Ready To Leave Your Corporate Job And Start Freelancing? Here’s What You Need To Know

By on February 16, 2016

By Kathy Caprino−

Part of the series “Living and Working Better”

Intuit projects that more than 40% of the workforce will be made up of freelance workers by 2020. Other research shares that by the end of this decade over half of the private workforce will be independent. If these projections holds true, millions of Americans will transition into a freelance career over the next four years

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To learn more about how corporate professionals can transition seamlessly and effectively to the freelance life, I caught up with Constantine Anastasakis, Senior Director of Business Development and Strategy for Fiverr, an online marketplace that matches freelancers with buyers ranging from SMBs to major corporations. Fiverr reports having facilitated more than 25 million transactions since 2010 across more than 100 categories of services.

Constantine shares his tips for freelancer success:

Kathy Caprino: Constantine, what do you think are the key criteria and questions one should consider when thinking about the transition from full-time to freelance?

Constantine Anastasakis: Any successful freelancer will tell you that the transition from a full-time career to independent work is challenging, especially if you want it to be lucrative. Compared to a corporate career, the world of freelancing can be unpredictable and intimidating. While issues like finding work and creating income stability are often seen as the top barriers to doing more freelance work, it’s important to remember that it’s been done successfully by thousands upon thousands of others. Preparing for the transition before diving right in can help make it less choppy.

Before you start freelancing full time, consider doing it as a side gig first. Redd Horrocks, one voiceover actress on Fiverr who earns six figures annually, started working independently on Fiverr while she held a full-time job as a stage manager for an event production company. At first, she used her side gig to help her pay off thousands in credit card debt. Once she paid off her debt, she started banking her income from her full-time job and using her freelancing income for living expenses. Redd’s success didn’t happen overnight, and she didn’t start freelancing thinking she’d make six figures right away. She set small attainable goals, like paying off one credit card, then moving onto the next. Eventually, she saved enough to make a down payment on her house and still had a deep savings bench that eased the transition to freelancing full time.

It takes hard work, persistence and patience to successfully transition into a freelance career. While it won’t happen right away, you have to start somewhere. Freelancing on the side (while working a corporate job) first is a good way to mitigate some of the risk, save money and decide that you really love it before taking the plunge.

Caprino: What do you think differentiates very successful freelancers from those who struggle?

Anastasakis: Most freelancers have the passion and drive to be successful, but many don’t know where to start when it comes to finding clients. Look at starting a freelance career like starting a business from the ground up. You have to build a strong customer base, then fortify and expand that base. Whether you’re working in a more traditional environment or through a marketplace, the reality is the same: your clients are everything.

Successful freelancers service their clients with any eye towards organic business growth. They develop individual relationships with new customers to convert them into long-term customers. Eventually these relationships will pay dividends down the road without outbound marketing efforts. A strong network will always reap multiplier benefits.

One freelancer who can speak to this is Ryan Heenan. He sells custom jingles and animated videos online and has more than 4,000 positive reviews from his buyers. His secret? He builds personal relationships with his customers by asking a lot of questions up front, specializing his offerings and following up to make sure his customers get what they need. As a result, about 40% of his customers are repeat buyers.

Caprino: What do freelancers need to know that they weren’t aware of as corporate employees?

Anastasakis: One of the worst mistakes new freelancers can make is selling themselves short . You see it time and time again: a new freelancer offers to do too much work for too little money  in an effort to over-service their clients. While you should always provide top-notch service to your clients, you have to know the market. If you’re going to start selling copywriting services, research what other freelancers are charging for copywriting. You want to be competitive and you absolutely want to keep in mind your experience and breadth of portfolio, but charge your clients what your skills are worth.

You should also differentiate your offerings to help them stand out. You can do this through a variety of tactics including offering a wide portfolio of work to create a simple buying experience, or utilizing marketing tools like videos to draw attention to your services and offer greater visibility. Another essential step is to carve out a niche for your offerings. You can be a video photographer and specialize in only one type of video photography or style. It may seem counterintuitive and limiting, but it actually enables you to charge more for your services thanks to the unique set of offerings.

Once you determine what services you’ll offer and how much you’ll charge, learn how to market those skills. Corporate employees certainly know what they’re good at, but many don’t know how to promote themselves. Don’t underestimate resources like Coursera and Udemy, where you can learn valuable marketing skills. You can also turn to other freelancers to find marketing materials on a budget. As you expand your network, you’ll find new customers and gain new insights into the services you can offer and how your value-added services differentiate you.

Caprino: How can people research and determine accurately if they’ll end up enjoying freelance work and make it a success?

Anastasakis: Freelancing is quite different from most full-time careers and the transition starts with a frank inward discussion. Think about your personality and your interests. Freelancing requires you to work alone (a lot), be solely responsible for the work you produce and to always put your clients’ needs first.

Are you a self-motivated person? Can you devote time each day to developing your freelance career? If you’re the type of person who needs a set schedule to be productive, you’ll probably have to set that schedule yourself. To be a successful freelancer you need self-discipline and accountability.

Also consider what makes you passionate. As with any job, you’ll be happiest doing something you love day in and day out. The great thing about freelancing though is that you’re not stuck doing one thing forever. As I mentioned earlier, once you build up a clientele, you can start to offer additional services that will add variety to your daily tasks and more depth to your portfolio.

Caprino: To offer some inspiration, what are the latest data/stats on freelancers, and the potential success they can achieve?

Anastasakis: : According to Inuit, 60 million Americans will be freelancing by 2020, making up more than 40% of the workforce . In fact, the number of Americans who voluntarily quit their jobs climbed to the highest number since April 2008 in November, as 2.8 million Americans left an employer. As the freelance workforce continues to rise, millions of Americans will branch out on their own and more and more resources will be available for people who want to start freelancing. As with any job, there’s never a guarantee that you’ll be a success, but if you’ve ever considered starting your own thing, now is a great time to start taking steps.

Caprino: Anything else we need to know?

Anastasakis: A great deal of freelancers limit themselves to local work and immediate needs in their communities, which while effective, is a fairly traditional approach to freelancing. There is a much larger market for freelancers if they look beyond their own backyards. The beauty of freelancing is that you not only can work from anywhere, but you can also work with clients from anywhere. Using a global platform can make a big difference in the initial lift it takes to build a customer base. For many new freelancers, a strong local or professional network may not exist and the overhead of time and energy required to build one is intimidating. Leveraging a massive global marketplace allows a new freelancer in Boise, Idaho to do business with a small business owner in Paris. That same mechanism will also help new freelancers build out their portfolios. While experience can’t be bought or sold, it can be accelerated.

The transition into a freelance career isn’t easy, but we’re at a unique juncture in the way people work that’s making freelancing even more appealing. In part thanks to technological and societal shifts, freelancing today allows you to work from anywhere, be your own boss and explore a career you may have never thought possible. By preparing for the transition before making it, you can jump in with the confidence that you made the right choice.


As one who left corporate America after 9/11 and launched a coaching and consulting firm, I know that Constantine’s tips are solid and helpful, for sure. I’d also add this: When you’re considering making a leap to another career or going freelance, you need to “try on” this new direction – physically, behaviorally, financially, and emotionally – before you jump, to make sure it’s something you’ll thrive at and enjoy. So often, professionals fantasize about chucking their unhappy and stressed corporate life, only to find that the new direction is not what they dreamed it would be, and their professional strife follows them in this new chapter. Here’s more about the 5 biggest mistakes career changes make and how not to leap before you’ve tested out if this new direction is right for you.

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Kathy Caprino has appeared in over 100 leading newspapers and publications both nationally and worldwide, including the Wall Street Journal, L.A. Times, Chicago Tribune, The Washington Times, SELF, Glamour, MORE, and on national radio and television. For more information, visit and connect with Kathy on Twitter, Facebook and LinkedIn.

About Kathy Caprino

Kathy Caprino, M.A. is a nationally-recognized women’s career coach and work-life expert, executive trainer, Forbes contributor, writer and speaker dedicated to the advancement of women in business. Author of Breakdown, Breakthrough, and Founder of The Amazing Career Project, Kathy is President of Ellia Communications, Inc. -- a leading career and executive coaching and training firm helping professional women build successful and fulfilling careers of significance, and reach their highest potential. For more information, visit or write to [email protected] Connect with Kathy on: Twitter, FB, LinkedIn.

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Ready To Leave Your Corporate Job And Start Freelancing? Here’s What You Need To Know