Travel With Type 1 Diabetes, With Jason Robinson, Nomad Experiment

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What is it like to clear $50k of debt in four years, quit your career in your late 30’s and go full nomad, and then get diagnosed with Type 1 Diabetes? Here’s how Jason Robinson managed all that like a rock-star, with his Nomad Experiment mindset. 

Related articles & interviews you won’t want to miss:
Starting a Podcast While Traveling Full-Time, with Anne Claessen
Creating Digital Nomad Visas, Summits and More, with Olúmidé Gbenro
How to Create a Location Independent Lifestyle, with Jason Moore
The Best Travel Medical Insurance for Long-Term Travelers 

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What is traveling with type 1 diabetes like? Jason Robinson of the Nomad Experiment tells us how, with a lot more info on getting out of debt, making career transitions, and more. #NomadExperiment #TravelWithDiabetes #DiabetesTravel #JasonRobinson #DigitalNomadTravel

Introducing Jason Robinson

As a working class kid from Ohio, Jason didn’t even realize that moving away from his home state was an option until he was in his 20s. At age 39 he had only been to two countries outside of the U.S.! He always wanted to travel, so he figured there was no time like the present. 

He adopted an “experiment mindset,” and a few years and many methodical experiments later, he eventually transitioned to being a location independent nomad.

He details a lot of these experiments in his first book, The Beginner Traveler’s Guide to Going Nomad. It’s full of tough love, tips, and strategies to help people finally kick-start their travel lifestyle.

Jason had to dig out of $50k in debt in his 30s, so he’s a huge proponent of simple but effective budgeting. And in late 2020, at age 42 during the Covid pandemic, he was diagnosed with Type 1 Diabetes, adding to all the new things to figure out. 

In this interview we discuss:

  • The ins and outs of making a big career transition (especially when it involves leaving a cushy job). 
  • How and why he cleared 50k of debt in a very short period of time. 
  • What it’s like to travel nomadically as an insulin-dependent Type 1 Diabetic (including some great tips about how to approach travel insurance companies about pre-existing conditions and traveling with months’ worth of prescription medications). 
  • Some of Jason’s “Nomad Experiments”, including testing out van life, buying a one-way ticket to Mexico (never having traveled internationally before), sleeping away from home for at least 1/3 of the year, and more. 

Click here to heck out our informative and fun chat!

Interview Transcript: Jason Robinson, The Nomad Experiment

Making a Total Lifestyle and Career Change

Nora: I want to start off with life transitions because you, of course, were in your late thirties when you decided to make a pretty significant life transition in your lifestyle and your career.

I was 30 when I sold everything to travel long-term. I found, certainly when I did it, I would imagine when you did it as well, and for many people who are in their thirties, forties, fifties, even sixties who are looking at making a big lifestyle change, one of the big objections I often hear is “it’s too late”.

It’s too late for me to make a big change. It’s too– I’m too old. I’m too set in my ways. Or, it will be dangerous from a career perspective. I’m wondering what was happening for you in your life when you decided to make this career transition and what have you done since then? 

Jason: I always knew that there were options for traveling late in my twenties.

Some of my friends around me started traveling kind of crazy-like. I had a friend and his fiance who sold everything to travel Eurasia for eight months on like $18,000 and started to learn about hostels and all these things. The seeds were planted early for me. But again, I grew up just not traveling.

Having seen those things when I was early thirties, I tried my first hostel. I tried couch surfing. Very slowly, started touching these worlds of travel, but domestically in the United States. Cyclically with my business I became a freelancer, contractor, self-employed, however you want to call it, in my late twenties.

But I was always very dependent on the place I was in, Charlotte, North Carolina. I had clients that were large architectural clients in Charlotte, and it was kind of tying me to that place. Essentially, after cycle after cycle of these big projects, I realized that I was going to need to get out from under them if I wanted to try this world travel thing in that direction. 

Middle to late thirties, my dog Brody, who was with me for 16 and a half years, finally took off. That was kind of what allowed me to open up my life and say, okay, if you’re going to do it, this is the time to start doing it.

To talk to your question about people saying that you’re kind of late in life, or it’s too late to get started. I was just talking to quite a few people in the past couple of days about that theory. In reality, those of us– if we assume our adult life starts at 20 years old, at 35, you’re literally less than two-thirds through your adult life.

Assuming you’re going to live to 70, 80 years old, you’re maybe a quarter of the way through your adult life. There’s many ways to look at that and to kind of rationalize– life is very long. I love the idea that life is short, but life is also long.

Life is short, so live it quickly, live it now, but also realize that you can change directions many, many times throughout your life. When you look back, they’re going to look like the blips on the timeline. They’re going to be pretty small moments compared to the whole long lifeline. 

Nora: Yeah, absolutely. I think that that level of perspective is definitely very important. It’s never too late, because if you assign yourself a life sentence to something that you’re not really interested or happy or satisfied in doing, boy, that makes your life a lot longer and not in any of the right ways.

The Nomad Experiment Mindset

Nora: Kudos to you for making that realization. The transition for you, though, of course, it was a whole new world for you. The seeds had been planted, but you didn’t have that experience. So you adopted this experiment mindset. Talk to us a little bit about some of these experiments you did.

Jason: My old website used to literally be called The DGTL Nomad. Like the letters. It was terrible. I was talking to my mom in Ohio when I was like 37 years old. I hate using all these numbers, but they’re fairly irrelevant, but obviously they’re relevant. I was talking to her and I said, “It’s called The Digital Nomad. I don’t even know what that is. I know it’s something I might want to be, but I don’t know if I want to be it.” I said, “It’s more it’s like an experiment. It’s like a nomad experiment.” All these bells went off in my head. This conversation literally happened and everything just went whoa, that’s exactly what it is.

Of course I looked up all the socials on it. How does nobody have all of these things? And I bought everything right there. The minute I started viewing everything as an experiment– I am wildly analytical. That’s what I get paid for as a graphic designer, and a brand designer, is to really think through all of the avenues.

I’ve done that my whole life. So for me to– for someone to adopt this mindset of “It’s just an experiment. You don’t have to win, lose, pass, fail. It’s not black or white. It’s just a fact-finding mission. It’s just an opportunity for you to see one way or the other, then make a decision and move forward to the next thing.”

Once I grasped that, it really just changed the way that I was allowed to experiment with one more thing to find out whether the conjecture that I liked it was true, or whether I really liked that thing. That was only five years ago, but the things that have happened within those five years, once I opened up that door, are just mind-boggling whenever I look at my momentous moments timeline of things that have changed or happened, or events in my life over the past five years, it’s mind-boggling. And it’s all because I kind of opened up that door.

Jason Robinson working location independently out of a jeep after a career transition

Jason Robinson’s Career Transition

Nora: You just mentioned that you’re a graphic designer, then you mentioned before that you were working in the architect– were you working as an architect or you were working in that field? So what was the career transition that you experienced? 

Jason: I went to college as a graphic designer, brand designer specific. That was my emphasis throughout my career. I migrated into signage and way-finding design. Major airports, there’s thousands and thousands of signs, and a lot of them are elaborately designed. Somebody needs to tell you what they look like, how they’re built, where they’re placed, exactly what words are on those things. I designed these massive– or I helped design these massive programs for large architectural buildings, a lot of airports and things like that.

That became what I was known for in Charlotte, North Carolina. I had a lot of architects coming to me to be on their team as the local guy, the boots on the ground. That was where these three to five-year contracts with massive projects, they would start to overlap.

I’d have a five-year project, and then three years in I’d get this other five-year project, and three years in I’d get this other five-year project, where I couldn’t get out. I had to really make this choice at some point to say, okay, if you want to travel nomadically, if you want to not be tied to a place, you’re going to have to make a decision about your lifestyle and your clients.

Nora: What decision did you make and how did you make the transition? 

Jason: I had literally looked at the decision the proceeding five years and the proceeding five years, like on almost clockwork, it was like every five years, this opening showed up between massive projects and this time the opening showed up and I was like, “Oh man, I’m going to have to deal with this whenever they call me for my next big one.” 

And sure enough, I had two separate architects that I worked with regularly, one out of Nashville, one out of Charlotte. They were bidding on the exact same project and it was gonna be a ten-year project in Charlotte. They both wanted me on their teams. I was going to get that job.

I had to call them both that day and say, “Look, I’m making a direction change in my life. I love working with you all, but I’m making a decision,” and kind of talk them through that. One of them wasn’t very happy. They thought that I just didn’t want to work with them. I called them a day or two later. I was like,” No, really guys, this is just me making a change in my life.” Once they figured that out, everybody’s just gung-ho, like “Go for it. Love that you’re doing this.” 

Nora: It’s interesting as well that they were unable to see a way to continue to work with you on a location independent basis. I mean, obviously this was pre-pandemic, so perhaps, they’d have a different way of working now, because I would say being a graphic designer, generally speaking, is a very digital nomad friendly career. If it wasn’t in terms of what you were doing, then how did you make that transition? Did you move into a different field with different clients, or did you just find clients who were willing to hire you remotely

Jason: More specifically, that was probably more my choice than a dictation of choice. I probably could have continued to work with them. As a guy who grew up very blue collar, not with these big budgets, not with these multi-million dollar projects that people are running in airports and things like that.

My brain still has a hard time getting around the kind of money that corporate America throws around. I probably could have looked at those architects and said, “Hey, I’m going to be on these teams, but I’m just not going to be in Charlotte. You’re gonna have to fly me in and do the same things that you do whenever you come to Charlotte. I’m just going to do those things.” 

There was a point in my life where I said, “These projects are not making me as happy as they are just paying my bills.” That’s a huge, important theme for anybody listening to this podcast, is it’s not just about the duckets, you need to figure out whether this is fulfilling for your life.

Just because the job is a good one and just because you’re grateful to have that doesn’t mean that it’s the thing you should be doing. That’s where I was. I knew that there were other things that I enjoyed doing more, or things that I at least wanted to attempt to do. A lot of, a lot of people say, “Why are you throwing this away? Why are you giving all of this up?” That’s what a lot of digital nomads or people that change their lives, they get that from their family. They get that from their friends or other people that don’t quite understand things. 

I have a huge problem with that mentality because, the way I see it, anything you have done up to this point in your life, you can likely do again, and you can do it just as well, if not better. You may have to take a pay cut. You may have to have some backup plans, but in reality, you can almost take a step back to those things, unless you’re burning bridges, unless you’re just not being a good human being or a good businessperson. 

I knew I could make these changes and if I needed to go back to those things, more than likely I could do that. I had good relationships. It was just a matter of saying, “Is this the right thing for me? Or are there potentially better things out there for me?” 

Nora: That resonates for me very much because that was one of the things that gave me the courage to make that ultimate leap into selling everything and selling my financial planning practice and hitting the road, was the knowledge that I could come back, and I could start a new financial planning practice, and I could do it 10 times better than I did at the first time because I would learn from all the mistakes that I previously made. 

I also did not burn any bridges with the company and the people that I were working with. I happened to know that– I had a bunch of clients who said, “Hey, listen, we’re all for you doing this, but if you want to come back, we’ll be your client again.” There is something to be said for making sure that you don’t burn any bridges, but then also to have that knowledge that everything you’ve done up to this moment is instrumental, and can be instrumental in the future if you want to make more changes. 

Jason: I don’t think I answered the, “What did I do next”? Essentially, from that moment forward, and I lost about 90% of my income based on cutting those ties at that moment, from that moment on the way that I led every new design relationship was with the reality that I could be working from anywhere in the world.

The work that I’m going to be doing, the communication I’m going to be keeping, all of the products that a client looks for from me as a designer, those are going to remain the same. The difference might be time zones. The difference might be a little bit more flexibility and just a couple of realities.

That has never been an issue. If anything, it’s been interesting. They go, “Oh, wow, that’s really cool. I can’t wait to see where our next meeting is from.” As with most folks that you talk to most of the time, the family and friends, even though reluctant in the beginning, they usually come around and they’re enamoured by this new lifestyle and what it can bring.

That’s what I had to do to kind of rebuild my income so that I could be location independent

Getting Out of Debt to Travel

Nora: Speaking of income, you mentioned, of course, that you had dug yourself out of a heroic amount of debt very quickly in your thirties. Now you have this budget-minded mindset. Can you talk to me a little bit about how you got yourself out of debt and how you apply some of the financial practices that you have, or things that you’ve learned, in your current lifestyle.

Jason: Can I just say that I love that you called it “a heroic amount of debt.” That makes it sound so awesome. That was so cool. I love that. It probably would have been a lot easier for those four years if I would’ve thought about it that way.

The tipping point for me was I was 28 years old. I was with somebody who I thought was maybe moving towards marriage and kids, and she clearly thought differently at that point. And we parted ways. When we parted ways, I realized that I was so far in debt that I wasn’t going to be able to support a relationship, or I was going to bring so much stress and those types of things to any later relationships that I didn’t want to be in that place.

It really wasn’t about me. It was about future me and who I might end up with. Which, spoiler alert, still hanging out solo. I said to myself, “I don’t want to be in this position again should these life events come up.” That was really the precipice or the beginning– I’m not sure if that’s the right word to use– that the beginning of the thought process. 

Essentially, I went out and I bought two books. I read them cover to cover in one night. I cut up all my credit cards. I just dramatically changed the way that I was leading my life. I told my friends and family, “I’m not going to be buying Christmas gifts this year and I’m not going out to the bar.”

I think I gave myself $10 every two weeks for what I called entertainment, which included my go-out-for-a-beer fund. I was so strict for those four years because I knew once that was done, it was going to be great. I had no idea how much stress all of that money and that debt had on me back then, until now I live debt free and I make sure my number one priority is to not be in debt.

Even if I start to inch that way, I’m like, “All right, dude, stop everything. Do what you need to do and get your shit straight.” It took four years. I paid off everything except for my mortgage at that point. There’ve been some bumps in the road ever since, obviously with medical conditions and things like that, things get expensive and you just gotta figure it out. 

Once you learn how to live lean– number one, it doesn’t feel lean, because it actually seems to open up your opportunities. It’s just the biggest thing that anybody can do. I know that sounds easy when you glaze it like that, but it’s the most important thing people don’t know they need to do if they’ve never been out of debt.

Nora: It sounds like reading these two books were pivotal for you in creating all of these new financial habits that now, of course, serve you very well in your current lifestyle. So, what were the two books that you read? 

Jason: The one book that I didn’t fully finish was The Seven Habits of Highly Effective People, which I assume the seventh chapter was “finish all the books you start reading”. The other one was The Total Money Makeover, Dave Ramsey. The way that book used to be written was you did it in order, which, you’ve seen my book and it actually takes on that mindset of you can do these things in order, or you can do them out of order. There might’ve been a seed planted back then, but essentially, the old Total Money Makeover, I’m not sure how it looks now. You only read as much as you can accomplish. Once you get to a point where you haven’t done these things, well, you need to stop everything, accomplish these things in your financial life, and then you can keep moving forward.

I think I only ended up reading half of that book too, because the first half was “Get your ass out of debt.” The next half was “Start investing and start doing those different things.” It was quite a few years later and I learned how to do those things on my own, regardless of that book. Just the mentality of that book, of, “Know where your money’s at. Know what it’s doing. Know every penny that you’re spending.” 

Even though that sounds heavy, it’s so easy for me now on a daily basis, especially since my life’s a little bit easier. I’m just not spending a lot of money on a regular basis. I think if people don’t know where their money is going all the time, if you ignore the $5 cups of coffee a week and the $6 beers a week, well all of a sudden, you’re up to $60, $70 a week, times 52 weeks a year, those hundreds, if not thousands of dollars that you just kind of ignore, and that’s a massive amount of money to be ignoring in your life. It’s something I could talk for days about. 

Nora: You and me both, because I’m a big proponent of creative conscious spending and “conscious” really is the important word here. Really think about every dollar that you’re spending and where. Is this enriching my life in a way that is worth the money that I’m spending? Dave Ramsey calls it The Latte Factor. All of those lattes: are they really enriching your life that much? Or is there an alternative that will be just as satisfying to you, but cost a fraction of that trip to the coffee shop every day?

And that can be applied on a variety of different levels. Especially, of course, in the full-time travel lifestyle, because, as you well know, full-time travel can cost as much as you want to spend. But it can also cost a lot less. It really depends on what it is that you want out of an experience, how much that costs, and then, of course, weighing whether or not that’s worthwhile. 

One of the tips that I have, one of the techniques that I have regarding budgeting in general, but also regarding now making your spending more conscious is, I track every dollar I spend. I do it with an app. 

Note: If you’re looking for options for travel expense tracker apps, along with a bunch more useful apps for travelers, check out The Best (Must Have) Travel Apps (25 of My Personal Favorites).

It’s very easy. Every time I spend the money, I just input it into the app. And I input the money without judgment. I don’t feel guilty for the money that I spend, but some part of my brain knows that I’m going to have to put it in the app. Perhaps that’s what triggers that process of thinking, “Okay, do I really need this? Is this going to help me in my life, in my career, in whatever it is that I want to achieve?”

Jason: The thing that I know us travelers, we also do, especially when we’re in the United States, things cost so much for us in reality compared to a lot of the places we travel to. You start to see it through the lens of travel and you start to see it in the, “What would this cost me in Portugal where I’m at right now, or what would this cost me in Mexico?” 

For instance, if I’m going out for that $6 craft beer or $6 beer in the U S. That’s literally half of a night’s stay in Mexico in some of the nicer hostels that I stay in, or that’s a six-pack of beer that I can enjoy with friends in Mexico. You start to see things through this lens of, “Do I really want to spend this money right now?”

You do still need to be spontaneous. And I think that’s the easy balance now, is staying out of debt, knowing that you’re strong with your finances, but also knowing that you need to live, you need to allow yourself those moments. It just seems to become easier once you get out of the way of setting up those things.

Jason Robinson, unintentional expert on diabetes travel

Traveling with Type 1 Diabetes

Nora: You had a really tough diagnosis of type 1 diabetes. I read an article that you wrote that was very detailed about how to travel with a medical condition. I had not even considered this kind of thing. You really opened my eyes up a lot about what it is to travel with various forms of meds and prescriptions, and how do you refill these abroad or get the extras. 

Please, tell me what it’s like. Please tell me what the process was of getting this diagnosis and how you felt, and then how you’ve been able to deal with it from a location independent and a travel perspective. 

Jason: Yeah. First and foremost, for those of us that don’t understand what diabetes is. A lot of us don’t understand what diabetes is. I had no clue, even though I had heard the word a million times. 

Essentially, within about 30 to 40 days, my eyesight completely went from perfect to, I couldn’t see anything. Then it went from nearsighted to farsighted to nearsighted. Literally flipped back and forth every couple of days. I was drinking a gallon and a half of water a day. I had cotton mouth too. I was drinking all this water, but I would go on a bike ride and I had crazy cotton mouth and couldn’t speak because it was so dry. I lost 30 pounds in about 40 days, or sorry, 20 pounds in about 30 or 40 days, and I don’t have a lot of weight to lose. I went from 165 to 144 in about a month. 

Obviously, by that point I had done some research, figured out what it was, more than likely, and went back to Charlotte and was diagnosed type 1 diabetes, which type 1 is an autoimmune disease.

Type 2 is often partly genetic, often caused by a sedentary lifestyle or lack of exercise or bad eating habits can all contribute to these things. Often, genetic. Type 1 diabetes is an autoimmune disease. Essentially your body just woke up one day and said, “I’m going to attack myself.”

When you hear “type 1 diabetes”, that means our body’s not making insulin. It’s because our body is attacking our pancreas and we’re not making insulin anymore. I am now an insulin-dependent type 1 diabetic. Essentially, I have to take insulin at every meal of the day, as well as some other times, to make sure that my body can process the foods that I’m getting in and deal with the sugar.

So there’s your quick 101. There’s a lot more to it, but essentially I was diagnosed with that and immediately thrown into this, “How do you afford these things or what do you afford?” I’m still figuring all that stuff out because, as we know, certain medical issues in the U.S. are pretty frustrating.

Diabetics typically spend on average $10,000 a year, whether they have insurance or not. These are averages. Essentially, I sold my house, went nomadic. Eight months later, the pandemic hit. Eight months later, I was diagnosed type 1 diabetic. And now we are about 8, 10 months after that.

I got to the point where I was like, “Okay, well, you’re not just going to sit back and not travel because of COVID. You’re going to allow the world to get back to where it needs to get to, to be able to do that.” Then I had to figure out, if you’re going to travel, you need to figure out what the type 1 diabetes.

A lot of travel medical insurances don’t deal well with pre-existing conditions. They kind of expect you to come at it pretty darn healthy. If you aren’t coming at it pretty darn healthy, they kind of say, “Heh, go find something somewhere else.” 

There’s a few health insurance, travel medical insurance companies that do cover pre-existing conditions, or some of the ones that don’t immediately, you can do things like get a medical clearance that says, “This person is fit to travel when they’re getting this policy. If something comes up with their pre-existing condition during their travel, we couldn’t have seen that coming because they were managing that condition.” These are a lot of things that I had to learn in the past few months was make sure that my doctors say, “Yes, you’re fit for travel.” I got it in writing by almost all of my doctors.

I also have a heart condition and a kidney condition, so I had to have all three of my specialists say, “No, you’re managing all these things well. There’s no reason for you not to travel.” Therefore, if I have a problem while I am traveling and I have my travel medical insurance, what they’re going to do is they’re going to say, “Wait, you got a problem with your diabetes. You shouldn’t have been traveling.” And we’re going to say, “Nope, I am. They said I was fine. There’s no issues.” Therefore, they’re going to cover those claims should something come up with my pre-existing conditions. 

Beyond that, I looked like an amateur drug mule coming into Portugal, because I literally had to get, from my doctors, five months’ worth of my medications and insulin. I came here with eight insulin pens, a bunch of needles, probably 300 pills for various different things. Having those medications printed out, having medication printouts from my doctors in case I got asked questions at the borders, or coming through customs and immigrations, or let’s say two of my insulin pens got frozen on the airplane, and now I need to figure out how I get more insulin because that was bound to happen, eventually. It just so happened on my first flight out of the country as a new type 1 diabetic. 

I am stopping at pharmacies. I’m asking questions here in this country. I know that the insulin is cheaper here. Medical is cheaper in a lot of different countries, compared to the U.S. It’s a pretty blanket statement that we can get behind. I knew that insulin is available here. 

Everybody around the world has medical conditions. These were some of the mental hurdles that I just had to get over and say, “You are not in this by yourself. There’s a lot of people around the world dealing with similar things. How do they do it? What do they do whenever they need these things?” I already know what the cost of insulin is here. If I need to replace those pens that are ruined, I know what I’m going to have to spend. It’s the cost of doing business.

I’m not going to not travel. I’m just going to figure it out. That’s why I’m going to now write about these things a little bit more to help other people, not just with the transitions in life and the transitions to being nomadic and traveling and just starting to travel. But obviously, I now have this new angle to help people with, because I got to learn it and I got to figure it out. So hopefully I can write it in a way where it’ll help some other people. 

Nora: I’m curious from an insurance perspective, how are you able to find an insurance company that was able to recognize that you were managing a pre-existing condition and ultimately to give you the insurance? 

Jason: I use InsureMyTrip, which is an aggregator. With InsureMyTrip, you can essentially go on there and they’ll pull in policies from different travel insurance companies that are highly rated. Then you can narrow them down by the things that you need. You can literally look at the ones that do cover pre-existing conditions, or you can dig into the paperwork because some of them don’t just come right out and say, “We cover this. We cover that.” 

This is the adulting part that sucks, where you actually do have to just kind of dig in and start reading or make some phone calls. I find it really odd that as a grown-ass adult, I have the hardest time just picking up the phone and calling somebody and asking what I think are stupid questions sometimes.

This person on the other end of the phone doesn’t know who I am. I’m going to hang up and they’re not going to think a thing of me, but for some reason I get– I think a lot of people get tripped up in that. Just pick up the phone and start making some phone calls and ask questions and ask them of two or three different folks.

If you didn’t know what questions to ask on the first one, by the second or the third one, you’re going to go, “Oh, wait, I forgot to ask this.” Or, “I’m learning that.” That’s what I had to do here. I did my research. I read the things I needed to read. Then I just started making some phone calls and made sure that I understood those things and I understood how to execute them, and what that might look like.

 I said, “If I had a problem, how do I follow through with a claim or this, that, or the other?” Before I ever bought any of these plans. That’s what those folks are there to do is to make sure you understand what you need to understand before you buy their policies. A lot of people just don’t do it. We just want to ignore those things because they’re messy and it’s boring and yada, yada. At some point, you can’t do that because you’re just in the dark. 

Nora: I always tell people to read their insurance policies from cover to cover. It’s soul destroying work, but it’s really important because when such a time is going to happen, that you have to make a claim, boy, you better know exactly how to do that because there are– right from the time that something happens to you, there’s a certain set of procedures that you have to follow. Otherwise, the insurance company may not cover you. 

Also too, I want to underscore, I’m going to second you on InsureMyTrip as a great way to have really specific filters for what kind of insurance policies you’re looking for. They will definitely spit out the companies that you can work with. Also, to work with an insurance company. If they do a medical questionnaire and then come back with a, “Okay, so we’re going to give you an exclusion for this condition.” Go back to them and say, “What do you need in order to remove this exclusion? Do you need a doctor’s report?” Because they will reevaluate. 

I’ve had that happen in the past where they’ve put– I had a heart murmur when I was like 16 years old and 20 something years later, they’re, “We’re going to exclude any condition that has to do with your heart on the road.” I’m like, “Are you kidding me? This was an exercise induced asthma that I had a million years ago.” Eventually, they did remove that exclusion because they realized, with the doctor’s report saying, “No, it’s okay.” 

Like you say, if you get the report saying “I’m fit for travel” or whatever it is the insurance company needs you to say, it can definitely– they will restructure your policy accordingly.

Jason: The term they use often is a medical waiver. Essentially, your doctor is saying, “This person is fit for travel.” Sometimes they use different terms, but that’s the low-hanging fruit term that you’ll probably see.

Jason Robinson’s Nomad Experiments 

Nora: I really want to talk more about some of your nomad experiments because in your book– your book is very fun. You’ve got a lot of tough love in your book. Definitely. But it is written for people who don’t have much or any travel experience, are not really sure even where to begin in terms of adopting a nomadic lifestyle. You did it with so much fun in terms of your nomad experiments.

What are some of the experiments that you did that ultimately helped you launch a new lifestyle? 

Jason: Again, early on, I started trying hostels and trying couch-surfing, and that was 10, 12 years ago. It was just a matter of finding– that was well outside of my comfort zone. What do I need to do to get into my comfort zone?

That was finding a hostel that I felt safe enough going to, because that’s one of the things that people don’t want to try. “Are they safe? Are they dirty? Are they the same?” Well, find a fancy one? Figure out the things that make you feel comfortable, at least trying to take one of those steps. 

I started trying those things early on. In my late thirties, I had never really traveled domestically very much. I was always a little bit fearful of traveling solo, just because it’s always easier if you can have somebody there to hold your hand and teach you how to do things or show you the ropes. I wasn’t doing those things. 

Finally I said, “Okay, you got to start trying.” I took some domestic trips. I would take a five-day trip to Philadelphia. I would take a five-day trip to Portland. I could work while I was on the road. That might sound expensive, but when you’re staying in hostels and when you’re using a travel miles to get free flights, and you’re still working on the road, it’s really just about– for somebody who has created that flexibility for themselves, it’s just picking up your life and dropping it into another place for a week.

Those first experiments in my late thirties were just start traveling domestically a little bit. I always thought about van life and I’ve conjectured for two or three years that I would like van life. I’m like, “Dude, before you just sell your house and go buy a van and think that that’s going to be awesome. And then do you just hate it? Maybe you should try it.” 

I went and bought a shitty old van that was already built out. It had a camper. It was ready to go. It was an old ’85, 1985 G10 baby blue camper van. You can see that on the Nomad Experiment. Just search for “van”. It’s gorgeous. I went to Shenandoah National Park and I camped there for a week. I worked out of the back of the van. I hiked the Appalachian Trail, some parts of the Appalachian Trail there. I did what I thought van life might look like, which was live in a different place. Also, get my work done. Also, get my exercise done. Do all of those things. And I tested it. 

You have to move beyond conjecture and “I think I’m going to like that. That sounds awesome.” You got to give it a try. That’s where my mindset was, “Well, let’s give it a try.” Probably the most important ones, and there were many, but probably the most important one was– three years ago I said, “Okay, You’re still traveling domestically, but what are you going to do to really push your comfort zone?”

I gave myself a goal to not sleep in my bed a quarter of the year. To not sleep in my home a quarter of the year. Whether that was just staying at a friend’s house or staying in a different city, that was pushing me to try to not use my house and my home as a crutch. Once I got through that year, I was like, “Well, that worked out pretty good, but progress is only progress if you keep moving forward. So I said, “Well, what are you gonna do next year?” And I said, “Well, let’s do a third of the year.” So that was 122 days. I did that. 

By the time I did that, that was– between those two years was also my first trip to Mexico. That was my third country. I bought a one-way ticket to Mexico. Because, back to that whole conjecture thing. “Do you really think living out of a backpack and traveling the world with only the things on your back is going to be fun? Maybe you should give it a try.” I bought a one-way ticket to Mexico, and I just said, “All right, I’ll start in Mexico City and see how long I go. Maybe I’m uncomfortable after four days and I just decide to come home.” That’s fine. That’s an experiment. Learn what you’re going to learn and move on.

I stayed in Mexico City for a week and then somebody said, “You should go down to Oaxaca. It’s smaller, and you’ll probably like it more.” I said, “How do I do that?” And they’re like, “Go buy a bus ticket.” So I bought a bus ticket, went to Oaxaca. Then I ended up in Puerto Escondido with four or five new friends that I met in Oaxaca.

Once I got through that second year of 122 days not sleeping in my bed, my comfort zone of my home, what used to be my comfort zone, what I’ve used to go home to and go, “Oh, I’m so calm here, and I get to go to my garden and I get to do these things.” It became more of a stressor to me than travel had. They flipped. Because all the chores and the maintenance and all of the things that came with my home were not as good as the freedom and the exhilaration and just the amazing things that travel were starting to bring to me, not only from an outside-of-me standpoint, but growth inside of me. 

I realized at that point I was like, “All right, I don’t need to do any more experiments. I’m ready to really try what’s next.” That’s when I decided to sell my house and– people ask me, “Do you miss it? Do you look back?” It’s been two and a half years and I’ve literally driven by that house three or four times. And the only reason I drove by it was to make sure that they didn’t cut down my favourite Japanese maple tree. ‘Cause I’ll be having some words if they did. 

I haven’t missed it at all because of these new growth experiences that I’m able to have in this current chapter of my life. If I wake up tomorrow and I want to get another mortgage on a house, I can do that. If I wake up tomorrow and I want to be in one place, I can do that. But right now I’m open to all the things that this is bringing. 

Nora: This is perfect because this ties back to what we were talking about earlier with regards to career transitions and the knowledge that you can always change tack if you want to, and adopting this experiment mindset is a fabulous way to ease yourself into new things, but also not to make any drastic measures that you might later come to regret.

Van life is a perfect example. I had a– I didn’t even view it as an experiment, but I had a six-week camper van trip. Which is when I realized van life probably isn’t for me. Good. Lesson learned. Tick. I’m glad I didn’t buy a van. Like you said, just being able to dip your toe in the water and see how it feels. Of different ways of living, different ways of traveling, different time periods of traveling.

I always suggest if people are looking at traveling long-term, or even full time, you don’t necessarily sell everything yet. Right? Take a test trip. Go away for a few months. See how that feels. Maybe you will realize that it’s not your cup of tea, or maybe you’ll realize there’s a different way to do it than how you initially envisioned.

Your mindset of the experiment is a brilliant way to try new things out and to ease into a transition that might otherwise seem really overwhelming. 

Jason: This is also, just a quick side note, this is also a way to disarm your friends and your family. The ones that are looking at you going, “What, what are you going to do?”

With the one-way ticket to Mexico, I sat down at a corporate dinner with eight people and they’re like, “You’re going to do what? Is that safe?” All the silly things you hear. I looked at them, I was like, “Eh, it’s just an experiment. If it doesn’t work, I’ll come back.”

It really does give those around you, who can be a lot of pressure on your life, the ability to go, “Okay. They have it under control. It’s not that big of a deal. They’re fully capable.” It really does help to disarm your family and friends, especially if you’re really trying some crazier things, what might be considered some crazier things.

Nora: I hadn’t even thought of that, but that is another brilliant way to be able to frame it for people in your life who may otherwise not understand the decisions you’re making, and to make sure that they will support you in that way. 

Well, I feel like we could go on forever. And I think we could. We could go on for another couple of hours, but I do want to wrap this one up and I want you to please tell us where people can find your book and where the people can connect with you online.

Jason: The Nomad Experiment. That’s my website. If you want to check out the book, go there, look in the shop notes. You can find it on the website very easily. The next best place to follow me is probably on Instagram, which is Instagram/thenomadexperiment

I do love photography. I mixed that photography with some of this other self-help, motivational, philosophical stuff about travel and overcoming some of these hurdles.

When I’m not writing a book, that’s where I get my photo and words fix is to kind of have some of those conversations on Instagram and I love when people reach out to me on there.

Final Words

Nora: Do you have any final words that you would like to leave with us? Something that you would put up on a billboard to tell the world? 

Jason: Just stop waiting. Just stop waiting and start figuring it out. Sooner rather than later. You’re never going to be ready. No matter what we’re talking about, you’re never going to be ready, so you might as well just get started at it now. 

Nora: Awesome. Brilliant advice. Thank you so much for joining me today, Jason. It’s been a pleasure.

I’m Nora Dunn, otherwise known as The Professional Hobo, and I will catch you next time.


You might think clearing $50k of debt in four years, quitting your career in your late 30’s and going full nomad, and then getting diagnosed with Type 1 Diabetes might stop most people, but not Jason Robinson. Using the experimental process and a great deal of determination, he was able to accomplish all this. Now he is helping people finally kick-start their travel lifestyle and learn how to travel with diabetes and other medical conditions. As Jason says, “Just stop waiting.”

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2 thoughts on “Travel With Type 1 Diabetes, With Jason Robinson, Nomad Experiment”

  1. Hi Jason,
    Thanks for sharing us about your story. I inspired on how you love and passionate traveling. Beyond of your illness, you pursue your traveling. Keep sharing about you.

  2. Good job Jason. Good job Nora for sharing his inspiration. Folks make many excuses for not traveling. But all occurs in the mind, so once you face the fear fueling excuses in mind, anyone can release any excuse to circle the globe.


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