Top Nine Lessons I’ve Learned From Three Years of Full-Time Travel as a Digital Nomad Entrepreneur

So we have been traveling now for over three years and in today’s episode you’ll discover what’s worked and what hasn’t as it relates to my experience in running a location independent business as a digital nomad. Welcome to the podcast, everyone. My name is Eric Dingler and I am a full time digital nomad entrepreneur traveling around the world with my wife and our four teenage kids. And we are having a ball and we are very thankful for the company that we own is able to do this, this, this side hustle that never was supposed to be what it is. This side hustle, though, that turned into a full time thing that gives us the freedom that we have to live this amazing lifestyle. And now that we’ve been doing it for a couple of years and so many people ask us about it. My wife and I are trying to help others. We want to not just inspire and, you know, people that that’s great, but we really want to help people answer your questions, equip you to have success with this because it’s a big thing and we realize that. And so my wife, she’s got her podcast, Digital Nomad Family podcast, where she talks about the family side and the travel side and all of that. And here on Digital Nomad Entrepreneur, I get to talk about the business side and I’m going to jump right into that. But I got to just quickly say, it’s so interesting right now to be recording this because I am recording this in my childhood bedroom. We are back in the United States visiting my parents for Thanksgiving. Marissa’s parents as well. They live very close to my parents. But we’re we’re parked at my folks house. They’ve got the room and space for us. And I was standing here getting ready to record. And it brought this memory back. I used to you know, I used to have this tape recorder. All right. And I used to tape into it. Sermons that I would preach, you know, in speeches that I would give. And they were all things that I had heard other people say. But I would come home and and I would imitate that and be them and and record that into a tape recorder. And here I am, like, oh, my gosh, I don’t know, 40 years, you know, 30, 35, 40 years later. Actually recording into my my phone. I record my podcast into my phone, but recording my podcast into a phone in my childhood bedroom. So just kind of, you know, struck me as interesting, if you will. And I thought I would share it. So there you go. If you’re like, Eric, this isn’t why I tune in. I don’t care about this. Well, good news. Let’s we’re going to get right into the content of today. So let’s talk business for a little bit. What have I learned from personal experience? Worked and hasn’t work specifically as it relates to a location independent business? Well, the first thing is that his work I’m going to cover this. I’ve got let’s see, one, two, three, four, five, six things on what work and three things on what didn’t work. And I want to cover the the six things of what worked first. So number one is having a flexible routine. Now, a lot of people think that routines are set. I used to always you know, I used to have a very set routine. Before we came, digital nomads and I tried to emulate that on the road. I’d get up at 5:00 in the morning, I would have my coffee, I’d have a breakfast. I go for a walk. I did my journaling. I did all these things. I really worked to try to keep that, and it just doesn’t work like that. In this lifestyle. There are too many missed opportunities. It was too challenging because we never I never knew what my time zone was going to be from from, you know for any given period of time in the into the future. And and we relocate sometimes during the week because sometimes it’s travel faster, cheaper, not faster, but cheaper to travel during the week. And not always. A lot of times we travel during the weekends, but I had a lot of Mondays where my routine didn’t work as I had to come up with a routine to make sure I was getting the important things done, but I had to build flexibility into it. So I how I finally figured out how to do this is I have a no meeting Monday policy. I don’t ever schedule meetings on Mondays. It’s no meeting Monday. And the reason I do this is when we arrive into a new city and I talked about this in a recent episode about how I choose my co-working space, but by having no meeting Monday when we arrive into a city, I have all day Monday with the freedom to take a breath, to walk around the city, to find my co-working space, to get things set up and make adjustments there. Then the rest of the time we’re in that city. I’m able to take Mondays to really get organized for the week, catch up on anything I didn’t get done the weekend before. Maybe take an extra three day weekend if you want, but I really like having that. No meeting Monday now. I always work on Monday. I don’t just take a surprise three day weekend. I don’t problem with that. It’s just not my personality to do that. I like working, so I’m going to be working those Mondays. Now, the next part of this flexible routine is I used to have very set, like from this time to this time every day I did this, from this time to this time, I would do this or Monday, Wednesdays and Fridays at 1030, I would do you know I would check QuickBooks, you know, and every Tuesdays and Thursdays at 1:00, right after lunch, I would do this certain type of activity. And what I’ve done is I’ve gotten rid of all of those blocks on my calendar and I keep Monday blocked off. I now keep Wednesday blocked off for no meeting Wednesday and I’ve got a few standing meetings that on Thursday. Why one on ones with my direct reports on my team. On Friday mornings I have our leadership team meeting and then the rest of Tuesday, the rest of the time slots. On Thursday I have a public calendar link and I let these people schedule themselves on my calendar. Now on Monday, I got five different blocks on their one hour blocks. I’ve got a prospecting hour blocked off. I have a quick book slash financial slash money management time blocked off. I’ve got a time block of leadership. I’ve got a time block of projects. Just project time. I’ve got lunch. I’ve got a little half hour slot for for lunch. Just a little 30, 30 minute one. And then what I do is on Monday, when I’m in my co-working space, when I’m all set up, I just I use those times. I meet those times. And then on Tuesday, when I get to the office and I get set up, I one of the first things I do in the morning as I look at my calendar and I slide each of those time blocks from Monday onto Tuesday, but I slide them around when people schedule meetings with me and I might have to shorten them or things like that. But then it takes me, you know, just a few minutes to do that. But then my Tuesday is set and I’ve got my meeting scheduled and then I’ve slid these time blocks in. And then on Wednesday morning I slide the time blocks over from Tuesday to Wednesday and I set up my Wednesday. I’m going to work. And then on Thursday I do the same thing. I slide each one over on my calendar, put them in and around when I’ve got appointments and, and when people didn’t schedule appointments and I do the same thing on Friday and then Monday they’re on my calendar again. There’s those are said as recurring events on my calendar. And when I move them on Tuesday or Tuesday morning, when I move them, I just click only this event that all events in this series just only this event and that breaks it out of the event. And then I go, I’ve got my flexible routine and this has worked really well for me. It’s, it’s bringing together for me the flexibility I need, but also time blocks, you know, a block calendar blocking or working in time blocks, which works for me. But for this lifestyle, I needed some flexibility in that. Okay. So that’s the number one thing that I would say that I’ve learned is works for me that is very different than when I wasn’t a digital nomad, when I wasn’t a digital nomad, my calendar, I didn’t have to have that kind of flexibility in my calendar. Now, as a digital nomad, I do. All right. Number two. The second thing that I’ve learned that works is really my portable office setup. You know, I’ve really had to get very comfortable with not ever working with paper of any kind, having my iPad. I use an app called Good Notes. Took me some time to get that all situated and organize the way I like it. And I’ve got that. I experiment with a couple of different computer stands portable. Q Keyboards or not keyboard but laptop stands and the one I’m using right now and absolutely it’s amazing. It’s two pieces of wood that lock in together and then boom, my laptop sits right on it at the perfect angle. And so I was great. I got rid of my bigger one. I got rid of my portable keyboard. Just my my office is really strong. You know, it’s been streamlined down. And so I’ve got it super small. Everything fits right in my backpack. I can pack it up real quick at home, get back the next day. So I’ve got a, you know, just my portable office at home. I’m going to try to describe it here on the podcast, but spending the time to get that right has really made a big difference. And it’s it’s again, different if you’re not location independent, you’re not to worry about this stuff. But being in a portable office, I had to make I had to really work that out. All right. Number three. Number three is having a solid team. Now, if you’re just starting out and you don’t have the ability to hire, you’re not ready to hire you either. Financially, you’re not ready to hire from a leadership perspective, you’re not ready to hire. You know, I started when I first started out, I didn’t have a team, but I employees, I should say, but I still had some team. I had my business banker that I just built a relationship with and was able to get some advice from him. A CPA, you know, that does my taxes, my financial planner, a coach. So I still had a team. Team. Does it mean people you pay, having a team can be having the right mentor around you, a partner. You know, there’s there’s all kinds of ways to have a team. Now, I have employees on my team and I’ve got a staff and I’ve got other leaders and things like that. So now I kind of have it in place, but it’s so important to have the right people, so you got to take time and focus on that. But having the right team, so super important. All right. Number four. The fourth thing here is really my frameworks. If you’ve been a podcast listener for a while, you know I love frameworks. I’ve got a whole bunch of them. But the three that have been the single biggest and most important frameworks for me has been OPI three. And if you’re not, if you don’t know what any of these are, OPI three you can listen to the last episode just before this. When I talk about one persona, one product, one pathway, that’s my business model. And I look at that every single day. What’s the you know, what’s the problem solving for who? Who are we trying to help? What are we trying to help them with? That’s the first one. That’s the persona. Then I have the product. Okay, what is our prior product? Is this how do we make it better than it was yesterday? How are we constantly making improvements to our product? And then third, the pathway, how does somebody go from not knowing us? They becoming a customer, not just anybody, but the persona. How are we getting in front of our persona? How are we communicating to them? What are we communicating to them, where and all those things and what’s the pathway they take from becoming aware of us all the way up to purchasing from us? So that’s the three framework. Then I’ve got my core five, my and you heard me talk about those a few minutes ago. If you were paying attention, you heard me mention several of these that I talked about my movable time blocks I the leadership time block wide because the first system there are five core systems your business is going to have to have to be successful. And the first one is you need a leadership system. And so I have a time block every day where I spend on leadership. Now, each day I do a different thing. So on Monday I review the weekly reports. All of my team has to submit a weekly report. It’s just three simple questions and I review those on Monday. They have to submit their reports on Friday and I take Monday to review reports. And so I’ve got something different. I do on Tuesday and something I do different on Wednesday. On Thursday, my leadership I don’t need that time. BLOCK Because I have one on one meetings with the people that I lead. And on Friday I have my leadership team meeting. So on Thursday and Friday, I am developing my team. I’m investing time into my team, I’m coaching them, I’m, I’m leading. And so that’s what I do on Thursday and Friday. But I also have to have a system where I’m growing as a leader. How am I learning? Because I am the capacity of my business. So I have to have a leadership system that’s the top of core five. I’ve got leadership and then you’ve got lead gen, lead conversion, collecting and managing the money and then project management. And then the third system is the marketing momentum framework that I don’t just use for my business, but this is the framework we use as the really the heartbeat of our product that my digital marketing agency sells. And it’s, it’s our marketing strategy is what this third one is. How do people become aware that they need our service when they’re considering getting help for this service? What are they consider? How do we become the clear and obvious choice? What’s their purchase experience like? What’s their onboarding experience? What’s their customer journey experience like? And then the fourth one is how do we take our customers so they’re not silently satisfied but the raving fans and how do we build upon their the relationship we’ve worked with them. And so that’s, that’s our marketing momentum framework. So having these frameworks have been really key. All right. The next two things I want to share of what works for spot number five and six. Here are two tools that I use. Two tools that I use that I think would work will work for. Well, the second one well, sorry. The second one, you’re going to have to be a mac user for it to work. But my entire business is built on a mac ecosystem. You know, I’ve got a MacBook, I’ve got an iPad, I’ve got my iPhone, my AirPods. Like it is just a nice setup. It’s my tech stack, my, my, my physical hardware tech stack. And so, so that wasn’t our work. But this next one, we’ll see where 0.1, two, three, four, 5.5. This is an app and I’ll link to it in the show notes, but it’s a tool I use called Open Phone because I’m constantly changing SIM cards and always getting a new phone number. We no longer carry a carrier service for our cell phones from the United States. We used to, but it was just so expensive and wasn’t really necessary because we were limited on data and just different things like that. And it’s just so much cheaper. We we’ve got a 50 gigabyte SIM card in Chile for 30 days for $6, 50 gigabytes of data. For $6. For a man like. Come on. That’s so stinking cost effective. And so we’re just constantly now changing SIM cards, getting chips for our phone. So open phone gives me a set phone number that never changes. I can text with it to clients. They can text me, they can call. I can set hours, change the message based upon the hours I can set up called text back. So if they call me and I’m not able to answer it, the system sends them a text message. Like there’s a lot of great things. And open phone. So I really, really like that app. I would strongly recommend checking it out to give yourself a really reliable professional business phone number. Oh, excuse me. All right. So number six here of what has worked is this. And it’s set app, city app, set app. I pay. I think it’s like $10 a month and I have access to all these amazing tools for my Mac. I’ve got clean my mac, I use paste I use an air several A.I. tools from it. Now it I just there’s so many I use in there. Bartender sip. The list just goes on and on. There’s a VPN in there, clear VPN. And so there are a lot of tools that I’d be spending a whole lot of money on or just wish that I had that I, that I maybe couldn’t afford because I didn’t want to spend that much money on them. But I get it. Offer us a monthly subscription of, like, ten bucks. It’s absolutely insane. I don’t know how they do it. They do it. I’ve used it for several years and again I’ve got a link to set app in the show notes also on my resource page on my website. So if you’re a mac user, I would strongly recommend you check those tools out. All right. So those are the six things that I have learned from what has worked for me, having a location, independent business. All right. And has really helped me have the business, the freedom to do this. Now, what hasn’t worked, the three things that haven’t worked are the three things I’m going to share. But before I do, I want to take a second and slide a really quick personal little commercial in here, if you will. If you are trying to figure out where your business is, what what part of open three or core five you may need to be working on, but just you want a health check of your business of where it stands. Maybe you’re finding yourself constantly trying to figure out what to work on next. Like, that’s a big like why I don’t know what to work on next. Or, you know, you’re frustrated, you feel stuck, you know. And so if you’re if you’re kind of stuck or overwhelmed or frustrated or confused, like if you’re having just like this this just should be easy or I feel, well, I want to invite you to get a snapshot of the health of your setup, your structure, really, by taking an assessment, it takes about four or 5 minutes. And I’ve created this assessment based on o.P three and Core five. And what it does is for the people that take it, I’m able to they see the results, I see the results, and I’m able to follow up and say, hey, you know what this look like? The area that that’s holding you back right now, this looks like your bottleneck. Here is something you can do to work on that. Here’s a resource. Here’s a here’s a book I listed. Here’s a podcast I recorded about that. Here’s a video have on that. Here’s a tool. I’ve used this all of this in my my business. Like, you know, I step in there and help you out as I can with resources I have. And so if you want to see the results for yourself, for your business, if you want to get this just you’re going to all you need to do is go to D and E podcast dot com forward slash scorecard. All right D any digital nomad entrepreneur D and podcast dot com forward slash scorecard. All right. So back to the content of this episode, what hasn’t worked? And then I’m going to wrap things up with this week’s leadership tip of the week. So. Number one out of the three things that haven’t work. Number one, my lead gen strategy. You see the lead gen strategy that I had when we were in our you know, in the States living in Norfolk did not translate well to the digital nomad lifestyle. And so it took me a while to rework my lead gen strategy. Now, luckily, I had a book of clients and we were able to continue going back to our clients and upselling them into additional services that they needed, increasing our wallet share and growing our business that way, getting referrals from them. I bought a couple of small web design businesses from people and brought clients in that way. And so that that kept us growing for a couple of years. But it wasn’t a long term strategy, wasn’t super reliable. So. It took a while, but starting out, I had to rethink lead generation. So whatever you’re doing, if you haven’t hit the road yet, if you’re not traveling yet, you got to spend a little bit of time wrestling with your lead gen strategy. But that was something that that broke for me. So that was, number one, what didn’t work. I’ve got a newly gen strategy now that is working. I’m not ready to share too much about it yet just because I don’t have enough. I don’t know data yet to to show it is an actual case that I really want to be able to share with you. It’s going to take a couple more months because there’s always a a runway of time on this. And once I have it really fine tuned down and I’ve got results that are repeatable and I’ve done that with a couple, you know, I’ll, I’ll work this through with some one on one coaching clients and when they have success with it. And the success that I’ve had is is replicated by others. Then I’ll be ready to share it more publicly here. But I do want to share something with you until I figure out how to help other people replicate it. So just know that that’s coming down the line. But that’s something I really had to wrestle with with my Legion strategy. And part of it is just my personality. It was what it was a big part of it. And you kind of have to know yourself in this. But but legion strategy was one. Okay. The second thing that didn’t work. My bank card, to be honest, I had a I have a debit card with our bank and I didn’t really think I needed a a debit card or a credit card, really, that wasn’t through our bank. And so I didn’t have one because I was like, what? When am I going to be buying? I’m not going to be buying anything. And if I do, it’s all these digital things. And so I didn’t think about it. And I wish I would have, because as we traveled and I started using co-working spaces and then one time I had to have a repair done to my laptop. I’d use my business bank card, and every single time I use it outside of the United States, I have to pay an international transaction fee. And I hate fees. I despise those kinds of things. And so I have had to get a card that I could use outside of the states that has no international transaction fees. But it’s working out because it’s another card with lounge access and some other travel benefits helped earn some, you know, rewards, points and things like that So it gives us another tool in our tool belt for that. We have some personal cards, we get that kind of stuff on, but my wife talks more about that kind of stuff on the business side. You’re going to want to have a good business card that’s got some nice travel that works well with travel. Just keep that in mind. Okay. The number three thing that didn’t work for me was working from the Airbnb, and I spent a long time working from Airbnb’s two years working from the Airbnb where we were. And I thought it was amazing. I thought it was gold because it was so easy for me to be to just be right there. And I could step out and, you know, have breakfast with the family and I’m having lunch with the family. And if somebody need something, they just come to my office door and we didn’t have any extra cost with that Then it just I thought that was the bee’s knees. Until we were went to Buenos Aires and I thought, Oh, I’m just going to try a co-working space. Oh my gosh, I never want to go back to not having one. I get so much and. Well, you know what? I’m already at about 27 minutes in this episode. I don’t want to take up any more time talking about something I’ve already talked about in another episode. If you haven’t listened to it yet, I have an episode where I talk about this, where I talk about how I choose my co-working space, and I talk about why in that episode, co-working spaces works for me because it wasn’t working, working from the Airbnb. If I was a solo traveler, just traveling with myself would have been would have been totally okay, but not with a family. Speaking of family, if you want to see some of the behind the scenes part of our lifestyle, what’s going on, you know, and more real time live action and stuff. Follow us on Instagram. We’re on Instagram. Family of dashes like a dash that you would put between two things family of dishes. I link to it in the show notes, but follow us on on Instagram. We post over there pretty regularly about our life, what what’s happening on that. So I encourage you to do that. And the other thing is, I would say this, you’ve made it to the 28 minute mark with that. And so that makes you a power listener and makes you a super listener, an amazing person. And because of that, I have a huge favor to ask. Would you please rate review? Make sure you’re subscribed. If you listen on Spotify, comment on the episode, but this helps other people find it. And that’s why I’m putting this out there so other people can find it, so they can get help from it. So if you’re enjoying the show, please review, subscribe, rate, share, do all the nice things, do all the nice things. You’re a nice person. Why wouldn’t you do the nice things you would? Because you’re a nice person. So again, do that. If you have any feedback, send my way. Now, if you have nothing nice to say, I don’t know why you’re still listening, but if you have nothing nice to say, then if you know you. But you feel like it’s constructive for me to hear what you have to say. I want to hear it. Email me. Erik at Disney Podcasts Gone. I don’t put it in a review. You’re you’re not actually accomplishing anything with that. You know, you know, you don’t have anything nice to say. Don’t say anything at all. But I still want to grow. I still want to improve. So if you have some constructive criticism, email it to me. Otherwise, if you’re listening still you don’t like the show and you don’t want to do that. I don’t know what’s wrong with you. Go find another show to listen to hurt my feelings. All right. This week’s leadership tip of the Week. Now, this is one that I need to think about it when I put it on my show notes with the leadership tip of the week this week this this week is tension can only be managed never eliminated. And this is true and leadership in work. It’s true in leadership in your personal life. Tension can only be managed. It can’t be eliminated. There is a tension that we feel as a digital nomad family between traveling and continuing the travel and being at home. In our passport country, you know, and being with family and they look at you and they like, are you guys going to keep traveling, do you think? Ever going to slow down, stop any time soon? And, you know, there’s a tension there and it can’t be eliminated because we have this desire to keep traveling in, this desire to be with family, and so we can just manage it. And this is true in leadership for your business. You’re going to have this picture of the ideal product, the ideal widget, and you’re going to think that you’re going to have this picture of what it has to be. And that’s great. There’s nothing wrong with that. But then you don’t have the reality of what it is today. It has not going to reach the stage you want it to be at yet night like nothing ever does. And it takes time. And so you have this tension between the ideal and reality. And if you break that tension, well, that means you’ve either sacrificed the the ideal or you’re not admitting to reality or your goal was never big enough to start with. And so there’s always going to be tension. So if you feel tension ever good tension is there. But it needs to be managed not for the sake of eliminating it. It can’t be. You’re not you’re not going to eliminate it. And that’s not the goal. And that took a long time for me to figure out that that was a hard lesson for me to learn because I always wanted to eliminate tension. I always thought tension was bad and tension had to be dealt with. But what I learn from a mentor. No tension. Just tension must be managed. Not for the sake of the goal, to eliminate it. It was a huge turning point for me in my mind. My personal leadership. And work in my family. Leading my family. Leading myself. And so tension can only be managed. Never eliminated. Huge, huge leadership lesson for you there. Well, friend, thank you so much for listening to this episode of the Digital Nomad Entrepreneur podcast. I look forward to reading your reviews and any emails that you send me. And yeah, it’s going to be good. I’m looking forward to hearing from you. So with that. Make sure you chase the big dream lead with courage and safe travels. Attention, passengers. We’ve now reached our destination. We hope you enjoyed the flight. Have a nice day.