Lessons Learned From Digital Nomad Living & What’s Next

sunset on the arabian sea goa india

The main purpose of my initial 6 month trip to Asia was buying time for cheaper living, getting some work done, a bit of exploring and pondering a few topics, which needed resolution. These goals influenced how I approached the average day and socializing. In this round about way, a huge step towards clarity has been reached and continues as I’m now traveling a few months through the U.S.

I’d like to share a few observations of a personal nature, specific to my life circumstances discovered while on the road. Everyone’s situation and goals are different. If anything these are like a journal entry to myself, however others may benefit from it, even if they seem like common sense. It’s only when you do something yourself, you can see how it really feels.


Need for relevant community

Moving around experiencing new sights and sounds is a definite rush. One of the things I found however was my growing lack of relevant subcultural communities to relate with, as I had in the States. I found this very isolating. Living in places for a couple of months here and there isn’t sufficient time to develop a fulfilling social structure. For some, the ‘digital nomad’ community is enough. In my view, this is just a collection of people who are working while traveling. It’s likely the only commonality shared. Ideally, those who stay a long while in one country can/should invest in learning the language and customs, while attempting to become a part of the community. And per my understanding, even then you may always been seen as an outsider. Most nomads however, don’t stay this long. I expected ‘something different’ and to dive into a new culture, however I didn’t anticipate how important this one point was, especially when you have nothing else familiar to fall back on for support. 


The heat. I really, really hate it.

A recurring theme mentioned on this blog, is my disdain for hot weather environments, despite being a Florida native and feeling stuck there for quite some time. The heat kills my energy, motivation and drives to go out and explore.

Full well knowing this, I decided to forge ahead to some of the hottest places on the planet like Thailand, India and Cambodia, due to the low cost of living. I’m not a shorts and flip-flops kind of guy; boots and pants is what I feel comfortable in. Many visitors to SE Asia feel right at home in this climate and thrive in it. Whereas, I’m typing this now in Seattle, WA with a 55 degree breeze coming into the window and I feel fantastic, energized and creative. Same thing when walking down the street in Portland, Oregon last week.


Lack of a home base

Part of the crafting a new life direction process was purging most of my belongs and giving up my apartment. The continuous logistical planning and getting settled in new locations isn’t really that fun, and a bit draining. Meaning there isn’t the psychological stability of knowing you have a familiar home to go back to. As an introvert, this is challenging. Also as a Pagan, not having a fixed place to meditate, imbue energy and do workings feels as ‘if I’ve lost something.’

At the moment I’ve been jumping between various hostels and AirBnb listings in the Pacific Northwest, after having camped at various festivals around the U.S. peppered with motel stays and friend’s house couch crashes in between. In Orlando, FL. I’m also temporarily renting a room at a friend’s rental home, which he’s in the process of getting rid of over some months.


Getting work done

I found co-working spaces the easiest environment to get solid work done, with coffee shops/cafe’s a close second. Working from my apartment (the one’s which had WiFi) was a last resort, as I prefer the buzz of being around others and it helps keep me focused. In a way, I feel more accountable to not waste time online, whereas it’s all too easy if staying home.


Sightseeing and tourist traps

I tend to like attractions where I can quietly explore on my own. Not a huge fan of group tours or the constant explanation of details. I like the wandering aspect of it to feel out the energy on my own. For example in Cambodia at Angkor Wat, I skipped both of the tourist lines, climbed up onto a ledge and entered through a window at the end of the ruins. A rewarding experience getting some quiet time to meditate in this old place at sunset.

I usually didn’t stay in any tourist areas, opting for more local parts of town. The catch-22 was the availability of daily interactions with locals, yet not speaking the local languages. This also means not interacting with many backpackers or expats either (unless a special trip was made out to those parts of town). I can’t say I’ve walked away with any resolutions of how to handle this in the future, since most stays are a couple of months or less, and travelers come and go.


Living in the moment

While on the move, I personally didn’t want to view every moment as something to record. In fact, everywhere you look is selfie sticks, small screens and posing. For me, this detracts from organically soaking up the energy of a place. It’s scents, sights, sounds and vibe. Your mind constantly rationalizes how moments should be captured. Using random locals as props for photographs isn’t my style. When I look back, many of my photos are of places and some ‘sneaky snaps’ of people in daily life, not with groups of people as I see others post. I passed up on a lot of extraordinary photo opportunities, and I can’t say that bothers me much.

I’d often look around cafés or expat hangouts and consider how things might have been a couple of decades ago when we couldn’t bury ourselves into a screen and needed to interact with others for entertainment, in lieu of reading a paperback book.



When reading this over, in some ways I’d peg myself as a ‘bad traveler’ of sorts. I found it a struggle to mentally compartmentalize the balance of work and play. I felt like I should have done even more exploring than I did, however the heat would just demotivate me and I’d guilt trip myself into need to work. I felt out of my comfort zone in many places, as even in the U.S. I often stand out, as my appearance is a bit non-mainstream. This felt even more noticeable in some places as I found myself trying to assimilate more into the local environments, and that just made me feel unauthentic and uncomfortable. Being an introvert who selectively interacts, continuously meeting new people can seem exhausting, requiring more alone time to recharge.

I still view this time period as a success overall, as I measure it. I found the resources, courage and planning to take another step towards a freer life. This entailed quitting the best job I’ve had, selling most of my stuff, leaving a comfy home base and activities/friends I enjoyed. Jumping head first into a place like India as a first stop was rough, but it made other locations somewhat easier. I don’t judge a trip outcome by how many friends were made, by how many sights were seen or the quantity of countries visited. I judge it by internal feelings and in the ways it changed my perspective.

I’m enthralled I got to see the funeral pyres of Varanasi, India , the Himalayas and Ganges River in Rishikesh, the ruins of Angkor in Cambodia, the electric vibe in Bangkok, Thailand , the temples in Chiang Mai, and the psychedelic beaches of Goa, India on the Arabian Sea. They are great memories I’ll never forget.

Being a perpetual nomad for years on end however, isn’t for me. In many ways, this trip reinforced my need to have a home base for most of the year and build local communities around me for the long run. In order to push my eCommerce consulting business further, I feel the need to stay put in a familiar environment for most of the year, without the guilt of ‘not exploring enough’ or feelings of isolation. Taking a few months of the year for travel to other countries and festivals is much more appealing.

I wanted to see what it was like to live/work/travel in far away exotic lands. And this I did.


What’s next?

One of the biggest issues I was pondering while away (and for years prior) is where to setup a home base that I could see myself living long term for most of the year. Meaning a walkable city with great public transportation, close to killer nature and a vibe I enjoy. I want to sink my teeth into a city and become a known participant of several different communities I enjoy, which takes months if not years. As I travel, I’ve found if I don’t view a place as a long-term candidate, I’m not fully committed to exploring it. I look for places where I can have repeated experiences in favorite spots. This to me, is more realistic then the one time thrill of seeing a truly epic sight.

To further complicate matters, there are several festivals and fire drum circles every other week in Orlando, FL, where I’ve lived for about 15 years that are my hands down favorite activity for many reasons. Other than these Orlando events, there isn’t much else I like about the State. Meaning this isn’t a good enough reason to stay forever in limbo so to speak.

Not to mention, setting aside the time to figure out how to grow my business.

I’ve been debating these points for years, which caused much inner turmoil and restlessness as the answers weren’t clear. These were too many things to try and tackle at once, causing me to shut down many relationship opportunities, friends and social gatherings. It took direct bold actions and learning through experience to shed light on the necessary solutions.


What make sense to me at this point is to…

  • Moving to Portland, Oregon as a home base. I’ve written about my past trips here in great detail, it’s felt like a perfect fit on all 3 visits here. I’ll be looking to rent a room in the dense, walkable parts of town, which could take months to secure, as the market is highly competitive.


  • I have no plans to ever drop hundreds of thousands on a mortgage, yet I don’t want to continue renting. A strong possible solution is to acquire a very small home in the next few years, of the 250 sq. feet on wheels variety to own a home mortgage free. This point deserves it’s own post, as it’s a complex topic for legal and logistical reasons. This would require coming up with a sizable chunk of money around $30-50k cash, as I’d hire a company to construct it. It will also require lots of networking to eventually find someone in a good part of town, willing to let me park it on their land, for whatever compensation we negotiate. Once finished and parked in a good location, it could also be used for rental income when traveling, since the aesthetics will be very unique.


  • Pickup a remote full time job AND increase my consulting income to acquire this needed cash surplus. I did this before over a three-year period. Before my last job I was down to $43 and then walked away with $31,000. Once I’ve accumulated enough savings, I’ll determine how to work less again and spend more time on hobbies.


  • Ensure my income streams allow the flexibility to attend my chosen festivals around the U.S., while having a home base to come back to and a grounded feeling. Exploring foreign lands will still happen, but for a smaller portion of each year.


To me, this is the best of both worlds (freedom of long term travel & home base with social circles). So there you have it. For me, the logistics of ‘what’s next’ have been a constant struggling point for many years. It took quitting my job, and embarking upon this digital nomad lifestyle to learn through direct experience what felt right.

It feels like a giant weight has been lifted from my shoulders, and the path has finally become clear! A great feeling.


  1. Brilliant post. I especially like “relevant subcultural communities to relate with”, and also the heat. I have been on the road 18 months now, mostly thailand. I solved the heat problem by digital nomading in Dharamsala (McLeod Ganj) India, with added advantage of spectacular hiking and ridiculously cheap ($300-400/mth). But I feel considerable (and sometimes painful) social isolation. The bottom-line here is that (1) there is no better place for “sub-culture communities” than the US, and (2) digital nomading is inherently distancing from your typical adventure-traveller, as the latter are traveling for thrills and new environments, whereas I view digital-nomading is more of a purposeful thing, be it business development or cultural awareness or personal development. Even in places with strong digital nomad community like Chiang Mai or Ubud, that fact alone does not create a basis for connection because what you have in common is only the fact that you are running an online business (think about it: are your friends people in the same business as you, usually?). I have discovered there is no single optimal environment that meets all of: cost, natural beauty and climate, focus and productivity, and social network. The Tiny home solution is interesting, keep us posted!

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