The 20 Most Fun Self-Employed Jobs

fun self employed jobs

What are the best jobs in the world? We’re not just talking here about the best paying or the most rewarding. We’re talking about the most fun as well. Fortunately, in a world where almost any information imaginable can be easily crowdsourced, there’s at least a popular consensus.

Ranker, a site that proudly proclaims itself as the place on the Web to “vote on the best (and worst) of everything” has come up with an answer. What surprised us (though maybe it shouldn’t have) was how many of these jobs could be filled by a self-employed person or solopreneurs too.

So, with that in mind, we’ve gathered some information from Small Business Trends and across the Web to get a better idea about what’s involved in starting and running one of these businesses. Think of it as a startup primer for some of the most popular and fun self-employment opportunities around.

Editor’s note: watch a video featuring the top 10 jobs that are fun.

Video Game Player

Plenty of people play video games for fun, but you can actually do it for profit too. In fact, website e-Sports Earnings has actually created a list ranking the top 100 players based on earnings. Professional gamers earn money by winning contests and streaming their games, allowing them to earn sponsorships, reports Business Insider. There are actually over 60 gamers who earn more than $100,000 in a year.

Voice-Over Artist

This isn’t necessarily a career that many people link with self-employment. But as with many jobs in the entertainment industry, being a voice-over artist involves building a personal brand and finding your own work.

Companies, including big names like Apple, contract out voice work to entrepreneurs like Susan Bennett, the voice behind the iPhone’s Siri.


fun self employed jobs

People love chocolate. So why not make a business out of it? But be ware, writes food expert Stephanie Zonis, a columnist for food enthusiast site Sally’s Place. Behind all the glamor is some pretty stiff competition and a lot of hard work. First, with its rising popularity, the market has become very crowded.

The work also requires, (beyond just a love of chocolate) considerable knowledge, skill and the ability to handle long hours and a very repetitive production cycle for the product.  You don’t necessarily need culinary training, but it can come in handy. In any case, Zonis recommends working or even volunteering for a chocolate maker to get some practical  production experience. And since you’ll be handling the business too, you’ll also need to think about marketing, packaging etc.

Toy Maker

Toy makers can use a variety of different techniques to create their products. Small manufacturers can use wood, fabric, or even plastic molds.

But probably the technology that has most transformed the toy making industry and put it within the grasp of solopreneurs is 3D printing. It allows creation of toys and many other products that can either be used as prototypes of be sold online or in small retail locations.

Personal Shopper

As great as getting paid to go shopping may sound at first blush, there’s much more to providing the right kind of service and creating a sustainable business than might at first be apparent. A personal shopping service may be operated in conjunction with other services, say, an image consulting business perhaps.

Here shadows one such business to see how a solopreneur combines the talent of finding that perfect item with a potentially more important business that helps people feel better about themselves and how they look.


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Craft beers are growing in popularity. And with that growth comes more and more opportunities for home brewers and microbreweries to succeed. In fact, the industry has even produced a kind of microbrewery crowdfunding all its own. Think Kickstarter for microbreweries and you’ll get the idea.

Microbrewers can start as home brewers and eventually expand into sustainable small businesses with additional employees.


Becoming a professional winemaker requires a love and understanding of wine but also a lot of business sense. It can, however, be done as a solo or very small venture, if you have the proper space and resources, reports WineMaker in a list of tips about what it takes to go pro.

Graphic Designer

Preston D. Lee runs a site completely dedicated to freelance design. So obviously it is the go-to destination for information on starting a business like this of your own.

Here blogger John Brook shares some tips you must consider when starting your own graphic design business. An important early step is to assess your personal talents to determine the services you can best and most efficiently provide.

Concert Promoter

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Working in the music biz can be an exciting venture. But how do you get into the music industry if you have no musical talent. Not to worry, concert promotion is still an option, though you’ll certainly need some marketing and basic business chops here. Concert promoters work with musicians, venues, and labels to gain buzz for shows and events. It can be a lucrative career, as reports in a story about a concert promoter who has been at it 50+ years.

Interior Designer

Being an interior designer involves planning and designing spaces for individual and commercial clients. For a self-employed person, this means building up a client list and portfolio. But it doesn’t necessarily require a physical location or large staff. In fact, services like are making it even easier to connect designers and clients. So even the marketing aspect of the business is being simplified making it easier than ever to go it alone instead of working for a larger firm.

Event Planner

Solo event planners can be responsible for organizing events of all kinds from meetings to corporate events. Entrepreneurs can create a niche in the market by specializing in specific events, including concerts, corporate retreats, or art exhibits.

Landscape Architect

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Landscape architects plan and design outdoor spaces including parks, yards, and other open areas. Becoming a landscape architect normally requires some education and a license. But entrepreneurs can create their own brand and client list.

Fashion Designer

Fashion designers can build their own brands and sell their creations online or in small retail locations. There are plenty of different niches in the industry, so designers can find a way to stand out. Plenty of fashion design entrepreneurs have reached huge success.

Stand-up Comedian

Becoming a successful stand up comedian might seem fun, but it requires a lot of work. Most comedians work other jobs while honing their craft and trying to find gigs. But once you’ve built a personal brand, you can set your own schedule and choose where you’d like to perform.

Wardrobe Stylist

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There are quite a few jobs that fall under the description of stylist, as it turns out. But a wardrobe stylist, in particular, writes Alexandra Suzanne Greenawalt, who herself works in the field, is generally the supplier and curator of clothing and accessories for a movie or commercial. The career is closely related to that of fashion stylist, the person who supplies or curates clothing and accessories for a fashion shoot.

Greenawalt goes on to list some of the other niches in the field in a post on her site: They include  hair stylists, personal stylists and image consultants.


Another small business option many may not think of at first is operating as a professional magician. Magician and balloon artist John Reid operates his own magic shop called Tricky Business. But this was also the sixth year Reid was invited to perform at a special Independence Day event at the White House. How did he get the gig? The same way so many other small businesses do. It came in the form of a referral, Newsday reports.

Romance Novelist

Electronic publishing has opened a lot of doors for would-be professional novelists. Those interested in romance novels can aspire to write their own and go through channels like Amazon if traditional publishing isn’t an option.

Dog Walker

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Pet sitters and dog walkers help pet owners in their area care for their furry friends. This is a business that doesn’t require a lot of overhead cost. You can build a client list with local advertising or even websites like

Personal Trainer

Personal trainers can work for health clubs and other institutions. But they can also operate on their own as small business people. Tech tools like Fitmob, available only in San Francisco at the moment though the service plans to  expand, connects trainers with clients looking for a workout, as TechCrunch reports. There are certification programs available and after that you can work on building a client list and personal brand.

Public Relations Specialist

Public relations is an industry that can lend itself to so many different niches and specialties. If you have an educational background in PR or a similar field, you can start by working with one or two clients to build up a portfolio.

We hope you’ve found this overview helpful. For more on the topic of self employment, see these other Small Business Trends articles:

7 Questions to Ask Before You Go Solo

10 Steps to Become a Self-Employed Consultant

Jobs that Increase Your Odds of Being in Business for Yourself

Fast Answers About 1099 Forms for Independent Workers

Make the Transition from Employee to Self-Employed Entrepreneur

Wine Maker Photo via Shutterstock, Chocolate Photo via Shutterstock, Beer Photo via Shutterstock, Concert Photo via Shutterstock, Garden Photo via Shutterstock, Fashion Photo via Shutterstock, Dog Walker Photo via Shutterstock

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Annie Pilon Annie Pilon is a Senior Staff Writer for Small Business Trends and has been a member of the team for 12 years. Annie covers feature stories, community news and in-depth, expert-based guides. She has a bachelor’s degree from Columbia College Chicago in Journalism and Marketing Communications.