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Rose-colored glasses have never been your style. But you consider yourself more of a realist than a pessimist. Sure, you can picture all of the potential problems that could arise in any given situation. That’s precisely what makes your skill set so valuable. Side hustles for pessimists are the type of money-making opportunities that can go well — or poorly — depending on how well you’re prepared. And your ability to see the shoals in otherwise smooth water makes you more prepared than most.

Side hustles for pessimists

Side hustles for pessimists often involve high-stakes situations where the ability to complete the job effectively rests on understanding the risk ahead of time. That gives pessimists the ability to create one or more contingency plans to ensure success. The reward for your pessimistic planning is almost always high pay. After all, not everyone can emerge from the dark side victorious.

Here are five industries where pessimists can thrive and the online platforms that connect you to money-making opportunities in those industries. 


Accountants do far more than simply add and subtract numbers. To compile financial statements for public companies, they must consider a wide array of business risks that could jeopardize the company’s future. These factors range from competitive threats to supply chain issues; legal challenges to fads. Underestimating those risks can get your accounting firm sued. So good accountants know how to ferret out the negative and assess the severity of the risk. The bright side? Seasoned accountants earn six-figure salaries.

The best places to find flexible work in accounting include Robert HalfBookminders and Acuity Financial.


Believing that people are out to get you doesn’t make you paranoid. It makes you vigilant about looking for unlocked windows and doors. If you’ve got the skills to find vulnerabilities in computer code, you can make a fortune in cybersecurity. Pay often exceeds $100,000 annually even for lower- and mid-level experts. And demand is so great that top tech companies subsidize online training programs, so you can learn the job inexpensively during your free time.

A variety of online platforms can help you find full, part-time and temporary positions in this field. These platforms include Toptal, Braintrust, Catalant, FreeUp, and Upwork.

(Click here to sign up with FreeUp)

Delivery and ride share

You don’t have to be a pessimist to drive for a ride share or delivery company. But you’re likely to make more money if you are. Why? You aren’t going to jump on random job notifications hoping that an undisclosed tip might make it worth your while. You’re going to look at the job’s promised payout, “surge” payments, bonuses, and the chance of a return fare. As a pessimist, you expect traffic. And you understand how gas prices, maintenance, and repairs impact your bottom line.

Thus, you’ve calculated your car’s mileage in both city and highway driving, and have worked that out to a cost-per-mile. You’re also playing “app poker,” which means you have a fistful of driving and delivery apps open anytime you’re on the road. That allows you to jump on the most profitable and proximate jobs, flipping from ride share to delivery as the best opportunities arise. Moreover, you schedule your work hours around traditionally high-demand periods when surges proliferate and down-time is rare.

Even with today’s record gas prices, you can earn net pay of $30 to $40 per hour doing all of these things. But succumb to wishful thinking and you’d be lucky to take home minimum wage. The best ride share and delivery apps are Uber, Uber Eats, Lyft, DoorDash, and GrubHub. You may also want to check out apps that arrange rides for kids before and after school, such as Zum, Kango and HopSkipDrive.

(Click here to sign up with DoorDash)

Project management

Project managers are needed whenever jobs are complicated enough to require more than one person, department or company to complete them. These jobs involve everything from engineering to logistics; film production to manufacturing.

Project managers understand the process from launch to finish; develop a reasonable schedule for delivery; and communicate with every contractor, supplier, and team member to keep the job on track. Because project managers work in widely diverse industries, the best place to find these jobs depends on the industry in which you work.

For those in creative fields, WorkingNotWorking and Creatively are good choices. Engineers can find project management work through SMA Inc.; financial and technical project managers may want to tap job opportunities through Robert Half.

Property rentals

Renters can present a litany of risks. They could get injured; break or steal your stuff; ruin things; commit a crime on the premises — or just fail to pay rent or vacate. However, all the risks are best addressed with a combination of renter background checks, deposits, and insurance. A smart pessimist will assess the risks and mitigate them with a combination of these tools before handing over the keys. 

The best places to find renters depend on what you’re renting. You can rent your house to short-term tourists through Airbnb, SabbaticalHomes and VRBO. You can rent a room to a long-term renter through a site like Nesterly. Or you can rent your house by the hour through Giggster or Peerspace. You can also rent storage space through Neighbor; swimming pools through Swimply, and cars through Turo.