Packing In A Career For Long Term Travel – Ups, Downs & Observations

Long Term Travel - Isle of Skye
Amazing Experiences in Skye – Scotland

I have been asked the question fairly frequently on my travels: What exactly is it like to quit a career to travel the world long term? In the opening acts of my journey I would have responded with something akin to: ‘I guess it must feel a bit like it does when you retire’ and after slapping the asker on the back I’d probably yell for another beer… However as time has drifted by and I have emerged from the initial honeymoon stages of the journey I might respond with the more accurate and thoughtful answer of: ‘It’s both amazing and exciting, yet not without its trials’.

The reality of long term travel is quite different from the ‘honeymoon period’ we enjoy in the opening stages of a long trip; and so it follows that a big difference between long term travel and a short vacation is simply the fact that vacationers never emerge from this ‘last day of school’ honeymoon period; their journeys are simply just too short. On the other hand  the long term traveller inevitably breaks through this invisible barrier, emerging into unfamiliar and unexpected territory.

So what happens when this brief period wears off? Well the realities of long term travel sink in, the tiring reality of constantly moving, the expenses, occasional boredom, disputes between travel companions etc.. all realities of long term travel that holiday makers fail to experience on any real level (except maybe expenses.. depending on where you go/stay/do).

These more negative experiences mingle with the positive new experiences we all enjoy while abroad and long term travel becomes a realistic mix of great, frustrating, amazing, annoying and ultimately memorable experiences.

I’m certainly not saying that it sucks, far from it, it’s an amazing, wonderful, enlightening and character building experience that I believe should be as much a part of our education as high school, yet it’s naive to imagine there won’t be trials and tribulations along the way, things that are rarely considered from the outside.

I had an interesting conversation with a wealthy property owner I know before I left home, we spoke about my upcoming trip and she kept stressing how lucky I was, and how she regretted never doing the same before she became tied down with ‘life’. I was left with the distinct impression that given her time again she may perhaps have made different choices. Happily for me, this chat reinforced my decision to leave (or perhaps just pause) my career; and helped to lay to rest the last fears I had that I was making a mistake in leaving my home, a job, a career and forgoing a whole bunch of money to go vagabonding.

So what’s it like being a homeless nomad after quitting a well-paid career to travel the world?

Well, there are ups and downs just like back at home, good times, bad times, exciting times and boring times, there are moments of wonder and moments of regret. I get worried, tired and stressed but there are also fantastic rewards, amazing sites, places and experiences and there always seems to be another city to explore, just around the corner..

The Best Bits of Long Term Travel (condensed into just 2 points)

Long Term Travel - Isle of Skye
More Incredible Memories in Skye – Scotland

Amazing New Sites & Experiences – I have seen some truly amazing things and have had some unbelievable new experiences. Hiking through Death Valley, snow camping in Yosemite, walking on cracked sheet ice in Canada, leaping canals in Venice, hiking across the Isle of Skye in Scotland and partying my way all across Europe and that’s literally just the tip of the iceberg, I could go on and on about the amazing things I have seen and done in the last 9 months.

Amazing People – People make these experiences infinitely more meaningful, some of the best moments have been shared experiences, catching up with old friends, forging new memories with temporary travel companions or making new friends along the way. It’s the people that make the experiences and sites the more personal and the more memorable.

The worst bits of Long Term Travel (not to say that they’re not valuable, just unpleasant)

Travel days – 18 hours sitting next to Charles Manson on a Greyhound in America wasn’t exactly a highlight, nor are airport security lines, neck cramps, Salmonella poisoning, getting lost on the subway, arriving in a new city at 3:30am with nowhere to go or dragging a pack 5km’s across a city after tearing some intercostal muscles… yep actual travel days are never the most pleasant of times. Yet they are a part of the experience that I think make the rewarding parts more valuable and let’s be honest, keep things somewhat more interesting too..

Travel is tiring – There are some days, I’m so tired from walking, sites, trains, busses and people that I feel like I almost need a holiday.. then I remember where I am…

Boredom & Monotony – As a long term traveller you can’t just go around ‘site seeing’ all the time, it does get old and occasionally awesome places like for example the house that Guy Fawkes was born in become: ‘that stupid bar where I kept banging my head on all the doors because people were just smaller back then..’. The forest can occasionally get lost.. behind the trees.

Homesickness – There’s also the inevitable homesickness that occasionally rears its melancholy head (often along with a hangover). Usually the pangs happen when you’re sick or tired or generally just uncomfortable somewhere far from your comfort zone. The last time I was going to Dubai as the final stop in a larger trip, I was so eager to get home, I almost didn’t enjoy the city at all.

General Observations about Long Term Travel

Time Travel – Time changes while abroad long term, it slows down and doesn’t seem to slip through your fingers as easily. A constant sense of novelty actually slows your perspective of time while at home, work seems to fast forward your life, it’s actually very strange.

Rat Race Stress – Occasionally I think about home and ponder that somehow I’m being ‘left behind’, that everyone I know will be miles ‘ahead’ of me when I finally return. A ridiculous notion I know, and some clear headed thinking cuts through this mirage as does reading some Seneca, which I do occasionally when I find myself in this mindset.

Long Term Travel - Isle of Skye
Long term travel is a character building experience

Inner Space – I have more time to contemplate things while abroad, life, myself, the world around me; I observe people and places everywhere I go and reflect on everything from religion to consciousness a world away from my home. You have more time to really think while you travel, mingled with new experiences, it’s a potent mix for new ideas and philosophies.

Size Matters – I have found that the world is actually a very small place; countries are separated by invisible lines, cultures and history may change but people are people everywhere I go.  We all want the same things, for the most part.. a notion that challenges many social boundaries.

Environmental Concerns – A distressing part of travel is to see the disturbing ways that people treat the environment all over the world. Occasionally I observe people to be more like a virus than intelligent, sentient beings and sometimes try to imagine how much better off our world would be without us. It’s unpleasant and disturbing to see how many other cultures treat our planet like it’s someone else’s problem..

Gratitude – Long Term Travel helps put your life and your home into perspective on a world stage. It is a wonderful experience in that it reminds us each to be grateful for the opportunities and people we have in our lives, both at home and abroad.

Enlightening – It’s a travel cliché yet it’s quite true that travel broadens the mind. It’s a perspective shifting, enlightening experience that I believe does make you a better, more functional and worldly person. Are you going to come home as a wise Gandulf type character and use words like ‘ thought experiment’ instead of just ‘thinking’? No, but you might notice the difference in a more subtle way. Here’s a petty example; before I left home, I had tried maybe 4 or 5 different types of German beer, now having spent weeks in Germany, maybe 40 or 50 is more accurate.

Expectations are a trap – Expectations are funny things that so often overshadow reality in such a way as to make it disappointing. I have learnt that in my travels, expectations are forms of closed mindedness and thus should be ignored in favour of an open mind and simple curiosity.

Travelling is a skill – You learn to travel better as you go. You’ll make mistakes early on in a trip, fall for a scam, spend too big early on or something similar, yet these ‘mistakes’ are part of the ride. Ensure you learn from them and recount them not as regrets but as a valuable part of the experience and you will become a better traveller.

In Conclusion

The paradox of travel is: the more you travel the more you realise how much of the world you have yet to see and so, the more you must travel…

Like having the wisdom to understand you are not wise..  (a library is all about the books you haven’t read, not the ones you have), travel appears to me, to be an unending journey; there’s always another city to explore, friend to meet and new experience just around the corner. By visiting one city you must miss another, is this frustrating or does it open many new possibilities? The correct answer is both.

Packing it all in and leaving a career to travel the world long term is one of the best things I have ever done (and plan on continuing to do throughout my life). I plan to continue living a life in which curiosity is paramount and exploration itself is a reason enough to explore, and what better way to live this philosophy than through world travel.

Quitting a career to travel the world long term has been a rewarding and eye opening experience where the downs have been just as important as the ups and the journey itself is as valuable as the destination. Has it been hard, frustrating, trying and tiring? Absolutely, and yet do I regret anything? Only not doing it sooner.

About Author


Hi, I'm Pete, an ex-cubical slave and corporate love monkey currently writing my way around the world. My background is in branding, digital marketing, media and I'm probably about a level 10 at moustaches.


  1. Marc

    Very nice write up. As someone who spent 18mths travelling as I turned 30 you cover off the pro’s and cons very well – the travel, generally via the cheapest slowest mode of transport going (hey, you’ve definitely got the time) definitely sticks in your mind for years to come, and despite the discomfort at the time is not something you would trade off against anything else (that being said 48hrs of straight bus trips from Manali in Himachal Pradesh in Nth India down to Mumbai to catch a flight is not something I would recommend). Your general observations and conclusion also mirror my own thoughts from my own travels. Wish you the very best of time going forward and am only slightly envious that I’m not still out there

    1. Thanks Marc, your trip sounds amazing, have yet to get to India actually but i’m looking forward to it.. and that bus ride doe snot sounds like much fun.. but still, like you said, they’re the things you look back on and remember. Great to hear from a like-minded traveller.

  2. Haha just found ur site through and noticed you are only a few days ahead of my own travels. I also quit my job and packed up to travel indefinitely (well at least for 365 days but prob more at this point).

    I am doing a photo a day project while I travel which you may find interesting:

    You are sooo correct about needing a holiday from your holiday. I have been going for 4 months now and cannot wait to get to the greek islands to lay about for a few days and have a break from moving about.

    Maybe I will bump into you somewhere in the world!

    Cheers, chris

    1. Nice one mate! The site’s fantastic, some really great images! I’ve been tossing up the photo a day thing but I think i’m just too unorganized to keep it up.. haha Stay in touch and let me know how ya go, maybe we can have a drink somewhere awesome!

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