How Freelancing Is Changing Work

Hayden Brown grew up with parents who were out to change the world. Her mother worked on women’s empowerment issues, and her father helped develop a national park in the Himalayas. For a time, the family lived in Nepal.

“It really instilled in me the value of spending one’s life doing work that has a real impact on others,” she said. “To this day, that is my parents’ ethos.”

Ms. Brown wanted to make a difference, too, but resolved to do it in the private sector rather than in the nonprofit world. That led her to the consultant McKinsey & Company, and ultimately to UpWork, a site that matches freelancers with employers. Ms. Brown joined the company 10 years ago, and became chief executive in January 2020, just as the pandemic hit.

To hear Ms. Brown tell it, UpWork is making the world a better place, one freelance job at a time. Those advertising their skills on the site are not gig workers like Uber drivers or TaskRabbit handymen, but rather accountants, graphic designers and even lawyers. UpWork’s marketplace for talent allows workers to find new jobs, and companies to find help in a pinch.

At the same time, Ms. Brown acknowledges that a company like UpWork exists only because the social contract between employers and employees has been so fundamentally altered in recent generations. Gone are the days when most people worked for one company for their entire careers and retired with benefits and a nest egg. Instead, professionals often jump from employer to employer, and sometimes industry to industry, all the while hunting for their next gig and stringing together side hustles.

Given all this, it’s no surprise that freelancing is on the rise, and that business at UpWork is booming.

This interview was condensed and edited for clarity.

Is UpWork back in the office yet?

We reopened our Chicago office; our San Francisco office is pending reopening, kind of; and we’ve permanently shut our Santa Clara office. We’re watching what’s going on with Delta. We’ve always been a very remote-oriented company, given our business model, and we’ve basically said we’ll be remote-first going forward.

Why did you shut the Santa Clara office?

We heard from our team members that they didn’t want to come back into it. They are working from home, and it is working so well for them. People were commuting, and some of them had an hour-plus commute, and they were like, “Why would I commute an hour just to sit at a desk?”

Did living in Nepal as a child affect your career at all?

It had a huge impact on me. Prior to my family moving overseas, I had grown up in my Small Town, U.S.A. Having lived in Kathmandu for maybe two years, I remember vividly my first trip back to the United States, walking into an American supermarket, and what had been so normal before was suddenly so abnormal. Just being confronted with the prosperity and the abundance of the U.S. and that supermarket setting, compared to what I had grown used to in Kathmandu, really struck me.

Given that your parents were involved in nonprofits, what made you gravitate toward more market-oriented solutions to some of these big problems?

I had seen the nonprofit world through my childhood and their experiences. I saw the positives in terms of impact. I had also seen a lot of the drawbacks in terms of some of the bureaucracy, the pace at which NGOs make decisions, the limitations they sometimes have in terms of access to talent.

What I didn’t feel like I really understood because of my upbringing was the business side of the world, which I could see was having such a profound impact on shaping people’s lives, for better or worse. That led me to go to McKinsey to get this crash course in business, and I fell in love with that.

What did you take away from your McKinsey days?

It gave me a bit of fearlessness that I got early in my career, because it put me in the room with senior decision makers. I learned very quickly that they didn’t really know any more about a lot of things than I did as someone fresh out of college.

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Is that not a little crazy that big companies pay McKinsey a huge amount of money to have people who don’t know anything about these topics come up with the answers for them?

It is. But I think it also speaks to that value of the beginner’s mind-set, this idea that sometimes the most valuable perspective is kind of uninformed. I kind of apply that even now, as a somewhat new C.E.O., in approaching problems and saying, “Look, I may be new to this” or “I haven’t done this before.” So it is crazy, but I think there may be some method to the madness.

One of the other takeaways I had was, early in my tenure at McKinsey, I had a manager who gave me some very harsh feedback. He tore me up in my performance review for not interviewing our clients in this extremely direct and hostile manner, which was his style. He had a military background and would be very confrontational. It was the first time in my career that I had really had to step back and think about feedback and say: “Am I going to internalize this? Do I really think he’s right, and is this style going to serve me and advance my objectives? Or am I actually getting really good outcomes, but I just disagree with him about the method and where is he coming from?”

There was a gender element there, but I realized that while it’s good to get harsh feedback, you also have to look at it critically and say: “You know what? That’s not for me. I have to be kind of true to who I am and move forward.”

How do you explain the rise of the freelance economy?

People want more flexibility and control over how they work, where they work, who they’re working for and really charting their own path around their careers in a different way.

At the same time, the pact around what an employee-employer relationship looks like has been weakening over time. Over the course of several recessions, most recently 2008, the social contract has been shown to be not what it was several generations ago.

As newer generations enter the work force, millennials and Gen Z in particular, they’ve seen that the contract for employment is broken and say, “That’s not for me.” They have a much more kind of empowered idea around how they’re going to build their careers that’s much more autonomous and not related to a single firm. It’s much more about skills that they have, portfolios that they’re building. They feel like that’s where they have safety and security. Being tethered to a single employer actually feels more risky to them.

And I think people’s mind-set has shifted with the pandemic, and we’ve seen now a sea change in people really re-evaluating their relationship to their work. They’re saying: “Wait a minute. I need some different things. I want to draw boundaries in different ways. I want to have a different relationship to my work than I did in the past, where I am much more in control.”

Do you think that social contract between the employer and the worker is broken forever in this country?

I think the fundamental flaw in the American system is that so many of our benefits, including things like health, are tied to employment status. That is really the original sin of the system that we are living in today.

The fundamental structure of the social safety net that we have in the U.S. is predicated on a model that I think is just old and outdated. Trying to go back to that would be moving in the wrong direction. Because when you talk to workers, they don’t want to sign up for a 9-to-5 job. They actually want more of that flexibility.

There’s a chicken-and-egg conundrum here. Are there more freelancers now because companies have been reducing their full-time head count, or are people really opting out and choosing to freelance?

We are not seeing companies shrinking their work forces because they’re really going to freelance talent. We’re in the early innings of the adoption of freelancers across the economy. That means for most companies, they’re using freelancers to augment their full-time teams, to prevent their teams from burning out by having this virtual talent bench of skilled freelancers who are at the ready and doing a bunch of work, and that can flex up and down.

So much wealth in this country is being created through equity these days. Is there any way for freelancers to enjoy some of that upside?

I don’t think there’s a great pre-existing model for that, and some of the archaic models of regulation and legislation in this country have yet to be updated. So it’s something that we need to keep pressing on as we look to evolve how our country deals with some of these regulatory areas that are really dating back to an era of work that we have so far moved beyond at this point.

What role do you think the office is going to play for companies in the years ahead?

Basically, all of the work we enabled prepandemic was online, and that’s still true today for all the obvious reasons. The amazing thing about what happened in the last year and a half is that everyone got so comfortable with remote work. It was partly a tools and technology thing, learning how to use Zoom or whatever. But I think the bigger thing was the cultural shift, where people realized it’s actually working pretty well. Remote work is just work.

The virtual office, I think, is going to continue to be ever-present for basically every business that’s doing some kind of knowledge work that can be done remotely. And it can be such a level playing field. People are talking about how women and minorities are contributing at higher levels on Zoom, because everyone’s Zoom square is the same size, or how parts of the organization that were kind of peripheral before suddenly are not disadvantaged in terms of access to leaders or information. Companies that choose to lean into that will really have a competitive advantage in terms of access to talent, in terms of creating a workplace that will be attractive to top talent that want to work in a place that is open and transparent and hard charging.

Are we going to have a freelance C-suite any time soon? A freelance C.E.O.?

Why not?

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