by Niall Doherty

A friend recently asked me if I was worried that the vagabond lifestyle I intend to undertake would result in me missing out on those deep and meaningful relationships which usually take time and commitment to develop. Another buddy recently made a case that having a few quality close friends certainly beats having a bunch of casual acquaintances.

These are legitimate concerns and I’ve thought long and hard about them. I’ll give you some of my resolutions at the end of this post. First though, I thought it would be a good idea to ask people who are already living the vagabond lifestyle to share their first-hand experiences. I was delighted to get back thoughtful responses from Colin Wright of Exile Lifestyle, Chris Guillebeau of The Art of Non-Conformity, and Benny Lewis of Fluent in 3 Months.

Colin Wright, Exile Lifestyle

Colin moves to a different country every four months, as elected by his readers. Right now he’s in Thailand, having just completed an epic two-month road trip across the United States. His thoughts on relationships as a location independent professional:

Basically, so long as you’re able to slightly adjust the way you approach relationships, you’ll be fine.

What I mean by this is that as Americans, we’re fed a VERY specific idea of what it is to be happy (a la the American Dream) from a very young age. Disney movies, sit-coms, Saturday morning cartoons, they all reaffirm this philosophy, and at the end of the day it leads back to consumerism (but that’s a different conversation).

The end result of this programming is that we believe the only legitimate reason to get into a relationships is if it will potentially end with marriage, kids, a dog, a trampoline, etc. Unfortunately, if you’re traveling this goal may not be realistic, as being in a long-term relationship can be a special kind of torture (and make you miss out on all kinds of opportunities), and building a relationship while you travel in the first place can be incredibly difficult due to time and geographic restrictions.

The important thing to keep in mind is this: you can have very strong connections with people without there needing to be marriage in your future. In fact, I would argue that these connections can be even stronger because there is a time limit.

It’s like the difference between spending your whole life saving for retirement (and only then letting loose and having old-man fun) and saving a little now, but mostly enjoying your life while you’re young. Relationships are an investment, and though you SHOULD leave yourself open to the possibility of something longer term, you should also most definitely allow yourself to enjoy life now with life-minded people who may not be looking to wait for retirement to enjoy everything the world has to offer.

What this means in practice is mini-relationships. Since I started traveling I’ve had only a few of these (I’m picky), but the ones I’ve had have been great, if short. Unfortunately it seems like I never meet someone I really like until I’m about to leave the city they live in, so I’ve had a few whirlwind weeks of dating and excitement and fun. Leaving really sucks, but it’s good in a way, because then we both have a time-limit and neither feels like we need to get hung up on little problems like couples normally do. What reason could there possibly be to argue if you both know that you’re only together for a week?!

SO, there’s that.

When it comes to non-romantic relationships, I would say that traveling gives you the chance to build more, stronger relationships than you could have staying in one place.

Sure, if you live a static lifestyle you can meet a handful of people and get really close because you’re always around each other, but in a way this is kind of like saying your brother is your best friend…well of course he is, you’ve had no choice but to be around him for 20+ years.

On the other hand, there will be people you meet while traveling that you are able to interact with in person for only a handful of hours (or less!) that you stay in touch with and reconnect with and learn from and teach for the rest of your life. I already have a few people like this in my life, and I wouldn’t give them up for the world, despite the fact that we’ll likely only see each other in person every couple years, if that.

The Internet definitely gives us a lot of ammunition when it comes to building relationships, too, because it allows for quick followup and incredibly casual rounding out of a person you only met briefly. There was a girl who I shared a few afternoons with in Lima that I ended up staying with for a week while in Auckland. She’s a super-rad person, and if we hadn’t been able to keep in touch via Facebook and email, we may never have been able to get to know each other better.

So I guess my main words of wisdom are don’t worry! The way you approach and manage relationships will change a bit, but the opportunity to create even stronger bonds more than makes up for any initial uncomfortableness you may feel about the prospect.

Chris Guillebeau, The Art of Non-Conformity

Chris is on a mission to visit every country in the world before his 35th birthday in 2013 (he’s about 80% done as of this writing). He also just released his first book — The Art of Non-Conformity: Set Your Own Rules, Live the Life You Want, and Change the World — which I’ve already devoured and highly recommend. His thoughts on relationships as a vagabond:

It’s not a problem for me for a couple of reasons:

1. First and most importantly, I do have a home base (Portland, Oregon) and I’m there at least as much as I’m elsewhere. I don’t go out or do much when I’m home, but I have a small group of close friends that I see often there.

2. Second, much of my community is online — so wherever I am, I spend a lot of time connecting that way. I understand that some people feel that online relationships are superficial, but I don’t share that belief.

3. Lastly, as I travel now I meet with readers and colleagues wherever I go. Again, some people might feel that those relationships are superficial, but that hasn’t really been the case. Instead, I’ve found that I have a ready-made community in many parts of the world. I wouldn’t trade that for anything.

Benny Lewis, Fluent in 3 Months

Benny is a fellow Irishman. When he was 21 years old, he spoke just English fluently. Now he’s 28 and speaks 8 languages fluently, having immersed himself in many different cultures over the years. He’s currently living in Budapest, on a 3-month mission to become fluent in Hungarian. His thoughts on relationships as a well-traveled polyglot:

I have reached a sane balance, but I haven’t reached a perfect balance just yet. I have accepted that many relationships I have must be somewhat superficial, while I will work to make them as deep as possible despite my short stay. I maintain relationships with all good friends online and meet up with people again regularly, which is always fantastic. Facebook and MSN have been essential in making sure that I keep in touch and then help me see the people again to form even deeper bonds.

Maintaining romantic relationships is notoriously difficult because as a traveller you already have this stamp of sailor-with-a-girl-at-every-port that will make so many girls sceptical, even if you are genuinely interested. And I have seen long-distance romantic relationships break down so often that I would never attempt to keep one alive myself unless I was absolutely sure she was “the one”. I am honest about this from the onset. Ironically however, many of my romantic relationships end actually because she has to travel away! The circles I associate with means I spend time with other travellers a lot, but I’m a more “fixed” traveller so when something seems to be going well it ends because she has to go home or elsewhere. As I said, irony – people expect me to be the one going around leaving broken hearts all over the world 😛

So my “words of wisdom” on the topic are that most of us are still figuring it out ourselves 😉 Travel makes you wiser in so many ways, but in other ways I’m just as confused as any other 28 year old about these matters!

A few of my own thoughts on relationships as a vagabond:

Quality vs. quantity

A common argument is that you’re better off having a small, tight circle of real friends than a massive sprawling web of shallow connections. But that’s only looking at quality vs. quantity from one direction. The assumption being made is that you can only have so many deep and meaningful relationships because you only have so much time; you need to spend lots of time with each person to form a deep and meaningful connection.

But what if we apply the quality vs. quantity concept to time? What if we cut out all the small talk and the time sitting together, speechless, watching crappy TV shows? What if we started being more upfront with each other from the start instead of trying to feel each other out, waiting to see if it’s safe to share how we really feel? What if we started making better use of what little time we have with each other?

Sometimes a minute is all you need with someone to change their life or vice versa. If you fail to see the potential in those meetings, it’s unlikely you’ll ever be a part of such change.

I take solace in the fact that I’ve gotten much better at introducing elephants and being myself around people from the get-go. I believe these things make a huge difference in the quality of my relationships.


Either/or thinking is not thinking with integrity. I believe you can have a handful of those thriving, long-term relationships while also building and maintaining many casual acquaintances. You don’t have to choose one extreme or the other; you can maintain a balance.

I’m satisfied with the balance I maintain. My cousin, back in Ireland, has been my best friend for more than a dozen years. (We only talk once a month via Skype, but we’re still as tight as ever.) I’m single now, but when I’m in a relationship I treasure the close and intimate connection. I have several friends here in New Orleans who I enjoy spending regular time with, and several more back in Ireland who I’ll always consider best buds. But I also have friends on Facebook who I’ve never met. Usually, at a party, I try to meet and connect with as many people as possible, even if there’s a good chance I’ll never see those people again.

And then there are the in-between friends; people who I haven’t spent a lot of time with, but what time we do spend together is always quality. We get right to important stuff, talk deeply and listen carefully. I may not get together very often with such friends, but I believe I know them and that they know me better than many couples know each other. You can form deep relationships quickly when you’re constantly working on your awareness and you have a genuine interest and curiosity in other people.

No worries

So, am I worried about missing out on those deep and meaningful friendships as a vagabond? I can’t say that I am. If anything, I’m excited about finding more of them. I understand and respect the fact that some people prefer to maintain a small circle of close friends, hanging out with the same few people every weekend, but that’s not for me. I enjoy meeting new people too much, connecting with different folks in different ways, seeing what I can learn from everyone who comes into my life.

Many thanks to Colin, Chris, and Benny for their responses above. I hope you’ll take some time to explore their websites. I’ve learned a lot from each of them.


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