Ben Keene on dreaming, starting a tribe & living on an island with three kids

[01:35] Paul: Today I'm talking with Ben Keen, who describes himself as someone that helps people do work that matters to them and the world. We'll dive into the many, many adventures he's gone on in his life over the past 20 years. We're also going to dive into his recent return from Koh Lanta, where he spent 6 months with his family, including 3 kids, living on an island in Thailand. Welcome to the podcast, Ben.

[02:08] Dreaming: Thanks, Paul. Great to be here.

[02:09] Paul: I was trying to make sense of the many adventures you've been on over the years, and a word that kept popping up in my head is the word Dreaming. You seem like somebody that likes to dream big and help others dream big. First, does that resonate? And just curious, where does that come from?

[02:30] Dreaming: Yeah, I mean, it's nice to be reminded that that's— they are— it can look and feel like that from the outside. I guess for me, it's— I've been fortunate to get into that habit or mindset, or sometimes a bad habit of trying to turn big ideas or dreams into reality. And yeah, it's, it's funny because I feel like I constantly sort of ask myself, oh, when am I going to, you know, grow up and try and do something? I thought, you know, having a family would lead to that, but obviously in recent times it's led to more adventures. Um, so yeah, the dreaming thing has always been— I think it was, you know, from my family and from my education was always like, chase, chase the opportunities, chase what matters to you. Um, and then just being part of friendship networks and projects, I guess, earlier on in life, which helped me, give me confidence to go and do these things.

And yeah, it's fun. And I think I get almost as much pleasure out of helping other people try and make that happen as well. So mainly around startups, but very much tied to the way of working and often where they work as well and changing their lifestyle.

[03:41] Paul: Yes, you've been doing these things for about 20 years. How did you first get into helping people carve new paths and doing that yourself as well?

[03:52] Dreaming: Well, the honest answer is I escaped the professional or corporate life before it even began. So you can say that was naive because I never went off and made any money that way, even though that path was sort of laid out in front of me. But I was in one of those at college, one of those evenings where big companies come along and they give you lots of beer and pizza and then say, hey, it's great, come and work on this. A lot of my friends who are studying anthropology or business studies or politics, and I thought, ah, interesting people doing interesting things. And they were all in this queue to sign up for these graduate recruitment schemes or consultancy programs. And, um, and guys, what's going on here?

And they're like, no, this is what happens. So I was a bit naive maybe, but I just felt like, well, that's not something I want to do. Go on that secure path, rejects a little bit of the things that I feel like I'm curious about matter. So I went off traveling like so many of us do. And I got involved with a small travel startup. I was their first employee and we see, you know, my job was driving Land Rovers around West Africa up to Timbuktu and back.

And, you know, that is an education, getting people around that part of the world. And it's incredible. And so that was my apprenticeship, I guess, in trying to turn dreams into reality. And then a couple of years later, I sort of, this travel company was getting more established and I was spending more time in an office. I was like, oh, I'm getting itchy feet here. And it wasn't my business, so I had the freedom to, to move on quite quickly.

Um, and the area that I was curious about was helping people who were— who weren't 18, um, or 19 years old who wanted to go off and do big trips, take career breaks, sabbaticals, um, try and think about what might be next in their lives. Um, but there was a lack of guidance online. So this was 2004. A long time ago. And so I made a little blog called Career Break Cafe, and the idea was just to help people, give them guidance about how to make this transition. And that started to get a little bit of momentum, but the business model was selling banner ads and skyscrapers down the side of websites.

And it doesn't matter how passionate you are about the content and the impact of the work, that sales model kills you very quickly. So Yeah, so that was running out of steam after a few months, but I got in touch through it with a guy who, you know, this was the time of MSN Messenger, Hotmail accounts, and MySpace. So we have to, you know, we're jumping back a little bit. And this guy got in touch, exactly, got in touch on MSN and said, hey Ben, I've read your travel blog and career break blog. It's really interesting, but I'm from the world of music, and MySpace was exploding at the time. There was a British band called the Arctic Monkeys who went to number 1.

Their first ever single went to number 1 in Europe and around the world. And it was like, you know, they were the most successful British band since the Beatles. And yet they didn't have a big production company behind them. And everyone was like, how did they get this traction? And it was— the music was good, but it was also because they built this huge following on MySpace. And so there was this moment in the music industry where people were like, ah, something is shifting here.

And, you know, 20 years later, obviously, that's really— we are 15 years later, that's normal now. But at the time, it was really new. And so this guy Mark got in touch with me and said, I'm interested in whether we could create a MySpace but for travel. So the idea was very simply, could you pick a destination in the world and build a social network or community around it online that would engage with the place and so on. And the thing— this seems very normal as we talk about it right here.

[07:30] Paul: Yeah.

[07:30] Dreaming: But in 2004, it was, it was a big leap and then sort of an imaginative leap, or it was for me anyway. Um, but what I liked about it was two things. One was that in community-based tourism or ecotourism or voluntourism, which I was doing a lot of at the time, um, you have this— you have two big problems. One of the big problems is that people aren't necessarily engaged with the project before in a sort of meaningful way, understand the culture. So they get there and it takes time to learn all that things and you can get some challenges around responsible tourism. And the second is the business model, right?

People come once, it's one-off thing, you work hard to get that sale. And I thought maybe there's something here where people could support a project or a destination over a period of time rather than just for their trip. And that was That got me really excited. And so anyway, we launched Tribe Wanted. I launched it with this guy I barely knew about a month later. And we'd found an island on Google in Northern Fiji.

And we found a landowner that was looking to lease this island right off the top end of Fiji, away from the main tourism.

[08:38] Paul: Yeah. So I want to slow you down a little there.

[08:41] Dreaming: Okay.

[08:42] Paul: Just because It seems like there's a bigger leap from getting, uh, experimenting with some of the startup stuff and going to, I'm going to pick a spot on an island and build a tribe. What, what was the shift or like what was your mindset during that time?

[09:01] Dreaming: I think so that, so this, these trends that we've, we've just, I've just been talking about with the social networks and the travel and community tourism and potentially bring those together. The question that we asked ourselves then was, if we were going to try out this kind of project, have an online community and a destination and some sort of support or connection between the two, where would we do this new sort of tourism experiment? And for us, it was really clear we would want to do something that was almost like the opposite of what a digital or an online community would be, a remote place in the world. So I've always been a an island maniac, I guess, like many people drawn to these remote, beautiful islands around the world. So that's where we decided. So we started hunting for islands online.

And of course, what you find when you Google islands for sale or for lease is a millionaire playground. It's all superyachts and big dollars and so on. And there's plenty out there, but it wasn't really our domain. We'd both just graduated from uni and we didn't have much cash. So So yeah, that was the leap, but then it got hooked. How can we, how can we make this happen?

And of course crowdfunding was the model we were thinking of, but this was pre-Facebook, pre-Kickstarter, certainly in the UK these things hadn't arrived. So we were just thinking about how can we do this with a PayPal button basically, and, you know, getting some attention online. But we found this island, and there's a contact of a contact who said, are you for real? And we were like, well, here's our business model. And off we went. And yeah, and we basically, I went over to Fiji and agreed a lease with the chief and the local government for 3 years.

And they said that the agreement basically said, okay, you can do this, but you need to pay, I think it was £20,000, something like that. So about a third of the lease fee over within the next 6 weeks. So that was then when it got real. So I was like, okay, we've got to raise $20 grand in 6 weeks to make this thing happen.

[11:06] Paul: Was there a moment in that when you kind of just stopped and said, oh shit, I just agreed to build a tribe on an island for 3 years?

[11:15] Dreaming: Yeah, well, the only— the investment was the flight to Fiji at that point. Yeah, but that was okay. The thing that pushed— I think pushed me over the edge, and it was a really mundane thing in the end, that like made me go, I really want to give this a go, was the fact that here in the UK you can travel on around the country on trains with a young person's card. And it's, um, I think it's up to the age of 26 and you get like a third off your travel. And I just look— I remember when I was working on this project online and I looked down and I saw my card and it was about to expire that month or something, and I was going to be no longer a young person. And so I thought, you know what I should do?

I'm going to be an adult from next month, at least in terms of getting cheaper travel. I'm not getting cheaper travel anymore. I should really go and do something much more serious like trying to rent an island. So that was the little spur to push me into action, was just like a change in the life stage that I was at, I guess. Instead of getting a proper job, go and try and rent an island. So yeah, we put it out there, and I think it was April 3rd, 2006, tribewanted.com, and it was like a full-page website.

A designer friend helped it. We paid £400 to make it. We had PayPal button on it for 3 types of membership and the smaller membership was about $180, $200 and that was a week on the island but there was no, you know, a year's membership to our tribal community. And that was the proposition. It wasn't much more detailed than that because we didn't know what was going to happen. And we put it out online, hit publish, didn't tell anyone, any of our friends, or I didn't anyway.

Managed to persuade someone we knew who worked in PR to get a press release out. And then nothing happened for 48 hours. So we just assumed, okay, well, the last 2 months of planning and the trip to Fiji was fun, but clearly this is way too crazy an idea. So never mind, we gave it a go. And just as I was letting that disappointment kick in, I woke up and I got a bunch of messages coming in from friends. They said, hey, I've just seen you in in the paper and there's something about an island and what's going on.

And it was picked up by, I think, an intern working at the Metro newspaper, which is like these free papers that get given out in cities. And we were like a page 3 feature, like a kind of crazy kooky project. And it was like an ad for the project. And that day I think we got £10,000 worth of membership sales. And what happened off the back of that was that, that was, that was like the press release that all the other mainstream media. And then, you know, digital media picked up.

So within a month, we had gone crazy, at least for us. So that was the beginning. So it was really exciting. And then there were lots of challenges afterwards, but we ended up moving to Fiji and living there for 5 years and building this community.

[14:05] Paul: Yeah. Was that a bit scary the first moment you got that payment, which basically said, okay, now I need to follow through on this and make it happen?

[14:15] Dreaming: Well, there's this wonderful thing about commitment, isn't there, in life? Like, when you commit, the magic really starts to happen, whether that's with a new project, a relationship, or an adventure, or whatever it is. And I think that was the moment for sure, you know, because you've made— you've put the word out there, and then someone says, go on then, turn this dream into reality for me too. And then tens and then hundreds and thousands of others jump in. And then you're like, okay. And so it's really exciting, but quickly it feels quite pressurized, or it did, especially as we didn't really know how we were going to do it.

So, um, but it was really exciting, and I think there's, there's probably not many moments in life, um, where you can have a real go at something without too many other responsibilities around you. Um, and so we timed that well. And yeah, it was an exhausting, uh, year or two because there was lots of ups and downs with the project, but it No regrets. And it was— it led to many other great things and a lot of good friendships.

[15:14] Paul: I know you've talked a lot about this experience, and I actually found some amazing early YouTube videos about the whole experiment. So I'll link to those if people want to dive in. I definitely encourage people to check that out. But when you reflect on that experience today, what are the 1 or 2 big reflections that you often just keep coming back to?

[15:36] Dreaming: I think so. So first of all, emotionally, there's one of just like the pure adrenaline and excitement of creating something new and being part of something really special, especially as a community. Um, in Fiji, that was, that was a wonderful experience. Um, but also the emotions of the, the, the stress, financial stress that it created. Uh, you know, the, all these promises that we made. Um, so yeah, it was a really intense time for me, that first year or two.

In terms of lessons, it was kind of like doing a, you know, a 10-year MBA in 6 months and life lessons. So I think the biggest thing I learned is that you're, you know, whatever you think might be possible is possible in terms of getting it going. You just really have to commit to to something if you really wanna make it happen. But also I think one of the big lessons I would, in terms of doing it differently, I probably would've not right at the start because it would've been hard to get people's guidance and support at the start. But quite quickly as we got the project up and running, I would've got a lot more, especially business guidance, I think. But it's hard at the time 'cause things are moving really fast.

And so it's hard to stop and pause and think, okay, how should we do this? Things are just moving. No, I think it was just that the learning was like, just go out there and make these things happen when you get the chance. The only thing you need to ask yourself that I always do with any project is try and jump forward a little bit and say, okay, if this did work or this did get momentum, what does my life and my work and everything look like in 6 months, 1 year, 2 years' time? Is that good? Am I happy with that?

Am I happy with the fact that this is going to be all-consuming? That this isn't gonna pay well for a little while, that this is gonna be experimental in places. And that's if you are in that frame of mind and you're ready and you've got all your time and energy to put into it and you care about the project, that's great. But you might also be at a different stage of life like I am now, where you have some different commitments with family and a home and that kind of thing. And so you have to say, does it fit in with that? And so learning what those red lines are in your own life where you're not going to negotiate, and then making decisions around how you start, build, and grow a project or organization around that.

But that's, that's the wisdom that comes 20 years later.

[18:02] Paul: Fantastic. Yeah, I'm sure it was a bit more challenging and all over the place back in the moment.

[18:09] Dreaming: Yeah, it was. But I mean, we had some crazy things happen. Just really briefly, we had a guy in California who I think was younger than us at the time, he wrote a blog, 5,000-word blog saying, istribewanted.com a scam? And of course we were flying up. It used to be like things like Digg before Reddit and those sites. It was a site called Digg.

And we were like a positive news story on Digg and that was driving amazing SEO and all this stuff. We were on the verge of being a big viral story online. It certainly felt like that for us. And then this guy wrote this blog which was like a bunch of red flags. And this was his kind of— it was his way of blogging. He would just pick interesting new projects that were out online and he would critique them quite heavily and then drive loads of traffic his way to pay his ads.

Anyway, so it was really annoying, but you know, it was, it was nothing that we could really do about it. Um, but of course people don't know, so they read this thing and then suddenly it's the top search thing in your— it's almost above your own domain name. Yeah, and it didn't go away for 3 or 4 years, and there was nothing legally we could really do about it. He had no— of course, the frustrating thing for me in that situation is that he had no responsibility, right? So he just wrote this blog and off he went. And a lot of people clicked on it because it was a compelling headline.

Classic conspiracy sort of theory for us anyway. But the impact was huge. I mean, we went from taking £500 a day to £50 a day memberships after that. So all those that were excited but had doubts and came across that would obviously held back until they saw it happening for real in a year's time. So that was the crazy thing was that he said at the bottom of this, this rant, this blog, he said, if you really want to go on a great adventure island holiday, I'd recommend National Geographic Expeditions. So I was like, okay, great.

And 2 years later, that's a very good recommendation. We'll try and be one of 2 years later, we were covered with a cover story of National Geographic. So I sent it to him and said, you recommended us all that time. Thank you for the recommendation. But of course, that didn't undo the damage that had been created by that. So I think we see that still now, right, online, where at one moment, the speed of success and failure can happen really quickly.

[20:37] Paul: I think people are more aware of that now too, right? That negative headlines are going to drive more traffic and people are a little more skeptical of it now.

[20:47] Dreaming: Yeah, I think so. And my instinctive reaction when that came out was, because we were getting traction in the States, was to take it on, right? I said, look, let's go on, let's sit down, let's do, you know, let me have a podcast with them. Let's go and have a conversation face to face or at least record a conversation with him so I can answer all his questions. And the advice we got from the States was, I guess, more traditional kind of marketing or PR advice, was like, no, you're just— these are— this is just a kid on the internet. You really want to be focusing on getting on Good Morning America and all this stuff.

And I was like, okay, all right, I don't know how it works. And I think that was probably the wrong decision, because if we really engaged with him, maybe he would have gone, okay, fair enough. But there we go. That happened. So we had that, the scam accusation. Then physically on the island in the first 6 months, once we were up and running, we were building this village, people coming to stay, we were working with our Fijian friends.

We had a fire in the first 2 weeks. There hadn't been one in 15 years. And it was just an accidental fire started by one of the local farmers, but that was pretty dramatic. And then we had a, in Fiji itself, there was a political coup. So the army took over the, the country. It was very peaceful.

It was kind of like the most calm political uprising you can imagine. Everyone just carried on, you know, in their coconuts and watching rugby. But yeah, that happened and it created negative headlines around the world, which impacted tourism and obviously us as well. And then once that had just got— we got over that, there was the biggest cyclone in a decade or something. And so that knocked over most of the infrastructure that we built. But You know, just, it's a kind of like, is someone telling us not to do this project?

But, so the first 6 months were intense, but we got over that and then we had 5 wonderful years on the island.

[22:36] Paul: Wow. So as that wrapped up and you decided to leave Fiji, where was your head at the time? How were you thinking about making the transition away from that?

[22:47] Dreaming: Yeah, so the business model was tough. We put a lot in upfront and some of those challenges I've just shared like impacted that. So I borrowed money to keep it going and so on. But we, yeah, it was, we didn't, you know, another lesson was like we didn't charge enough money, obviously, for the experience at the start. And so we got into debt quite quickly, plus we invested way too much in the online community. We were building all the components from scratch.

So yeah, it was, the project was in debt and, you know, extending the lease longer term would have cost us a lot more. So the business model needed to change. So I said, look, I'm stepping out now. The infrastructure is there, the local community carried on building new partnerships. That's carried on since then, not at the same level, but they've kept the island going. The transition for me was quite a hard one because it'd been everything for a while.

But what was exciting was that there have been loads of people because of this, the amount of publicity the project had got, get in touch, "Hey, this model is obviously clearly a success. Let's go and do it here or here." in all these places around the world. And it was amazing. So it was like obvious places like other beaches and islands around the world. But then we had offers come in from like the city of Detroit and, you know, just really interesting places or like somewhere in the Arctic Circle. Just to build these interesting different kind of community experiences.

The problem was we didn't crack the business model. We didn't have the Airbnb scalability on that side. We had a really exciting community tourism and online project but it wasn't. We hadn't nailed the business model. So that was— we did end up doing 3 other projects which were all in their own way really successful. So we spent a year living and working in Sierra Leone in West Africa, and the opportunity there, there was some funding and a good partnership opportunity to go and support the development of an ecotourism project on the beach, a beach near Freetown.

And of course, When you think of Sierra Leone, typically people who will think of, you know, blood diamonds and Ebola now, and, you know, a lot of poverty. But it's a remarkable place in terms of culture, and it's beautiful on the beaches and everything. So we wanted to play a part in trying to help change the story, um, and lots of other people are doing that as well. So that was really great, and that ran for 5 years, and then it got passed on to the local community, although Ebola obviously had a big and that had a big impact, of course, locally, but also on people who were planning to travel there. And then we've been running a project in Umbria in Italy, which is obviously a little different, for the last 6 years now, and that's still running. So that's— it's like a sustainable farm.

It's, you know, make olive oil and wine, have their own pigs and cows and horses. It's a beautiful place. It's like the original good life. So my business partner, who's Italian, set that up and we've been going there for a few years. I'm not involved personally with that now because I've moved on to other things, but yeah, that's still going. So you can go and live or spend a few weeks on this beautiful farm and eat and drink the best you ever have.

[25:59] Paul: I'd love to dive into some of your work with the Escape School. And I noticed, I mean, you've worked with people, especially early in your career, you talked about helping people take mid-career sabbaticals. Uh, you basically designed your 20s doing all sorts of different things, different experiments, trying to figure out technology, the internet. How— what drew you to work with the Escape School, and what do you think are some of the differences in terms of how people were approaching designing their own paths when you started there, and maybe 10 years prior when you were starting out?

[26:36] Dreaming: The story of the Escape School, or Escape the City as the organization is called. So this was set up by two guys who are, you know, like yourself, had been in the world of corporate consultancy, and they were, they were in their late 20s, and they were sort of, you know, the economic crash had just happened, Lehman Brothers had just gone bust, and they were like, oh, something's changing here, and we're not happy in our jobs, and we want to go and do, go on big adventures, start our own businesses, have more positive social impact in the world. And they couldn't find the community organization that would help people like them make that transition. Because it felt like a big deal to them to walk away from this world that was very— seemed very safe, or where they were supposed to be, you know, ticking their career boxes.

So what they did, because they had each other, they egged each other on, and they started running little meetups and a Monday newsletter, which was like the top 10 escape opportunities in the world. And they were just exciting jobs. And adventures and opportunities. They would share this and this mailing list grew. And so that's been going, that mailer's been going for, you know, 8 or 9 years now. And it's built, you know, a big following.

And it's still, even if you love your job, it's a great email to get on a Monday, like 10 really cool opportunities in the world. So that was how Escape the City started. And then it's been on a mission since then to try and help people find, you know, escape whatever job they don't really want to be in and move into more fulfilling work for them, whatever that looks like. And so I was, they kindly invited me to one of their sort of kickoff parties in London to talk about the story I've just shared with you, you know, the Tribe Wanted story as an example of here's the kind of crazy stuff you could be doing instead of working in London. And so I shared that and halfway through I realized there's 600 quite frustrated corporate professionals in this room. It was a big turnout in this room.

They've all had a few drinks, They're all a bit like, oh, come on, give me some clues as to how I can do this. And I'm basically showing a bunch of holiday pictures as far as they're concerned, right? So I was like, right, come on, think, think, how can we— how could I try and help these people here with a bit more of a realistic jump? And so I remember that, um, a good friend of mine who runs this incredible project called Right to Dream, which is a leadership and sports academy in Ghana in West Africa, and it's now the best football academy for girls and boys in in Africa, and it's an incredible project. You can check it out, Right to Dream. And he was looking for someone to help develop their Paralympic, the disabled athlete program, and to try and get some para-athletes from Ghana to the London 2012 Olympic or Paralympic Games.

And anyway, I mentioned this, and like, a friend of mine was looking for someone to help with this sports development project. And it was really exciting. Anyway, I mentioned in passing, and then afterwards, of course, loads of people were like, Ben, well, tell me about that project in Ghana, that job in Ghana. So, um, I interviewed a few on behalf of my friend, of the people who came forward, and made my recommendations. Anyway, 6 months later, when I'm in Sierra Leone, my friend calls and said, Ben, you remember, um, uh, the, the lady you recommended for the job? She's doing a great job.

Anyway, she's coming to Sierria Leone next week. Could you look out for her because it's her first trip there? I said, sure. Anyway, she is downstairs now with my 3 children, our 3 children. So, so that's how the relationship with Escape the City starts, is that I, I met my wife, um, at their launch party. So since then I've kind of been like, I owe these guys.

No, so that was—

[30:08] Paul: that's a big duty to them.

[30:11] Dreaming: Yeah, exactly. This is what happens when you turn up to these kind of events. You meet people who are trying to do similar things. So yeah, we worked in West Africa. Susan and I worked in West Africa on these different projects. Then we came back to London and I got back in touch with the Escape the City crew and I said, how's it going here?

I think we're going to come back and settle in the UK for a little while, maybe try and start a family, and I'd love to see if I can help you guys with your project. And they just started this exploring this idea of a education for people. Because it's all very well having the most exciting opportunities in the world, but they kind of fly past like silver bullets. They're very hard to catch. When you're sitting in your corporate job or your law firm account, like, oh, you know, astronaut relationship manager for Virgin Galactic, how do I even think about making that change? It's, you know, chief experience officer for Airbnb, which these people may be qualified for, but it feels like such a big psychological shift, right, to think about those opportunities.

[31:13] Paul: Yeah, I've talked to a lot of people and so many people just frame it as all or nothing too, right? So it's, I'm in this job and it, it's basically in this job or I have to blow everything up and start a new life. And yeah, I, it's often much more subtle and slower in terms of shifting mindsets, redefining success. Putting people through small experiments, making them feel uncomfortable. But, um, yeah, how have you thought about some of those small things to help people start to make those, uh, shifts? So you—

[31:47] Dreaming: what you've just described, Paul, is, is the kind of model that we, um, and we— so for the last 5 years, building this Escape School to help people make this transition, it's the model that we've, that we focused on, which is small steps. So you start with a something's pushing you away, right? There's something that's not quite right, or maybe a big thing that's not right in your work or your life. And then there's some pull factors like, oh, I've got this entrepreneurial itch I want to scratch, or I need— I always wanted to go on this big adventure. I want to work on that problem in the world. How do I start to explore it?

And of course, it's not an either/or. It's not suddenly I go from management consultant to social entrepreneur in like just like that. It takes skill shift, emotional shift, psychological shift, people shift, you know, social network shifts, location shift often. So it's a significant number of changes and that takes time. But the main— we focus on, and this is what we've done at Escape City, but I also focus on with my other projects as well, focus on 3 things. One is who you're working with or who you're spending your time with.

So it sounds obvious to you and I, but like, if you want to explore this new world of work or digital nomads or social entrepreneurship, whatever it is you're curious about, then you need to start spending time in that space. And that doesn't mean you change your life to go in that space. You just need to start experimenting or exploring it. Go to events, go on a one-off trip. You know, all your readings around this subject, all your social media, change your social media feed to follow these people and these projects. And that's the first step.

And then the second step is to start to do something that's more than just following things, it's actually acting. So it's like, how can I add value to any of these people or projects, what they're doing? Okay, Paul's got this really interesting guy called Paul, he's got this podcast, I'm really interested in his stuff. Hi Paul, I'm curious about this. Could I help you in any way? You know, and then suddenly it's like, oh right, I'm actually contributing to this and I'm learning about it and so on.

And then the third thing is obviously just getting that into a, you know, more and more steps. And at some point looking at your business plan, your financial plan and saying, could I cut down to 4 days a week? Could I go freelance? Could I go part-time? Have I got enough savings to then give me a 6-month or 12-month runway to try this new life? And so on.

And what I've learned about people who go through this, helping, you know, probably 1,000 or 2,000 people now through the Escape School and outside as well, whether it's starting businesses or doing other things, is that people often will wait until they're at breaking point in terms of the pain levels before they really act. And that's a dangerous place to get to because obviously then you're you're unstable in many ways. But also, you know, it doesn't have to be this sort of like jump off a cliff. It can be the smaller steps. And when you're working in this, this so-called new world of work that we're in, you realize that it's messy, that there's no clear path. It's not like a graduate scheme where you go up a ladder and that's it, or, you know, you're in the armed forces.

And that's the old world. It's not this three-stage career. It's like the portfolio career. It's multiple identities. It's up and down cash. It's different locations.

It's, you know, and that's the hard thing. It's getting used to being that adaptable person that goes up and down. And I still struggle with that sometimes. Like, I wish, especially with young kids, I wish I had that regular 9 to 5. Not often, but I do sometimes wish that. And I think my wife probably does as well.

But yeah, that's what we've learned.

[35:31] Paul: How do you think about what you do next and where to spend your time or what to experiment on?

[35:39] Dreaming: So we have this thing we've sort of developed at Escape School called your good idea criteria. Okay, and these are essentially your non-negotiables when you're looking at new opportunities. So they are a mixture of your aspirations, your dreams, and the things that you would love to spend all your time doing, and your reality. So your resources, your time, your money, your networks, your skills, etc. And what it spits out at the bottom is like, okay, here are the things when I'm looking at scanning for opportunities, or I'm daydreaming about things I'd love to do, or I'm looking about where we want to live. These are the things that are kind of my, my benchmarks for saying yes or no to them, or at least looking a bit more into it.

Um, and so for me, for example, it's got to fit around my family. That's the number one thing. And it's got to bring enough money, and it's got to you know, give me enough time with my family. And then number 2, it's got to be able to say, okay, is it a creative process? Am I having a positive impact? Is it got potential to scale?

Um, and then the third thing, is it fun and adventurous? Um, and of course not every project will be like that, but those are my kind of criteria. And then it's all about just staying connected with projects and people that are exciting.

[36:47] Paul: How did you decide to start something like the Rebel Book Club? Or maybe you can tell us what it is first. But I'd love to just hear like maybe some of the practical, like really tactical steps of how you actually did that.

[37:02] Dreaming: Yeah. And I think it's the mindset that's crucial here because it's such a contrast to the Tribe Wanted project, which was a wildly ambitious thing. This is quite a sort of mundane— it's really fun, but it's quite a small, like simple model. So Rebel Book Club came about when I was in Bali. 4 years ago, and I was running a little remote startup program, really just to— as a way of funding our time there for a few months, um, and out of Ubud, this famous co-working space in Bali. Anyway, I had a group of 20 people who would check in every day and how you doing on your projects, and it was just about accountability and helping them, uh, move forward.

And, uh, one of the guys who was on that, um, he's also called Ben, and we talked about— we were comparing Kindles And we realized that we both had a problem, a really big problem, which was that we had loads of similar books that were unread on our Kindles. They were between 10% and 20% read. We're like, what's going on here? We're downloading them, we're starting them, we're not finishing them. Mainly startups, mainly like, you know, business, science, biography, you know, all nonfiction basically. So we decided, let's let's have a, you know, do a little book club.

So we did one in Bali and we had a meetup at the end and a cocktail and so on with 10 other people. And it was great. I was like, oh, this is fun. But obviously that's just a book club and people have done that for decades or centuries. But we thought, what I suggested was that, well, when we get back to London next month, and he was heading home too, why don't we set this up? Because I think this is great and it helps solve a problem for me and I think there's something here.

Why don't we set this up where we say, right, every month we're going to read one non-fiction book and a different theme each month, so we, we keep changing, and we're going to hold you, or the members, the people participate, uh, accountable to finishing the books. So we'll nudge you, we'll help coach you through it, um, and then at the end of the month we'll meet up somewhere physically and, uh, we'll have a cocktail and we'll, you know, see how we can get something out of this book and apply it to our lives. So it's not a critique of the book, it's like, what in this was interesting, insightful, and how might we take it back into our lives? So it's like useful reading. And we'll charge people for the opportunity to be part of this from the start. So the goal on day 1 was like, could we get 15 people to give us £15 in 1 month to be part of this?

And we'd pick a book and off we go. And so we created a simple landing page. We use GoCardless, which is, you know, subscription direct debit model. And a button and we had a little application form, which we used Typeform for, and people would apply. So we just wanted, 'cause we wanted to make sure that the people who were coming on board were really up for this and they were like-minded and so on. And it, yeah, between us we got 25 people in that first month and it's grown every single month since.

Next month will be our 50th month or 50th book. And we've now got over 500 and there's been times where it's been stagnant steady and other times we do little bursts. And we're now running in 4 cities, mainly in London, but we're just starting to open up European cities. And it's just one of those projects that, you know, for 4 years now has just been fun, but it's also been financially sustainable, started to pay a little bonus every year. And it's made a really positive impact. And it's, you know, last week we had 150 people come to our meetup in London with Kate Raworth, who's the author of Doughnut Economics.

Authors start coming now, which is amazing. About this future model of economy in the world that we live in. And it was, you know, we're Skyping in our other cities and we're having chats online. And, you know, it's still a pretty simple model, but it's fun and it's got potential to grow. And the thing I think one of the reasons it's worked is that we never put a lot of pressure on ourselves or onto the idea to be a big success. So it's like the lack of ambition is kind of The reverse psychology has made it sort of almost a success.

And also, we haven't had the time. So the two of us who've worked on it, this has been very much a side hustle or a side, you know, it's a 2-hour-a-week project. Now it's, for me, it's a 10-hour-a-week project. It's grown. But, you know, for 3 or 4 years, it was just very much like, okay, Sunday night, log in, update, new members, new book, go. And that would be it.

So it's been great.

[41:25] Paul: That's fantastic. I think there's such a key lesson there in terms of how you approach that. You didn't start out saying, I need to have a 500-member book club, right? You just invited people to an in-person event, said, okay, maybe there's something here, and then kind of kept it simple and did the digital version, but also didn't make it super grand in terms of ambitions, and then just basically saw what people were reacting to. I love that approach. And I think it's just so much more possible with today's tech tools that I think, especially a lot of people in the corporate world, aren't aware how easy it is to do some of these things, mostly because they're not exposed to some of the tools that their organizations just hasn't embraced yet.

[42:15] Dreaming: It's wild. I mean, see, this weekend, so the last two days, I've just kicked off the 9th program I've led on this at the Escape School for the stuff we call it the Startup Accelerator. It's a 3-month part-time program for people who are curious about trying to build a business. Or more than curious, they're serious about it. And the big, the 2 big things that really help them is one is the cycle, you know, move from like thinking to doing. So like, right, this week, guys, you're going to do a business model.

You're going to talk to 10 customers. You're going to mock up a landing page. You're going to go out there and try and sell this. It's just like push, push, push to act. And then the second thing is just curating that toolkit for them. So it feels, I think, a little bit now like once they realize, oh, you can build loads of stuff online really cheaply, then it's like, where do I start?

Because 5 years ago, they were like, it was like WordPress and maybe one other web building tool that you could do without hiring a developer. Now there are 100. At least, and the no-code kind of revolution or trend. We actually— I was doing startup trends in one of the sessions over the weekend, and I was like, you know, we put the no-code, no worries as a trend and like the maker movement as a trend, because in the last 5 years, suddenly they are like— these are people are building, as you are, remarkable and exciting careers using this toolkit.

[43:40] Paul: Yeah, definitely. I run a lot of stuff using no-code tools like Coda. Even things like this podcast are running on Anchor, which are now free to publish your podcast on all the platforms. So it's nice.

[43:53] Dreaming: Well, we're just about to launch our Rebel Book Club podcast, so we'll look into Anchor.

[43:59] Paul: Fantastic. So all these experiments are great business models, companies. Then you have a few kids. And I imagine approaching something like deciding to live on an island with 3 kids is a little bit of a different thought process than starting a business abroad or launching a digital business.

[44:25] Dreaming: Yes. Yes. It's, yeah, it's been fun. So August last year, we we put our house on the market about a year before that. So we put our house on the market, I think the month that the Brexit referendum had gone through. Great, great timing that.

So basically people have stopped buying houses since then because no one knows what's going to happen to the economy here. So yeah, we hadn't sold our house because we wanted to move out to the country a bit more. And anyway, so we thought, hold on, why are we looking at potentially renting and going to live in the country? Down the road, you know, 50 miles from where we live. Well, you know, if the only thing at the moment that's tying us here is, well, our eldest daughter is about to start school and I'm still doing some work with Escape the City in London, but other than that there's nothing physically tying us here. Why don't we, why don't we use this as an opportunity to go and, you know, go live somewhere differently for a little while?

And I, you know, I came home with this thought and you could just see my wife going, oh no, he's— this isn't—

[45:25] Paul: he's not joking.

[45:29] Dreaming: Yeah, he was like, come on, you remember we met on a beach in Sierra Leone, this is what happens. So yeah, so then our criteria were very simply, some of it was very different. We were going to escape winter, 6 to 9 months, someone that was different to, you know, culturally and climate to where we were living here, somewhere hot, and somewhere with good Wi-Fi connection so we could work remotely, and somewhere where there was some kind of international small international school. And actually, that third factor was the thing that narrowed it down, because otherwise there's loads of cities, especially in Southern Asia, where you can live great, obviously great online connection and in the tropics, or you can live with a— you can find international schools. But the problem, you know, they're all in big cities and we didn't want to be in a big city.

So then I was looking at places like Ubud again, but we've been there before. And then And then I found Koh Lanta in southern Thailand. So this is near the south of Krabi and opposite Phuket on the Andaman Sea. And Koh Lanta is this 20-kilometer island and it's still developed for tourism, but it's more low-key than Phi Phi and Phuket and elsewhere around there. And I was scrolling on Google Earth and as I was going down the road and I was looking at all the kind of bars and hotels and places, I saw this like Global Village School. On the map.

And I was like, what's that? And I clicked the link and I was like, oh, this is small school, it's been running for 5 years, international school for families who are visiting or living on, on the island. And I was like, oh wow. And then literally 100 meters further on from the school there, I found Cohub. Um, wow.

[47:08] Paul: Google Earth?

[47:10] Dreaming: Yeah, I was just scrolling through across the island. So yeah, and I was like, wow, those are the two things we're looking for. So this is it, we're going. So we made— we then— the decision, the time between making the decision and leaving was 6 weeks, which if you're by yourself, maybe that's not that long, but as a family, that's quite a short period of time. But I like that because it pushed us to like pack down the house quickly, pack down our lives here, pack up our bags to go, and then without too much thinking, because I think you always feel that transition time with whatever, however long it is with like the planning.

[47:43] Paul: It's like planning a wedding a year and a half from now.

[47:46] Dreaming: Yeah, exactly. So we did it and we moved there in early October and we came back a month ago. So we were going to get— the goal was to be there 6 to 9 months and we ended up being 6 months mainly because we couldn't get our education visas which we were hoping to get which would have made it easier to stay longer. And secondly, the house here, the rental wasn't quite as good as we thought. So it was a couple of things built up and we felt like, oh, we've done a good 6 months here. But it was brilliant, and the highlight package is strong.

And of course, the kids had a great adventure, and they'll always have that as part of their story in their early years.

[48:26] Paul: I'm living a bit nomadically now, and people often say to me, "Well, you can do this now, Paul, but once you 'get serious' or have kids down the road, you surely can't do anything except have a full-time job." do these things. Did you get any pushback from people taking your kids abroad?

[48:47] Dreaming: No, we didn't get pushback. We got a lot of— I think people have learned that probably with me anyway, all the stuff we've talked about this morning. But I think the— oh, hello. Not long, 10 more minutes. Just talking about you. Yeah, that's Isla.

Yeah, we, it was more a case that I looked at the business model like quite, you know, family business model. And I realized that, okay, worst case scenario is it's going to cost us a little bit to do this. Best case scenario, we come back in profit. And I think it ended up costing us £1,000 a month extra than we were spending, than we were, yeah, than we were having come. So we lost a little bit, but then I didn't do a lot of work. And we did a lot of time with family and just enjoying the experience.

And I did a lot of time taking care of the kids as well. So it was fantastic. But of course you've got to go into these things with your eyes open. Like the Instagram version of it looks incredible, but the reality is that we were checking for snakes in the garden. We were, a lot of mosquitoes. The climate was intense.

Between 10:00 AM and 4:00 PM, unless you're inside or air conditioned or asleep in your hammock, it's not that, it's too hot, especially for a 3-year-old. Or 2-year-old. So that was hard. And there's less structured activities than you'd have in a town in England where, you know, kids have got loads of things to do. So that was— those things were challenging. But the upside was that, apart from being in the sun for the winter, um, was that we hung out with a— we got to know a lovely group of families who were all there for different reasons.

So 10, 15 different nationalities, a lot of dual national Children at the school, so half Thai, half from another part of the world. And so it felt really— but it was low-key. It wasn't sort of big global international school. It was just people who were there for the lifestyle. And, you know, we escaped the winter and escaped all the politics of this country at the moment. And yeah, I'd recommend it to anyone, but you've got to go into it with some energy.

You've got to go into it with the expectations that it's— yes, you won't have— you're not going to have the cold winter, you're not going to have the coughs and colds of the kids, you're not going to have these things that might be hard work here, but you're going to trade that in for something else, you know, like skin issues or heat exhaustion or, you know, so it's— there's always— wherever you go, it's going to be challenging. But we— what I like about doing that kind of thing is that when you're talking about it here, people go, wow, that's crazy. How's it going to go? I wish we were brave enough to do something like that. And then you get there and you realize you're the light. There's a lot more hardcore families than you.

There's people who've been living there for years or traveling around the world with all their kids and driving a tuk-tuk or whatever it is. And you're like, okay, but that's what's fun. You connect to that next sort of stage. So yeah, we, we had a wonderful time and we're very glad we made the effort, but it's a significant amount of energy to make that transition physically and emotionally, you know, back and forth with the family. So I don't think we can do it too regularly.

[51:59] Paul: Yeah. Is there anything different you're thinking about in terms of raising a family and designing work and life since being back from that?

[52:08] Dreaming: I don't think dramatically. It just emphasized to us two things. One is spend as much time as we can with the children, especially these early years, together as parents. Although that's intense, there's ups and downs with that. The trade-off is that you build these wonderful relationships with them. And nature.

So we've come back to it. We're not in London, but we've come back to a busy town surrounded by beautiful countryside, but we're craving more nature. So that's why we want to get out to countryside. So, um, so yeah, those are the two, two big lessons in terms of work. Um, so it's an interesting time for me because I've got good projects going on and I'm working again with Escape the City, um, a little bit. But this is a time where I'm exploring what else could I— what do I get my teeth stuck into next, the next year or two?

Um, and that's just, uh, you know, an exploration phase at the moment. But I don't have that much time to explore, so trying to do that occasionally when I'm having interesting conversations like these.

[53:06] Paul: I'd love to close with perhaps some reflections in terms of what you've seen. You've obviously experimented in many different ways with how to live life, how to design work around that. What do you, what do you think have been some of the major shifts in terms of just people's expectations around what they expect from work? It seems especially in the last 10 years, a lot more people are almost expecting to kind of design a career in life similar to what you've been doing over the past 20 years. Have you— yeah, have you found something like that, or a continued shift towards people's expectations raising in that?

[53:45] Dreaming: Totally. And I think there's some big trends going on globally that are accelerating. Obviously, you know, last 20 years we've seen communications channels shrink because of the internet, and therefore travel has become a very different seems a lot easier to get around the world, and then Wi-Fi being available so people can start working more remotely. So those trends, and also the fact that people are able to, you know, more and more people are freelancing, there's more and more opportunities to do that kind of work, all that's accelerated that stuff. But I think that maybe one of the big differences now is also the expectation of, because of the, uh, you know, 20 to 30 year old is not is, you know, the values alignment for them between what they— what matters to them in life and their work is now completely integrated.

And so this idea of going and working in a certain job that isn't quite right in terms of what matters to them is quite a big challenge, whereas maybe in the past it's like, no, this is what you do, and then you go outside of work, you do things that are important to you outside of work. So that's shifted things. And we're seeing that disruption in big companies around that, because demands are being made, which is great. And this B Corp movement and all this stuff is just fantastic. So yeah, it feels like a really exciting time. Of course, alongside that, you've got a lot of trends that are chaotic, whether it's economic or environmental.

And so I think it's, you know, the mental health of this generation coming through now who feel like the world is Yes, it's their oyster in the sense that they can create opportunities for themselves, their connections, their tools. There are lots of sort of paths to— different paths to follow now, and lots of amazing resources like your podcast to inspire them and guide them. And the flip side is that it feels chaotic. It feels like, wouldn't I be better just to stay put and, you know, do what's sensible? But I think there's ways of de-risking this, all these transitions, and both financially and psychologically and, you know, in terms of the CV as well. It's like, it's just about telling your story and why you've made these decisions.

And I think one of the best books I've read on this topic is called The 100-Year Life. I don't know if you've come across it yet, Paul, but it's a really cool book.

[56:07] Paul: I've heard people reference it.

[56:08] Dreaming: Ah, yes. It's a brilliant book because it really goes into detail about the shifts, especially around the length of our careers and the fact that, you know, if you're 20 now, you've got more than a 50% chance of living to 100. And that's the shift in mindset then for that generation. And so what that means is that you're thinking about multiple careers, multiple identities, you know, 'cause you're gonna be working or, you know, building projects, living your career for 60 years or so rather than 30 or 40. That is a big mindset shift that's gonna kick in over the next decade. And therefore, what does that mean?

Do I spend the first 10 years exploring and trying, you know, trying out stuff before I commit to something? And then I do something for 10 years and then another thing and then another thing. So I think those kind of reinventing your career and reimagining work exactly as you're doing is gonna become more and more frequent. But yeah, I think it's a time of flux in the world of work, and that's exciting and terrifying for those that are caught up in it. And I think my last reflection would be just if you're kind of curious about all this stuff, you're listening to these podcasts, you're reading these books, and you don't know how to start taking the steps, the first step is just to be on listening and reading and watching is to go and start spending time with people who are doing it, whether that's in meetups, in real life, right? Not just online.

Meetups and events in communities like Escape the City in London and others around the world because that will accelerate your mindset and the opportunity. And before you know it, you'll be recording a podcast in Taipei.

[57:48] Paul: [Speaker:TYRONE] I love it. I fully embrace that advice. I'm so grateful to a lot of the people I met in my own path. I have a link now on my site where people can just book curiosity conversations with me. Being able to form that first friend or that first person that's thinking or living in a different way can be much more impactful than no matter how many books or side things you're starting.

[58:16] Dreaming: Of course. It's a combination, I think. For me, it's like the hybrid of everything. I'm going to have to apologize and run away because I can hear my children. The reality of life is kicking in. I got to go and help.

But thank you for, thank you for your time and your interest.

[58:31] Paul: Fantastic. Thank you for the conversation, Ben, and I will link up to the Rebel Book Club and everything else you're involved in and continue to wish you the best of luck and continued adventures.

[58:43] Dreaming: Thanks so much, Paul. Take care.