Jonathan Kalan shares insights from creating and running Unsettled, one of the leading nomadic travel programs.

Science shows there are neurological benefits to blowing our own minds on a consistent basis and that, conversely, failing to do so causes brain atrophy.

Jonathan Kalan joins us today from Unsettled, a semi-structured retreat program with activities co-created by its participants designed to inspire and cultivate personal and professional growth. Jonathan was a photojournalist in a past life exposed to different perspectives in his coverage of events around the world and felt compelled to develop a platform that would help others gain perspective from traveling. In this interview Jonathan shares what it was like going through the TED Residency program in the early days of Unsettled, the value of diversity amongst their program participants, how their retreats work, who they’re best suited for and his take on the future of the nomadic travel space. Enjoy!

Show Notes

Time   Topic
0:02:37   What is Unsettled?
0:04:14   The philosophy of co-creation where the participants create the curriculum
0:06:50   It’s about giving people time & space to break out of their routine and create something together
0:07:05   What’s the origin story of Unsettled?
0:10:13   The TED Residency incubated Unsettled over a 3-month program
0:11:01   What does the statement “there is no truth” mean?
0:14:49   What’s your big idea worth spreading from that TED Talk?
0:15:46   Ways to continually push your boundaries and challenge your world view without traveling
0:16:39   Be Unsettled: embracing discomfort as a catalyst for how we change as humans
0:18:32   What kind of traits does this type of lifestyle engender?
0:19:57   On the dangers of dopamine addiction of constant stimulation from hyper-mobility
0:21:58   Who is Unsettled for?
0:24:26   Value of diversity “only 40% of our participants are from North America”
0:25:27   How does Unsettled fit in within the landscape of nomadic travel programs?
0:27:23   The value of curriculum co-created by participants
0:28:33   Can you talk about how the retreats actually work?
0:30:00   Do you have communications infrastructure for alumni to keep connected after the program?
0:31:22   What if anything can you share from your roadmap? Where do you see this going?
0:33:26   Have we hit peak nomadism or do you see this space only growing from here?
0:36:19   Are you proactively doing things to develop the diversity you have or is that just coming on its own?
0:37:13   Anything you read or listen to on a regular basis?
0:38:13   Any travel hacks you can share?
0:39:08   Any mobile apps you recommend?
0:40:46   “What’s actually holding you back and what’s the worst that can happen?”
0:42:08   Who is this not for?


Unsettled website
No such thing as a fish podcast
New York Times The Daily podcast



Image 1 of 17


Speaker 1 – 00:00 – Nomad, nomad, nomad podcast.

Sean Tierney – 00:21 – How do you know what you know? Is there a such thing as a single truth or does everyone just experienced the world in his or her own reality and what can we do to constantly blow our own minds and push ourselves outside of our comfort zone to see the world from multiple perspectives? These are the questions we’ll explore today with guest Jonathan Kalan, cofounder of Unsettled a travel platform that emphasizes cocreation of experiences by him for its participants in a former life. Jonathan was a photo journalist exposed to many perspectives and atrocities and it was driven to create a platform that would help others gain the perspective of experiencing multiple truths firsthand. We’ll talk about what it was like going through the Ted talk, a residency incubator program. Uh, this was a springboard for Unsettled early on the dangers of the dopamine addiction that comes with a constantly seeking novel simplicity of stimulation from hypermobility.

Sean Tierney – 01:18 – We’ll talk about how to constantly push your boundaries, change perspectives without leaving your own city. Ways to do that. The traits that the nomadic lifestyle tends to foster and much, much more. Jonathan is a very well spoken, just neat individual, so without further ado, here is my conversation with Jonathan Kalan of Unsettled. Nomad Podcast is supported in part by nomad prep, an online academy that teaches you everything you need to know to take your job on the road and crush it abroad. Enroll today at nomad, and get your first four days of training completely free. Nomad prep. Take your job on the road and take on the world. All right. Welcome Jonathan Kalan to the podcast.

Jonathan Kalan – 02:01 – Thank you very much. Great to meet you.

Sean Tierney – 02:03 – Me too. You now you are the CEO of Unsettled.

Jonathan Kalan – 02:08 – That’s correct.

Sean Tierney – 02:10 – And so I heard you describe it at one point on one of the interviews as a. was it study abroad for adults? I guess that’s kind of the elevator pitch. It’s the longer form explanation of what Unsettled is.

Jonathan Kalan – 02:22 – That’s a great question. There’s a lot of ways to describe what we do and I think it’s, um, it’s almost a good problem to have because it means we’re doing something a little bit differently. So, no, I think conventionally in the easiest way to describe what unsettled does is we run two weekend 30 day coworking, uh, treats professionals, towards creatives and people who are going through, we’re seeking to go through kind of professional transition in incredible destinations all over the world. So, um, you know, why we call it in some ways to study abroad for adults as an enough worker, as somebody who, who is an entrepreneur who works in the creative sector. Um, I think it, as you move along in your career, you sort of have less and less opportunities to actually dive into experiences, allow you to meet new people that allow you to challenge yourself, to allow you to get perspective in a way that is beyond just, let’s say backpacking through a country.

Jonathan Kalan – 03:16 – Um, and so, you know, we looked at unsettled. It’s really a shared experience about the people just sort of like a study abroad, you know, in your early twenties, um, because we provide freedom and flexibility to do what you want, right? We don’t have a guided program, a structured program. We are very designed and what we do and we take a very experienced designer lens to every experience that we run, but it is something that has this interesting mix between structured, um, you know, for a longer period of time, two weeks or a month in these places is. So. Yeah, I mean that’s, I think the easiest way to describe it or maybe the catchy way to describe it. It’s a lot of depth and sort of how we do what we do.

Sean Tierney – 03:56 – Yeah, for sure. It was on your site, you say cocreation is important to you guys. So it sounds like this is a program where it’s truly the people that come onto our half the curriculum, like they can bring their own skill sets and teach a course on whatever, but it’s really created by the members it sounds like.

Jonathan Kalan – 04:14 – Absolutely. Yeah. This is, I think a philosophy that we have to travel and communication in general is that, you know, people don’t just want to be passive consumers of an experience. Especially, I think the kinds of people that go on Unsettled, the kinds of people who tend to went to work and travel and, and who are looking for more, have there been experiences abroad is that they’re not seeking to be passive consumers. They want to be active creators, right? They want to go somewhere and be a part of a community, contribute to a place, contribute to others’ experiences. Um, sort of like a choose your own adventure, right? They don’t want to be told what to do. They want to create an experience around what they’re seeking out of that. And so, um, you know, we take that approach to how we design experiences. You know, we do have different workshops, events and programming that we run, some core ones that are for us that are around how do we build community over this period of two weeks or a month. I mean, we encourage participation. How do we help people achieve their goals, keep themselves accountable and connect people around things that they’re interested in doing or exploring over the two weeks or the month.

Jonathan Kalan – 05:17 – But it’s all designed around, you know, what do you have to give them, what do you want to learn? And so everybody’s coming from unique backgrounds, like you said, we’ve had farmers, CEOs, designers, developers, people from 70 countries around the world and all ages, all have a different set of experiences and backgrounds to share in our, I think most of the product platform for that to joe and to run an experience that is designed around, you know, each participant being able to, I think live the best version of themselves, contribute to the community in the way that they want to and get what they want from that experience. Um, and that’s designed around obviously the people that are on the experience, about 15 to 20 people is designed around the people in the location. So people in Buenos Aires, Bali or Cape Town is designed around the place itself and what that place has to offer. So what is it the Bali has to offer that’s different than Cape Town. It’s different than Morocco. And then obviously the purpose, which is what are people seeking out of this experience, right?

Jonathan Kalan – 06:15 – Is it growth? Is it time to start, is it time to finish something? Is it time to get something off the ground? Is it time to take stock of what you’ve been working on, where you’ve been and what you want to do over the next five, 10, 15 years of your career? So, you know, I think when you bring those together and truly about giving people time and space to break out of their routine but then create something together and as a result in the end, it’s completely different for the last one. You know, we never have the same experience as a result of just the way we designed it.

Sean Tierney – 06:46 – That’s pretty awesome. Can you talk about the origin story? Like what, what were you doing for this? I know I saw you were a photo journalist for awhile. We’re like, what? What compelled you to start this company?

Jonathan Kalan – 06:56 – Yes. So, so I was a photo journalist for a long time and journalist as well. I was based in Africa and the Middle East and you know, for most of my twenties I actually never had a office job. Right. I had never had to go in nine to five and work in a single space. I’d always been working remotely working for myself, freelancing and it’s an incredible lifestyle and I think having the freedom to choose and having the freedom to live that life and decided you know, where you want to go and what you want to work on, it is. It’s an incredible privilege and an incredible luxury. I think for me, it’s sort of a double edge sword, right? The ability to choose to live anywhere that you want to live and work from anywhere that you want to work is both exhilarating and can also be lonely.

Jonathan Kalan – 07:42 – Right? I think a lot of people who may be listening to this podcast are, you know, a lot of people that, um, you know, sign up for Unsettled or these other programs. I sort of reached a point where, you know, it’s amazing to have this global network, but unless you actually see them and spend time with them, like how are you driving meaning from those relationships and how those relationships actually adding value to your license. So, um, myself and my co founder, Michael, we, he had kind of a similar backstory. He was an editor. He worked for MIT for four years running a publication for them but never stepped foot on the MIT campus in Boston. So, um, we actually started by organizing a sailing trip for about 30 of our friends and it was just chance to kind of totally unplug, not work related, um, and was a way for us to really just connect, you know, get together, have a great time. And I think through that week it was, I think one of the most inspiring weeks of my life because the depth of conversations about work life, love, spirituality, everything in between.

Jonathan Kalan – 08:42 – We have that space to really dive in and you think it’s a pretty contained space. You know, we had four boats, each is about eight people in the square meterage of it, but you’re tiny and you’re stuffed in there and it’s a pretty experience. But let’s do that. You build really strong relationships. And so a lot of us on that trip started thinking about, well, how can we, how can we put an blend this into our lives more often, right? Why do we have to go sailing for a week? Why can’t we go and actually bringing our work selves with us and be productive and carry on these types of conversations, these ideas, this room inspiration we’re getting from each other in this exchange. And so we, um, we started running a couple of experiments with friends and you know, about, uh, about two years after we kind of ran that first sailing troopers when we lost on several full time. And uh, so we went into the Ted residency and kind of started picking things up and about mid 2016.

Sean Tierney – 09:33 – So was the Ted residency. So you had the idea for this and then the Ted residency followed that. And then the talk that I saw was basically you guys already had this idea in motion at that point?

Jonathan Kalan – 09:43 – Yeah, exactly. So we applied to the Ted residency with Unsettled this sort of our project to be incubated and you know, it was an incredible experience. And if anybody has the opportunity to apply for it, I highly recommend it. It’s an amazing group, amazing support network. Um, you know, we’re, we’re the first class, so we were very much an experiment for them on how they build community and incubate community, you know, over a three month period in their office. And so, um, yeah, it was a great way to meet really interesting people to challenge ourselves to have the support of Ted and to test out some of the ideas we had for kind of designing experiences and building community with this really global community of people who were at Ted. So it kind of served as an incubator for us. The way that we think of community and the way that we built out Unsettled from there.

Sean Tierney – 10:30 – Yeah. So if you’re listening or watching, I highly recommend you check out his ted talk. It’s only like six minutes long, but it’s really, it’s brilliantly done. And you said something in it that I want to touch on and you said, uh, or the whole thing was called the power of privilege. But you said there is no true like you made the statement that there is no truth, which is a bold thing to say, but I agree with you and can you unpack that a little bit and explain to people listening? What does that mean?

Jonathan Kalan – 10:54 – Yeah. I think in the world of fake news and just watching the series a, the fourth estate and a lot of the ideas, you know, sort of where it is truth lie and that was pretty present. And so, um, for me, the idea that there is no truth just comes to everything is perspective. Um, you know, our realities are formed by the perspective is that we have and by the situations that we grew up in, and I think, you know, oftentimes it’s really only through seeing the world through somebody else’s eyes and being able to understand, you know, what they’ve been through and what they’ve gone through. I mean something as simple as just being able to be empathetic to what their experience is. Um, you know, there is so many competing ideologies and thoughts and ideas and perspectives and realities in the world that I think, you know, yes, some things are fundamentally true.

Jonathan Kalan – 11:46 – Like this table is, would, you know, this wall is white, um, but, um, somebody may be color blind and that maybe this isn’t white or maybe this isn’t proud or maybe this isn’t a gray, you know, and I think to understand where people are coming from to understand what they’re looking at and understand how they view the world is really understand how we can exist in coexistence as humans. And so I think the talk was tied around how privilege is the ability to sort of see multiple perspectives to experience multiple realities for me to be able to embed myself in the midst of a revolution in Egypt and understand what people are going through. Not completely, but at least see it through their eyes and to understand that, you know, if I was in their situation, would I view things differently? Um, you know, as a Westerner who grew up in a democratic city, I was taught to believe that democracy is right. But living other places, some people think that democracy is not the best way. Right. And so it’s, it’s about how do we challenge our assumptions and use that to understand other people’s realities.

Jonathan Kalan – 12:46 – And I think travel is, is one way to do that. Um, I think it is one way to understand what privileges we have and what privileges we don’t. Um, and so yeah, it’s, it’s a, it’s a lot sort of unpacked within that, but it is an exploration of how privileged truth and perspective is sort of tied together.

Sean Tierney – 13:06 – Yeah. It reminds me a lot. I don’t know if you’ve seen this clip, but there’s somewhere a clip. It’s like a five minute clip with an ex CIA agent and she’s talking about, you know, how she oversees talks to these people and she’s saying like, you realize from their perspective, like all these movies that we grew up with, Star Wars and Independence Day and like the rebel up against the big empire. She says, you realize to these people we are that evil empire and it’s purely a matter of perspective.

Ex CIA Agent – 13:35 – He said, is it to us to the rest of the world, you are the empire and we are Luke and Han. You were the aliens and where Will Smith? But the truth is, when you talk to the people who are really fighting on the ground, on both sides, and ask them why they’re there, they answer with hopes for their children specific policies that they think are cruel or unfair, and while it may be easier to dismiss your enemy as evil, hearing them out on policy concerns is actually an amazing thing because as long as your enemy is a subhuman psychopath, that’s going to attack you no matter what you do, this never ends. But if your enemy is a policy, however complicated, that we can work with.

Sean Tierney – 14:24 – Um, so I guess what’s the ask of that Ted talk? Like what, what was the, uh, what did you want people to do differently who are listening to that Ted talk

Jonathan Kalan – 14:34 – that’s your big idea, worth spreading and think it’s seek the difference in life. For me, I’ve always sought to take a different path or to challenge myself. So for me, the call to action of that really is what can you do to challenge your perspective, right? What can you do on a daily basis, on a monthly basis, on a yearly basis to continue to push yourself outside of your comfort zone and see things differently, to be able to understand how other people view this world and whether that’s simply on a daily basis reading a conservative newspaper, if you’re really reading liberal newspaper, if you’re conservative or if it’s traveling to a place you know, solo to really understand and immerse yourself in it in a new culture environment. If it’s, you know, there’s small actions that you can take, um, you know, not just big actions like quitting your job and traveling the world and trying to understand all the cultures in the world. They’re never going to accomplish that. But there’s certain things that you can do to continually push your boundaries and challenge your worldview.

Jonathan Kalan – 15:33 – And I think the idea is that when those opportunities come up, take them right. Somebody invites you to dinner that may be different from you, that you may have not had an experience with their community or understanding and they want you to join the family, take it, you know, go. Um, those sort of opportunities I think come more often when you’re traveling, but even in your daily routine, I think there’s ways to incorporate that in. And if you live in a big city like New York, I mean there’s a ton of communities here. There’s so many ways to engage with people who may view the world differently than you see things differently than you. If only you take those opportunities, I think you will have a greater understanding of the world that we live in.

Sean Tierney – 16:11 – Yeah. Well I like that it’s baked into the name itself. Be unsettled, right? Like it’s almost like this positive discomfort we talked about in another episode, but it’s this notion that the discomfort is good. Like putting yourself in uncomfortable situations because that’s how we grow. Right?

Jonathan Kalan – 16:27 – Absolutely. Yeah. And the name is, you know, we chose it intentionally. Provocative name was unsettled because it is about turning something that is often perceived as a negative and translating into a positive and saying that, listen, we’ve felt unsettled in our lives at some point. We’ve all felt that feeling of something’s not right here. I’m not comfortable. How can you own that? Embrace that and say that’s a good thing, right? That is actually a catalyst for how we grow. That is a catalyst for how we change and how we evolve as humans and I think in the world that we live in today where change is happening so, so quickly, right? On a technological basis, on a social basis, on a political basis, on a, on a professional basis, right? We sort of always are being demanded to be at the top of art game and so I’m being unsettled to me is about being able to embrace that idea of uncertainty and embrace that idea of not knowing and embracing that idea that you know, things are going to change, so where can I take ownership of that, of that change, right?

Jonathan Kalan – 17:26 – We’re going to take ownership of how I change or how I adapt to that change and it starts with just making yourself uncomfortable over and over and over again to understand your own internal process of how you deal with uncertainty and change.

Sean Tierney – 17:41 – I’m glad you bring this up because I’ve always had this thought and we talked about it again in a different episode, but that we get basically tested on the road, like the all things being equal. If you had two people and you have one person who’s got a nomadic existence and one person who’s got the sedentary existence, that person has just continuously faced with these little challenges every day of things that they don’t know. They don’t know that if they build like, I dunno, it’s like doing pushups for resilience or skill training. You know, there’s, there’s some, uh, what, what other traits. Yeah, that’s maybe a better question. Like what traits do you think that this type of lifestyle in genders and people.

Jonathan Kalan – 18:18 – I love that I was going to say, resilience. You nailed it. Is building resilience. Um, you know, I think in the economy today, I’m just speaking from a professional perspective, it’s being able to understand the global economy, being able to be adaptable to different situations and environments and having that sort of flexibility and, and exercising that muscle of, you know, how do I adapt to change, right? With any industry that are changing incredibly rapidly and I think the travel and living and working remotely and sort of living this nomadic lifestyle I think prepares you for that. I’m far more than just staying in one place. Um, I think it on a converse, I think it can also maybe subtract from other parts of, of the human experience that can be essential building relationships and how to sustain relationships. If you’re moving from one place to the next all the time, you can sort of potentially build that patterns and habits of um, you know, sort of fleeting relationships and loose ties and loose connections

Jonathan Kalan – 19:17 – and I think actually hurt us internally and sort of why on certain focuses so much on building community and building really strong community of that period of months so that you can then stay connected and kind of move all over the world with these people, which does happen. But um, you know, I think it does exercise those muscles of resilience and it does also maybe feed into tendencies of avoidance score of I’m kind of hyper mobility that you have to just be aware of. And I think it’s always a sort of conscious understanding of what am I doing, why am I doing it? What am I hoping to get out of this? And you know, I asked that myself to myself every single month, right? When I’m traveling and I’m working, I sit and be intentional about fuel. Where am I going this month and why am I going there? Right? What am I hoping to get out of that as opposed to just drifting through life? Just trying to experience as much as I can.

Sean Tierney – 20:08 – Yeah, definitely. So I went through Remote Year and I can definitely testify, I mean 99% the best thing I’ve ever done, but the negatives would be we set the bar for stimulation so high and you’re just like the amount of stimuli you get when you, if you’re, if you go back to a normal, you know, sedentary existence, you just feel like just so under stimulated, you know, like there’s not like

Jonathan Kalan – 20:32 – It’s like taking ecstasy, right? You’re like, oh my God, that’s incredible. Oh, this is reality. Well, how do I get back up there again? And I think, you know, travel and adventure and it builds this from Tokyo, you know? But how do you balance that with something that’s more sustainable and more long lasting? Right. I think you’d probably agree that most long lasting thing out of your experience was the people that you met and the relationships that you’ve formed and those probably continued to this day and you’re meeting up with them all over the world. And so, you know, that’s what we find as well, is that there’s this isolated experience that is this incredible blast of inspiration, of excitement, of exploration, of experimentation. Um, but then when that’s done, you need something that continues. I think the relationships and how you build community after an experience is actually sort of the long lasting value of how you carry that on, into your daily lives. Whether it was the mindset that you had, whether it was the routines that you changed or the things that you explored during that intentional sort of period of working and traveling or experiencing. Um, the people are the ones who help you carry that forward.

Sean Tierney – 21:40 – Well, so people who, who is this for, we’ve got, let’s say there’s people already on the road, nomads who have been doing this for awhile. And then you’ve got people who are listening maybe who are thinking about trying the location independent lifestyle. Do you cater to both groups or who? Who, who’s the ideal candidate for you guys?

Jonathan Kalan – 21:56 – Yeah, that’s a really good question because we do have a really diverse community and part of that is by design. So I would say roughly one way to break it out is about a third of participants on unsettled. Let people who are entrepreneurs, freelancers, yeah, CEOs, consultants, people who either are living this lifestyle already or have the ability to kind of have this freedom and flexibility built into the lives and unsettled kind of fits a specific need for I really want to explore this place. I want to do it with a group of people that’s going to challenge me and help me grow. And um, so that’s about a third. I think another third are people who may have more traditional corporate jobs and are taking a sort of semi structured sabbatical or they maybe run their own company and have sort of just gotten the time and space to be able to take an experience like this. You know, it may be reached two years, three years of their company and say great, like I can finally kind of work remotely for a little bit.

Jonathan Kalan – 22:52 – Um, and then the final third I would say are people who are really looking for a more structured sabbatical, right. There are people who’ve quit their job, who are in a major, you know, intentional career transition where maybe they’re thinking about going back to school and maybe they’re back in school and studying and they look at, at the time with Unsettled as being a space to think about those next steps to be productive in a way other than just sitting out on a laptop and granting out for six, seven hours a day. Um, they look at it more as a space to find clarity, to develop new ideas, to meet people who are gonna, inspire them. And I think, you know, we bring those groups together and it. And it works really well because, you know, you’re not just all sorts of entrepreneurs working on an idea. You know, you’re not just all people who are in transition and asking big questions. But it’s actually that the sort of compliments and mixing of ideas between the two that really I think the challenges people to grow.

Sean Tierney – 23:46 – Yeah. Well definitely the diversity. Again, speaking only from what I know I’ve never done Unsettled, but uh, that diversity of age of backgrounds, cultures, that was, it would not have been the same experience for our group on Remote Year. We’re were that not the case. And so I’m glad to hear that you guys purposely try to mix it up like that.

Jonathan Kalan – 24:03 – Yeah. People find this surprising. Is that only 40% of our participants in North American? Right? So we have about 60% from Africa, Asia and Middle East, South America. Great. You’re up. Um, and, and that’s, you know, part of it intentional and part of it is just, I think we stumbled upon a need that is far more global than just, you know, you’re burnt out corporate executive in New York or you know, you’re a remote worker from the Netherlands. So I think um, you know, we’ve intentionally kind of curated that and it adds a lot to the experience of having that diversity of age where most people assume again that this is something for people who are in their early twenties. Our average age is about 35, so we do spend quite older I think than the average that is because people are looking for sort of more of an intentional travel experience. They’re not looking to party, although we do have a good time, they looking for something that’s going to add more value to their, to their career in their lives at that stage. So yeah, we’ve had people from like 1974 and everything in between.

Jonathan Kalan – 25:06 – Well, it’s a good segway because my next question was going to be how do you guys differentiate. I mean there’s a, there’s a whole landscape now out there, these kind of programs, but you guys, I would argue Rome Wifi Tribe Remote Year. Those are the ones that I kind of think of in terms of like the upper echelon. How do you position yourself against those and someone looking at all those. Why would, why would this be appealing for them? Why? Why is unsettled? Who’s it right for you?

Jonathan Kalan – 25:33 – Sure. I mean, all those guys, Remote Year Hacker’s paradise, they’re all. I mean, I think running great companies doing amazing things. I think they all fit into the market and it needs a little bit differently. I mean, Rome is really a housing provider. Remote Year is for promote the, around the world and promote job I think where Unsettled comes in is you know, we’re really that place that gives you time, space and structure to break out of your routine and get inspired, right? It’s not just about working remotely, right? It’s about going to a place and exploring with, you know, an intentional group that is, I’m looking for a meaningful experience, looking for a community that’s going to challenge them and inspire them and looking for something that is, um, a bit more than just I’m going to go and work and travel. Right? It’s why we spend so much time on designing experiences and cocreating experiences.

Jonathan Kalan – 26:24 – So I would say the differentiator is if you want an experience that is going to give you an active role in that experience. If you’re looking for something that’s going to be a catalyst for conversation or change, I’m Unsettled is, is I think a stronger fit than maybe a program that is just designed around, you know, working remotely and traveling. So it comes down to the community, it comes down to diversity and it comes down to just how we connect participants and you know, I think the best thing is actually to speak to our alumni and let them speak to them themselves because they can say it so many more words than so many, so much more stronger words that I could about what that experience actually means.

Sean Tierney – 27:05 – And hearing you describe it, it reminds me almost of. Have you ever heard of bar camp? Like the unconference was their thing that

Jonathan Kalan – 27:12 – I’ve heard of it.

Sean Tierney – 27:13 – It’s this notion of like a self created conference where you show up and people kind of gravitate to groups and someone says, Oh, I’m going to lead a talk on this. And so that like, it’s very like emergent behavior in a conference versus like this is the agenda and these are the talks that are doing,

Jonathan Kalan – 27:28 – It requires you to show up with unsettled, like you have to show up and you can show up however you want. You can attend everything that we do. You can not attend everything that we do. You can make family style dinner on Monday night so you could just kind of sit there and hang out and enjoy the conversation in any food somebody else makes for you. It’s entirely your choice. And I think that’s the beauty of the experience that we curate and how we, how we run our programs. And so, um, you know, it is a bit, is a bit different, but it’s something that we, this is what people are looking for. At least the people come on Unsettled

Sean Tierney – 28:01 – and you do. So these retreats and so that it’s multiple months in the same location. It’s not like boom, boom, boom, boom. It’s like you go for. Or you can go for up to like three months in a location. Or can you talk a little bit about how it actually works?

Jonathan Kalan – 28:15 – Yeah. So we, we, we have, there’s two programs right now. One is sort of just one month and one is two weeks. So we have some destinations that run for a month, some that run for just for two weeks or people who really can’t quit your job or can work remotely full time. Um, and so, you know, we’ll be in one location for maybe six to eight months out of the year. So Buenos Aires for example, you know, we ran three months in a row, but most times it was just a whole new set of participants each month. So a lot of people, most people come for just one month or just one, two week experience and then they come back maybe a couple months later for another trick or another destination. Um, you know, there’s no requirement is signing up for x number of experiences. Um, you know, we get a lot of alumni who, who do come back and join either our sort of month long trips. Again, we also run a week long adventure trips for alumni. So we do a big sailing trip every year, kind of in honor of our, how we started, you know, we’re running one later this year in Thailand

Jonathan Kalan – 29:14 – and so, you know, we’re offering a lot of um, like community, but sort of flexibility to pick and choose and say great, I want to be in Buenos Aires in April and then maybe I’ll be in Barcelona in June and then maybe I want to go to Cape Town in November. Um, you know, we get peoples who fully agency and flexibility to choose the months that they want to sign up for one month, sign up for five months. It’s entirely up to them.

Sean Tierney – 29:37 – Those people have a method like through you guys to stay in touch or is, do they just like develop Whatsapp groups amongst their own or do you guys actually have infrastructure for them to keep in contact?

Jonathan Kalan – 29:47 – Yeah, we’ve been building infrastructure. We have about just over a thousand alumni around the world now. And so we, Whatsapp is obviously very strong communication for it, for the retreat itself. So kind of post retreat, how they stay in touch. And then we built some internal systems, Facebook groups and other things that we’ve built out to keep connected and then sort of running more events in different cities and just finding ways. And actually to be honest, most of it has happened organically, so I would say any given week there’s four to five alumni meet ups happening around the world that we’ve had absolutely no pardon, we haven’t aligned who’s I think got 11 or 10 people from on Bali trip, um, to join her on a safari in Tanzania later this year. So these kinds of things are happening really organically and we’re sort of trying to add some structures to support people but not obviously take control of it because we worked a lot of communities and seeing how they grow. And for us it’s important to understand what people are looking for first before you come in and say, here’s what you need.

Sean Tierney – 30:49 – Got It. So it’s ala carte monthly or, or two weeks. Um, come and go as you choose, find a new program, stay in touch with people when you’re developing the infrastructure to really melded the community together. That’s awesome. Where do you guys see this going? Like if you’re what you’re able to share, like where, what’s your roadmap with this thing? Do you, what do you envision?

Jonathan Kalan – 31:14 – I’ll try to keep it simple as possible. You know, we look at living Unsettled as not just a month, a week, a day, a moment. It’s a way of. It’s a philosophy, right? It’s an approach to life like we talked about before, you know, how can you live on, settled in every moment and take the choice that allows you to embrace uncertainty and embrace the unknown it. So how do we integrate that into people’s lives and make it more accessible? I think everybody is looking for some elements of unsettled and as we grow it, I think, you know, we’re going to continue running incredible month long experiences and incredible two week long experiences. We’re going to expand the number of destinations that we run. I think we’re going to diversify the kinds of experiences that we run and just always seek to improve what we do. You know, our, our vision is to really run world class experiences for that. That help people live more boldly in every moment and I think in doing that we’re constantly discovering what people are looking for and reacting to that as our community grows,

Jonathan Kalan – 32:13 – we’re looking to serve our community and say what else can we do for this group, for those looking for experience, challenge them and so, you know, we’re keeping an eye on I think just the entire space and market and what people are interested in when it comes to travel and work and this lifestyle. But also, you know, as we grow a community, being responsive to their needs and what they’re looking for and how we support them as they grow. You know, I wouldn’t be surprised in two years or three years from now that unsettled has, you know, 20,000 people, 30,000 people around the world who’ve been a part of our experiences, if not many more.

Sean Tierney – 32:48 – I was going to ask you the space itself, it’s like the other day, I understand we roam a, they actually folded from what I understand, but then you’ve got like we work that has an $8 billion in funding or something like with a b, 8 billion that they’ve raised. So you got these kinds of, like different views on the space. I mean, it seems like it could be huge. Uh, have we hit peak nomadism or do you see this thing going, like only more and more people going location independent?

Jonathan Kalan – 33:15 – That’s a great question. Um, I don’t think we’ve hit peak nomadism. I think it’s, it’s such a combination of factors and things happening right now, whether it’s the devolution of the workplace, it’s allowing people to live this lifestyle, whether it’s the ease of travel that’s allowing people to just pick up and go across the world and you know, a day’s notice. I think all of these things are opening up more opportunities. And so I think you’ll see the industry develop in a way that serves different needs. You know, we work towards a very specific need office space. They’re really good at creating office space and experiences around office space and you know, their growth is very much tied to the sort of small team or independent worker all over the world who needs a place to work for us for catering to people who were seeking experiential travel and who want to combine the professional, limited their life with travel. Other programs are seeking more like a specific professional skills. Right? So a coding boot camp in Bali for example, is for somebody looking to learn a specific skill.

Jonathan Kalan – 34:14 – So I think, you know, there’s so many opportunities as people look to. I’m blend more parts of life together, but also maybe separate them out and then I think you’re going to see this space grow in a number of ways from the actual accommodations and operation side from the types of experiences that are offered to the specificity of the kinds of travel experiences that people are looking for. Um, I feel like we’re really only at the beginning of.

Sean Tierney – 34:43 – I hope the diversity stays though because as it does become more specific and focused, um, to me it would’ve been a shame if it was just a group of traveling salespeople on Remote Year and our job, you know, like if that would have ruined the diversity of it. So hopefully you can keep that, uh, the diversity there.

Jonathan Kalan – 34:59 – Yeah. And I think it’s really a matter of just opening up to the rest of the world and saying, hey, like, just because you know, you know, just because the typical model is a coder from San Francisco who’s chatting out in the world and sort of just living cheaply just because that’s the stereotype doesn’t mean that’s the truth. Back to, you know, one is the truth. There’s as many people in Istanbul or in Oman or in Beirut who have the capability to work remotely as maybe somebody in New York, San Francisco and you know, it’s really about saying, has anybody opening this up to that? Does anybody offering this to that? Right. So it’s actually a conscious effort of, of companies and people in this space saying, you know, there are people from all over the world, we’re looking for these kinds of experiences. Are you offering it to them? And we said, absolutely we want to because we know the value that can be gained with keeping that diversity.

Sean Tierney – 35:51 – Did you guys actively, because if it’s 60 percent foreign, so Remote Year was much more skewed to American people. I think. I’m just curious like did you guys actively go and seek out and promote to those folks to get that level of international diversity or is that just naturally what’s kind of come to the website?

Jonathan Kalan – 36:11 – I think it’s coming through a result of early on our own networks, um, you know, just the sort of organization stations that we’ve been heard of in the travels that we’ve had in our own personal networks in building this from the beginning. Um, and then from there onwards, I think it was or has been a targeted approach to really bring together a really amazing international community. So, um, you know, I wouldn’t say it’s something that we’ve, uh, you know, made a very structured approach towards, it’s just kind of always been our philosophy of how do we build the global community and this is the way that we do it.

Sean Tierney – 36:44 – Very cool. Alright, well I’m gonna switch gears here and go very tactical. Just some specific like Tim Ferriss, he type questions to ask you. Hmm. Is there anything you read or listened to on a regular basis? Like what’s you, how do you get your information? Is there any sites or blogs or podcasts or anything that you personally find yourself going back to you?

Jonathan Kalan – 37:04 – I’m a big podcast guy listening to the New York Times the daily for Bullshit. I listened to. There’s no such thing as a fish. It’s a great podcast from the guy’s cute, hilarious or tidbits of facts. Um, BBC sort of broadcast podcasts. I’m the, yeah, there’s nothing that I have been sort of a routine at the moment. There’s a great newsletter is called, I think it’s called on human innovation on human experience. I’m going to forget the name, it’d be in Paris, but it’s one that I do love reading. It’s by. Oh, I forget the name.

Sean Tierney – 37:43 – We can put it in the show notes.

Jonathan Kalan – 37:45 – Yeah. Um, that’s about it. I’m not, I’m not, I’m not great with routine as we’ve been in the company implies. So

Sean Tierney – 37:55 – Right on. What about, uh, any travel hacks, things that you’ve kind of picked up from, you know, wisdom from the road that you could share with fellow nomaders,

Jonathan Kalan – 38:04 – travel light and always bring a toothbrush in your carry on. I think that’s, that’s a pretty solid rule. Um, no, I mean I think the thing that saved me most traveling over the past year or two is a little backup battery for my phone that’s been like the number one thing and her phone plan that allows me to get data internationally for free. I think those two things that made life incredibly easy or I can land in Nicaragua can land anywhere in the world pretty much and instantly be able to connect you with my data and you know, work if I have take a call. So that has saved me a ton, a ton of time and effort. Um, other travel tips forthcoming. I think about that.

Sean Tierney – 38:47 – Fair enough. What about any apps that you find yourself using it regularly? Any mobile apps that make life easier on the road?

Jonathan Kalan – 38:54 – Not a big APP guy to be honest. Um, you know, I tried to, I try to limit my technology, use as much as I possibly can because I’ll spend 15 hours a day sitting at a computer. I will try to, for the rest of it. So no, no travel app, so I’m not a big fan of travel apps, um, beyond google maps and it’s kind of probably my most used.

Sean Tierney – 39:19 – Fair enough. Fair enough. Someone listening, they want to do this. What’s the, what’s the advice? I saw you guys having an application process on your site? Is that just send them to

Jonathan Kalan – 39:31 – Yes. And it to be and uh, feel free to have them recommend you or how they heard about us and a little discount. I would really say before applying, understand what do you want out of this experience, right? What are you looking for for a month or for two weeks? Right? Are you looking for an adventure? Are you looking for personal growth? Are you looking for just in time and space to work remotely or are you looking for, um, you know, to complete a new project, uh, understand kind of what you’re looking for and I think that’ll help us help you think about where to go and timing and all of those things. So we’ve got an amazing admissions to him who take hundreds of calls every, every week who are really great at kind of understanding how we can best help people with Unsettled and where they want to go. So they would be more than happy to chat.

Sean Tierney – 40:23 – Cool. So be introspective, thinking about what you want to get out of it. What about this, the last question, but to that person who’s listening, who’s, who’s never done this before, who is actually on the fence and not sure if this type of lifestyle, uh, you know, if there’ll be able to hack it. Um, what do you say to the person who’s considering it for the first time?

Jonathan Kalan – 40:41 – What’s actually holding you back and what’s the worst that can happen and if you don’t have a great answer to either of those, go for it. Did you do have a good answer to them? See if we can work around it. And I don’t think it did. I mean it, it’s, it is interesting because it’s not for everybody, right? It’s not for everybody. Um, but I think what would I say is kind of to what I spoke about earlier about embracing that Unsettled that uncomfort is try something right. At least take an experiment. At least go for two weeks, at least go for a month and see if this kind of lifestyle is for you. Um, and I think companies like Unsettled and others in the space allow you to sort of have a soft landing contest, this kind of lifestyle out before quitting your job or going remotely full time. And I think that’s a real value add. So if you are on the fence, think about what’s the worst that could happen. And is there a way for you to make yourself comfortable experimenting. You’re trying it for two weeks or a month and see where that could take you.

Sean Tierney – 41:44 – Who is it not for suddenly asked me? Maybe that’s a better question. So you said it’s not for everybody. Have you seen it go wrong for some people? And if so, what are the characteristics of the person who this doesn’t fit for it?

Jonathan Kalan – 41:57 – Yeah, that’s a really great question. Actually. I would say it’s not for people who aren’t interested in creating a community. Some people just want to travel solo and don’t want to be a part of the community. They just want to kind of in between. And I wouldn’t say, you know, go off and traveling solo. It’s a different kind of adventure, right? We’re not competing for people who want to go spend a month or two people who come to Unsettled those people who’ve done that and have reached a point where they actually value being a part of a shared experience. So I would say that’s a big one. Um, second, most people who aren’t interested in contributing and just expect everything to be handed to them. Um, I would say that’s not what we do. We’re not a guided tour, we’re not there to pamper you were there to take care of you and give you a platform and to make you comfortable and to make you feel ready for whatever is to come. Um, but you know, we’re not a guided tour, so I would say that’s an expectation that definitely wouldn’t align. Uh, and then the third I think is most important. It’s just don’t be an asshole. That’s pretty much been a slime is be open to new people and the, it is a new perspectives if you’re somebody who’s going to challenge everybody who comes here with from the not the best fit.

Sean Tierney – 43:05 – Cool. All right, Jonathan, thanks so much for taking the time. You’re listening is the website you can go and apply there. And uh, yeah. Thank you so much. I really appreciate you being on the show.

Jonathan Kalan – 43:17 – Thanks a lot Sean. It’s a pleasure.

Sean Tierney – 43:19 – All right, see ya. Okay. That was my conversation with Jonathan. Hope you found that useful. If you have a question for Jonathan, you can leave a written comment below his episode on You can also record a quick video question using your Webcam. So nomad podcast is now syndicated by all kinds of platforms. If you’ve been listening via audio or on any of the audio only platforms, I would challenge you to actually switch it up and maybe check out the next episode on video. All the videos are found on the website and vice versa. If you’ve been watching the videos, maybe consider going to your favorite podcasting platform in subscribing. Next episode. Listen, while you’re in the car on your commute or on a run is Jonathan would say, shift your perspective here. Constantly seek to, uh, choose a different angle and how you consume the content.

Sean Tierney – 44:11 – So if you’re considering doing a nomadic travel program, you can save up to $300 off select programs simply by applying via our discounts page. You’ll find that link in the footer of our website under the program discounts or simply go to to apply for any of the available programs. Their note, if you do apply to the program itself, it doesn’t validate your opportunity to get the discount, so be sure you apply via our form. No matter podcast is supported in part by nomad prep, an online academy for aspiring digital nomads taught by yours truly, and that teaches you everything you need to know how to successfully make the transition to this lifestyle of the digital nomads. Get the first four days of this two week program completely free by going to Nomad prep. Take your job on the road and take on the world if you enjoyed the content thus far, the greatest compliment you can give is to actually share this with a friend.

Sean Tierney – 45:07 – I know we all have someone we know that it’s talked about going remote, taking their job on the road. We’d love it if you’d share the podcast. Alternatively, maybe consider sharing it on your social media, posted to your Facebook. Send a tweet out, I know now Instagram, you can actually take the Instagram posts and share it to your story so we are Nomad Prep is the handle across all social media, so if you feel so inclined, we’d love it if you shared the podcast to spread the word. As far as upcoming guests. In keeping with this trend of interviewing founders, I’m going to be talking to the founder or the co founder and CEO of Remote Year next week, so very excited to talk to Greg Caplan. He’s a neat guy. I’ve met him a couple times in person and he is always just full of energy, so that should be an interesting conversation.

Sean Tierney – 45:58 – Lastly, if you are a blogger and you are currently traveling, consider adding yourself to This is a travel platform. Again, something I run on a volunteer basis right now, but it syndicates the blog posts of people currently on the road so you can find that and just click the submit button in the header to add yourself there or to apply. Okay, so we’re getting great feedback so far. If you’ve listened this far, thank you so much for tuning in. As always, uh, it’s, it’s just a blast and it’s an honor to have this role of kind of helping distribute this information. So until next time, it’s a big world out there. Get out and explore it and I will see you on the road.

Speaker 1 – 46:45 – Nomad, nomad, nomad podcast.

Personal Site
Current Company
Current Title


Sean is host of Nomad Podcast, author of the Nomad Prep eCourse to help others successfully transition to the nomadic lifestyle. Sean is also founder of Problemattic, a global movement to mobilize knowledge workers for good. Read more from Sean on his personal blog or his business blog.

View all posts

Nomad Podcast is a series of conversations with nomads, founders and domain experts to help get more people unstuck through transitioning to a nomadic lifestyle. Add your email to get special access to private AMA sessions, pre-release products and other VIP shiz.