Always prepared for the worst? These side gigs are for you

Austin Moody poses for a photo as he sits a his home work station in Tampa, Florida.
Believing that people are out to get you doesn’t make you paranoid — it makes you well suited to a job in cybersecurity.
(Steve Nesius / Associated Press)

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.


These side hustles 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 such planning is almost always high pay — after all, not everyone can emerge from the dark side victorious.

Here are five industries where pessimists, skeptics and worrywarts can thrive and the online platforms that can connect them to money-making opportunities.


Accountants do far more than simply add and subtract numbers. To compile financial statements for public companies, they must consider a wide array of risks that could jeopardize the business in the future. These factors can include competitive threats, supply chain issues and legal challenges. Underestimating the 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 Half, Bookminders 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. Annual pay often exceeds $100,000 even for low- 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-time, part-time and temporary positions in this field; among them are Toptal, Braintrust, Catalant, FreeUp and Upwork.

Delivery and rides

You don’t have to be a pessimist to drive for a ride provider 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 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 affect 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, allowing you to jump on the most profitable and proximate jobs, flipping from providing rides to delivering as the best opportunities arise. Moreover, you schedule your work hours around traditionally high-demand periods, when surges proliferate and downtime is rare.


Having an upbeat outlook is a tremendous advantage for those pursuing artistic and people-oriented side jobs.

July 17, 2022

Even with 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’ll be lucky to take home minimum wage.

The best ride 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.

Project management

Project managers are needed whenever jobs are complicated enough to require more than one person, department or company to complete them.

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. The best place to find this work depends on the industry.

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 opportunities through Robert Half.

Property rentals

Renters present a litany of risks: They could get injured, break or steal your stuff, commit a crime on the premises — or just fail to pay rent or vacate. All the risks are best addressed with a combination of 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 to a renter.

The best place to find renters depends on what you’re offering. You can rent your house to short-term tourists through Airbnb, SabbaticalHomes and VRBO. You can rent out a room for a longer term through Nesterly. Or you can rent your house by the hour through Giggster or Peerspace. You can also rent out storage space through Neighbor, swimming pools through Swimply and cars through Turo.

Kristof is the editor of, an independent website that reviews moneymaking opportunities in the gig economy.