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.

35 Reactions
  1. Magician? MAGICIAN?? What about juggler? Ventriloquist? Well, I should be too offended I’m a voice over artist as well. But if anyone reading this is looking for entertainment… please.. check out my website 😉 Willing to travel…

  2. I guess these jobs are fun because they are mostly fueled by passion. It’s funny how you put video gaming on top. While it is an industry that’s worth looking into, it is not really that open to the public. You have to be an expert in a game in order to be considered as a professional gamer.

    • You definitely have to be an expert in several of these fields in order to make it work, but people who are really passionate about them can usually find a way.

  3. Great list, Annie!

    I’ll admit to having one the fun self-employed jobs listed.

    I was a Voice-Over Artist.

    It was a blast!

    I would do it now, if asked.

    The Franchise King®

    • That sounds like fun! I don’t think I’d have the voice for it, but it seems like it would be a fun thing to try out.

    • Martin Lindeskog

      Joel: Would you mind doing a voice-over thingy / announcement clip for my new podcast show at some point in time?

    • Just to say – website is the place to get gigs for voice-over artists . Good luck!

  4. I wouldn’t want to be a chocolatier, but I’d love to be a professional chocolate taster! I also wouldn’t mind being a personal shopper (but for a particular niche) or a voice-over artist (I’ve done two gigs in the past).

    • I would also love to be a professional chocolate taster – where do I sign up?

      • Hehe! There probably are professional chocolate tasters out there somewhere! I just don’t know where 🙂

        …but if I ever do find where to sign up, I will be squealing excitedly back here to let you know 🙂

  5. The brewmaster I know, while passionate about the quality of what he is producing, works 12 hour days and is in the red financially while trying to support a young family. The dogwalkers I know work harder than just about anyone — and the skill set involved goes way beyond an understanding of animals – remember that you are outdoors in all weather and you are dealing with anxious pet parents, elderly pets, potentially dangerious situations with aggressive dogs, insurance policies, etc. In fact, I just watched my partner struggle for nearly two hours to get up and go to work because his body is so exhausted from 7 years of walking dogs. The graphic designer I know meets up with our self-employed group once a month at the end of the month to make sure she carves out time for her invoicing, because, strange as it might sound, it can be very difficult to find the time for necessary administrative tasks when you are are working on client projects, especially if the clients are demanding and keep changing their preferences. While all of the jobs here have elements of fun, remember that, like anything, it is the hard word that makes people successful at them. A surface level “Look at how fun these jobs sound!” article does not paint the true picture of self-employment. Sacrifice and extreme hard work are involved in all of these options.

    • Spot-on with this comment. Professional pet sitting is a career fueled by a passion for pets. But it also takes hard work, business skills and customer service know-how – in addition to pet-care knowledge about the vast array of companion animals pet owners have. Top that off with working on all of the weekends and holidays that the rest of the world is celebrating. Rewarding, enjoyable, fun? Sure, but it also takes a special kind of dedication and love of animals – and their owners – to be a professional pet sitter.

  6. Martin Lindeskog

    Annie: Have you seen the movie, Chocolat? The main character is opening a chocolatier during lent…

  7. Martin Lindeskog

    How about tea taster / blender / trader? Please stay tuned for my book on tea, tea blends and direct trade from tea plantations in India.

  8. Sometimes it becomes important to listen to your heart, basis on which a work or employment to be chosen. Yes money making is one of the most important criteria, but earning the same while living with passion can really be a fruitful idea.

  9. Beware of secret shoppers, find a reputable company. This act of goods for cash is a front for some money laundering exercises.

  10. I think Skin Care maker is the most fun (and farmer)!

  11. Hi Annie, I couldn’t read anything after Chocolatier! I hear all the hard work aspect. But chocolate tasting for a living? Where do I sign up?

  12. I am 14 and I don’t know what I want to be?? iv been thinking but I don’t know.

  13. I made a very nice living selling ladies clothing. I would call on small offices staffed primarily by women. I came around once a month and when summoned. I traveled to NYC, LA and Vegas four to six times annually to buy. I have a jewelry business now, but it has become more physically taxing than I prefer. I am retired, but looking for something that requires no lifting to keep me occupied. This s an interesting list.

  14. Hallo Annie.

    I know. I am late to reply for your article here. Haha.
    But I feel tempted to do so anyway.

    Thanks for providing us with this list.
    This is really an interesting list, and I for sure know you could have mentioned a lot more.
    But you had to decide which you select to write about as well, right? 🙂
    I think you did a pretty good job.
    How long did it take you to create it?
    Because often you don’t see the work that went into an article after all:

    Which is reasearching, creating the idea. Searching and researching for the graphics.
    And one task for sure – last but not least – is to put it all into in easy readable
    and understandable form. So it sounds simple.
    But this is not always easy to do.

    And how did you learn all this?

    Thanks. 🙂

    ~ Holger

  15. Well written with illustrative images. So mostly art is like self business.
    SO procuring clients can be difficult at times. Don’t forget to get listed on b2b portals like

  16. Excellent, what a webpage it is! This weblog provides valuable facts to us, keep it up.

  17. Hi Annie, all i would like to know how to start these careers as i do not see a link. Thanks

  18. Hey,
    This is a nice one .. Are these the only self employed jobs in USA.

  19. Hey,
    This is a nice one .. Are these the only self employed jobs in USA.