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The 5 Mistakes You're Making When Talking to Your Nomad Friends

Updated: Aug 14, 2023

Digital Nomads Catching Up

Your nomad friends have something we need from you, and it’s uncomfortable for us to ask: please ask us about our travels!

The holiday season is upon us, and many of us will be returning home for the first time in months, or in some cases, years. We’re so excited to see you and catch up on everything we’ve missed in each other’s lives. We are pumped to hear about your engagement, so proud about your MBA program, and bewildered that you have full-on adulted and purchased a home during our absence. While your experience in these last few months has surely been different from our own, we are genuinely excited for you!

When the conversation eventually shifts back to ourselves, it can be… a little uncomfortable! Look, we get it. From an outside perspective, our lives seem pretty unconventional. It can be hard to know where to begin. While our accomplishments are less traditional, they are still things worth celebrating. We’re out here learning languages, summiting mountains, getting diving certifications, starting companies, pushing our limits, and learning new things about the world and the people in it every day. We want to share that with you! Here are some pointers on how to get the conversation started.

First off, let’s cover what not to ask, and why:

1. What’s your favorite country?

We get asked this question a lot, and frankly, it’s boring. We have a hard time answering this because it is one-dimensional. Countries are so multifaceted and have a lot to offer. We learn about them on a deeper level by spending more than a week in each. I have a favorite country for food, a favorite for nightlife, and another favorite for outdoor adventures. I have formed a generic answer to this one just to have something to say when it is inevitably asked, but it’s not a very personal or thoughtful question and often solicits a flat response.

Instead, try What country surprised you the most?

2. So… are you seeing anyone?

Nomad dating is, in a word, complicated. We’re often moving around too frequently to date locals, and sticking around long enough to properly date invites visa complications. Dating other nomads is also tricky. It’s a big commitment to change your travel plans for someone else early on, and like a sitcom in its 10th season, there's a limited or non-existent degree of separation between the nomads you’ve dated, and every other nomad. It’s a tangled web and a small enough community. If I am seeing someone, it’s likely the least interesting thing I could talk to you about. No offense to them, but I’m doing some pretty interesting things in my travels! This question makes me feel like my success is being measured by my progress toward marriage and settling down, and it’s just not the path I’m on right now.

You can still ask about it, just don’t let it be the first or only question you ask me!

3. Wow, tell me everything!

Where do I begin?! How might I sum up months or years? You will likely get a top-level overview of the order of countries I went to and some of the activities I did there. This question doesn’t show that you’ve kept up with me or paid any attention to what I’ve been up to. I beg of you, ask me something specific that you are genuinely curious about!

Instead, try I saw you were in Istanbul last month, it looked incredible! What was the food like there?

4. Did you enjoy your vacation?

Oh, how this one irks me. It’s not a vacation. It’S nOt A vAcAtIoN. IT’S NOT A VACATION! This is a lifestyle we’ve chosen, and most days, it’s not glamorous or luxurious. On our Instagrams, we’re leaping off waterfalls, swimming in infinity pools, and sunbathing somewhere tropical. In reality, many of our days are spent in cramped airports, trying to sneak our too-heavy carry-on through the gate. Others are on ten-hour bus rides without AC or running from cafes to coworks trying to find a half-decent wifi signal before our big meeting. We’re working while traveling, and that requires a lot of concession. Don’t get me wrong, we are extremely fortunate to have the opportunity to do this and we don’t take that for granted, but please understand us when we say we’re not on spring break.

Instead, try What are some of the biggest highs and lows you’ve had while nomading?

5. Nothing.

Sometimes when you don’t know what to ask, you don’t ask us anything at all. This one hurts the most. It makes us feel as if you don’t approve of our lifestyle choices, think of it as a phase, or are just uninterested. We’re not following a traditional path, and maybe you don’t understand it or can’t relate to our experiences. Start from anywhere! What is a nomad? What are you working on? Would you someday want a home base here, in another country, or not at all? It’s important that our family and friends from home support us or at least try to understand us. A little effort goes a long way.

Instead, try Are you finding travel fulfilling and meaningful?

Now on to the fun stuff, what you should ask us!

I have a delightful friend from home who is the poster child of a good conversationalist. After our catch-ups, I feel all of the warm-and-fuzzies. What is she doing differently? She is asking me very specific questions that show she has been paying attention. Beyond that, she asks me things I know she is genuinely interested in hearing the answer to. I come away feeling that in an hour's time, I have shared the most interesting and impactful moments of my last few months.

The way she words her questions resembles a not-so-structured version of the STAR method. The STAR method is a technique often used in job interviews, to solicit a well-rounded story from the interviewee.

Situation, Task, Action, Result

Here’s an example of some STAR questions in the context of travel:

Your time in Tanzania looked like nothing I’ve ever seen before. Can you tell me what a day in the life was like there? I’m wondering if it was easy to balance work and all your weekend adventures in that environment.

Why this is a great question: You paid attention to what country I was in and what I was doing there. That is so appreciated! We know our lives can be a lot to keep up with, but anything specific you can remember shows us that you care. This is general enough that I can think of specifics that you’ll find interesting. You specified a place, asked me to describe my experience, and how the result affected my experience.

The group you were with in Mexico City looked like so much fun! Can you share with me one of your favorite group adventures while you were there?

Why this is a great question: It’s very specific! We’ve had a million adventures together and I don’t have time to share them all. However, I can certainly pick out my best stories. These are fun for me to tell and hopefully, fun for you to listen to.

You were feeling pretty burned out at work before you started traveling. Has that changed? Can you tell me about some of the new projects your working on and if you’re enjoying that more?

Why this is a great question: If I’ve taken the leap and left my desk job to start freelancing, or decided to give entrepreneurship a go, that’s a big deal for me! I’ve taken a potentially less financially stable path in exchange for freedom and time. If I’m finding success, that’s an accomplishment I want to celebrate. If I’m still struggling to find my footing, I’d love your support.

As digital nomads, we make new connections and have intro-level conversations every day. We hope for more from our friends from home who have known us for years. We miss you, we love you, and we want to share all of our incredible experiences, pitfalls, wins, and losses with you. Your support and comradery make a difference to us. We want you to know that we are happy, safe, making strides, and fulfilling our goals just like you.

5 mistakes youre making talking to your nomad friends




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