The gig economy promises easy money and flexible work, but not all side hustles actually deliver on that promise. We asked ChatGPT to identify which popular side gigs consistently lose people money.
“Some side gigs can end up costing you more money than they bring in, especially if you don’t carefully track your expenses or underestimate the time investment,” the artificial intelligence explained. Here are the biggest money-losing side gigs to avoid, plus why they drain your wallet instead of filling it.
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The Transportation Trap: Rideshare and Delivery Gigs
Rideshare Driving (Uber, Lyft)
Why it loses money: Car depreciation, gas, insurance and maintenance often consume most earnings. Many drivers don’t account for the true cost of putting 20,000-plus extra miles on their vehicle annually.
“After all expenses, some drivers earn less than minimum wage, especially in areas with low demand,” ChatGPT wrote. The AI pointed out that surge pricing is inconsistent, and unpaid downtime waiting for rides can devastate your actual hourly rate.
The hidden costs: Vehicle depreciation alone can cost $0.50-plus per mile. Add gas, increased insurance premiums and accelerated maintenance, and your $20-per-hour gross pay might become $8 net.
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Food Delivery Services (DoorDash, Uber Eats, Grubhub)
Why it loses money: Similar vehicle costs as rideshare, but with additional risks. Tips vary wildly, and base pay often doesn’t cover true operating expenses.
“If you drive during slow hours or in poor areas, earnings drop significantly,” the AI warned. Accidents or traffic tickets while delivering can wipe out weeks of earnings, and you’re responsible for all costs as an independent contractor.
Amazon Flex and Courier Work
Why it loses money: You cover gas, tolls, parking and vehicle wear while Amazon sets the delivery time frames. Routes often take longer than estimated, cutting your effective hourly rate.
“If you’re late or have delivery issues, you risk being deactivated,” ChatGPT explained, highlighting how platform-dependent gigs offer no job security despite requiring significant personal investment.
Creative Pursuits That Drain Bank Accounts
Crafting and Selling Handmade Goods (Etsy, Craft Fairs)
Why it loses money: Startup costs for materials, tools and marketing often exceed early profits. Most crafters undervalue their time when pricing items.
“Time spent crafting often isn’t accounted for in pricing,” the AI observed. When you factor in Etsy fees, shipping costs and the hours spent creating each item, many crafters earn less than $5 per hour.
The math problem: If you spend four hours making something that sells for $25, minus $8 in materials and fees, you’ve earned $4.25 per hour before taxes.
Freelance Photography and Stock Photos
Why it loses money: Equipment costs are substantial — professional cameras, lenses and editing software can cost thousands. Stock photo sites often pay pennies per download.
“Time investment in editing, scouting and shooting often isn’t billable,” ChatGPT wrote. Many photographers spend hours on unpaid tasks for every paid shoot.
The Biggest Money Pit: Trading as a ‘Side Hustle’
Day Trading and Crypto Trading
Why it loses money: “It’s gambling if you’re not experienced,” the AI stated bluntly. “Many people lose money chasing trends.”
Trading fees, taxes on short-term gains and emotional decision-making compound losses. Studies show 80% of day traders lose money over time.
“This is one of the fastest ways to lose money under the illusion of ‘hustling,'” ChatGPT warned. The AI emphasized that volatility can eliminate gains instantly, making this more speculation than legitimate side work.
Property and Platform-Dependent Gigs
Airbnb Arbitrage (Renting To Re-Rent)
Why it loses money: Vacancy periods mean no income while rent continues. Furnishing costs, cleaning fees and platform commissions reduce margins significantly.
“Local regulation changes” can instantly kill profitability, the AI wrote. Many cities have restricted short-term rentals, leaving arbitrage hosts with expensive leases they can’t profit from.
Streaming and Gaming Content Creation
Why it loses money: Equipment costs (gaming PC, microphone, camera, lighting) can exceed $3,000. Most streamers spend hundreds of hours before earning anything.
“Most streamers earn very little unless they build a large following,” ChatGPT explained. The time investment rarely pays off financially for casual streamers.
Red Flags: When Side Gigs Become Money Pits
ChatGPT identified key warning signs of money-losing side gigs:
- High startup or recurring costs that eat into earnings
- Unpaid or undervalued time that doesn’t appear in income calculations
- Dependence on platform algorithms or inconsistent tips for income
- Bearing all risk with no stability or benefits
The Smart Approach to Side Gigs
Before starting any side hustle, the AI recommended setting a budget and tracking all expenses meticulously. “If you’re doing a gig just to try it out, that’s fine — just set a budget, track your time and expenses and reassess often.”
- Calculate your true hourly wage by dividing net income (after all expenses and taxes) by total time invested, including unpaid tasks.
- Track everything for tax purposes, but don’t assume deductions will make unprofitable gigs worthwhile.
- Set limits on how much you’ll invest before seeing returns, and stick to them.
The bottom line: Not every opportunity to make money actually makes money. The most successful side hustlers choose gigs that truly add to their income rather than just keeping them busy while draining their resources.
Before jumping into the gig economy, do the math. Your time and money are valuable so you must make sure your side hustle treats them that way.
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This article originally appeared on GOBankingRates.com: We Asked ChatGPT Which Side Gigs Are Actually Losing You Money — Here’s What It Said
