Workforce Wanderlust

What will our work become in an itinerant world? British-Australian entrepreneur, Kate Kendall, weighs in.

Aaron Foley

Taking destiny into their own hands, digital nomads are finding they can control how, when and where they work. By 2020, this figure is projected to be 40% of the total workforce.

In this episode, we speak to Kate Kendall, CEO of freelance platform CloudPeeps, who sees this new interconnectedness as a gateway not just to a new way of working, but to understanding each other more deeply. 

The Where the World’s Moving podcast is a BBC Storyworks Commercial Production, presented by OFX.  It explores our ever-changing world, and how technological and social shifts are enabling collaboration, contribution, and human progress.

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Podcast Transcript 

Ross Dawson: Hello and welcome. I'm Ross Dawson, a futurist, speaker and author, hosting the Where the World's Moving podcast series presented by OFX, a global money transfer specialist for Where the World is Moving. Through this podcast series, we explore our fast moving, ever changing world and some of the extraordinary technological and social shifts that are shaping business and society, driving collaboration and globalization and supporting human progress. To find out more about the exciting ideas in this podcast and the rest of the OFX series go to

Ross Dawson: Since we left our ancestral cradle in Africa tens of thousands of years ago to populate the planet, humans were born to wander. More recently, technologies of connection have made it far easier for us to express our innate desires to explore and experience widely. Now, an array of new digital platforms are allowing work to be far more fluid and flexible, able to be done from anywhere. So what will work become in an itinerant world? To help us understand this emerging space, who better to talk to than Kate Kendall, CEO of freelance platform CloudPeeps. Welcome to the program, Kate.

Kate Kendall: Thank you for having me, Ross.

Ross Dawson: You have lived a very itinerant working life. You've been based in Melbourne, New York, San Francisco, Brisbane, have I left any out?

Kate Kendall: We were in Berlin a little bit too and Bali for a bit in 2012 as well.

Ross Dawson: That's pretty diverse. So what is it that's kept you moving from place to place in the course of your working career?

Kate Kendall: So I started out as a journalist and then I really got into social in the early days. And when I was kind of meeting people in that community, I noticed that a lot of web developers were starting to work remotely and travel all over the world. And I was always someone who got a job out of university and didn't do the kind of year or two backpacking. And so I had a little bit of wanderlust and I was like, oh, this is a great way where I can still work on my goals and still work, but also see the world. And that about 2010, that was when companies were getting a little bit more kind of trusting with people working remotely. And so I started doing community management, social marketing as a freelancer for companies while I'd travel, and then that led me to kind of pick up more permanent home such as when I was in San Francisco. But yeah, it was really drawn out of a place of, Oh this is great. I can see the world and learn more and expand my mind, but also keep working.

Ross Dawson: That's living the dream. What do you think the real value is to people off experiencing, working and living across different countries and cultures?

Kate Kendall: I think it is just so key and already in the past, I think especially for years since platforms like Slack came along and have really kind of revolutionized how companies communicate internally. It's just that so much thing is, if you can talk to someone across different boundaries, different places in the world, you're just really thinking about user experience and a kind of holistic approach to doing something when you are connected, deeply connected to different humans all around the planet. I remember sometimes when I was working with some of my team in America who might not have had that experience as much when they were kind of creating copy or doing campaigns, it was very, very US centric. They didn't realize that if it was summer in the US, it might not be summer elsewhere in the world. So I think the more that you have that information and that knowledge that there are so many different experiences at any one time on this planet, you really can create much better experiences and solutions for them.

Ross Dawson: It is a global world, global business. So unless we've experienced it for ourselves, it is a bit theoretical.

Kate Kendall: That is so true. And even on a local level in the Australian startup community, when companies used to launch here, they often were the kind of local version of what had launched in the US and now as you see, so many companies are going global from day one. People have to think globally when they're launching. It's just so important.

Ross Dawson: More and more people are able to, just live the dream as a word to be able to say, well, I want to work but I don't need to be tied to one place or even to one job. So they're becoming freelancers, independent workers, so what do you see is driving this rise of independent work?

Kate Kendall: Yeah, well, I say this as a millennial and I know millennials can have a bad rap that when the global financial crisis happened, a lot of people really went from going, I have security, I can have one job in my next 10 years, I can have benefits, everything will be okay. And I think everyone just really saw that collapse and realized that there is this thing of perceived security where having a job doesn't necessarily mean anything to do with security and you can create your own security by creating your own business or taking responsibility for yourself. And so, there is this kind of saying where our grandparents generation might have had one job in their lifetime, our parents' generation might've had five and now we have five at any one time. And I think as many people kind of try to say, oh, that's not a good thing. I think that it means that a lot of people are now really focused on the job to be done rather than filling hours at a desk.

Kate Kendall: And so freedom and flexibility are absolutely huge drivers. The other driver is education and impact. So some people who are just realizing they're not having any impact by sitting at a desk between 9 to 5 and even much longer and by going externally, they can pursue their dreams and passions and still earn a living.

Ross Dawson: Yeah, it's actually a really interesting point around the security. I mean, I feel more secure in having my own company than I do in a, with the C.V people having corporate jobs where you just never know what's going to happen next.

Kate Kendall: Yeah, absolutely. And I think that's where a lot of people, once they're okay with risk and we are seeing a huge shift to this entrepreneurial mindset as well. It's not just the independence, it's people who are now thinking of themselves as yeah, businesses, micro agencies, and now they're operating with much more risk appetite and entrepreneurial mindset.

Ross Dawson: So speaking of entrepreneurial mindset, you saw an entrepreneurial opportunity in this world of more and more freelancers around the world. So your company CloudPeeps matches the freelance marketers with clients. So what was it that you saw changing, which led to this opportunity?

Kate Kendall: When I was freelancing myself, I was kind of forming a little network of people that I trusted, other freelancers, other indie professionals in their kind of marketing community social media space. And at that time, there was really zero trusted online marketplace that any, I guess, skilled professional, especially from places like the US or Australia would work. So this was happening offline, offline referrals. And so I just kind of started getting companies come to me saying, I want to hire a community manager or a social media manager. And then I also had the talent pool. So it started very organically out of my own need to go, Oh, I really love remote work and here's the vertical that I work in. So why don't we start a quality driven freelance platform for these kind of people. So it was really about creating a tribe and then also allowing clients to access really skilled, high communicating kind of talent that they might not have had the opportunity to otherwise.

Ross Dawson: What technologies are already in place to support this evolving future of work? And how do you think this will develop moving forward?

Kate Kendall: Yeah, well, there's so many then stats on this, but that by 2020, 40% of the US workforce will be independent. So we are saying this being such a huge shift and a lot of people at the moment are already having a side gig or a side job that they're doing around full time work. So I think that work really needs to understand that people are driven to flexibility. They're driven to remote. They really want to empower themselves to pursue their dreams and to work in great cultures. And so that's where a lot of employers really need to catch up and start offering that. And you've seen that with the expansion coworking spaces and all of those other places that this independence is going. So I think it's already happening so fast, that it's not, we know, will it happen more?

Kate Kendall: You might think of organizations in the future of being made up of little pockets of independent professionals that are coming together to work to that greater goal. And the other thing that's being disrupted at the moment is business models in general. So you've seen the rise of kind of equity crowdfunding, and a lot more people getting involved in business ownership. And so I think it will be changed so much in the future and we won't even know what an organization might appear to be as it is today.

Ross Dawson: Sounds breathtaking. Are you saying that organizations are moving fast enough at the moment?

Kate Kendall: I think that, obviously the one organizations that are kind of really succeeding, a lot of tech companies. So tech companies, I think this is ingrained in their culture, that they are very fast with innovation, they will change how people work. And even when I'd go into bay area companies, head offices, they were all often, some people are in meetings, but a lot of people were out of their desks or on their desk talking on Slack. So the idea that they have to be in this office and be monitored isn't kind of current anymore. And so I think a lot of companies, if they really want to kind of innovate and stay relevant, they need to change and change a lot more than they have been doing because it's just, everything's happening at such a greater speed than it did in the last century.

Ross Dawson: Yeah. So if professionals can live and work where they want, where do they choose to live? So you mentioned you'd worked out of Bali for a while and other people I know travel the world, they go from place to place and keep on working. So what happens? Do talented people then sort of just choose their favorite city or beach in the world or do they just keep on moving? Or how does this change the nature of where those people that can do the work they want choose to live?

Kate Kendall: Yeah, so this digital nomadism I guess is the broad term or location independent. And I wasn't nomad for many years and it's changed a lot since the early days because there's so many more coworking spaces in communities now. And one site that's really great for checking out where to go is Nomad List. So Nomad List is an index of the top cities for nomads and it will have places like Chiang Mai in Thailand or Ubud in Bali, Lisbon in Portugal. So it's based on a variety of factors such as internet speed, cost of living is such a crucial one, and I saw that in San Francisco where the average cost of a one bedroom apartment is $1000 plus a week. So these cities are just not affordable now for even teachers and doctors, it's just not affordable, let alone creatives and independents.

Kate Kendall: So that's also been a big shift where people have started to move. But really it's all over the world that people might go and they may stay for one to two months at a time, sometimes longer, sometimes shorter, and then go to the next place. And I think it's quite interesting because it also brings kind of questions around what it is to be a citizen of a place and also a tax residency. So that's where a lot of things like healthcare and other like insurances, they're trying to catch up to service this new market. There are other downsides and the criticisms of the movement too, which is that it is a lot of affluent individuals that can go and are they giving back to the local economies. But I think in general it is still very emerging and things are not quite as established yet.

Ross Dawson: So let's say you're young or perhaps not so young and you think that sounds awesome, I'd love to do that. So how do you get there? What do you do to be able to live this nomadic lifestyle?

Kate Kendall: Well, I would definitely say to get a buffer first. So I think anyone who kind of quits their job and hasn't done any financial planning around it, that can be a tough way to start. So a lot of people I've seen have kind of saved up a buffer, started to build up some sort of freelance practice or even started selling products and services online so that they have that remote income. And they've looked at passive income streams too, they might sell a course on Udemy, all these kinds of ways that you can make money online and then they might even be employed full time and still and then quit their job. And then start by becoming a minimalist, which is kind of what I did. I sold a lot of my possessions and I never quite got down to the 50 things or less things. But I did have quite a small kind of travel set up and then you basically book a flight and you go to your first destination and meet fellow nomads. You join a space or find a space that you can work into, continue to bring in revenue.

Kate Kendall: And there's different parts. I think it doesn't have to be all or nothing that you're nomad or you are in one place. I've seen people become nomads and then buy a house and then be a nomad again. And so, the only thing I think the biggest challenge is, is families because obviously if you start getting, if you have children and then they have to go to school, it's much harder to just leave every three weeks and pack a small bag and go somewhere. So that's also been something where people are like, I'm going to get rid of all this stuff. I don't need a massive mortgage. I don't need to earn all this income that then pays that mortgage. I'm going to live leanly and focus more on my wellbeing and dreams and creating.

Ross Dawson: Yeah, absolutely. These are what you can call global citizens. Do you think people feel that their identity is beyond a nationality or a place that they are far to spencer in the whole world at large?

Kate Kendall: Sorry, I was born in the UK and moved to Australia when I was 10. It's almost what I've known is to move or to be a kind of global citizen in a way. And a lot of people have been in the same boat where they might have lived all over the world or immigrated at some point of time. So it's less I think about this is my identity that is tied to this nation and this is where I'll always be. And there are, I think it is a lot bigger than just kind of obscure movement because even places like Estonia, have got now the e-Residency where they have offered digital residency to set up to use the kind of infrastructure that Estonia has for businesses and access to the EU while not being a physical citizen. And I think that it's just so interesting to see a country that might have dwindling population, attract new people to kind of build that economy even when they're not based there.

Kate Kendall: And I'd love to see places like Australia almost test that same model to attract more businesses and kind of independence here because they might not be able to even afford Australia. But there's parts of Australia that I think are really great with the business and access to things. So that's kind of happening as well. And a lot of people are moving across different places all the time and keeping to one tax residency. So it's kind of complicated, but I think that it's already happening. It will happen more and more and the world will become one global place.

Ross Dawson: Well, I can certainly hope so. And certainly every nation will benefit from attracting those people that do wander, that do have the global perspectives, that do have the talent and are choosing somewhere to hang out.

Kate Kendall: Definitely. And America has been one of the leaders in that, in the talent war for a while and it's great to see that that is kind of changing and other countries are now attracting top talent and with Australia as well it was part of a program that was bringing Australians who are based overseas for a while back to Australia to, kind of it's the anti brain drain as people were saying, and bringing back and bringing those experiences. So, I think that it's a great time to be in Australia as well.

Ross Dawson: If you're enjoying this episode, listen to the rest of the OFX series at

Ross Dawson: In the world of work, in terms of where people physically work, you mentioned co-working spaces which are growing rapidly. Do you think that we will shift out of offices while we start to see the big offices in central business districts empty out or will we move to co-working spaces, will we work from home? How do you think this will play out in terms of where we physically work?

Kate Kendall: I work out of a large co-working space on Collins street in Melbourne at the moment and it occupies all nine levels and there's offices for larger teams, there's offices for five person teams, there's hot desking and then there's even dedicated desks. So it really caters from that. You might just pop in for a few hours right through to you're building your team there. And corporates have tended to even buy coworking space memberships as ways to engage local communities, attract more talent and to offer that flexibility. So I think space, like these buildings that would have traditionally been massive corporations have now been divided up into co-working spaces that can cater to all business sizes. So I think offices are just changing in themselves, they'll still always be there, but it's how we use them that's evolving. A lot of people are also working on the road when they travel.

Kate Kendall: So Airbnb has options now that you can kind of look for work friendly spaces. And then people are also working from home and the internet is really, the speeds have improved. Although there are criticisms there, but I think that it has improved. Tools again, like Slack and Zoom have made it much more easier to connect remotely. A lot of work is now tracked and accountable online with project management software, task management. I always say it's really hard to hide online with your work and not be accountable because people can see what you're putting in Dropbox or Drive, what are you ticking off and things like that. So I think there's a greater transparency actually by working online and that leads into the less need to physically see someone work to know that they're working and that's driven the shift in the office spaces as well.

Kate Kendall: There are people working in cafes as well. There are blended cafes and co-working spaces, so it's really kind of shifted the whole office space, paradigms just changed.

Ross Dawson: In some senses, the future of business is becoming community, community of customers or communities of freelancers. Where do you see the role of community evolving?

Kate Kendall: I kind of go two ways on this because maybe if you would've asked me a year or two ago, I would have been yes, everything's moving towards community and organizations should be communities. And I agree that there is like an internal community aspect of the kind of talent and the engagement and the culture that is at play. But I've kind of tended to less think that now all organizations need to have a community. Sometimes just delivering a product in a very set, scalable, repeated marketing channel can be enough. Not everyone wants relationships with everything at any one time. And I think as the world's become a bit noisier, people have tended to choose less communities to have a deeper involvement with. And that's what really drew me to community in the first place. That it was around connecting and connecting deeply and building relationships. And so I think for me, community is really around that involvement and that those relationships and that impact and it has to be a really healthy community to be a true community

Ross Dawson: From where we are today and moving forward, what do you think of the fundamental technologies that are assisting this evolving, more fluid, global world of work?

Kate Kendall: It's kind of been a bit complicated with remote work because there's two schools of thought. There's the always on, what they call the green dot or the presence whenever you're on a messenger or Slack, it's set to on and continuous. So it's this kind of continuous communication that's done in real time. And there's pros and cons to that because obviously it helps with transparency and you know where someone is, even if they are remote. But then there's also this kind of impact of, it's like someone knocking on your office door every five seconds. I think that the true kind of remote work is when you can be based anywhere around the globe and work on different time zones and not rely on the kind of same continuous communication. It's much more disparate and it can be done asynchronously.

Kate Kendall: And companies like Buffer have been really trying to pioneer that. So they'll still have their old hands on, but they will not expect someone to kind of reply at all hours. And so that's one part where I worry about the future of tools. If they do, then end up taking more time and we are more connected and we're online at all hours. I think that's bad for boundaries and mental health of employees or workers as well. So then the tool, and then different tools that are kind of catered to those pathways. So there are project management tools that allow you to kind of work and be focused on what you're achieving without having the messaging aspect. But right now I think the tools that we're seeing a lot are all focused on messaging and people have them, sometimes they allow you to pro slack and then there're times where they need to kind of set a status to our way and go back to email. So the tools are catching up basically for the behavior.

Ross Dawson: Yeah. That's interesting. So, of course, this is not just about technology and while freelancers may readily be able to take to this world like ducks to water, in corporates it's a very different old way of working they've had. In a larger organization, how do you shift the culture to make remote working, not just acceptable, but just the way which things are done? How do larger organizations, more traditional organizations, shift to enable this new world of work?

Kate Kendall: Yeah. I think that it really does start with the CEO because if the CEO doesn't understand it and doesn't get it and the values aren't inherent in that CEO or that founder, it's really, really hard to change the whole culture of an organization. And organizations, in order to truly have their shift, they need to be really trusting and understand what it is to trust team mates. And not every organization has that and not every organization can have that. So I think if someone did want to make the shift first up, they really need to understand it. So it's not only just the CEO and the culture and the values, it's also who you hire. I'd say there's a different hiring process for someone who is going to be remote versus someone that is going to be in house.

Kate Kendall: And with remote, when I was hiring a lot of remote professionals, I'd really look for someone who is really self motivated. So one of the early criticisms to remote was, well, if you're working from home, are you just going to spend all your time doing laundry or whatever? And after a while, if you don't have any self discipline and you can't motivate yourself to get to work or you want to watch midday TV or any of that, I mean, you really aren't the right person to be working remotely in the first place. And this relates back to the broader conversation of us moving to that independent or that entrepreneurial mindset where we're responsible for motivating ourselves. And I think true leadership relates into this, which is leading people without having to manage them and say, do this, do that.

Kate Kendall: If we start moving to this self-driven, but collaborative model, then we can all kind of coach each other and have a bit more of a web network than just one person saying, okay, well, you've got to be here on the dot, you've got to be doing this and that. And I guess, and I think a lot of the younger workers are fine with that model. I think that education's changed, so people are kind of coming through realizing that it's more self learning now. So they're responsible for that and responsible for themselves at work and everything. So to me it's just you really need to hire those people and it's a slow change. It's hard to just kind of click your fingers and say, we're remote now. And you can have a combination as well. Start with some parts of the organization. So you might have your tech teams, they're able to work remotely, but then you might find that your sales team still want to work part of the time in an office and kind of motivate each other and compete to hit some goals.

Kate Kendall: So it also depends on the discipline, which is why it's great to have a variety of different spaces and setups.

Ross Dawson: As a society, what is it that we should be doing to push us more towards that positive future of work.

Kate Kendall: I often talk about the freelance economy and then the US it's the 1099 economy and you've seen a lot of on demand platforms be kind of criticized and even sued for the treatment of their communities, if you call them or the kind of workers. And I think that there's a huge opportunity to recreate what employment classification looks like as part of that. So I think it needs to be government led as well. We can't kind of go fully independent or fully remote and then lose a lot of the kind of things that made work protected. You may travel and be nomadic, you might not have superannuation or all of those things. So I think we need to look at work not only from allowing people to kind of pursue their passions and create their dream businesses, but also from a really macro perspective, what will this look like in 50 years' time? Especially as the population ages, new workers.

Kate Kendall: So, I think that's really important. So other parts of the future of work, I think it's just, it's such a kind of almost a broad statement. I tend to be a bit practical about it and look at the next few years as just how then can people create businesses and really stay at it as well. So if the, I do see a lot of freelancers that might start with the first year or two and then it gets difficult and they look for full time work as well. So it's about creating the tools and the services that can help everyone thrive if they do choose to work in a different manner or set up their own business. And then obviously companies need to really think about how to offer the benefits or the ways of working that people really want to seek.

Ross Dawson: Yes. So how about from an individual perspective? We've got to change your world of work. There's some new jobs, new skills and new capabilities to be able to work in this flexible manner. So what would you advise a person who is looking to create a prosperous work life moving forward in terms of any skills or capability that they should be approaching?

Kate Kendall: Yeah, I think they should almost create a business plan or a career plan for themselves and think of almost their skills as themselves as a product, that they are kind of marketing out there. So say if you were a marketer and then you did want to start your own business, you kind of have to look at your positioning. I mean we hear words like personal brand a lot now, the death of the resume, people are using LinkedIn and portfolios a lot more. So I think that a lot of the way that work gets connected and matched isn't through this traditional, you have a paper resume and you, or you have a pdf and you send it around to people and hope that you'll get picked out of hundreds. So I think it's really about understanding yourself as a product and what you offer and what value you offer as well.

Kate Kendall: I think people need to really look at what skills are most in demand and how to service those and provide value in that space. And then also ask themselves what they really want in life. They want more, if they're are a working parent, they may decide that, hey, I'm actually looking to optimize for flexibility over financial return and just kind of make a check list of the things that offer most. I often look at impact as well and mission. So I like to work or collaborate with mission driven organizations. And there's a lot of B Corps and people now that are looking at that social impact of what they do. And that's also a huge driver for millennials as well, with that impact and having a positive effect on the environment. It's really about understanding what people want and then working backwards and trying to create that from there with a place of a plan.

Ross Dawson: Absolutely. So Kate, you've shared with us some fantastic insights on the changing world of global citizenship and fluid work and what's coming next. So thank you so much for your time and your insights today, Kate.

Kate Kendall: No problem. Thank you so much for having me.

Ross Dawson: To find out more about how OFX is helping their customers move money around the world. Go to This podcast is presented by OFX and is a BBC StoryWorks commercial production.

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