I Tried to Start a Side Hustle Every Month for a Year: Now I Owe Everyone and Their Dog


I Tried to Start a Side Hustle Every Month for a Year— Here is My Eye-opening Experience 

I thought side hustles would save me.
I thought they were the answer to rent, groceries, and my unhealthy subscription to three streaming platforms.
I was wrong.

Here is the truth. You will hear stories about people who start an online store and pay off their student loans in six months. You will see TikToks of women who sell custom mugs and move to Bali. You will hear about freelance writers who “work from anywhere” and still have health insurance.

You will not see the unpaid invoices, the boxes of unsold product, or the credit card bills that chase them in their sleep.

I know, because I lived it for one year. I started a new side hustle every month. Twelve businesses. Zero profits. Too much debt.


Month 1: Dropshipping

The internet told me dropshipping was “low-risk.”
Buy nothing. Sell everything. Let someone else handle the shipping.
I signed up for Shopify. I linked to an AliExpress supplier. I bought Facebook ads.

The problem was no one wanted my “ergonomic avocado slicer.” The few who bought it got theirs three months late. They emailed me. They wanted refunds. I refunded them. The supplier kept my money.

Loss: $740


Month 2: Candle-making

I saw a video of a woman making $3,000 a month from soy candles. I bought wax, wicks, scents, and jars.
I burned my fingers.
I smoked up my apartment.
I sold four candles to friends at cost. The rest sat in my closet until the summer heat melted them into one giant vanilla-scented blob.

Loss: $280


Month 3: Etsy digital prints

No inventory. Instant downloads. Passive income.
I spent a weekend designing inspirational quotes in Canva.
My designs were bad. Fonts looked like ransom notes.
I sold two files. Etsy took its cut. My net gain was $1.20.

Loss: $39


Month 4: Reselling sneakers

Sneaker reselling is supposed to be easy. Buy rare shoes at retail. Sell them for more.
I joined a sneaker “cook group” for insider tips. Membership was $50 a month.
I bought two pairs of Nike Dunks for $300 total.
No one bought them. I still wear them to the grocery store.

Loss: $350


Month 5: Affiliate marketing blog

I wrote 20 articles about “best ergonomic office chairs.” I paid for hosting, a domain, and SEO tools.
Traffic was low. My first affiliate sale was a $90 chair that earned me $4.50.
Google changed its algorithm. My site disappeared from search results.

Loss: $412


Month 6: Food truck idea

I saw a used hot dog cart on Craigslist. $1,800.
I borrowed money from a cousin. I had no permit.
I got shut down on day two by the health department.
I sold the cart at a loss to a guy who sells lemonade.

Loss: $600 plus my cousin’s disappointment.


Month 7: YouTube channel

Niche: Budget travel tips.
I spent $700 on a used camera and microphone. I edited videos for hours.
I uploaded ten videos. I got 96 subscribers.
I made $0 because you need 1,000 subscribers to monetize.

Loss: $782


Month 8: Dog-walking service

This was supposed to be easy money.
I printed flyers. I handed them out. I got one client.
Her dog was aggressive. It bit my leg. She didn’t pay me.
I stopped answering dog-walking inquiries.

Loss: $48 plus a tetanus shot.


Month 9: Online course creator

I bought a course on “How to Sell Courses.” $499.
I created a course on “Time Management for Busy People.”
I learned that busy people don’t have time to watch courses.
I sold zero copies.

Loss: $499


Month 10: Farmers market stand

I made artisanal granola. I rented a booth for $150.
It rained the entire day. Foot traffic was dead.
I sold three bags.
I ate granola for breakfast, lunch, and dinner for two weeks.

Loss: $196


Month 11: Instagram thrift shop

I thrifted clothes. I styled outfits. I posted them online.
Instagram’s algorithm buried my posts.
I shipped one order. The buyer returned it.
I gave the clothes to Goodwill.

Loss: $215


Month 12: Mobile car wash

I borrowed my uncle’s pressure washer. I advertised on Facebook Marketplace.
One person booked me. Their driveway had no water hookup.
I refunded them. I returned the pressure washer.

Loss: $38


The math

Twelve months. Twelve side hustles.
Total expenses: $5,379
Total revenue: $34.70
Net loss: $5,344.30

Debt: Two maxed-out credit cards. One cousin who won’t talk to me. A dog bite scar.


The pressure to monetize everything

The US has a $1 trillion student loan problem. Wages have stalled while the cost of living rises. Social media feeds are full of “passive income hacks” and “quit your job” success stories.

It creates a loop:

  1. You feel broke.

  2. You see someone’s side hustle win.

  3. You think you can do it too.

  4. You invest money you do not have.

  5. You lose money.

  6. Repeat.

A 2023 LendingTree survey found 44% of Americans have a side hustle. The average monthly income is $473. But averages hide the truth. Many earn nothing. Many lose money.


The red flags I ignored

  • I started businesses in niches I did not understand.

  • I trusted strangers on YouTube who make money teaching people how to make money.

  • I underestimated costs like permits, advertising, and equipment.

  • I thought passion was enough.

  • I ignored market demand.


What I learned

  1. Do market research before spending. Search for competitors. Check demand on Google Trends. Read real reviews.

  2. Start small. Test an idea with the least money possible. If you sell a product, buy or make a few first.

  3. Track every expense. Use a spreadsheet. Do not “wing it.”

  4. Avoid debt for experiments. Use only money you can lose.

  5. Question “passive income” claims. Many are marketing funnels for expensive courses.

  6. Know your skills. Align side hustles with what you can already do well.


How to keep a side hustle from becoming a side disaster

  • Focus on one idea.

  • Give it three to six months before starting another.

  • Get feedback before launch.

  • Price for profit from day one.

  • Plan for taxes. Side hustle income is taxable.

The Take Away

You will see people making side hustles work. Some build real businesses. Many do not.
If you want to try, protect your wallet.
Do not start twelve in twelve months.
Do not believe the avocado slicer hype.

My year taught me this: sometimes the best side hustle is keeping your day job and your evenings free.

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