Should I take the plunge? Push me over the edge!

Hey everyone!

This will be a throwaway account - I will sign up properly once I’m ready to embark on this exciting new journey. However, I need some support and advice before taking the plunge. I think this post is about to get a tad lengthy given that I need to explain my circumstances, but if you stick with me, you could possibly become a huge influence on my life and one of the catalysts for a drastic lifestyle change! (Scroll to the bottom for the TL;DR version)

First up, I am 26 years old, currently living in Australia. I work full-time in a web development/designer position, and have been employed for almost 6 months. Previous to this, I was running my own graphic and web design business, and I did this for about 3 years. Why did I decide to go back to working “for the man”? A few reasons: more money, more security, less headaches. I own my own apartment and my expenses exceed $2000/month, so I needed to increase my income in order to live more comfortably.

I’ve recently discovered the “digital nomad” phenomenon, even though I actually kind of lived this lifestyle while travelling for 3 months (US/UK/parts of Europe), but the difference is I always stayed with friends or family and was never alone. I also never considered moving overseas to where expenses are low and building my business and other passive income ventures - until now, that is. I would love to have more time to work on some of my own projects that I have started over the years (e.g. finish writing my first novel, have more time to work on an online game that I started with a couple of buddies, blogging/vlogging, maybe even start setting up new online businesses like dropshipping, etc.)

I’ve been thinking about moving to Chiang Mai in Thailand. I’ve been doing a lot of research online and it seems like this is one of the biggest digital nomad hot-spots. I would also love to visit Thailand and experience the culture, people, and food. However, all I see online is the positives about being a digital nomad. Nobody seems to talk about how lonely it can be or the downsides to this way of life. For all of you out there that are currently living this lifestyle by yourselves (without partners), be frank with me! What’s it like? Do you get lonely? Do you find it hard to go out and meet new people? Are the people you meet always temporary companions, or are you able to cultivate meaningful friendships with others that extend past the “business” side of things? I’m a bit of an introvert at heart, and I have never gone out to a club by myself or anything like that in my life - it’s always been with friends. However, I know that I would have to put myself out there if I decide to pursue this lifestyle. Honestly, this kind of excites me and terrifies me at the same time, but I know that it would be a great experience!

Another issue that I face is with my family. My parents are very… shall we say… “invested” in my life. They take a lot of interest in what I do and how I should be living my life. I say this in the most positive way possible, but sometimes I wish they weren’t so protective and paranoid about the world. My mother in particular worries all the time, and this is what she thinks of the whole idea: It’s dangerous. People will rob me. What if I get sick? She thinks the healthcare system in Thailand is horrible (despite her only knowledge of Thailand stemming from documentaries she has watched pertaining to the sex industry). Drugs. Hookers. Corruption. Loneliness. “You’ll be taking several steps back in your life/career if you do this.” I mean, I could go on, but this post is getting long enough. How can I convince my family that this will be something positive and that I am not crazy for wanting to do this?

Is the whole thing worth it? My life right now is not bad by any means. I have the well-paying job, I have the apartment, the car, the (what some consider) “perfect” country. Am I not being humble? Do I not appreciate what I have? These are questions my parents are asking me. But alas, I am unhappy. Even though I have it beyond “good” when compared to other people, I am still not satisfied. I can’t stand the 9-5 lifestyle. I am getting sick of my job and the people I have to put up with. I’m watching my life pass me by as I am getting older and older. I really want to experience more of the world and have the ability to work on projects that actually make me happy. Tell me I’m not crazy for wanting to drop everything to pursue a nomadic lifestyle!

I’m going to try to wrap this up now. Let me give you guys a breakdown of what I would need to do in order to become a digital nomad:

  1. Rent out my apartment (It’s been renovated and has new expensive furniture. I am definitely afraid that someone will come in and wreck it all, but hey, I wouldn’t have much choice).

  2. Quit my job and get in touch with my old clients again (I think I could easily start getting freelance work again from my previous clients, so I probably wouldn’t have an issue with getting by).

  3. Book my tickets and do all the preparations (Vaccinations, changing my address so my parents get my mail, sort out accommodation for Thailand, get my visa in order, etc. etc.)

It’s a huge change with a fair few financial risks, and all it boils down to is: Would it be worth it? Here’s a brief run-down of the questions I need answers to in case you couldn’t be bothered reading the wall of text above.


  1. How lonely does it get as a digital nomad?
  2. Is it safe to travel to Thailand? What are the risks? What should I be wary of?
  3. How has being a digital nomad worked out of you? Don’t just give me the glamorous version either! I want the gritty details too. :wink:
  4. Is it easy to make new friends that actually stick around?
  5. If you could do it all over again, would you?
  1. There are times that it can get pretty freaking lonely, especially if you come from some tiny niche of society and then realize that something like it barely exists anywhere else, so you end up in these long meaningless tedious conversations about pop culture while you would much prefer to be gouging your own eyes out. But, that may not be you. Me, I grew up at a top tier league university - yes, grew up on campus - I’m like an uber nerd. It turns out that I have a really hard time being interested by anyone that doesn’t have critical thinking skills, knowledge, experience and the ability to add more to a conversation than a parrot could.

Okay, back to the question…

On the upside, it will push you out into the world more, so chances are you will meet more people than if you were hiding out in your apartment and work.

Anyway, on to the other stuff…

  1. Is it safe. I have no idea, haven’t been to Thailand. I have an aversion for much the same reason as your mother, except I’ve actually been a target of trafficking - cute white girl, out on her own at a young age, need I go on. I’m wandering Europe at the moment - nice safe and tedious Europe.

But in general you need to decide what you define as safe. Do pick pockets make you nervous? Does the presence of militarized police to keep the “safety” make you actually feel safe, or do they make you want to back away slowly with a really big grin on your face in the hopes that that will think you’re just a dumb tourist and move on?

  1. It’s life. I needed work that wasn’t settled because I like to get up and move around. So, I made it happen. It’s pretty normal…from my perspective, anyway.

  2. There’s a certain amount of turnover. Social media helps to keep things semi-alive when you’re not around.

  3. Skip :smile:

You’ll be fine, probably :wink:

1 Like

Thanks for the reply, @Cee! You’ve been a target of trafficking?! That sounds pretty scary. If you’ve shared this story on the forum before, send me a link! I’m a 6’2" white male, so you’d assume that something like that should be of no concern to me, but still, you always have to keep your wits about you. I’m glad you’re safe and sound!

What line of work are you in that allows you to travel? It seems like you have a way with words, so my first guess would be that you’re somehow involved with writing. In terms of getting lonely, I think that’s one of the reasons why I want to go to Chiang Mai - lots of other digital nomads to meet and hang out with, so hopefully it wouldn’t be too much of an issue. Like you said, there’s always social media, Skype, and the internet in general to keep in touch with friends back home!

Thanks for your reply. :smile:

Ha, yeah, you’re probably pretty safe when it comes to trafficking. There’s no link on the forum about my experiences with it - those are stories best left for a therapist’s office or after a few rounds of drinks.

I can see the appeal of Chiang Mai. I’m heading for a resort town soon for nearly the same reason (and the beach - definitely the beach). I enjoy the camaraderie and diversity of people that travel, especially if they just happen to speak my language. I’ve been involved with Internations on and off for just that reason - they do regular casual local meetups for expats all over the world.

Personally, I do research and miscellaneous work for NGOs, financial companies, floundering start ups and the like. No one needs to see me in person for that :smiley:
Anyway, I’m not one of those “amazing start up” tales :wink: I just do my thing.

I’m more of an ex-nomad… but in answer to your questions

  1. You won’t be lonely from lack of people wanting to make conversation with you, and you won’t be in danger of being thought off as weird for heading to a bar alone. If anything, more jaded from having the same introductory conversations again and again…

  2. Thailand is pretty safe. Tourists are sacred cash cows which the local political agitators and mafias leave well alone, and whilst there’s petty theft and a few mostly obvious or inexpensive scams, you’re probably safer than at home, unless you’re in Thailand for the joys of getting paralytically drunk at full moon parties.

  3. Don’t underestimate the amount of distractions. I never finished writing my novel! But FWIW I did get my old job back (even for a lot more money) when I returned. I can’t imagine medium-term travel being viewed as much of a negative with most Australian employers, despite what your mum might think!
    Less glamorous side: inevitable sickness at some point, constant attention from hawkers, long, hot and uncomfortable bus rides, losing your temper at being overcharged and then realising you’re getting angry over a dollar, realising it’s a long expensive flight to your friends’ weddings.

  4. Pass. I moved around too much. Some localities have friendlier local people and more expats in it for the long haul than others

  5. I’m considering it…

1 Like

I’ve always been one to only have a very small group of very close friends. I haven’t got time for superficial relationships. This fact makes it nearly impossible for me to build meaningful relationships when I know I’m only going to be in some given place for a short amount of time. A couple of things though, I’m not really susceptible to loneliness - my upbringing probably had a lot to do with this, but also, I have cultivated relationships and I do have friends all over the world who I can have a chat with so loneliness is a non-issue for me.

I haven’t spent much time at all in Thailand, so I can’t really speak intelligently about anything specific to Thailand but the TL;DR is no, it isn’t safe - but having seen this topic discussed ad nauseam in every travel travel forum about every destination, I opine that asking if X is safe is the wrong question. The real consideration should be more along the lines of “are you capable of making sound decisions?”

Surely you’ve seen the photos of the family of 7 piled on to a motor scooter in every person’s blog post about Thailand. That image should be enough to leave you questioning the lack of highway safety laws. Assuming that you will, at some point, want to get from point A to point B you’re going to have to put yourself in an equally dangerous position, whether by private car or chicken bus or tuk-tuk, or longtail boat or something in between. There’s not much you can do to mitigate that risk. Aside from that, however, it really boils down to whether you know yourself well enough to know if you make sound decisions and judgement calls. Miraculously, even people who lack those skills do just fine in an overwhelmingly large number of instances.

One other question to ask yourself is “how safe is home?”. Surely you know people or at least know of people who have been violently attacked, raped, murdered or died in car accidents in your own hometown. Does this make your home less safe because these things happen or do you count your blessings and become more aware and thus better equipped to keep yourself out of these dangerous types of situations? The world as a whole is dangerous - remove wars and violence, remove automobile accidents and you’re still left with natural disasters that can strike anybody anywhere at anytime. You’re still left with disabling, disfiguring and deadly diseases which are often incurable. Live your life on your terms.

I started as more an analog nomad. I posses a skillset that took me all around the world. I loved the going to new places aspect of that. I loved the making four times as much as I would at home simply because I was willing to go someplace that my contemporaries weren’t willing to go. Imaging drawing “hardship” pay while living on a tropical island - I giggled like a schoolgirl every time I got paid. As much as I loved all of that, I became very loathsome of the fact that essentially I was working for the war machine. I’d picked up a smattering of digital skills along the way and had quite a few false starts at being my own boss. I tried to earn money by blogging and soon found I couldn’t write to the advertisers. I tried freelancing several times and found that I have exceptionally poor business skills - I didn’t want to be a businessman or entrepreneur. I thought I wanted to be knee deep in code, but trying to run a business kept me about as far away from that as I could imagine. Eventually, I had a very long discussion with one of my aforementioned close friends and she asked me some very hard, revealing questions. Her advice: “Find a job!” It took me a while to warm up to that idea. I’d had jobs and I hated them. What I needed was to be able to make a living from wherever the wind blew me. Little did I know that this is entirely possible - it took a few tries but eventually I found the job that ticked all the boxes for me. I make enough money to live comfortably in many parts of the world, I have no set hours, I can do it from anywhere with an internet connection, I work with a team of people who are all better than me and keep me inspired and driven to learn more & do more, I don’t spend any time hustling clients or chasing down unpaid invoices. I’m incredibly happy

See my answer to #1 - but, no. I do, however, probably have an easier time of it while nomading about than I did at home. I do find many more opportunities to connect with like-minded people and definitely engage in more stimulating conversations with the people I meet than I ever did with people back home.

1,000 times over. I couldn’t be happier.

1 Like

It’s true that much of what you read is a positive spin on the nomad life-- and true that there are times where it sucks, you’re lonely, miss your friends/ family, work isn’t going well, the power is out, blah, blah. (I write about the good and the bad, but here’s a post that is not-so-sunny…)

Still, if you want to do it, do it. Everything is reversible. If you hate it, quit. What’s the worst that could happen?

(And yes, Thailand is super safe-- I’m a single white female and was astonished at the lack of harassment compared to Latin America and Africa.)

1 Like

Not happy freelancing at home, nor working for “the man”? Great. But why do you think living in Thailand will make you happy? Does constantly changing scenery keep you interested and invested in the world and your life? Are you deeply interested in Asian culture, politics, or environments? If so, you might have a good reason to go.

Will you make strong, lasting friendships while abroad? Maybe. Some people are really good at it, others are not. Are you the kind of person who makes friends easily? How do you feel about meet-up groups or couch surfing? Are you the kind of person who is good at keeping up long-distance relationships? Personally, I am not. But I am a deeply solitary person and happy to spend weeks alone. Eating alone at a restaurant is not a problem for me; I am happy to spend time by myself, find a sunny spot, and watch humanity pass by. Does that sound good to you?

It is possible to connect with people in a meaningful way without striking up life-long friendships. You can have great conversations with people anywhere in the world just by asking questions and listening to the answers. But how tolerant are you of people who have widely divergent views? How will you take it the first time someone tells you how the thing you are most passionate about is incomprehensible to them? how your culture/religion/politics is deeply misguided? how inhumane your country is? And they will (ah, Australian immigration policy…). Are you up for it?

Also consider your relationship with possessions. Will you be happy living out of a suitcase with two or three pairs of pants and shirts? Pack a trial backpack to see what that really looks like. Are you ok with travelling in crowded, hot, stinking public transportation instead of your own car? Are you ok with geckos on the walls, giant centipedes in the ceilings (well, that was Indonesia not Thailand, but you get the idea), and mold in the bathroom of your hotel room? Or are you secretly expecting to live in luxury because “living in Asia is cheap” and, if so, can you really afford it? The cost of luxury living is not all that low, even in Thailand.

Are you going to get sick? At some point, yes. Make sure you have decent health insurance. Are you going to get robbed? If you are reasonably aware of your surroundings (and sober), probably not. Are you going to get caught up in drugs, prostitution, etc.? That’s up to you. Are you going to be happy? No idea. If you are not, you can always head home. And I agree that if you head home after a few years it shouldn’t be a big deal as far as your future career goes.

Most of us regret the things we did not do, the opportunities we let slip away, far more than the crazy things we did. Live your life.

Already many good replies. I’ll just add a very short version.

  1. If you feel like it, you can always meet someone. Hostels, bars, coffeeshops. There are also loads of forums, chats, meetups, etc. Very easy to make initial contact. It also tends to be easier to meet Western people, while in Asia because there are fewer of them.
  2. I feel safer in Thailand than I felt in many Western cities I visited.
  3. You need discipline and endurance. Just because you work from the beach, you can’t spend your day on Facebook. The job needs to get done. The client needs to approve your work. If you venture into a new area, you may spend the whole night at times.
  4. Yes, definitely.
  5. Also yes.