The Art of Living On The Road: Lessons from a Social Media Nomad
Founders Introduction
I always thought nomadic living was a black-and-white decision: you packed up your life and went off-grid—for good. But then YouTube happened, and a new wave of vloggers emerged. They made it seem like an even more unattainable lifestyle, gracing our small screens with idyllic profiles, breezing from beach to beach. Jealous? Definitely.
But what if it didn’t have to be an all-or-nothing decision?
What if there’s a vast middle ground to explore between society’s “norm,” with all its trappings, and the vlogger lifestyle of living out of a van and cliff-jumping their way around Asia.
This is exactly what came to mind when I started chatting with one of our customers, Andy, about his own nomadic experiences within the U.S.A. Intrigued, I wanted to know more.
Thankfully, Andy agreed to an interview, and I hope that beyond being a fascinating insight into his life, it inspires us all to reflect on our own lives and consider what small steps we can take toward a happier, healthier existence—one without so many of the limitations we like to build for ourselves.
Our blog last month (with Nick Hall) talked about defining our values and striving to live in line with them. It’s our hope that Andy’s story will inspire you in a similar way. For instance, if you value friendship, who could you visit instead of opting for yet another beach holiday? If, like me, you have immovable commitments, perhaps more frequent trips closer to home could be the answer. If you travel for work, consider staying with local residents or booking extra nights to explore more than just the airport lounges.
At the end of the day, our lives are enriched by people, places, and experiences. So, why not push yourself to "fill the void" a little more.
As always, we’d love to hear your thoughts or experiences, or especially if you have your own story of change and personal development. Feel free to drop us an email at info@hollowheadthreads.com
Warm regards,
James
The Art Of Living On The Road Interview
By Andy Whisney
The Journey and Inspiration
What was life like before you turned Nomadic?
It was pretty routine - maybe? I've been a freelancer digital marketer since 2017, so I've kind of been nomadic since then, though I never left my home state of Minnesota. So more nomadic in the professional sense, staying in hotels around the state, if that tracks.
What first inspired you to leave behind a more conventional lifestyle and become a nomad?
I’d thought about doing it since around 2019. It wasn't until my father passed away in 2022 that I realized I could really dive in head-first.
Was there a defining moment when you decided that traveling full-time was your new path?
The day I booked my first Airbnb in Austin, TX. It was so scary. One of my best friends lives in Austin, so that was a great excuse to go. Then once I booked that, I started looking at all other sorts of places considering where I could go to next.
How did you envision this lifestyle before you started, and has reality matched up to that vision?
I very much romanticized the idea! But I didn't really consider how much time and effort goes into packing, driving, getting acclimated to a new place, getting the dog comfortable - all of those "little" things get clouded by the idea of living on the road. Luckily now I've found a groove but finding it took a while.
Daily Life on the Road
What does a typical day look like for you while you’re on the road?
If it's a travel day, it's mostly driving. I look back and kick myself a bit for not stopping at places along the way, but I'm hyper-focused on getting to our new destination on time and in one piece. I drive a Toyota Tacoma and it gets around 360 miles per tank, so every ~300 miles we'll stop. Luckily my dog is a great travel partner - and she kind of knows the deal once we get everything packed up.
How do you choose where to go next, and what factors influence your decisions?
Last winter the focus was getting my dog, Pepper, to the ocean - while going to places I had never been. So it's mostly around the people, things and places I want to experience with my dog. The original idea, though, when the first Airbnb was booked it was simply to escape Minnesota for the winter.
What are some of the biggest challenges you face in everyday nomadic life that people might not expect?
Mostly routine-based. It isn't until a few weeks into the new place that I finally feel grounded. Things like going to the gym, going on a walk, finding the nearest grocery store are all crucial ways to get my footing sooner.
Social Media and Storytelling
How do you balance experiencing your travels with the need to document them on social media?
I struggled with that initially. I just try to make my experiences the most important and then if I feel like documenting them on social media, I will. But it isn't necessarily always on my mind to post about my travels on social or gather a huge following.
What do you hope to convey to your followers about life as a nomad?
If anything, that it isn't as crazy of an idea as it seems. You don't need to drop everything and move to Bali to experience the nomad lifestyle. If you're fortunate enough to work remotely, just try working from a new place for a week. Or a couple days. Whatever it is. It's simple enough to get a taste of the lifestyle. It’s up to you!
How has sharing your journey online influenced the way you travel and the connections you make?
I'm not sure it really has, to be honest. If anything, it's made me more open to experiences and saying "Yes" more often. I'll surprise myself sometimes when I say yes to something that me five years ago would've scoffed at.
Mindset and Personal Growth
How has this lifestyle changed you, both personally and professionally?
As I mentioned, it has put me in a much better headspace personally. I've felt tons of personal growth that I can largely attribute back to 100% of the time being out of my comfort zone. Professionally, it has helped me take my job more seriously. Not that I didn't in the past, I just know that I need to go above and beyond because my current clients are so cool with me working from anywhere.
What have been some of the most transformative experiences you’ve had on the road?
Everything from driving through a winter storm in the Rockies, to sunrises in Joshua Tree, to conversing with a sketchy but nice man on the beach in Eureka, CA, to listening to audiobooks that hit me at the right time. Everything can be transformative; your eyes just have to be open enough to realize it.
Do you feel an increased sense of freedom living this way, or are there unexpected pressures that come with it?
The only pressures are those I put on myself. To perform at a higher level for my clients, to get out and hike and walk my dog places she's never been - those kinds of things. Aside from anything else, just enjoying where the wind takes me.
Logistics and Practicalities
How do you manage the practical side of things like work and finances?
Work is usually pretty straight-forward. I'm pretty accessible for my clients and will always let them know if I'll be away for an extended amount of time. Finances can be tricky - being a business owner as well as a digital nomad, a lot of things are in flux. But I have a bookkeeping service that helps with things when I need them.
How do you prepare for potential emergencies or the unexpected while on the road?
I'm not on the road enough to really experience potential emergencies *knocks on wood* but I have, like, AAA for roadside assistance and an Apple Watch I can use in case of emergency.
Community and Connection
How do you maintain friendships and relationships while constantly on the move?
Friendships are an easy one. I typically know some folks each place I go, but all of my friends keep in touch via Slack. So, we all chat at least once/day. It's great.
What role does the nomad or traveller community play in your life, and have you found a sense of belonging within it or is this a personal journey?
I haven't met many other nomads - in person or via social - so there isn't yet a community that I've tapped into. It’s definitely a personal journey for me.
How do you handle periods of isolation, or do you enjoy the solitude?
I've always been very independent and have always really liked my alone time and my own space, so I enjoy the solitude. And I'm never fully alone - I've always got my dog Pepper by my side!
Reflections and Future Goals
Looking back, would you change anything about the way you started your journey?
Maybe waiting as long as I did. But if I had gone any earlier, I wouldn't have been around for my father in his final days so I'm really happy with how my journey started.
Do you see yourself continuing this lifestyle indefinitely, or do you have plans for a different kind of home base one day?
It for sure isn't sustainable - it's exhausting. I think I'm getting closer to finding a place to hang my hat, but right now I'm still in exploration mode. But who knows! That could change tomorrow.
What advice would you give to others considering a step or leap into nomadic living?
Just do it! Give it a try. Try it for a week. Try it for a long weekend. Try it for a regular weekend. If you can, just give it a shot and see if its right for you. If it isn't, at least you tried. What's the harm in trying hey?
Philosophy and Perspective
How do you define “home” now, and has that definition evolved?
I've warmed up the idea of home being a people, not a place. So when I travel I purposefully pick out places where I know people. I'm in Denver, CO as I write this and three of my best friends live here. It's a place I've visited often so I'm already pretty familiar with it and it has some sense of comfort. If I think to one of my more secluded stays - an A-frame near Yosemite for all of February 2024 - I was on the verge of cabin fever I think lol, at least for the first week. It had all modern amenities, so it was an incredible stay - but I didn't know anyone! I would only occasionally speak to someone when on a hike with my dog, or at the grocery store. I remember a maintenance person came by one day and I could've cried because it was so nice to talk to someone. So - that said - the community aspect is huge when defining "home".
What does success mean to you?
Honestly, just enjoying every day. I need to be better in recognizing how lucky I am to be living the life I'm living. If I were to tell 10 year-old me the kind of life I was living, there's no way he'd believe me. So that is success to me.
Do you feel this lifestyle allows you to live more authentically, and if so, how?
Absolutely. Being thrust into a new location, you can be whomever you want to be. It's a very freeing feeling. I think that authentic living creates that feeling of living more freely. It's very liberating.
What has traveling around America taught you about the country and its people?
That everyone is pleasant at their core and though we can disagree on things, everyone just wants to be happy.
Are there places or cultures that have resonated with you in unexpected ways?
The slowness of Joshua Tree was both refreshing and a little spooky. It's just a spooky place in general!
Final Thoughts
What has been the most surprising thing about this lifestyle that you wish more people knew?
That it isn't all it's cracked up to be some times! We all see the van lifers or digital nomads on social media - but it's a ton of work. Luckily, I've just been doing it in the States a bit, I imagine going overseas would complicate things even more. But yeah, it's much harder than people might think. The small details, lodging gets expensive, lack of community can make you feel isolated sometimes - there are just things that pop up that I didn't consider when I first started.
If you could capture the essence of your nomadic life in a word or phrase, what would it be and why?
Worth It. I say all of that after mentioning the negatives because what better way to push yourself outside of your comfort zone than to travel to a ton of different places and simply fly by the seat of your pants every day? I've noticed personality changes that I'm very proud of and I attribute that growth to this nomadic lifestyle.
You can follow Andy and Pepper's travels here:
Andy Whisney (@andywhisney) • Instagram photos and videos
