Shit Nobody Tells You About Being A Digital Nomad - Phil Hawksworth
11 months ago

Shit Nobody Tells You About Being A Digital Nomad

What’s it really like being a digital nomad?

There’s a million blogs, books and courses out there telling you how to become location independent, and how awesome your life will be when you do. Is that the full reality? Is it all roses?

Like anything in this world, being a digital nomad is neither inherently good or bad. It is simply a lifestyle choice that some of us have made. It has a lot of positives, but it also has some negatives. It’s not for everyone.

You will know if its for you. You will have a pull towards it in your heart. An inherent problem with authority and the idea of settling down with a cubicle job, miserable overweight wife and possessions you can’t afford on finance will make you feel physically sick.

Freedom will be your highest value and you will have been pursuing it across all areas of your life, whether you realise it or not.

Let’s look at some of the realities of being location independent. The shit that nobody tells you when they’re getting you hyped up on the lifestyle. It’s a truism that your biggest day to day stress will be finding good wifi in random places around the world. However, there are some medium-long term actual downsides to this lifestyle too.

Some of the things on this list aren’t actual negatives, but rather they’re important things you should know and utilise appropriately.

The first 6 months – adapting to freedom

The first few months are weird. You have ultimate freedom and constant new environment/experience. You probably haven’t lived like this since you were a small child.

If you had a job before, clearly you had no freedom. Even if you had a business and did have time freedom, you were still in your normal environment at home. Around familiar people and in a familiar routine.

Now you have all of this freedom and you will go crazy. You will party too much. Go out too much, drink too much, fuck too much and generally not do any productive work. It’s inevitable that you’ll divulge into hedonism and I think you should do so. It’s good for you to find your own boundaries.

You will end up over shooting – doing too much partying and hedonism – and after 6 months or so, when that wears off and loses it’s appeal, you will probably realise you’re not as happy as you thought you were.

The excitement of not having a job and being free wears off, it becomes your new normal and suddenly you’re not sure what to do with yourself.

You need to exert some discipline to get yourself into a more productive and sustainable routine. Without boundaries you end up in chaos rather than freedom. It takes self-discipline to recognise and fix that problem.


You will have a base city

Whether you are planning to or not, you will end up having a base city. Everyone does. The fact is, being on the road is tiring after a while. It’s not conducive to good work and even those of us who value freedom still need some routine and familiarity. It’s back to the chaos versus freedom conversation from the previous point.

A base city is like a quasi-home you can go back to and slip right back into your routine. I ended up falling into having Chiang Mai as my base city, partly through random chance. You might want to have a couple of base cities, on different continents or different parts of the world. For example, summers in Europe and winters in SE Asia.

The beauty of being location independent is you can come and go as you please. You can stay for as long as you want, and then you can leave – maybe never to return.

Truth is, nobody will want to be on the road permanently. It’s draining. The base city allows you to settle into a routine and get some work done. When you get tired of being there, you can leave and chase a new adventure.

You will usually leave to fill the gap of what you lack in your base city. For example if your city is quiet and doesn’t have much going on like here in Chiang Mai, you will leave to go somewhere more exciting and lively for a while. Until that gets too much and you crave the quiet again. This is the true freedom of being location independent.

It’s not that you are gonna be in a new city every week. Rather it’s the knowledge that you can move as and when you desire, to ensure you’re always living life on your terms and maintaining your happiness. There is no perfect city – as Jake observed – the beauty is, you don’t need the perfect city when you can move whenever you wish!


Be wary of your digital nomad guru

There’s the dictionary definition of being a digital nomad, e.g. you work remotely and live location independent; then there’s the identity of being a digital nomad. The cult.

Below is a podcast I did recently with Will and Brian. Among other things we discuss the digital nomad guru movement of people selling how to get rich being a digital nomad, by selling how to get rich as a digital nomad.

I don’t know anyone who identifies hard as a digital nomad that isn’t either selling the identity/dream, or just a wannabe. Usually the people who bought into the guru’s dream.

Unfortunately this guy often doesn’t actually have a business or any valuable skills, and runs back home to live with mummy after 6 months because they’re not cut out for being in business on their own.


Digital nomading is not a business. A blog is not a business

This is a follow on from the previous point and referenced in the podcast.

If you want to be permanently location independent, you need a fucking business. Something that actually generates enough profit for you to live on.

I know that sounds stupidly obvious, but all of the people buying into the guru’s identity dream don’t actually have a business. They seem to assume calling them selves a digital nomad, writing a travel blog and trying to affiliate sell how to be a digital nomad constitutes a business.

You might make some money like that, but the chances are you probably won’t unless you’re a hot girl, or willing to graft for free for 4 years before it pays a return.

Please, have an actual product or service people want to give you money for, or a skill you know is valuable and people will pay you for (freelancing) before you run off to a foreign land. I want you to succeed and live free, to do that you need to make sure you don’t jump the gun and buy into the dream without a reality to back it up.


You’ll have fucked up relationships

It’s a weird position to be in when you never stay in one place for more than a couple of months. Your relationships are always inherently transient, unless you meet a girl you wanna travel with. That’s unlikely; the digital nomad world is 90% male, or couples.

So you come and go from places, constantly getting to know new people and saying goodbye to old. It’s great fun fucking your way through 60 girls in a year, but that does get tiring and old after a while. You will start to crave something more long term and that is going to create all kinds of conflict.

Internally you have the pull for adventure and new places (new girls) versus the affection of a girl you’re dating wherever you are.

You go and come back, maybe she waits for you. Maybe not. If she does, you know she’s been sleeping with a bunch of other guys while you’re gone, but she’s still gonna get jealous about you doing the same thing – that’s the very nature of women.

If you don’t subscribe to monogamy anyway, dipping in and out of people’s lives every month or two just adds fuel to the drama girls will always inevitably bring up in non-monogamous relationships.

It’s great if you’re young and single, obviously. It’s perfect. Just be aware that at some point you will fall for a girl you have to leave, or you will want to settle into something more long term and that will create conflict with your lifestyle.

I don’t have an answer to this conundrum, because it depends what you want from life at the time. Your own desires will obviously fluctuate anyway – I just want to bring the topic up. I think it’s good to have an idea of what you do and don’t want from relationships, in order to create the boundaries needed to not get into drama.


Good friends are worth a lot

You’re not just having transient romantic relationships, but friendships too.

Personally as someone who doesn’t let people into my life easily, I don’t make a lot of friends on the road. Obviously if you’re an extrovert or generally not a grumpy Brit you will make more friends, but it’s going to be short, generally shallow relationships.

It gives you a new appreciation for good friends you do make. One of the reasons I come back to Chiang Mai a lot is because I have good friends here. After a couple of months adventuring, it’s good to come back and be around people you share deeper experiences with.


For a year people will ask when you’re coming home. After that they forget about you

It’s pretty funny. Normal people who have normal jobs and normal lives don’t seem to grasp your reality. They think you’re just on some extended holiday and will be back home soon.

I guess most people who have never been in business for themselves don’t actually believe it’s possible to make money online (or at all without a paycheck).

For the first year or so people will always be asking when you’re coming back. After that, they seem to figure out you’re not and they stop asking.

I’ve found a few people seemed to lose interest in the adventure stories and I guess had some resentment towards me living free while they’re doing the same old shit. It is what it is, but you will always be ‘weird’ in most peoples eyes.

You’re living an unconventional life as an outlier, so I guess it’s understandable.



Live is great if you’re pursuing the location independent lifestyle. There’s never been a better time to arbitrage your money, travel cheaply and live free.

Just go into it with your eyes open. It of course has some downsides and things you want to think about before jumping in, expecting everything to be sunshine and rainbows.

Two or three days a year you’ll end up in the wrong part of the world at the wrong time of year and it will rain. Imagine.


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  • Thanks for sharing your experience Phil.

    “summers in Europe and winters in SE Asia.” – sounds ideal to me! I was in Europe for 4 weeks last year and in Asia for 4 weeks a couple years ago. After a while, I just want to get back home, so having a home base is totally true, whether in the US or anywhere.

    It’s good you’re experiencing this lifestyle now. It’s really hard to do it once a family comes, if it comes. I tried so hard to do what you do between 2012-2015 and just couldn’t stay away from San Francisco for too long. Real estate holds me down as I bought a fixer in 2014 and couldn’t breakway.

    Maybe one day!

    BTW: I think blogging is the best business in the world!


    • This lifestyle definitely isn’t for everyone, you’re right there. Some people just like to be settled and have a home.

      Agree about family, I think that will settle most people down to one or two places. Constantly travelling is for single people.

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