Why High-Skilled Freelancers Are Leaving Corporate Life Behind

In some industries, there’s now one freelance “comprehensivist” where there used to be a team of specialists.

Published on Fast Company

On a sunny November day in San Francisco’s Mission District, inside the offices of Stamen Design (a studio known for cool-looking maps), I met what you might call a unicorn of the modern knowledge economy. Her name is Nicolette Hayes.

She and I sat down, and she walked me through her latest two client projects. The first was an interactive model of the Amazon rainforest designed for a popular geography magazine. The second was a visual design language for human emotion, where sadness was represented as a deep ultramarine blob with soft blurry edges. These disparate projects called upon a range of visual, interactive, spatial, and psychological concepts that many would struggle to understand, let alone weave together cogently.

“What once might’ve been a three- or four-person team is now simply Nicolette.”

Knowledge workers with polymathic competencies in multiple disciplines are still rare, but they’re becoming more and more common. Take Hayes–a Berkeley geography grad with a design masters from Pratt. She is a data-visualization designer who regularly handles user interface, user experience, visual design, interaction design, and design research on behalf of clients. What once might’ve been a three- or four-person team is now simply Nicolette.

Enter the comprehensivists

Buckminster Fuller might’ve called someone like Nicolette Hayes a “comprehensivist”–the opposite of a specialist. According to constructivist psychologist Spencer McWilliams, “Fuller was highly critical of disciplinary specialization, believing that it was originally instituted to support the interests of a power structure and keep intelligent individuals from knowing too much.”

The rise of comprehensivists in some sectors is coinciding with the broader gig economy trend: multi-skilled knowledge workers are increasingly able to ply their trade to a range of bidders on their own terms. Project-oriented fields like design and journalism have seen this coming for some time, in part because the deadlines they operate on make for easily definable gigs.

But more and more fields formerly thought of as “non-creative” are adopting creative processes, making their work more easily chunkable as well. As CEO of IDEO Tim Brown remarked in a recent IDEO U webcast, “The sign of an organization becoming more creative is the move from processes to projects–projects are inherently creative acts.”

Even industries like law and finance are beginning to fray around the edges, with top talent decamping for gigs. But whether a job is gig-able is now less about field and more about role. After all, someone still has to hire the freelancers. Leadership roles share DNA with their organizations and benefit from the sort of sustained, longitudinal engagement that’s harder to imagine a freelance model being able to accommodate.

Still, as more knowledge work goes project-based and the normalcy of 1099 labor grows, the more likely top-shelf multidisciplinary workers are to go it alone. Does this portend a future working world split into B-player company teams and A-player freelancers?

The future perfect

“Whether a job is gig-able is now less about field and more about role.”

To get a sense for the likelihood of top talent shifting away from the firm and toward gig labor, we first have to understand the conditions that brought about firm-based work in the first place. Here’s how I’d break that down:

  1. Knowledge limitations: Knowledge was hard to obtain and diffuse across specialists, necessitating teams.
  2. Productivity limitations: The pre-digital landscape demanded far more intensive time resources, necessitating teams.
  3. Networking limitations: An individual’s ability to source jobs usually couldn’t match the steady stream of work found at firms.
  4. Safety-net limitations: There were scarce substitutes for health, legal, financial security outside of firms.
  5. Cultural limitations: Postindustrial, pre-Millennial mind-sets just didn’t tend to foster a go-it-alone attitude on a mass scale.

With respect to (1) knowledge and (2) productivity, the sheer complexity of many workplace challenges historically meant that eventually no one person was capable of keeping the whole project in his or her head; there was simply too much to know and too much to do. But knowledge resources and productivity tools have improved vastly in the past five to 10 years. Even simple tools like, YouTube, Google Docs, and Adobe Creative Cloud have made cross-disciplinary knowledge dramatically easier for workers–especially independent workers–to pick up.

With respect to (3) networking, “platform” startups create efficient labor exchanges that rely on little more than individual pocket computing power. When talented individuals can easily find gigs, one of the only apparent advantages of working at a firm might be its ability to foster teamwork. But even gig platforms might be able to solve that, too. People can use their smartphones to find co-collaborators and coworking spaces on their own. Think Upwork, HourlyNerd,, and WeWork.

With respect to (4) safety nets, thanks in large part to the health care reforms of the past decade, gone are the days of sticking with a firm solely for the benefits. Legal and tax-accounting security used to be sticky, too. How else could the humble knowledge worker safely contract his or her time while accurately reporting income to the IRS? But these services are now a cinch, from and LegalZoom to and TurboTax, among others.

“Leaders need to prepare for the gig economy by focusing less on millennial retention checklists, which are table-stakes at this point anyway.”

With respect to (5) cultural limitations, knowledge workers are getting much more comfortable finding creative ways to earn a living in the digital landscape. Native digital culture has broadened millennials’ options in particular–their average job tenure is only two years versus boomers’ seven–which incidentally feeds back into (1) knowledge above. Millennials intentionally amass more job experiences and self-directed learning by age 30 than their parents or grandparents ever needed or desired.

A recruiting 'Battle Royale'

In earlier days of knowledge work, these limitations made firm-based collaboration not just desirable but necessary. As these conditions subside, however, the sheer necessity of collaboration evaporates. But people may still opt for it on the basis of nostalgia or merely habit, but it’s simply less crucial for a job well done.

As ever, the deciding factor will likely be economics. Harvard Business Review recently affirmed that over the past two decades, time spent by managers and employees in collaborative activities has ballooned by 50% or more. In the end, firms and people will do what they can afford. As more pieces of complex assignments can be handled by one individual, they likely will be. And this bodes well for the comprehensivists.

But it leaves hiring managers in a vulnerable spot. If firm employment is no longer sticky enough to hold top talent in place, what else can managers do to keep their companies staffed with A-players?

Back at Stamen, Nicolette Hayes reflected on this question: “Lone-wolf contract work does benefit from a broad skill-set,” she conceded, “but it isn’t necessarily the preferred work style of the comprehensivist.” She pointed out that she thrives in “alone-together situations,” which are certainly hard to produce outside of firm walls, no matter how cozy the coworking space.

“Alone-together situations”–where lots of people work collectively (and often collaboratively) under a shared banner toward some shared goal–could be the differentiator recruiters and hiring managers need to highlight.

The value proposition to A-players could even be framed as a question: Just how alone–or not–does an intelligent social animal want to be? Where does freedom end and loneliness begin? Increasingly, knowledge work is a creative act, at the heart of which are human needs, including the need to be social. For many, this need is best answered with firm-based employment.

The bottom line, though, is that aspiring corporate leaders need to prepare for the gig economy by focusing less on millennial retention checklists, which are table-stakes at this point anyway. Besides, the new gig-economy recruiting battle won’t be old-fashioned firms versus millennial-friendly firms. It won’t even be established firms versus startups. It will be firms generally versus freelancing.

The argument has to be made that firm life is good–nay, better–than going solo. If businesses and their leaders can highlight the socially rewarding aspects of sustained collective work, they’ll be primed to compete for top talent in the talent market of the future, even as it reinvents itself.