How Freelancing Changes Work


Hayden Brown grew up with parents who wanted to change the world. Her mother worked on women’s empowerment and her father was a national park in the Himalayas. For some 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,” he said. “Until now, that’s my family’s ethos.”

Ms. Brown also wanted to make a difference but decided to do so in the private sector rather than the nonprofit world. This led him to consultant McKinsey & Company and eventually UpWork, which pairs freelancers with employers. Ms. Brown joined the company 10 years ago and became CEO in January 2020 just as the pandemic hit.

To hear Miss Brown say, UpWork is making the world a better place, one freelance job at a time. It’s accountants, graphic designers and even lawyers who advertise their skills on the site, not gig workers like Uber drivers or TaskRabbit mechanics. UpWork’s talent marketplace allows employees to find new jobs and companies to find help when needed.

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

Given all this, it’s not surprising that freelancing is on the rise and business at UpWork is booming.

This interview has been summarized and edited for clarity.

Is UpWork back in the office?

We reopened our Chicago office; Our San Francisco office is waiting to reopen, sort of; and we have permanently closed our Santa Clara office. We’re watching what’s going on in Delta. Given our business model, we’ve always been a very far-focused company and basically said we’re going to be remote first going forward.

Why did you close the Santa Clara office?

We’ve heard from our team members that they don’t want to come back. They work from home and this works very well for them. People were commuting and some had over an hour of commuting and were like, “Why would I commute for an hour just to sit at a desk?” they said.

Did living in Nepal as a child ever affect your career?

It had a huge impact on me. Before my family moved overseas, I grew up in my Small Town in the USA After living in Kathmandu for maybe two years, I remember very well the first time I went to the United States, walking to an American supermarket, and things that were so normal. before it suddenly became very abnormal. Compared to what I was used to in Kathmandu, I was really struck by the prosperity and abundance of the USA and facing that supermarket environment.

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

I saw the nonprofit world through my childhood and their experiences. I have seen the positive aspects of the effect. I also saw many disadvantages in terms of some bureaucracy, the speed of decision making by NGOs, the limitations they sometimes have in terms of access to talent.

What I couldn’t really understand because of my upbringing was the business world of the world, and I could see that it had such a profound effect on shaping people’s lives for better or for worse. This made me go to McKinsey to take this crash course in business and I fell in love with it.

What did you get from your McKinsey days?

Being early in my career gave me some fearlessness because it put me in the same room as top decision makers. I learned very quickly that they didn’t know more about many things than I did as a recent college graduate.

Isn’t it a little crazy that big corporations pay McKinsey huge sums of money to have people who don’t know anything about these issues find the answers?

This. But I think it also touches on the value of a beginner’s mindset, the idea that sometimes the most valuable point of view is a little bit of ignorance. Even now, as a somewhat new CEO, I apply this when approaching problems and saying, “Look, I might be new at this” or “I haven’t done this before.” I mean, it’s crazy, but I think it might be a method of insanity.

One of the other takeaways I’ve gotten is that early in my tenure at McKinsey, I had a manager who gave me very harsh feedback. It ripped me apart in my performance review for not interviewing our clients in this highly direct and hostile manner, which is in his own way. He had a military background and would be very belligerent. It’s the first time in my career to really take a step back and think about feedback and say, “Am I going to internalize this? Do I really think he is right and will this style serve me and further my goals? Or am I getting really good results but disagree with him on the method and where it came from?”

There was a gender element there, but I realized that while it’s good to have harsh feedback, you have to look at it critically and say, “You know what? This is not for me. I have to be honest about who I am and move forward. ”

How do you explain the rise of the free economy?

People want more flexibility and more control over how they work, where they work, who they work for, and how they really chart their own path around their careers.

At the same time, agreement on what an employee-employer relationship looks like is weakening over time. During several recessions, most recently in 2008, it has been shown that the social contract is not what it was a few generations ago.

As the new generations, especially the Y generation and especially the Z generation, entered the workforce, they saw that the employment contract was broken and they said, “This is not for me”. They have much more empowered ideas about how to build their careers and are much more autonomous, not just one firm. It’s more about the skills they have, the portfolios they’ve created. They feel like that’s where they have safety and security. Being tied to a single employer actually seems riskier to them.

And I think people’s mindsets have changed with the pandemic, and we’ve now seen a huge shift in people who are really re-evaluating their relationship with their work. They say: “Wait a minute. I need something a little different. I want to draw borders in different ways. I want to have a different relationship with my job than in the past, I have a lot more control here.”

Do you think the social contract between employer and employee in this country will be broken forever?

I think the fundamental flaw in the American system is that many of our benefits, including things like health, depend on employment status. This is the real sin of the system we live in today.

The basic structure of the social safety net we have in the US, I think, is simply based on an old and outdated model. Trying to go back to that would be going in the wrong direction. Because when you talk to workers they don’t want to sign up for a 9 to 5 job. In fact, they want more than that flexibility.

There’s a chicken-egg riddle here. Are there more freelancers now that companies are reducing their full-time staff numbers, or are people really choosing to stop freelancing and go freelance?

We don’t see companies shrinking their workforces because they’re really going to freelance talent. We are in the early stages of freelance adoption across the economy. This means that for most companies, they use freelancers to empower their full-time teams, keeping their teams from burnout by having this virtual talent bank of talented freelancers ready and doing loads of work. bend up and down.

So much wealth is created in this country through equality these days. Is there a way for freelancers to enjoy some of these benefits?

I don’t think there is a great pre-existing model for this, and some archaic models of regulation and legislation in this country have yet to be updated. So it’s something we need to continue to focus on as we try to improve how our country deals with some of these regulatory areas that actually go back to a working age far beyond at this point.

What role do you think the office will play for companies in the coming years?

Basically, all of the work we enabled pre-pandemic was online, and that still holds true today for all the obvious reasons. The surprising thing about what’s happened over the past year and a half is that everyone is so comfortable working remotely. It was partly a matter of tools and technology, learning how to use Zoom or whatever. But I think the bigger thing was the cultural shift where people realized that this worked really well. Remote work is just work.

The virtual office will continue to be always available to basically any business that does some kind of information work that can be done remotely. And it can be such a level playing field. People talk about how women and minorities are contributing to Zoom at higher levels because everyone’s Zoom square is the same size, or how parts of the organization that were once a kind of peripheral aren’t suddenly at a disadvantage in terms of leaders or access to information. Companies that choose to move towards this will truly have a competitive advantage in terms of access to talent, creating a workplace that is open, transparent and attractive to top talent who want to work in a challenging place.

Will we be a free C-suite soon? A freelance CEO?

Why not?


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