Lifestyle Design & Long-Term Travel (What They Don’t Tell You)

paraguay bus
Instagram travel: Behind the scenes.

I really don’t want this post to come off as yet another spoilt brat travel blogger, whining about how hard their life is because they have to actually set their alarm for tomorrow’s safari, or that they, like – totally understand abject poverty because they once ‘slummed’ a night in a four-star hostel in Phnom Penh.

I hate that s**t.

For the record, I love my weird way of living. With exception of a short period where I kind of lost my mojo and got a little down in the dumps – I’m the happiest I’ve ever been since I left home four years ago. My dreams seem more reachable, I know what I want (and what I don’t) also, I can pretty much drop everything and go live anywhere in the world that tickles my fancy at any given moment.

And I’ve earned the right to do so.

With regards to online income – I really struggle to think of anything more aligned to ultimate freedom. Being location independent whilst bringing in cash opens up doors that I could never have imagined if I stayed at home and took the usual route. I’ve crossed off most of my dream destinations in the last few years, grown in confidence, lived/travelled in just under 50 countries and as cheesy as it sounds – I got to know the real me.

This less than conventional life is what I always dreamed of, but it’s not for everyone and it’s often too romanticised, so I don’t want to feed the misconception that everything is always sunshine and rainbows when you take this path. I’m also not one of those lifestyle design bloggers who look down on anyone who has a stay at home career, a 9 to 5 job, or hasn’t been backpacking in their lives.

Do what you want, as long as it makes you happy and you’re not hurting anyone. Isn’t that what we all truly want after we drown out all the bullshit – happiness?

So I figured if I’m going to continue selling this lifestyle to people who are interested in it – it’s only fair that you get to know about all sides. Today I’m going to pinpoint the not-so-amazing parts of long term travel/lifestyle design, those that the lifestyle design bloggers tend to miss out. The type of truths that Instagram would try and implement a gagging order for if it knew what was coming.

Running Away From Your Problems

passive quote

I know. I know. I can already hear a thousand travel bloggers screaming; “I’m not running away from anything…I’m running towards something,” armed with an arsenal of Mark Twain quotes to throw in my face. Calm down, slip into the hippy pants that you purchased during your ‘spiritual experience’ watching Family Guy reruns in a cafe in Pai and hear me out…

I don’t think that everyone who chooses this life is a lost, hopeless soul running away from something, but they definitely do exist on the road. Even someone like myself who likes to look my demons in the eye and work out my issues can have the propensity to use this lifestyle as a distraction tool.

You can definitely shake off a lot of negative emotional shrapnel if you’re away from a toxic environment, which you needed to escape – but I’m afraid personal, deep-rooted issues can’t be eradicated by a change of geography and you can never run away from yourself. You can’t outrun the truth. It always catches up with you.

Be real. Write it out. Meditate. Read more. Hang out with people who lift you up and love you for the dickhead that you are and call you out respectfully. Work out what’s holding you back and make a conscious effort to fix it day by day and don’t be so hard on yourself. Every day you wake up really is a chance to start again.

Lack Of Focus (When Travelling Long Term)

Imagine trying to work in these conditions...
Imagine trying to work in these conditions…

Some of my friends who choose this life don’t seem to have this problem, but I believe they are an anomaly. Long term travel is a major distraction to your core goals and life focus. I’m already resigned to temporarily dropping two major projects at the moment, one which is just starting to bear fruits of success – because I’m about to go on a long trip with one of my best mates from back home. But I couldn’t resist as I am of the belief that happiness is better when shared.

My advice; if you want to work on building something online, it’s better to stay in one place for a while than to bounce around backpacking. Travelling long term takes up a lot more mental bandwidth than you think. It’s not all peace sign photos on the beach and beers at dawn.

It’s also trying to not get scammed and running around searching for a place to stay every day. This can get exhausting and you’re better off rewarding yourself with a trip after knuckling down and hustling for a while.

Romantic Relationships Are Harder

I’m not the one to be a Bridget Jones type and to feel like I can’t function if I’m single. It’s good to take a bit of time out alone and I also think dating is so FUN (if you don’t – you’re simply doing it wrong) but is there really anything better than being in a loving, nurturing relationship, where you grow together as a collective as well as an individual?

All good on paper, but speaking as a heterosexual man it’s a little harder to get right when you live like this. I don’t have the exact numbers, but I’m pretty sure that most people who choose this life are men. And men are hairy and ugly.

Couples who stay together in this lifestyle tend to want the same thing and share the same vision. It’s either that, or one person has to sacrifice a hefty chunk of happiness in order to be together. I’m not saying it’s impossible – but it’s certainly trickier.

Business Bipolar

emojo roller coaster

“I’ve made $X this month. I’ve arrived. I’m on my way! Knock out the champagne and let’s toast to the next level!!!”

Next month: “I’ve worked 60 hour weeks for a month and I haven’t made a penny. I’m an idiot to think this would ever work and I should just get a job like a normal person.”

Unless you’re a member of the upper echelons of lifestyle design like Tim Ferriss – the chances are you’re going to have to spend a hell of a lot of time (and financial investment) working on something that you have absolutely no idea you can make money from. It’s terrifying.

With sexy stories like “ditching the boss” to be your own, it’s hard not to be seduced into this lifestyle with open arms. But a monthly paycheck does offer a certain level of comfort and you kiss that goodbye when you go down this road.

Letting go of something you’ve spent countless hours/weeks/months/years on because it doesn’t work is heartbreaking – that’s if you do manage to detach from your ego, which doesn’t want to let you ‘fail.’ I echo the sentiments of the aforementioned Ferris if you want to have a crack at this life (and are in the privileged position to do so) – save up enough money to live in a cheaper country of your choice for six months and work your balls off on your idea. Make it your priority and make those months count.

As an added not-so-great bonus – sometimes friends and family don’t understand that you still have to actually work for your money. It’s not rare for someone to take things personally if you can’t meet up or drop things and chat at the last minute. ‘Self-employed’ seems to translate to ‘open all hours’ to some people but in reality it’s not the case. Switching off is also a nightmare and it negatively affects my sleeping patterns when working with people in different time zones.

You Trust Less

Last night I was sat around a table with fellow travellers talking about a conundrum that we face on the road; to trust, or not to trust. That seemingly polite guy giving you directions when you’re lost? Yeah, now he wants money and he’ll be pissed off if you don’t cough up.

You can’t even trust taxi drivers in most places and the tax that you pay for your western privilege is you’re a walking target for people to rip off. You become immune to bullshit on the road, grow tired of being constantly treated like a mug and you learn to spot a trick pretty fast after a lot of practice.

But what about those occasions when someone just wants to be amiable and connect with you on a human level? The truth is the road hardens you and as much as you want to give the benefit of the doubt – you probably shouldn’t.

It’s all about self-preservation and most importantly staying safe, but this permanent state of distrust isn’t always the best way to go about life and it doesn’t feel good to be default cynical all the time.

Getting a Good Cup Of Tea Becomes An Actual Life Goal

I’ve seen every crime against tea known to man. Milk in first. Teabag on the side. Lukewarm water. More milk than water. Lipton?! It’s enough to make a tea connoisseur weep.


Like I said, I didn’t want to sound whiny – I just wanted to throw out the ‘other side’ that isn’t really talked about a lot. This life isn’t for everyone, but for those who want it – the tough times are definitely worth it. When you have a few good months of business and you have that awakening moment of how lucky you are to be where you are and that you’ve completely redesigned your own reality – you’ll wonder what all the fuss was about.

Japan Friends

You can always try it out and go back to what you know if it doesn’t work for you.

Did I miss anything out?

Anthony Middleton

Former loser who took a risk. Visited over 100 countries. Trying my best to not get skinny-fat during Covid.


  1. Alex P on November 19, 2015 at 11:18 am

    Great article! Too many travellers and bloggers just post what my wife calls ‘instagram travel’. Just a momentary snapshot of life, carefully selected and filtered and edited to seem as pretty and attractive as possible.

    …as for being a couple that stays together – maybe we’re just lucky!

  2. Adam Brooks on November 20, 2015 at 3:25 pm

    This was a great read…. I feel your pain on the Tea situation!

  3. Algarve für Entdecker on February 13, 2016 at 12:40 pm

    Thanks for this great post! I was brought up in different countries abroad. And I loved it. But – other than traveling as a blogger – at that time my family and I stayed in one place for 3 to 4 years. And we had enough time to adapt to a different culture and to different people.
    Travel blogging in as sincere way means to get prepared for the journeys and destinations ahead – which gets harder, the older we get.
    Regards from Berlin, Germany! Alex

  4. Chris Vincent on February 16, 2016 at 6:10 am

    Soo…I felt like I had to post something after reading what you mentioned about “Couples who stay together in this lifestyle tend to want the same thing and share the same vision.” I couldn’t agree more about travel as a lifestyle. I had the opportunity to travel the world and funded myself doing contract web development type work several years ago. My wife owns a travel agency, which helps get trip costs low with discounts from hitting sales goals and the like – which makes it easy on us when we travel, now that we have kids. Anyway, I always enjoy reading your blog!

  5. Man Vs Clock on March 11, 2016 at 4:54 am

    Yep, travelling somehwhere is certainly very different to living somewhere. Very different beasts!

  6. Lucian on June 20, 2019 at 8:19 am

    Thank you for your sincerity! Regardless of the lifestyle we have, we will have advantages and disadvantages.

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Hi, I'm Anthony!

In November of 2010, I took on a mammoth challenge against the clock in a quest to upgrade my miserable life. I went out of my comfort zone and turned it all around. Ten years later, I’m completely location independent…

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