I working a normal job?"

I started in April. I went to the Target on Broad Street in Richmond and found the clearance section. It was a graveyard of products that nobody wanted — mismatched picture frames, seasonal decorations in the wrong season, and an entire endcap of weighted blankets that were marked down from $49.99 to $14.99.

Weighted blankets. The internet told me these sell well on eBay. People love weighted blankets, apparently. I bought five of them. $14.99 each. Total investment: $75. I also bought a few other things — a set of kitchen knives ($8 clearance, selling for $35 on eBay), a yoga mat ($6 clearance, selling for $22), and a Bluetooth speaker ($12 clearance, selling for $40).

I listed everything on eBay. Took photos, wrote descriptions, set prices based on what similar items were selling for. The listings went live on a Tuesday. By Friday, I had sold the kitchen knives ($35) and the yoga mat ($22). By the following week, I had sold the Bluetooth speaker ($40).

Total revenue: $97. Total cost: $26. Profit: $71. Not bad for a few hours of work.

But then the weighted blankets didn't sell. They sat on eBay. And sat. And sat. I lowered the price. Still nothing. I lowered it again. Nothing. I promoted the listings. Nothing. The weighted blankets that I thought were a guaranteed win were just five 15-pound blankets sitting in my garage, taking up space.

I kept buying and selling other things — mostly small electronics and kitchen items from thrift stores and clearance racks. Over four months, I made $89 in profit on items that actually sold. But I still had five weighted blankets in my garage and another three clearance items that nobody wanted.

The math on individual items can be great. I bought a set of vintage Pyrex bowls for $12 at Goodwill and sold them for $85. That's a 600% return. But for every Pyrex bowl, there are five weighted blankets sitting in your garage collecting dust. The average is less exciting than the highlights.

The biggest time sink was listing and shipping. Taking photos, writing descriptions, packaging items, going to the post office — it adds up fast. I'd spend an hour taking photos and listing three items, then another hour packaging and shipping two sold items. For a profit of maybe $15. That's $7.50 an hour, and I'm not counting the gas I spent driving to Goodwill and the post office.

What I'd do differently: I'd focus on one specific niche — maybe vintage kitchen items or electronics — instead of buying random clearance stuff. The people who make real money on eBay know exactly what sells and what doesn't. I was guessing, and my guesses were wrong more often than they were right. Also, I'd never buy weighted blankets again. Ever. For any reason.

Hustle #5: Selling Feet Pictures (The Joke That Went Too Far)

This is the one Sarah won't let me forget. I was scrolling through Reddit one night and saw a post that said, "People actually buy feet pictures. My friend makes $500 a month selling pictures of her feet." I laughed. I showed it to Sarah. She laughed.

Then she said, "You should try it."

"You're joking."

"I'm serious. Make a joke listing. It'll be funny."

So I did. I took a picture of my feet on the bathroom floor — I have ugly feet, by the way, I'm a man who wears sandals year-round and my feet look like they've been through a war — and posted them on a feet picture marketplace. The caption said, "Beautiful male feet. Very manly. $5 per picture."

I expected nothing. I expected it to be a funny story to tell at parties. I expected zero dollars.

I got zero dollars.

Nobody bought my feet pictures. Not one person. I posted the listing on a Monday, checked it on Wednesday, and nobody had even viewed it. I showed Sarah the listing.

"That's... unfortunate," she said.

"You said people buy feet pictures."

"People buy feet pictures. Just not your feet pictures."

She wasn't wrong. My feet are not photogenic. They're hairy, they're calloused, and I have a toenail on my left foot that grows at an angle because I once dropped a can of beans on it. If feet pictures were a stock, mine would be worth negative money.

Total earnings: $0. Total time invested: about 15 minutes (taking the photo, writing the listing). I'm counting this as a side hustle because I technically tried it, but really it was a joke that I should have kept as a joke.

Sarah still brings it up. "Remember when you tried to sell feet pictures?" she'll say, usually when we're at a dinner party or with family. "His feet were terrible," she'll tell people. "Nobody wanted them."

She's right. Nobody wanted them. And honestly, I'm relieved. The idea of strangers paying money for photos of my feet is deeply uncomfortable, and I'm glad the market validated my discomfort.

What I'd do differently: Nothing. I'd do nothing differently. I'd not do this. I'd keep it as a joke. The joke was funny. The execution was not.

The Total Picture

Here's the full summary over six months:

DoorDash: $980 earned over 2 months, about 87 hours of work. Effective hourly rate: $11.27. After gas and wear: maybe $9.

Fiverr: $340 earned over 4 months, about 30 hours of work. Effective hourly rate: $11.33. After platform fees and taxes: maybe $8.

Dog sitting: $315 earned for 1 week, about 168 hours (I was "on duty" 24/7). Effective hourly rate: $1.87. Effective hourly rate if you only count active time: maybe $6.

Reselling: $89 profit over 4 months, about 40 hours of work. Effective hourly rate: $2.23. Plus I have a garage full of unsold weighted blankets.

Feet pictures: $0. 15 minutes of work. Effective hourly rate: $0.

Total earnings across all five hustles: about $1,724 over six months. That's roughly $287 a month. Not nothing, but not exactly "quit your day job" money.

Total time invested: roughly 340 hours. That's about 14 hours a week, every week, for six months.

Effective hourly rate across all hustles: about $5.07. Five dollars and seven cents an hour.

For context, Virginia's minimum wage is $12 an hour. I could have worked at a gas station making almost twice what I made doing "side hustles." And I wouldn't have had to deal with aggressive chihuahuas, unsold weighted blankets, or the shame of nobody wanting my feet pictures.

What I'd Actually Recommend

If I had to pick one hustle to recommend, it would be freelancing — but only if you can write well and you're patient enough to grind through the first month or two. The hourly rate is decent, the work is flexible, and you can do it from your couch at 10 PM. But don't expect to make real money in the first month. The first month is about building reviews and reputation, and it's slow.

DoorDash is fine for quick cash, but the hourly rate is lower than it looks once you subtract gas, wear, and taxes. It's also unreliable — some nights you'll make $40, other nights you'll make $10. If you need consistent income, it's not the best choice.

Dog sitting can be great if you get the right dogs. Ricardo was not the right dog. But I know people who make $500 to $1,000 a month on Rover watching well-behaved dogs. The key is screening. Ask about the dog's temperament before you commit. If they say "a little aggressive," run.

Reselling works if you know what you're doing. I didn't. I was guessing, and my guesses were wrong. The people who make real money on eBay are experts in specific niches — they know what sells, what doesn't, and what to avoid. I avoided nothing and bought weighted blankets.

And feet pictures? Don't. Unless your feet are genuinely photogenic. Mine are not. Yours probably aren't either. Let's all agree to stop pretending this is a viable side hustle.

The Biggest Lesson

Side hustles aren't passive. They aren't easy. And most of them don't pay what the internet promises. The "make $3,000 a month from your laptop" posts are almost always from people who make money by selling courses about making money. It's a circular economy of optimism.

The real money in side hustles comes from either a specific, marketable skill (like writing, design, or tutoring) or from sheer volume (doing a lot of low-paying work over a lot of hours). There's no magic trick. There's no secret system. There's just work, and the question is whether that work is worth your time.

For me, the answer was mostly no. Five dollars an hour isn't worth 340 hours of my life. I could have spent that time with Sarah, reading, sleeping, learning a skill that would actually increase my earning potential at my day job, or just enjoying the fact that I have free time and I'm choosing to spend it doing something I like instead of delivering Chipotle to strangers.

The money was real. The time was real. And the chihuahua bite scar on my right hand is also very real, which is something I never expected to write.