No, We Won’t All Be Freelancers In The Future Of Work

Upwork CEO Stephane Kasriel has seen (and helped) the freelance economy take off. But that doesn’t mean he thinks we’re all fated to become “solopreneurs.”

No, We Won’t All Be Freelancers In The Future Of Work
[Photo: Jeff Sheldon / Unsplash]

There’s no doubt freelancing will play a major role in our future working lives. Over 57 million Americans took on freelance work in some capacity–that’s 36% of the U.S. workforce, up from 53 million in 2014. With a rising tide of people flooding into the freelance economy, our fourth annual “Freelancing in America” study, released earlier this month by Upwork and the Freelancers Union, now predicts freelancers will make up a majority of the U.S. workforce within a decade.


But while many of today’s workers are swapping long commutes, outdated workplace hierarchies, and the nine-to-five grind for the freedom to be their own boss and set their own hours, the fact is that not everyone will.

Traditionally employed workers are on the decline, but that model isn’t about to vanish. After all, plenty of people who do want to freelance fail; not everybody has the skills or temperament to do it successfully. And that’s not to mention all the people who don’t want to freelance and aren’t likely to change their minds. Instead, as I’ve argued before, future work teams may more closely resemble movie crews, with a core unit of traditional employees hiring specialists for results-oriented, project-based work.

With that in mind, there are four key criteria that the successful freelancers of the future will need to possess in order to stay competitive and succeed.

1. A Specialized Skill Set

While some have argued that high-skilled “comprehensivists” now have the upper hand in the freelance economy, specialization is more likely to win the day. It’s a matter of supply and demand: The more specialized your skills, the rarer they’ll be, and the more people will pay for them. Contrast that with easy-to-learn skills with low barriers of entry to training. If you can pick it up on Coursera or Lynda, so can literally hundreds of thousands of others. Plus, many of those skills are already threatened by automation and artificial intelligence.

Related: Why High-Skilled Freelancers Are Leaving Corporate Life Behind


Researchers at the World Economic Forum suggest that the average shelf life of many existing skill sets is declining, with employers already having trouble filling open positions. In fact, more than 80% of HR professionals find it difficult to attract people with the right skills, according to the Society for Human Resource Management. As a result, in the so-called “war for talent,” professionals who can offer a differentiated skill set for a particular project–especially those with IT and tech-related skills for which demand is high and supply is short–will have a leg up in the freelance marketplace.

2. High Demand Skills, Today And Tomorrow (Hint: They May Be Different)

This of course goes hand in hand with specialization, but the crucial added variable is time; today’s in-demand skills won’t be tomorrow’s. So forget what you’ve heard about the supposed perils of “job hopping.” That may lose you points in a corporate recruiter’s playbook, but if you’re comfortable moving swiftly from one job to another, you may have an easier time staying up to date in the freelance economy–by picking up fresh skills and experience with each new project.

This isn’t automatically good news for millennials and gen-Zers, though, who aren’t actually changing jobs more rapidly than prior generations, but it does represent an opportunity for anybody who can grow accustomed to constantly updating their expertise. Indeed, today’s freelancers have already learned this lesson; our study found current freelancers already skilling up more quickly than their traditionally employed counterparts.

The freelancers of the future will need to make this kind of professional development a regular, continuous habit. Think of it this way: We still use word processing software and talk on our phones, but you’d never list “Microsoft Office” on your resume in 2017. Likewise, “social media expert” won’t exist in 10 years, so it’s crucial to constantly reinvent yourself, building off the skills you already have. A designer five years ago is still a designer today, but instead of designing just for the web, she’s now designing for mobile or even augmented reality.

3. A “Solopreneurial” Mind-Set

Becoming a freelancer is a lot like running a business, except that you are now the startup. Like any good business model, your goal is to build a long-term profitable company that’s steady, stable, and not particularly risky to run. So it’s important to think like “solopreneur,” rather than someone haphazardly picking up one gig, and then the next, and then the next.


Related: 3 Signs You’re Still Thinking Like An Employee After Becoming Your Own Boss

Successful freelancers understand how to use their talents to get things done. Ideally, they’re strategic and selective about the work they do. But while technology can help you market yourself to potential clients, things can get pretty frustrating if you aren’t passionate and can’t stomach the inevitable salesmanship and self-promotion it takes to pitch yourself and grow a client base. Drive and determination really are key, and not everyone has it in them. There are no shortcuts.

4. Emotional Intelligence In Spades

You knew this was coming, right? There’s a reason we keep hearing about the importance of so-called “soft skills” like emotional intelligence in conversations about the future of work. But that doesn’t just go for traditional employment, where you’re more likely to interact with colleagues in an office setting.

Sure, technical chops that are tangible and measurable, like installing software or preparing tax documents, are part of what goes into any successful freelancer’s specialized portfolio. But interpersonal abilities–like communication, getting along with others, active listening, and empathy–are just as important when you work for yourself. That’s because the way you communicate with the client you’re selling to determines the strength–and potential lucrativeness–of the working relationship over the long haul.

Related: These Are The 4 Emotional-Intelligence Skills You’ll Need In The Future Workforce


So if being in front of people, asking questions, and managing multiple workloads sounds too daunting for you, then freelancing may not be for you. And yes, this applies just as much to highly specialized, in-demand technical fields like coding. Indeed, many of the most opportunity-rich jobs of the future aren’t obvious candidates for the freelance economy–and the emotional-intelligence factor is a big reason why.

Programming requires you to sit in front of a computer for long periods of time, and there’s a world of difference between managing clients and writing code. Just because you’re good at and enjoy the one doesn’t mean you’ll be good at or enjoy the other. So having great people skills might make you more competitive than someone with comparable high-tech expertise but not much tact in dealing with people. After all, it’s the human stuff that robots (so far) can’t so easily master.

For anyone who’s ready to put out their freelance shingle and say goodbye to traditional employment, you’re about to confront surging opportunities–just as long as you can check these four boxes confidently. If you can’t, though, don’t worry. Freelancing may be a booming market, but it isn’t all of our fates.

About the author

Stephane Kasriel is the chief executive of Upwork, where he built and led a distributed team of more than 300 engineers located around the world as SVP of engineering before becoming CEO. Stephane holds an MBA from INSEAD, an MSc in computer science from Stanford, and a BS from École Polytechnique in France