The Freelance Wave

The recent emphasis on flexible work has driven a massive surge in freelancing. Workers are ditching the notion of being strapped to a desk from nine to five in favor of digital nomadism, otherwise known as the location-independent workforce. With the right technology, the options of where you want to work are now endless.

PODCAST | 25m
November 18, 2020
S2:Ep3

Executive summary

  • Meet several expert and rookie digital nomads as they explore new ways of working
  • Hear about the past, present and future of freelancing
  • Insight on how technology is enabling employees to work wherever they want, however they want

Melanie Green (host):

A couple of years ago, I was sitting at my desk when I realized something. I can really work ... anywhere. All I need is my laptop and my recording gear. I could be on a beach, sipping a cold orange juice, sending an email. I think we’ve all had this realization at some point. And then, we all just kind of forget about it and get on with our day. Well, not all of us.

Travis Taborek:

So, yeah, I'm doing it. I'm leaving for Barbados in three weeks.

Melanie Green (host):

That’s Travis Taborek. This week on Remote Works, we’ll hear how he went from working in a basement mailroom to a sunny home office in the Caribbean. So grab some sun screen, and let’s look at the new world of the freelance digital nomad. My name is Melanie Green. You’re listening to Remote Works, an original podcast by Citrix.

Adam Ozimek:

Thirty-six per cent of the workforce freelances. And that's a little over five per cent of GDP.

Melanie Green (host):

That’s Adam Ozimek. He’s chief economist at an American freelancing platform called Upwork. Adam defines freelance work as anything that's project-based or temporary, and not a traditional nine-to-five kind of job. Many of the freelancers Adam talks about are only doing it occasionally.

Adam Ozimek:

Meaning they freelance maybe once a week or once a month, or even just a couple of times a year. So, because freelance is really, it’s a broad way to work, it's a very flexible, diverse way to work, a lot of people do it just a little bit. And so that's how we get, you know, over one third of workers participating in the freelance economy in a given year. If you want to look at full time freelancers, which are people you know, who are doing it in a more comparable way to your nine-to-five work in terms of how much they do it, that's 13% of the workforce is freelancing full time. So that's a subset that I think is an important number to think of.

Melanie Green (host):

Freelancing was already a big part of the North American economy, but the pandemic accelerated the movement to hiring more and more. According to a study by Upwork, two million Americans have started freelancing in the past year. This work now contributes one point two trillion dollars to the U.S. economy. That’s up over 20% in the past year. Adam Ozimek says the market for freelancers covers the gamut.

Adam Ozimek:
Freelancing includes low-skilled, selling stuff online and lots of temporary gigs, stuff like that. It also includes full time skilled professionals, like programmers. So we have everything from independent contractor who drives a cab to machine learning programmer who works full time and makes six figures.
Melanie Green (host):

While freelancing is not a new phenomenon, the massive shift in how and where we work has brought freelancing and more flexible ways of working into the spotlight.

Adam Ozimek:

It's not a modern invention that's disrupting the labor force, but it's a way of working that is flexible for both clients and freelancers. And it's always been with us. I think that there's a tendency to sort of play futurist a little bit and say, you know, we're always going to be freelancers someday. And I don't think that's the case. I think that freelancing is very valuable.
And a lot of situations, both the client and the business, and it will continue to be very valuable. That’s sort of a non-futurist prediction. We're not going through crazy disruption. It's just, this is a normal way of work and it always has been. The sort of more futurist way to look at it is that we are seeing a massive transformation of the economy, when it comes to remote work and overnight around half of the labor force was working remotely back in April. And so a lot of people are starting to work remote and they're finding that it's working better than they thought it would. And that's true both of workers and of employers, and there's a lot of synergy between freelance work and remote work. Remote workers are disproportionately likely to be freelance.
So I do think that while there have always been freelancers and there always will be, our corner of the freelance economy, the remote skilled work freelancer is definitely going to be an area that we see some growth in, as a result of this turn towards remote work. People trying freelancing for the first time, appreciating the flexibility and you know, the growing technological ability to find clients no matter where you are, no matter where they are.
Melanie Green (host):

The downside to freelance work is a lack of job stability. As permanent, full-time jobs disappear - many are turning to freelance work as a means of survival. But there’s something else at play too.

Melanie Green (host):

What does the word freelance mean to you?

Travis Taborek:

It means I work my own hours and that I'm my own boss. It means that I choose who I work for.

Melanie Green (host):

Travis Taborek is a 31-year-old digital marketer and writer based in the San Francisco Bay area. For Travis, freelancing and remote work sound like freedom.

Travis Taborek:

I choose what projects I work on and I choose when I want to work. It offers me a lot of freedom and flexibility in how I stay productive that I just wouldn't get an office job. It's really liberating.

Melanie Green (host):

Before going into marketing, Travis worked as a contract mailroom assistant at Google’s headquarters in Mountainview, California and at YouTube's headquarters in San Bruno.

Melanie Green (host):

Do you mind me asking how you got into this kind of work at all?

Travis Taborek:

I remember walking into Google’s headquarters on my first day of work and just being in complete awe of everything around me. I saw all these smart, ambitious people who are changing the world.

Melanie Green (host):

But the mailroom wasn’t ultimately where Travis envisioned himself.

Travis Taborek:

Being in that environment inspired me to pursue a career in the tech sector. I was like, okay, I'm still young. I still have my life ahead of me. I still have options. I could still work my way up here. I just need to find out what skills I need to learn. That was the position I started from.

Melanie Green (host):

Flash forward a couple of years. Travis went to a tech boot camp and trained to be a digital marketer. One internship and a few contract jobs later, he is now a Search Engine Optimization and Content Specialist. Working freelance gave Travis a range of experience on the job. And it gave him the time and opportunity to build the skills he needed to succeed. That’s all good. But working freelance requires that you take charge of your life. You need discipline and commitment.

Melanie Green (host):

What does an average day look like for you, working?

Travis Taborek:

I'll start by making a list of like the top three things that I need to accomplish that day. And then maybe a list of stretch goals or like sub-tasks that I can work towards. If I'm done with that, I'll sign on to Slack. I'll message my manager and say, ‘Hey here's what I hope to have accomplished today. And I anticipate it'll take me this long. If you have anything else you need, just let me know.’ And then I usually wrap up by around 4:30 or 5. Then I have a couple hours of downtime before I make dinner. In bed by 9 o'clock, get up and start over again.

Melanie Green (host):

Communication and organization are critical aspects of productivity, two things that are very difficult to master. It's clear Travis has done just that.

Travis Taborek:

For years, my life dream was to travel the world as a digital nomad, while working remotely. A digital nomad essentially is someone who's able to work from anywhere in the world as long as they have an internet connection. Could be Australia, Siberia, Europe, anywhere.

Melanie Green (host):

Adam Ozimek says that being a digital nomad is a great fit for someone who works freelance.

Adam Ozimek:

I've worked with people who are self-described digital nomads, and they have family all over the country, friends all over the country and sometimes all over the world. They like to be free to go and live and work wherever they want and to travel and to see people and to see places. And that's really tough to do with traditional employment. In terms of, you know, freelancing, tends to be more remote friendly than traditional employment.
Melanie Green (host):

Fun fact - according to National Geographic online, the phrase “digital nomad” surfaced around 1997 in a book called Digital Nomad by Tsugio Makimoto and David Manners. The authors argued that technology would allow humans to work from anywhere and return to the wandering ways of our ancestors. By 2019, over seven million American workers described themselves as digital nomads. The rise in remote working during the pandemic has brought even more interest to digital nomading. Why work from your cramped studio apartment in the city, when you could work on a beach?

Travis Taborek:

Digital nomad lifestyle encapsulated everything I ever wanted my life to look like. So my whole digital marketing career, the last couple of years of my life have been solely working towards that.

Melanie Green (host):

Travis’s freelance work gave him a perfect opportunity to try the digital nomad lifestyle. After carefully laid plans to work in Mexico were put on hold by the pandemic, Travis looked to other countries. And Barbados caught his eye. This beautiful Caribbean island offers sun, sea, sand, and special visas for remote workers.

Travis Taborek:

I heard about the Barbados Welcome Stamp Program, which is how I'm going to be living there. It's a special visa that they're offering to remote workers, such as myself. And I saw this, and I was like, this is perfect. This is exactly what I wanted.

Melanie Green (host):

To qualify, you need to be making over 50-thousand dollars a year and have health insurance. There’s also an application fee. But what Barbados offers in return is a great environment for working, glorious weather and a robust health care system. And of course, dependable WIFI. So Travis didn’t just jump into working remotely in another part of the world. He prepared himself. He researched places that would offer the infrastructure he needed to work effectively. He made sure he had the skills he needed for his new contract. Only then was Travis ready to embrace his dream.

Travis Taborek:

This is my chance to go for it. So, yeah, I'm doing it. I'm leaving for Barbados in three weeks. This is my heart's desire. Being a digital nomad is my life's purpose.

Melanie Green (host):
Adam Ozimek says that the new path Travis is carving out for his work - and his life - is one of the biggest reasons to consider freelancing.

Adam Ozimek:

Freelancing gives you the freedom to work when you want so if you want to spend a couple of days driving from one coast to the other then you can do that with freelancing and you get to choose when to work. It's a level of flexibility that's really difficult to replicate with traditional employment. And that's why a lot of people like it. So this is not a temporary adaptation for them. Although, you know, freelancing is useful as a temporary adaptation. For them it's a level of flexibility that they always want.
Melanie Green (host):

Travis’s story is pretty inspiring. He figured out what he wanted to do, and then came up with a plan to make it happen. Now, he’s headed to Barbados to start his new adventure. For a glimpse of how that might turn out, meet Elly Earls.

Elly Earls:

As a digital nomad has been doing this for nine years and as someone who's really interested in the phenomenon and how it develops, this year, has actually been quite surreal because I'd been talking to anyone who would listen about how great remote work was for a long time.
Melanie Green (host):

At the ripe old age of thirty-four, Elly Earls is a veteran freelancer. She’s worked as a freelance journalist for almost a decade, living and working remotely in south-east Asia, Spain, Bali, and now Germany. Her desire to combine travel with work took root in her childhood.

Elly Earls:

I grew up in Darby, which is a city in the Midlands in the UK. But my parents got jobs in Bangkok when I was 12. So I spent my teenage years in Thailand.
Melanie Green (host):

Elly has a few words of wisdom for people like Travis who are just starting their journey in remote work.

Elly Earls:
My advice for anyone getting started out is always join the digital nomad communities because the thing that everyone says to me and the thing that I also felt at the beginning of this journey, was that I wish I'd known that there were other people doing the same thing who I could talk to and who would get what I was doing and what I was going through. And, you know, if you're feeling a bit lonely, there's someone there to talk to who gets what your life is like. So communities like that are a real lifesaver. Although isolation is absolutely a challenge of this lifestyle, once you get into the nomad communities, the people are actually what really makes this lifestyle amazing. The interesting, smart, awesome people that you meet through these communities just improve your life so much.

Melanie Green (host):

Not only is Elly a freelancer, she researches and writes about freelance and remote work.
Elly Earls:

I was talking to a researcher the other day, who's doing his PhD in digital nomadism. He said that up until this year, there were three segments of digital nomads. So there are the freelancers, the sort of, small business owners or entrepreneurs, and then the remote employees. And previously, those first two categories had made up the vast majority of digital nomads. But he was talking about how now, because of the coronavirus and because companies have realized that their employees can work remotely it's that third group, the remote employees that is going to grow a lot over the next few years. And so the makeup of the community might change quite significantly, which could be interesting.
Melanie Green (host):

That means that Travis could have plenty of company on the beach. And it means that forward-thinking countries like Barbados could really benefit from the growth in remote work.
Kavi Guppta:

The future of work is going to come from all over the world. Not necessarily just in Barbados.
Melanie Green (host):

That’s Kavi Guppta, a writer and speaker who thinks a lot about the future of work. Like Elly and Travis, Kavi sees the many benefits of freelancing in the age of the digital nomad.

Kavi Guppta:

What is incredibly important is the choice of flexibility. Deciding what kind of work you want to do and taking on however much work you want to do based on your capacity and your drive and ambition. And also, maybe being more critical of the type of work you take on and having a choice in who you want to work for and how often you want to work for them. I think the length is then determined by you or the contracts that you take on as a freelancer. Now that's not particular to digital nomadism. That's just freelancing in general and that's existed for ages. But ultimately what we're now seeing is, as a freelancer, you get to choose who you want to work for. And as I guess in this context of a digital nomad, you get to choose where and when you want to do that work.

Melanie Green (host):

Elly would fall into the category of someone for whom flexibility - the ability to choose where and how she works - means everything. So much so that she doesn’t see herself moving into a full-time office job.
Elly Earls:

I've been freelancing for nine years and now I'm moving more into the entrepreneur group, starting my own business, starting my magazine. I think the possibilities of that are greater than any permanent jobs that I could have.
Melanie Green (host):

But like anything in life, there are no guarantees. Kavi warns that not everyone who ventures into freelance work is going to have the success Elly had.

Kavi Guppta:

Number one is trying to get contract or freelance gigs in industries or in roles that just aren't in demand. Second to that, a number of people are hiring for the cheapest possible labor that they can get. And so really sifting through a lot of that noise and finding companies or enterprises that really value quality and really value a good wage. That's your job to figure that out now because no one's doing it for you.

Melanie Green (host):

That sounds harsh, but it’s true - and not just in freelance work. We’ve always thought of working in a large corporation as bringing some kind of job security. But Kavi says that’s something of an illusion.

Kavi Guppta:

There's never been job security. There isn't now. I think we've been really attuned to this idea that no longer exists where a lot of our parents and grandparents work for one place for a long time - 50, 60, 70 years - then got that gold watch or that really lovely retirement package that comes out of it and the big party and the cake.

You're seeing it right now. I mean, COVID-19 has shown it, but also for a lot of people who remember the great recession in 2008 onwards, job security was nothing secure in the first place. We're already looking at ways to either create more casual labor opportunities in a good way for ourselves and individuals, but companies are also looking at ways to have to reduce their workforce expenses and be more malleable about how they could hire people and how often they could hire people based on their supply and demand issues that they have.

Melanie Green (host):

Kavi says that means we have to be flexible. We have to keep reinventing ourselves. Working freelance allows us to do that - whether working remotely or not.

Kavi Guppta:

Be prepared to have to probably do four, five particular reinventions in your lifetime around whatever skill it is that you are selling yourself for in the online marketplace of work. Be prepared that what you have now will no longer be the same job in maybe even two years time. Be prepared to also really understand what value you're providing to the organization that you're working with. Constantly assess - constantly assess - whether you are creating value or not. And if you aren't - if you’ve found that you aren’t - what do you need to do to reskill yourself or reposition yourself to be an in-demand value creator.

Melanie Green (host):

So what tools do we need to be successful in remote work? Kavi says we have to reconsider the importance of what we think of as soft skills.

Kavi Guppta:

Time management. Communication skills. Being overly redundant at communicating with people is so important. If you can't write a really good email or a really good Slack message or deliver a really good video or put together a really good meeting, you're going to fail so hard. And that applies in the physical workspace as well. These are not soft skills. These are absolutely important to your success, not only from a technical ability, but how you collaborate with others as well. So let me go back again. There’s time management, there’s communication ability, organizational ability, because you're actually managing so many different moving pieces on a project or a contract, being able to show that you're on top of it is so important. And I really, really hate when people call them soft skills because I don't see anything soft about it at all. Those are really hard things to master. So why can't they be hard skills?

Melanie Green (host):

Kavi also says that from an employer’s point of view, there are some hurdles to get past.

Kavi Guppta:

If you can't see them, you don't know what they're doing so you don't trust them. And so then you end up creating habits that constantly make sure that that employee or that worker, you're keeping tabs on them. I think trusting people to get the job done because you can't physically see them, or they're not physically sitting next to you, is a huge hurdle not only for employers but also for the person who’s being employed. And then of course, just the sheer number of meetings that you probably have to be involved in because they were so useful to the trust factor in a physical workplace. And you're trying to recreate that environment.

Melanie Green (host):

Ultimately, we need to have technology that works for us and enables us to create value in any situation. Like Travis, we need to set goals for ourselves. In the freelancer world, we’re responsible to the client but we’re also responsible to ourselves.

Kavi Guppta:

You really have to become your own manager. You have to become your own boss. And although that sounds great in the sense of ‘finally, I don't have to report to anyone’, it's actually brutal because you are now responsible for yourself. And the whole idea of being your own boss is sold quite a lot as a mechanism of freedom, but it really isn't. It means that you now have to be your accountant. You have to be your own coach. You have to be the person that makes sure that you don't procrastinate and actually get the job done because nobody else is looking over your shoulder anymore. Learning how to be your own leader is going to be one of the most incredible skills that you can take. And it does come back to having good time management, being a good communicator, being really organized, understanding how to really strengthen your productivity because you're the only person that's going to be responsible for yourself now.

Melanie Green (host):

Kavi’s promise - and warning - about self-sufficiency reminds me of a bird being nudged out of the nest. It's a long way down. But then there’s a big beautiful sky up above. There are risks but there are also rewards. I’m Melanie Green. You’ve been listening to Remote Works, an original podcast by Citrix. Subscribe and come back in two weeks. That’s at citrix.com slash remote works.

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