How To Make Lasting Friendships And Meaningful Relationships On The Move

Posted on / by Natalie Sisson / in Business Travel / 24 comments
Making friends Montage

This blog post is from some content that didn’t make the cut to my soon to be released Suitcase Entrepreneur book. I still cover this important topic but not in quite so much depth so enjoy!  

I bet you’ve experienced that chance encounter with someone special that was cut short too quickly because you had to catch a train, or you were late for your flight.

Or what about the time you met a great group of people on your travels but just a few days later you were heading off in different directions?

This is both the joy and challenge of taking the location independent route in life. I’ve experienced this a lot over the years and it certainly leaves you with mixed emotions.

As human beings, we naturally crave connections and a sense of belonging, and when you’re always on the move, this is one challenge you can’t avoid. At the same time it’s also very liberating.

I think it’s really important to discuss if you’re considering, or already travel the world and becoming more nomadic. That’s why I dedicated a significant portion of a chapter in my upcoming Suitcase Entrepreneur book to it.

Below I share exclusive content I didn’t end up including, but is still important to share. I want to cover the questions I get asked most often:

  • How do you keep your family and friends close when your thousands of miles apart and create a win-win experience for all?
  • How do you deal with loneliness or separation on the road?
  • What tools and services do you use to bring you closer to friends and strangers when you’re traveling or setting up in a new location?

Keeping Family Close When You’re Thousands of Miles Apart

Speaking from experience and numerous conversations with travelers from around the world, your family’s tolerance to your level of wanderlust are on a sliding scale that looks something like this:

8-10) Really supportive of your lifestyle and travels and keen for you to experience the world and find yourself.

5-7) Don’t really understand it at all but only interfere when they’re concerned, so long as you check in to show them you’re alive and not in prison.

0-4)  Not happy that you’re no longer within 5 minutes drive or in constant communication and really don’t understand this desire to see the world.

Of course there are varying levels on this scale, and the trick is to know understand how to make this a win-win situation for everyone.

My parents are 10/10 on this scale and for that I am eternally grateful. It helps that they instilled the travel bug in me at the tender age of 2 years old, when they took me on my first international trip. They’ve done the best possible job ofallowing my sister and I to fall in love with travel.

I’m also fortunate that my parents still travel frequently and we meet up wherever possible. For example, in 2008 they came to visit me in London before I left England.

A month later we met up in Vancouver, Canada, where they came to support me playing in the World Ultimate Frisbee Championships, after which we went on a road trip together.

In 2012 they came to stay with me in the house I rented in Amsterdam for a month over summer and then we both arrived in Berlin to spend two weeks together, and timed our train trips from different European cities to arrive within half an hour of each other.

When my sister lived in England I went to visit her and then we met up in Spain for a holiday together. She came to visit me when I was living in Canada and in Argentina, and I went home for her wedding in 2012.

Regardless of whether you have family members who expect to be able to reach you for nightly calls, or parents who couldn’t care less where you are so long as you don’t run out of money, the trick is to set up expectations in advance.

Here are three key strategies to keep close family ties:


The most important thing to remember is that you need to educate your family on `why’ you’re doing what you’re doing, and sell them on the vision you have for your life.

Often a lack of support comes from an inability for family members to see how you view the world, coupled with a lack of perspective from your side on how they view what you’re doing.


If you can align your reasons for travel or relocation with solid points of benefit, over time they will come to better understand your wanderlust. If you can align your values with theirs wherever possible it will make it easier to part ways.


They may never `get’ why you just had to head to a remote or dangerous location, or your need for thrill-seeking or go budget backpacking, so manage the amount of information you give them. I’m not suggesting you lie but acting first and seeking permission after is a solid plan. Like the time I told my Mum how fast I went on the motorbike with a friend after the fact.

It’s a handy acronym too, I am.

As in `I am doing this for….’, `I am going to go to …’, `I am going to keep in touch Mom’.

Keeping Close Friends When You’re Far

I’m fortunate to have a large group of friends and family scattered around the world who I catch up with whenever I am `coming to a town near them’, which is quite likely, given my travels.

I’ve found that no matter how many months or years it’s been, true friends will always pick up where we left off, just like old times.

Making friendsmontage600

We all know that true friends are hard to come by and great relationships take time to nurture. When it comes to friends it helps to split them into two categories.

Best friends you’ve had since…like forever.  These are the people who’ve known you for a lifetime, and have seen you in your diapers, or helped you through your first pimple, or high school romance.

For these folks you can apply the same principles as you do to your family, especially if you’ve lived all your life in your home town or village.

Adult friends : By this I mean people who you’ve become friends with after school, perhaps when you started working or realized that you were no longer able to relate to your childhood friends as you’ve grown up.

Leaving this posse behind will be hard, there’s no doubt about it, but absence makes the heart grow fonder, and it tests the bonds of friendships. Often you’ll find once you’ve been gone for a period of time, it becomes crystal clear to you which friends really matter to you and enrich your life.

The inverse of that is recognizing, once you’re far away, which relationships and connections you’ve been holding on to, that no longer serve a purpose, or were even limiting you in their nature.

Four tips to keep your friendships strong:

1. Touch base with your closest friends via text messages, emails, postcards or chats on social media sites to keep each other up to date on your news. Remember not to dominate the conversation with your amazing travel stories and worldly experiences, which will often make their every day lives pale in comparison.

2. Hangout virtually with video sessions on Skype or Google Hangout or Facetime. There’s a lot to be said for seeing someone’s face, as communication is 90% visual. It makes you feel instantly more connected and you can say a lot more in a shorter period.

3. Engage with them on how your lives intertwine despite the distance. This may seem obvious but one of the hardest things to deal with (speaking from personal experience) is sharing details of the life you’re currently leading with friends who are leading the life you used to lead.

When you’ve been away a long time, your return home can often seem somewhat disappointing when it feels like nothing has changed. Friends may even seem narrow-minded or sheltered in comparison to before you left to experience different cultures and expand your mind.  Be sure to acknowledge this and be aware of how you’re going to feel now.

4. Move on if your friends are not adjusting well to your nomadic tendencies or find it hard to reconnect each time you’re home and then lose you again. This may sound harsh but it’s part of life. True friends will be with you in life no matter what. Other friends will come and go and for each person who you lose touch with, you’ll meet plenty more on your travels.

Once again I’ve given you an appropriate acronym, them. As in it’s about them, not just you.

The realities of relationships

One of the most common questions I get from people I meet is how I cope with relationships when I’m constantly on the move.

So let’s get this straight right now, at the time of writing this I am single, with no desire or intention to get married or have kids. However if you’re an adventure seeking man, who’s tall, dark and ridiculously handsome, over 6 foot, with a great sense of humor, a sharp wit and you’ve got your life together, we should talk!

Ok moving on. For the longest time it seemed like an odd question to me because, as a citizen of the world, I rarely feel lonely or homesick and as a fiercely independent human being I relish the freedom of doing my own thing.

But when you’re in a country where getting married and having kids seems like the only option in life, it’s one of the daily questions you get asked. Take for example my trip to the Philippines where 8 out of the 10 conversations I had, especially with taxi drivers, went something like this:

Taxi driver: “Miss, are you married?”

Me: “No”

Taxi driver: “No, why not married miss?

Me: “ Why on earth would I want to get married?”

Taxi driver: Miss are you single”

Me: “Good guess.”

Taxi driver: Miss, how old are you?

Me: This a very personal line of questioning

Taxi driver: Sorry mam. So you are single?

And so it goes on. So if you’re a single traveler be prepared to have plenty of people question why you’re traveling alone.

Tips for solo travelers on the hunt for love

Be open to chance encounters (but don’t put yourself in a dangerous situation) and enjoy the variety of people you’re going to naturally meet as a result of your travels.

What about when it turns serious, and you think you have met the one, or at least one you’re prepared to divert your current travel itinerary for? I’d suggest traveling together for a few weeks.

There’s nothing like travel and living in each others pockets 24/7 to sort out whether you’re going to make a good partnership and this initial lust is meant to be.

It’s also a good idea, where possible to carry on with your travels and adventure and aim to meetup somewhere on a future date – whether this is weeks or months, to truly find out whether this person is in fact someone you really dig, or whether it was just a magical travel romance at that moment in time.

This is where I can hear you saying `That’s fine for you Natalie, you’re traveling the world as a single lady, with no cares in the world. What about me, I have a family and kids’.

Sure you have a point, it’s a lot easier to travel when you’re single, although you then have the challenges of being single in countries where you get hassled more for that very reason like India.

Managing partnerships across the high seas

I firmly believe, that even if you’re married with kids, travel is always an option, as is relocating to another country to live and work. If you’re looking for examples I can’t wait for you to read my upcoming book!

If your travels are going to see you and your partner separated for long periods, you need to seriously consider whether you’re cut out for the long distance thing, and if you both decide you are, establish a firm line of communication to keep the romance alive.

Tools mentioned like Skype, Facetime, social media, instant messaging and even letters and postcards, can all be great ways to stay connected. Most important I believe is planning your next rendezvous together to give you something to both look forward to.

Travel can do strange things to you and your levels of trust, intimacy and whether you engage in a monogamous relationship or not. You’re likely going to meet a lot of alluring people while you’re traveling and this can be very tempting to engage in or test the waters with, especially when you’re feeling lonely and have been apart from your partner for a long period of time.

This conversation is a pretty damn important one to have when you are in a relationship or considering going into one, and being on the move only intensifies the potential situations you may have to face alone or together.

As you an see life of a traveling nomad is both a rewarding and challenging one, not just from a business perspective, but from your own personal development, and that of your friends, families and people you create relationships with.

I’d love to know how you stay connected with those you hold dear in your heart in the comments below.

PS I’d love to see you on my book tour in Santa Monica this Sat July 20th, and the official book launch in Vancouver August 7th.