This is a meta analysis of all past interviews for this show and a distillation of the top 10 actionable insights that you can use to improve your quality of life.

This is the audio capture of the opening keynote Sean gave for Nomad Cruise X on 11/30/19. It’s the distillation of the top ten lessons extracted and distilled from all the guest interviews for this show. If you’re a new listener this is a great table of contents index to the current body of interviews. Happy New Year!

Show Notes

Time   Topic
0:03:15   Welcome and context
0:05:24   Sean’s Why
0:08:40   The methodology to this analysis
0:10:11   #10: Impostor Syndrome – Danielle Thompson
0:12:02   #9: Understand Brick Walls – Christiaan Oosterveen
0:14:08   #8: Hustle ’til it hurts – Andres Cohen & Johnny FD
0:15:26   #7: Start Small but Start – Diego Bejerano & Greg Caplan
0:16:42   #6: Ditch the Anchors – Matt Bowles
0:17:42   #5: Trust your Heart & Immerse yourself in positivity – Marissa Meddin & Khemit Bailey
0:19:32   #4: Prioritize your Health: Trevor Gerhardt & Ben Lakoff & Kara Mosesso & Bernie Miller
0:22:16   #3: Get Clarity on your Why: Matt Dunsmoor & Sondre Rasch
0:23:10   #2: Create 10x More Value than you Harvest: Alex Hillman
0:24:05   #1: F*ck Regret: Christa Romano
0:27:00   Questions


Nomad Cruise
Freelance Travel Network
Randy Pausch Last Lecture
Why We Sleep book
Matthew Walker on Joe Rogan’s podcast
Power of Calm program
Regret Minimization Framework


Dori: 03:16 This person I know here chroma the grievous cruises. He’s a, an entrepreneur or business rent, and he has a podcast where he’s interviewing nomads so far and he’s reviewed SUNY for nomads talking about their life, their challenges. And now he’s here to share the 10 insights that you learned from them. So whack on one stage. Sean

Sean: 03:51 Great. Thank you very much. My name’s Sean and like she said I have a podcast for nomads that is aptly named Nomad Podcast, so you won’t forget it. And yeah, I’m super excited to lead things off. So I want to do a quick poll before we get started. Raise your hand if you’ve been itinerary. In other words, you’ve been doing your job around the world for a year or more and you consider yourself a long time nomad. Okay, awesome. That’s a good portion. About 20% of them. Raise your hand if you are a fixed, you work in a, you have a home base and you’ve been working from one place. Okay. And then have you put your hand up, keep your hand up if you would say you’re an aspiring nomad, you’d like to try out this lifestyle of bouncing around the world.

Sean: 04:34 Awesome. Okay, cool. So hopefully this is gonna be useful, not just for you guys, but also for the people who’ve been doing it for awhile. Like my man Matt up here. [inaudible] But yeah, what I’ve done. So let’s see this down. There we go. So let me give you some stats first off. So as Dory mentioned, I’ve interviewed 34 guests so far on the show in the last year. It’s about over 200 hours of work into this project. It’s generated 776 pages of audio transcripts and that’s just over 400,000 words, right? And so my challenge here in the next 20 minutes is to distill all of this into 10 actionable lessons for you guys to help you have a better life. I think it’s useful to understand the why anytime you’re digging into something. So I’m going to quickly give you my personal why.

Sean: 05:27 My why is very simple. You guys, my why is to help others be gravity so that you can be free to do what you’re born to do. I went through the Simon Sineck process. This has been like crafted over a number of years, but this is my why help others be gravity’s can be free to do what you’re bored with you. So everything I do is couch around that. So I’ve been a nomadic for the last three and a half years. I’ve been remote for four and a half years working for a company called Pagely is the director of sales. And the first year before I was remote, I was working out of my apartment in Phoenix, Arizona. And you know, I was making good numbers, but I just was not thriving. I was not, I just felt like like slumbering through life. And I feel like this is not an uncommon thing.

Sean: 06:07 Like we kind of get winnowed in through like a series of career choices and whatnot and you kind of just get reminded, let you, they wind up in a rut basically. That’s how I was in that rut. And it took discovering the nomadic lifestyle to eject me from that. And I had a pretty awesome result. My sales numbers went up 70% the year that I went abroad. Social life just, you know, flourished. And just all these things just started clicking. My health got better. So no matter travel was like this kind of miraculous like shot in the arm of inspiration. It just like revitalize me in every possible way. And so this is my, why is this like why I’m spreading it. And to understand why is, I also think you’ve got to ask the why three times. So why is this important? So I read this article in the New York, Texas called the lost Einsteins.

Sean: 06:53 And the premise of this article was that at any given moment in the world were deprived of, would be Einsteins, in other words, kids that would been the next time sign and share these amazing inventions and creations just like their natural talents were flourished, but they’re not there. And that flower will never bloom because they were not given the same nurturing experience, the same opportunities as people who have higher socio economic status. And when I read this article, I got goosebumps but for a different reason. And that’s because I do believe that this is a true phenomenon. I believe that this is something that’s actually happening, but I also believe it’s happening in adults. I believe that there’s this adult slumber and that it’s more common than we think and that no matter travel could do for other people. What it did for me is that it can reawaken it, just bring people back to life, almost like a defibrillator just shock you out of whatever celebrity you’re in.

Sean: 07:47 And so that’s, that’s why I engaged in this project and then to ask the why that third time. Why is that important? It’s because I believe that the problems that we’re going to face as a world in the next decade are only going to be solved by creative inspired individuals. It’s not going to be people that come through an education system, which dulls, you know, basically rounds the edges and kind of like makes cookie cutter factory workers. It’s going to be people that are traveling the world exposed to all these amazing cultures and ideas and studying different fields and then coming into contact with other people that, you know, it would have been an improbable thing that these two people ever met, but it’s going to be this diaspora that creates the next crop of Einstein’s that we need to solve. The problems are going to face us.

Sean: 08:30 So this is ultimately the root cause of why I believe this is important and why I’ve dedicated so much time to this effort. All right, so with that setup let’s talk about the methodologies I used. So 400,000 words, and it’s a lot. It’s half a million, almost half a million words. I wanted to make sense of this. I wanted to do it in a methodical way. You know, I’m all about data science. Like how can we do this methodically? So so I thought, what have I fed all those words into a tag cloud and it made just one big word cloud out of this and say, okay, what’s the most used words in these interviews before I unveil it? Anyone have any guesses as to what words you’ve used to shout him out? If you do freedom could guess. Optimism, creativity, those are all great guesses in that I would say traits that are very common to the people I interviewed.

Sean: 09:20 Here’s the answer. This is the word cloud that came out of it. There’s a lot going on there, so I kind of added some emphasis to see the big ones, but we have to think really kind. No, we’re go right people. Yeah, so all very positive words. But it’s hard to draw any kind of conclusive themes from this, right? So clearly we need to go deeper. And the way that I did that, this led to the next thing which actually solved it is I went through every episode and the show notes, these are the show notes at the bottom. It’s basically a table of contents for the episode. Went through all 34 episodes, scour the show notes, and I started making linkages and I just went through because I had all these conversations so I know we said, but this helped me jog my memory and remember what we talked about and then I was able to start circling things and drawing patterns and from all of that process and merge these 10 things.

Sean: 10:09 So let’s without further ado, here is number 10 okay, imposter syndrome, you guys, we all suffer from this. This was a critical insight like this is Danielle Thompson. She’s a 25 year old entrepreneur from Canada currently living in Bali, but she’s been all over the world. I met her in Lisbon a few years back and then recently again randomly ran into her there, which is when we recorded this interview, which is 25 years old. She’s built a very successful business. She’s a freelancer and basically built a virtual agency. She got so much business, but she started farming it out, hiring people, turn it into an agency, and then went a step further and actually built online Academy and call it the freelance travel network to teach other freelancers what like the lessons that she had learned along the way. So interesting. Like 50,000 Instagram influencers. It’s ridiculous. So by any stretch, like this person is very successful.

Sean: 11:03 You can’t argue that a 25 year old, she’s very accomplished and yet she feels imposter syndrome. So this is something that just we all suffer from. And I think the key insight, and this is just a theme across most of the guests I interviewed had the same thing. So I think the takeaway here is that recognize that you guys recognize that this is not unique. Like I’m looking out over a sea of humans. How big, what am I doing here? Like I, I’m, I’ve never had some massive successful company or anything. Like I just interviewed a lot of successful people, right? So I feel like, well, what I know does ever be here, but I think this is like the insight is that we all have this no matter who you are, this, you know Danielle has this. So just recognizing, I think the key is recognize it.

Sean: 11:45 Say I hear you imposter syndrome, I hear you talking. I’m not going to listen to you. I’m gonna put you in this little box over here and say that’s nice, but I’m going to go about my wife because that listening to that voice will Rob you of giving your true gift. So that’s imposter syndrome. That’s number 10. Number nine, has anyone seen this? The last lecture? Randy posh. Raise your hand. Yes. So this is like a really good thing. I would like write this one down and put this on your list for something to watch. It’s like amazing talk. This Carnegie Mellon professor who is unfortunately no longer with us, but he gave a terminal cancer and gave a last lecture, which is brilliant. It’s amazing talk. But this is one of my favorite quotes from, he says, brick walls are not there. Keep, keeps out there.

Sean: 12:29 Just give us the chance to show how badly we want something. And so there’s another thing that I noticed is that many of the entrepreneurs that I interviewed would hit a brick wall. It’s like we all hit this low point and it’s not something to hold us back. It is that actually like the instruments that forges us, that allows us to prove how badly we want something. And I think perhaps no one epitomizes better than this guy. This is Christianne [inaudible] that’s a guy I met, a Dutch guy in Lisbon. Long story short, he’s tried to start up, ran out of money, didn’t have any money to pay anything. The 34 Euro insurance on his scooter is at his girlfriend’s house. One night cops come arrest them, pull them out of the house and he ends up winding up in prison and it’s in prison.

Sean: 13:16 And he’s reading this book by Richard Branson and he gets like this epiphany is like, no one’s going to solve this for me. Like I clearly have some limiting beliefs that have gotten me here. So I’ve got to figure out the neural hacking to get myself right. And he pulled himself out by his own bootstraps. He’s a professional speaker now, just ran a marathon and Elizabeth in three and a half hour marathon having never run before. This guy used his own techniques to teach himself how to run a three and half hour marathon, having never run like a five K. And so, so I think the lesson here is that these brick walls, you guys that we all inevitably face in hindsight it’s always easy to say like, Oh, that’s what that was. But it’s like when we encounter them in real time, you’re just like fuck this massive challenge and like this is terrible.

Sean: 13:58 But like just slightly tweaking your mindset and realizing that that is like kind of a gift in the skies to help you prove how much you want something. That’s what the brick walls are for. Okay. So number eight, hustle till it hurts. I don’t know if anyone remembers on the race from the last cruise. Awesome Panamanian guy just has more hustle in his little pinky than I think most of us do in this room. But he’s written his bike all over Panama has this really creative business. He’ll make these promotional campaigns and he’ll actually kind of put the cart before the horse. We’ll make a promotional campaign and then sell it to these major brands like under Armour and Nike and whatnot. So this guy is just like the epitome of hustle. I can’t tell all his stories, but if you listen to his episode, it’s just a mile a minute about all the stuff he’s done. And he’s incredible. Another person, I think Johnny FD, I’m sure a lot of people know this guy. You know, hustle till it hurts. Literally this guy went to Thailand, taught himself movie Thai fighting and which is getting hurt every night, but was making it work, was at least earning enough to then become a stupid diver instructor to then start a blog and write a book and a course. And he had now has like 18 streams of passive revenue, but that is just like just hustle man. Just made it happen.

Speaker 4: 15:13 And this is a public [inaudible].

Sean: 15:24 All right, so that was number eight. Let’s go to number seven. Start small. Let’s start. So this is Diego [inaudible]. We may meet him, I believe he’s, I know bond actually with wildlife tribes so we might get to actually meet him there. He started wifey tribe. It’s one of the most popular tribal programs out there. The way he did it, he didn’t come with some elaborate business plan and raise a bunch of money like the way he did it was literally just sending an email to a hundred of his friends and said, Hey, I’m going to go to Bolivia. Does anyone want to go and work with me just to try this out? And literally that’s how the whole thing started. They’ve got like five chapters now around the world. I just did one with them in Barcelona last month. But like that all emerged from just that one little step of sending that email to a hundred close friends and doing that.

Sean: 16:06 Similarly, this is Greg Kaplan is the co founder of remote year, which is arguably the largest travel program out there. Myself and Matt looked at it. This is same thing. You got started in a different way though. He put it a just a crappy landing page up and then closed, posted it to hacker news and within a month they had 50,000 signups to the program. Right? But it was there just like one little small step after another. They didn’t go out and raise it, touch, you know, a bunch of money, although they have sense, but it’s just the idea is you guys start small, don’t try to boil the ocean, start small, but start number six, ditch the anchors. So my man Matt bulls by the way, but we often get confused for one another. The other tall white guy with a podcast for nomads on the boat.

Sean: 16:52 So this is the kind of thing that to the extent you guys can go carry on only in the, for the people that are trying to travel a lot and go around the world, this has a huge impact aside from the tactical advantages, like physically being able to move through security faster and not worry about like, you know, the exposure of having lost luggage and all that. But I think Matt would attest that there is a larger factor that the eclipse is all those importance. And that is psychologically the lightness of being like deliberation from stuff that you have. Once you’re able to put everything you own in a backpack and just walk around the world with that, like you’re living proof at that point that you value the experiences more than you do this stuff. And so I highly recommend if you can get all your stuff into a backpack and just sell everything else, it is quite the way they do it.

Sean: 17:41 So Disney angers. Number five, trust your heart and immerse yourself in positivity. So this is another common theme across the people that I interviewed is that your ability to decouple this from this and to recognize like this can fool you, this can lead you astray and rationalize things that you think you should be doing and it gets this an audit mess, but these things can quiet this and then focus on this. You will be better served. And I think Marissa Medin, she was on the last cruise. She’s also involved with wifi tribe. She embodied this. She was working at Pepsi, had arguably a dream job working in the music promotions department for them. People like Beyonce, Jay Z going into, he’s like gala red carpet events. They’re like amazing job by every standard but was not fulfilled and did not necessarily have the supportive network. Her friends were like, well, why would you quit that?

Sean: 18:32 That’s amazing. Like you’re crazy. Don’t, don’t put that job right. But she wanted to do something else and did not have the support network. So you know what she did? She made it in the form of podcasts. She surrounded herself. She listened. She picked the podcasts and had them in her ear buds every day, giving her the support she needed to then eventually go and do what you wanted to do. So creating the network if you don’t have it. The other example of this, this is Kevin Bailey and Lisbon he worked for another big company. You may know Apple as the global risk assessor. He was traveling all over the world, same thing, arguably a dream job, but wasn’t fulfilled. And he found his supportive network in fiction. This guy was able to like the movies that spoke to him and the fiction, those works. He was able to find support in those characters, in this dialyze and have that be the supportive network to then turn that into a system.

Sean: 19:22 And now he’s actually helping others through this methodology. But again, like decouple this list of events. Cut number four, prioritize your health. The people that I interview all seem to have a focus on health. And this is my man Trevor Gearhart. He was the very first participant of remote year, first group. And he is just a CrossFit fanatic everywhere he goes. He finds a CrossFit boxes, the first thing he does in any city same thing. Someone you may know sitting up here, Ben Laycock does the same thing, right? I’ve been with this guy, he will pick an Airbnb based on the proximity to a CrossFit gym yesterday. I’m with him and we’re literally buying a kettlebell walking around here at a rock land and to find a 16 kilo kettlebell in his backpack. So, but he knows he prioritizes health and he puts that above everything else because he knows he needs to get a good workout it.

Sean: 20:16 Right? So if fitness and exercise is one pillar, I would say the other pillar is diet. This is Kara [inaudible]. She’s a certified nutritionist live a decade on exclusively plant based diet and she’s run 26 marathons, right? So she knows a thing or two about health. And her episode is amazing. It’s nomads I think were particularly afflicted with not necessarily having access, you know, and it’s like just more complicated to eat healthy, right? We don’t always have a kitchen if you don’t know where the health food store is. And it’s just harder. It’s tricky. But that’s why it’s up to us though, to take ownership to study enough of nutrition so we know that we can make it work wherever we are. All right, so if exercise diet are the pillars, what do you guys think is the foundation of health? There you go.

Sean: 21:05 Sleep. This is Bernie Miller. He’s a sleep specialist and MD for the Mayo clinic in Phoenix, Arizona. And this guy has been treating sleep disorders for two decades. I had him on the show because I wanted to learn more about what’s involved there. I’ve subsequently read a book. Has anyone read why we sleep by Matthew Walker? A couple of people. That is an awesome book. I would write that one down. If this is important to you. Really recommended. He was also into the Joe Rogan podcast. It’s an excellent podcast episode. But anyways, sleep you guys very important. It’s like everything else. If you’re, if you’re not getting good sleep then it’s going to unravel whatever you try to do in these other capacities. So it is literally a bell foundation. And I would argue there’s one more thing here with health is my man Rob price from Sydney, Australia stress, let’s say stress is like if the pillars, you know, exercise, diet and foundation sleep, the ability to mitigate stress consistently is like working with good building materials.

Sean: 21:59 And so he has a whole strategy for doing this. He spent like most of his life studying stress and developing a program called power of calm. But anyway, whether you use meditation or whatever your method is, you need a reliable method to combat stress gut. So it’s help clarity on your why is my man Matt Dunsmore, he is a facilitator for Simon Sinek. That’s the program that I mentioned that I went through. But gaining clarity on your, why you use or why is like your, just your essence, your internal, the just the thing that makes you who you are and getting more clarity on that just is like a force multiplier. It just gives you such more power over everything. And I think the guests who most epitomize this is this Andre Raasch, he’s the founder of safety wing. Some people may be using that insurance here actually for travel shirts, but he got very clear on that.

Sean: 22:49 You know, you face challenges both as a nomad, as an employer about just travel insurance. It was just a mess. And so he set out to solve it and to make it so that you could have that feeling of security, that safety net and feel supported as if you were in your home country no matter where you are. Right? So getting clear on your why is important multiplier. All right, number two, we’re almost there. Create 10 X more value than you harvest. This was a subtle shift. This is something that’s very consistent across the entrepreneurs that I interview. And it’s the idea that you know, when you think about entrepreneurship, you think about like creating a product and it’s selling it and then that’s the name of the game. But it’s subtly different than if you think about it more like creating massive value and then just harvest a small fraction of that.

Sean: 23:34 You will be successful. And so this is Alex helmet. I think episode 14, he created something called a 30 by 500 Academy where he actually gives you a framework for doing this. And sales Safari [inaudible] bonds, like his whole methodology for how you do this consistently. But this is something that was just consistent across all the entrepreneurs is they focused on this creative massive value and then just sipping a small sliver of that for themselves. Okay. Number one, you get a little like drum roll for this one as the final one here. All right, so number one, you guys, the number one lesson from all this fog regret, like this is a, this is something like just truly making decisions on what you’re going to regret at least down the road. And this is Krista Romano. She’s been, I think she’s on nomad cruise nine right now, but I think more so than anyone I interviewed, she has a really touching story.

Sean: 24:26 You guys, you’re more than a pretty face on Instagram. She’s actually a really sweet person and she had an an accident a week before in college. The week before she was scheduled to go on a study abroad program. She actually had a diving accident, dove into a pool, hit her head on the bottom. And luckily at that pool it had been like half a foot more shallow. She could’ve been paralyzed or worse, right? So she did not guys and not get paralyzed had vertebrae fused and recovered from it. And now Lynn’s very much carpet diem like bucket list everywhere she goes is all about like seize the day ready. But it’s that idea that you make decisions based on, I don’t want to regret this down the road. I don’t want to be on my deathbed and be like, I wish I had tried that business or I wish I had asked that girl out or I wish I had done whatever.

Sean: 25:12 Like you just want to live without regret. So actually I want everyone to just basically extend your arm right now. Everyone did this with me extending your middle finger and a count of three. Plug regret. Two, three. All right, you guys in summary here to wrap this all up? Oh yeah. By the way, regretted it. There’s actually like a legit decision-making theory called a minimization of maximum regret. You can look it up, it’s on Wikipedia. But in summary, recap all this imposter syndrome. It’s real. Don’t fall victim to it. Understanding what the brick walls are, whether therefore hustle until it hurts. Start small, but start ditch the anchors. Go carry on. Only trust your heart. Surround yourself with positivity, prioritize your health, diet, exercise, sleep and stress reduction. Declare you on your why. Create 10 X more value than your harvest and fuckery. Greg, you guys, we’ll skip the visualization exercise cause I think we’re just about out of time here.

Sean: 26:14 But these resources that you might go to nomadic, all these stories and more are there no matter I actually, this was just one project. I actually put all of this into an online course and I know David Danker is probably going to kill me for this, but I made a coupon code. It’s totally free. Anyone in the room who wants to do it NCX rocks. You can just use that. It’ll be good for the rest of the crews. So you can do the whole course for free and get all that there. And if you are a longterm know about it, there’s a good chance that I want to interview you. So see me at some point. We can also talk about making you an advocate. I have a fairly generous affiliate program and so that’s me scrolling on dubs almost social media. You guys, thanks for listening. Any, I don’t know if we want to do questions now or what do we open it up for questions? Is there a time a few minutes later? Yeah, we got time. All right, so anybody have any questions about this stuff? No questions. Oh yeah. Josh,

Sean: 27:13 Have you used these lessons to change the way that you live and have you seen a difference in the way that your life unfolds because of that? Yeah, absolutely. So in every way, like the health stuff was super important. Meditation has been pretty profound in terms of like presence and awareness and just like centered prioritizing health. Like for me, it kind of all, like I mentioned, like when I went abroad, I think it was a combination of things like being exposed to a lot of creative stimuli. Like I had been working in my apartment and it was just literally like I forced myself to go to a cafe every day just to see another human, like to get that interaction. But then like swing that pendulum swings too far the other direction and now you’re all over the world. You’re meeting amazing people.

Sean: 27:57 You know, I did remote year, so I was with the community of 75 people. And so I also had the other one plate, consistent tribe, but also exposure to everyone there everywhere else where I went. But yeah, no everyone of these things, I think the imposter syndrome recognize it like, again, cognizant of it, but afflicted behind it. So yeah, I think each one of these lessons has been very powerful. So how long did it take you from the podcasts or, yeah, so I just kind of did it. I don’t know, I just fumbled my way through the first. You’ll see like the early episodes are kind of a different format. And so I just started doing sort of recording on zoom and release them and then kinda got more professional and Matt actually getting a lot of good advice on terms of the format, how to refine it and be more professional about it.

Sean: 28:53 But again, that starts small, but just start. I think if you’re thinking about doing a podcast, the key is just to start, just like literally take your phone, you use the voice recorder. I know Paulette Bo rolls around with equipment. He’ll just like grab him ad hoc on the moment. I think it could is just do something, get going, and then once you’re in motion, it’s easier. Once you have that inertia of moving, I think it’s easier to refine it than it is to like the whole perfection is the enemy of good enough. Right? Like so.

Speaker 2: 29:22 Anyone else?

Sean: 29:26 Okay, cool. Thank you guys for listening.

Speaker 2: 29:32 [Inaudible].


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.

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