Interview: Michael Youngblood on Starting Your Digital Nomad Journey and Building a Community Abroad

8 min readMay 11, 2022


Image provided by Michael Youngblood from Unsettled

Michael Youngblood is the CEO of Unsettled, a global experience company for creatives, entrepreneurs, and independent workers. They offer retreats and coworking experiences for digital nomads around the world.

Michael is also one of Remote’s top remote work influencers for 2022.

We spoke to Michael about digital nomadism after the pandemic, and how aspiring digital nomads can start their journey even if they’re currently working a 9 to 5 job.

What do you think of the way remote work has evolved over the last couple of years?

The trends behind remote work have been happening for the last 15 to 20 years. The pandemic was a great accelerator, but the infrastructure was already in place.

Millions of people got to work in this new way because of the pandemic. So it isn’t surprising to see this growth, the resources were already there.

Many businesses are embracing this revolution by letting their employees work remotely. Destinations around the world are beginning to embrace it too and releasing things like digital nomad visas and tax incentives to move to new places.

Millions of people are working remotely today that weren’t doing it two or three years ago so it is here to stay.

Perhaps people who are resistant to remote work still haven’t experienced it properly because of the pandemic…

There are lots and lots of people who have had exposure to it. A recent Airbnb report found that 20% of all bookings have been for a month or more. It’s not the easiest thing to do. It helps if you’re single if you don’t have a family if you don’t own an expensive home or even a home with a yard.

But for many people, it’s not easy to travel while working remotely.

Some businesses, especially internationally, are beginning to look the other way or don’t have a policy if you’re working from home or staying domestically within the country. But I think the more elements you add to it, the more complex it becomes. It’s just naturally not that easy for everyone.

But there is still a segment of the population that will be combining work and international travel. And that’s not to overlook the major opportunities like domestic travel and regional travel.

Now that remote work is becoming more mainstream, what tips do you have for employees who may wish to become digital nomads?

Firstly, a lot of digital nomads are either self-employed or freelancers. So if this is something you want the freedom and flexibility to do, sit down and think, can you go freelance at this point in your career? What are the pros and cons of that? How might you do that? Can you just move from a full-time employee to a contractor role?

I would have people reflect personally on that question.

But in terms of getting your manager’s approval, it’s a conversation. I would say, sit down and think to yourself, what’s important to your manager right now and what’s important to you right now. Can you find a middle ground?

Then, my suggestion would be to find a location that is within a similar time zone. If you’re in Central Europe, maybe you go down to the Mediterranean, for example. But think about the time zone.

Secondly, I would make it really clear that it’s temporary, that it isn’t a full-time move. I think a lot of managers get nervous about the duration of travel and tax implications. But if it’s a more temporary trip, that’s going to ease the burden.

Then, it’s really important to make a compelling case. Have you built up trust with the organization? Maybe you’ve worked effectively throughout the pandemic? How are you going to continue to do that?

You could also position it as an experiment. Maybe you’ll take two weeks vacation in South Africa, and you could ask if you could extend it and work from there for a week or two. You could say something like, ‘I just want to see if you’d be okay with me working from abroad for a week or two around my vacation?’

Then lay out your plan, so for instance, are you renting a villa, or joining a co-working space? The more you show you’ve got a plan, the more your manager is likely to say, yeah, let’s give it a shot.

Also, I would say go to a single destination for a longer period of time. Digital nomadism often implies that you’re nomadic and you’re moving constantly, but when you move, you have to book plane tickets, search for hotels, set up Wi-Fi, find good places to work, and figure out where to eat. That’s a full-time job in itself anytime you switch locations.

So I would say, pick one destination and make that case to your manager.

Lastly, if there’s a health reason for doing this, then mention that as well. If you’re feeling burned out, tell them this is a way to recharge. Even something as simple as, ‘this is for my mental health, or my social health, or my physical wellbeing, so it is important to me that I do this.’

If someone is interested in a nomadic co-working experience, what are the first steps they should take to make it happen?

I would recommend just doing a Google search for co-working retreats to see what’s out there. Obviously, I think Unsettled is the best for a whole host of reasons.

But I would say they should do their research and maybe find two or three organizations that offer these experiences. It’s important to look at their audience as well, in particular the age and professional background of their audience. When you go on these trips, a major benefit is who you meet and how they end up impacting your life either as a friend or a contact in your professional network.

It’s also important to look at what’s included in the package. At Unsettled, we’re happy to answer any questions, so just reach out. We’re friendly. There are real humans behind the website.

So just come up with your questions and some information like where you want to go, when you want to go, and why you want to go, and share that with us in an email and we’ll get back to you.

How do you build community as a digital nomad?

It can be hard. I think a lot of digital nomads actually struggle with this, whether they admit it or not. People who are living this lifestyle are already very independent individuals, maybe fiercely so.

They’ve decided they’re going to make changes to their career so they can prioritize their personal travel at least as much as the team they work with. It takes a very strong individual to do that.

I think they also get out there and realize it’s very lonely. I would say, before you even start talking about apps or destinations, travel is an easy way to meet people. You just have to be willing to do so. You have to be willing to walk up to a stranger in the coworking space and strike up a conversation.

And you have to keep doing that.

Secondly, I would look for communities. There are a lot of communities out there for travellers and digital nomads. Look at the Facebook groups, consider travelling with an organization like ours that creates a community.

Also, start looking for local events. There are always events going on at digital nomad hotspots. So look for those events and be willing to pay for a tour that an organization is putting on, or be willing to pay for a dinner party that’s being hosted.

What are some of the benefits of a digital nomad experience? What do people take away during these trips?

I think people just feel that they are where they are supposed to be in life. When you get out there, you a make a decision, and you’re combining travel and work, you achieve this contentment.

And that’s a hard feeling to feel. I don’t feel it all the time for sure. I feel happy when I’m out there travelling.

I also think there’s a lot of stress involved. Travel can be stressful. I run a travel company, but I still get stressed when I get on an international flight to a destination I’m not familiar with. When I walk out of the airport, there are things to consider like, am I going to get an Uber, am I going to get ripped off by the taxi guy? Is it safe for me to be walking around at night in the neighbourhood where my hotel is?

There are very stressful things to deal with. But this comes with all types of feelings and experiences. I think these experiences make us stronger and more grateful. You have to have the down moments to have the high moments.

What are the top three destinations in terms of community for digital nomads?

Portugal has a very large and thriving digital nomad community, partially because of tax incentives and the price of living there. Even if you only go for a week, you can tap into that nomad community.

Bali has traditionally been one of the big ones. It’s always a great destination, but do check time zones before you go and make sure it works. It’s easy to find international communities of ex-pats there.

India is another one, where you’ll find a community of travellers and remote workers.

But really, anywhere you want to go, there are probably other people who are there as well and working remotely. It’s just a matter of doing research and finding them.

Where do you see remote work in the next five years?

I think over the next five years, we will see employers and startups provide a community for remote workers. That applies across the board, whether you’re a digital nomad or you’re working at home five days a week and your office is 10 kilometres away.

I think employers are going to look for ways to build community, whether that’s virtually or through a flexible plan where you come into the office one or two days a week.

This community building will be at the forefront, and we see it everywhere. We see it in the way hotels are designing experiences and creating apps for their customers and members to find each other.

There are absolutely going to be more travellers working remotely, but I think we’re really going to see this renaissance period around community building as a result.

‍ReadyTal connects companies with the best remote software developers around the world. Our candidates come from more than 60 countries and have passed robust language and technical assessments. If you’re looking for talent, get started here.




ReadyTal matches software developers with remote jobs around the world. We champion remote work through everything we do.