Are you an optimist? These are the best side gigs for you

An actor holding an Academy Award.
The odds are against striking it rich as an actor. But with an increasing number of streaming services clamoring for fresh content, the chances of making a decent living are not as remote as they once were.
(Marcus Yam / Los Angeles Times)

A pessimist might assume that side hustles for optimists are those too-good-to-be-true opportunities that turn out to be scams. But optimists know that there are some side hustles that simply suit their generally positive outlook on life.

It’s worth mentioning that optimists tend to be more successful than pessimists. That’s partly because they believe that setbacks are opportunities to learn to be more successful. And that can become a self-fulfilling prophesy.

When a pessimist might give up, optimists revise, regroup and try again. That can be a tremendous advantage with the artistic and people-oriented side hustles ideal for optimists.


Although almost any work pursuit can benefit from an optimistic outlook, we’ve culled these opportunities down to the relative few where optimism is a near requirement. These include jobs where you’ll need to overcome a lot of rejection before landing your first “big break” or sale, and those where pessimists simply wouldn’t see the opportunity or succeed in the long run.


The odds are against striking it rich as an actor. But with an increasing number of streaming services clamoring for fresh content, the chances of making a decent living are not as remote as they once were. Although actors can earn considerably less than minimum wage, average actor/performer salaries in the U.S. now exceed $59,000, according to

Better yet, the Bureau of Labor Statistics says that acting jobs are expected to grow at a much faster-than-average pace of 32% between 2020 and 2030. (The average growth rate for all professions is 8% over that period, according to BLS data.)

Good places to find acting side hustles include Backstage, Playbill, ActorsAccess and ExtrasManagement. Those willing to play character actors at private parties should also check out BeeBizy, a Los Angeles-based kids’ party site, where character actors can earn $200 for a few hours of work.

Business development and sales

If you listen to sales gurus — no matter whether they’re academics, authors or motivational speakers — they’re likely to point to one key factor in creating a successful salesperson: optimism.

This well-accepted notion got its start with landmark studies conducted by the University of Pennsylvania’s Martin Seligman.


Working with insurance giant MetLife, Seligman measured both aptitude and attitude to study retention and success of the firm’s salespeople. He found that optimism was the primary determinant of how successful you’ll be in sales. It was even more important than aptitude.

Optimistic salespeople earned between 20% and 57% more than their more pessimistic counterparts — no matter how well qualified the individual candidates. Subsequent research focused on real estate agents found even more dramatic results, with optimists outperforming pessimists by as much as 300%.

Sales experts have a lot of theories as to why. However, Seligman’s theory was that when optimists fail, they attribute the failure to something they can change. That makes them more resilient, innovative and persistent.

Sounds like you? Good places to find business development and sales jobs include Field Day, Robert Half, FlexProfessionals, FlexJobs and SkiptheDrive.


A pessimist may see a worn chair, broken table or grubby highchair as junk. But an optimist like you may see these as vintage items that can be refurbished and resold at a profit. And if you’ve got the ability to use a screwdriver and paintbrush, you may well be right.

It’s possible to make a six-figure living picking up free goods on CraigsList, Nextdoor and Facebook Marketplace and reselling them at a profit on EBay. Just ask Melissa and Rob Stevenson, who run FleaMarketFlipper. The couple not only make a full-time living this way, they now teach classes on how to do it. Rob says he and Melissa regularly get items for cheap or free and resell them for 10 times their original investment.

To be sure, the belief that you can take someone else’s junk and make it attractive and useful for others takes some optimism. But when getting items for free, the worst-case scenario is that you just throw the product out later, Rob says. However, if you need to pay for items you want to resell, Rob suggests you do a detailed Google search to make sure you don’t overpay.

Teaching and tutoring

What makes optimists ideal teachers and tutors is their propensity to experiment with innovative methods when old styles don’t work. This is pivotally important now, as millions of kids find themselves depressed and behind grade level often as the result of problems with online learning during the pandemic.

Teaching and tutoring sites continue to be swamped with students, which means jobs are plentiful. Some sites worth checking out:

Outschool, which encourages teachers to come up with innovative ways to teach serious subjects.

TutorOcean, which lets instructors set their own rates and specialties.

LessonFace, a great option for music teachers.

AmazingTalker, which specializes in language tutoring.

Virtual assisting

Who wouldn’t want a can-do assistant ready to manage your email, schedule your travel, post for you on social media and handle other tasks that you’re too busy to address?

Optimists have two advantages in this field. First, they’re more likely to get work, since virtual assisting is highly personality driven. Second, they’re likely to earn more because there are no standard rates in this field, so dynamic individuals can demand more.

If you find work through platforms such as Fiverr and TaskRabbit, you’ll set your own rates by the type of virtual assisting task you take. You might, for instance, charge just $25 per hour for email management but $35 an hour for travel scheduling. If you’re good at social media or WordPress, you can charge $75 to $100 an hour — or per job — for handling these more sensitive tasks.

In addition to Fiverr and TaskRabbit, you can find virtual assisting work with FreeUp, Boldly and Belay. However, these platforms generally have set rates of pay that vary by the freelancer’s experience and the site.

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