Until a half-century ago, entrepreneurship (the solo or hero variety), was taboo. The nerve of folks who made their living from customers and friends for that matter! Entrepreneurs, so it went, could not cut it inside the organisation — poor souls had to strike out on their own. Today this way of life is a bragging right.

The idea that so many could have it their way is deeply unsettling to some. “They’ll be back,” sceptics chime. Yet a popular report from freelancing platform Upwork points to an inevitable tipping point: the majority of American workers will soon be freelancers.

Many are opting out of trekking to and suffering in spirit-sapping offices. With the allure of creating meaning on their own terms, the world’s brightest talent continue to flee corporate life. Although some have built companies of their own, the majority prefer dancing with as opposed to in the organisation.

Our economy’s fundamental unit is no longer the company — it’s you. You can follow your nose, try out different things, and see where it takes you. But what does this mean for the future of work? 

While lifetime loyalty to a single company has gone the way of the dodo bird, Brand Me’s have flooded the marketplace. Every shrewd business, as a result, has become like show business.

Two decades since chronicling free agent nation, I caught up with author Daniel Pink to get to the bottom of where things rest.

Getting a Leg Up

At the turn of the century, Pink found free agents in every nook and cranny — even tracking down Betty Fox, an early yet elderly (at sixty-eight) internet entrepreneur. Using her knowledge, the web, and a bit of help from her son, she launched and sold an online business for seniors.

Like Betty, for those with a knack of leveraging technology, free agency can provide a one-way ticket to liberation. But for others, free agents or otherwise — work is still just a way to make ends meet. The net outcome of technological advances might mean an elite few are catapulted ahead while the rest are left waving in the rearview mirror. 

Not seeing the explosiveness of the change that would take place, Pink remarks:

“Remember: I wrote Free Agent Nation before smartphones and, equally more important, before widespread broadband! But that’s not all. It was also before Facebook, before Twitter, before the cloud, and before Uber, TaskRabbit, and the gig economy. In a way, the conditions I described back then now almost seem quaint. 

I’m hoping that this country will reckon with its ugliest truth: That the modern economy is leaving people behind. What’s happening has less to do with the form of work…and much more to do with who has skills that are in demand and who doesn’t. The fact that too many people who work hard and do the right thing can’t get ahead is the most urgent moral and economic issue we face.”

At its core, technology is simply about the way we make progress. The challenge then is in designing a better system of work that helps employees develop in-demand skills on the fly. As machines will soon eclipse the amount of work we do, more contractors and flexible working arrangements will play a significant role in the system. But so too will the ability to play nicely with our robot pals. If we rise to the challenge, it could be our greatest opportunity to flourish.

Beef Brisket Hash

Our organisations are failing us because they’re not built to function as engines for learning. Employees should get paid for both their intellectual property and what it is they’ll need to know. But what we still have are corporations that reward conformity over professional growth.

While the incoming workforce is being prepped for jobs that will soon be extinct, what they desperately require is the ability to learn how to learn. Our education system is rooted in standardisation and mass synchronisation but will only sprout through personal, situational, and reflective practice. Pink points to the biggest surprise in the learning revolution:

“The best example here…is YouTube. It has become the go-to source for all kinds of specialised learning — from playing chord progressions on a guitar to perfecting an Australian accent to preparing beef brisket hash to having a difficult workplace conversation…the key for organisations is to make it just as easy and effective to learn new skills inside the organisation as it is to do so outside the organisation.”

As a young person, you can’t sit out the future. You have to cultivate a growth mindset. And those organisations that liberate workers so they can follow their nose are simply practising good business. “Freewill — not free cola — quenches the thirst for meaning,” wrote Pink at the turn of the century. To thrive in the future, workers must be given the leeway for cross-domain thinking and creative problem-solving. Cultivating curiosity isn’t just trendy— it ‘s winning in the innovation game.

A Bossless Future

Gallup reports that just one in 10 managers have the talent to manage well. In other words, 9 out of every 10 managers don’t have what it takes. The next generation leader will need the kind of pedigree that Pink predicted twenty years ago, a great: party host + movie producer + baseball coach. Yet the evolution of this 21st-century leader is taking much longer than we’d hoped. Here’s Pink’s reasoning today:

“The real problem here, at least in my view, is two fold. First, the way we prepare leaders — in MBA programs and in many leadership development courses — hasn’t changed all that much. We’ve rubbed off some of the command-and-control rough edges. But most of these programs haven’t fundamentally rethought what leadership means in this much more fluid environment. As a result, managers resort to what they’ve learned rather than take the riskier step of more fundamentally refashioning what they do and how they do it.

Second (and it’s related), we don’t have many role models out there for this new approach to leadership. So not only are people not learning this approach in their professional training, they’re not seeing it in action in their organisations. Instead, they’re often seeing the same old approach — and worse, they’re often seeing this approach rewarded with promotions.

This alternative form of management is rooted in a networked way of thinking and doing. Leaders who understand that the talent war is just an endless game of Tetris have fastidiously responded and reorganised to better serve individuals and teams. The new credo for leading is more horizontal, dynamic, and distributed. In fact, the long view is to envision a future workplace where there simply aren’t bosses.

Whichever way, we should be looking to enrich the working spirit rather than quashing it. Pink does see this type of leadership prevailing in the end. “I’m just not sure whether the long term is 2 years or 20 years,” he remarks.

Working it Out

We need to redesign both our schools and organisations so that they continually nourish our minds. Students and workers alike need spaces that consistently feed curiosity and free them to stoke creativity. And while the future may not be evenly distributed — it can be a better place.

A long road lies ahead. Some might hold their breath, interminably waiting for their company to treat them as free agents. But since Pink let the cat out of the bag a tsunami of workers have jumped ship. They glee over the fact that going your own way is the only way.