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Long-Term Travel, Career, and the Uncertain Path to Success

Posted By in Travel Musings | 38 comments

Long-Term Travel, Career, and the Uncertain Path to Success

If travel blogs have one overarching message, my own included, it’s something like: Cast off your doubts, go traveling, and let the consequences be damned. The part that these inspirational messages tend to leave out is that quitting my job to travel long-term was, and still is, downright terrifying.

At the airport - ready to leave Canada

At the airport – ready to leave Canada

It’s true that the most challenging part, by far, was mustering the courage to leave Canada in the first place. But 2 years later, the doubts that once governed most of my decisions still slither up to the surface and demand attention. They rise up after skype conversations with friends who finally got the promotion they wanted, or saved to start their own business after putting in time at unpleasant jobs for the last few years. They struggled, and then they succeeded. Those are the moments when everything about my life: The serial expat lifestyle, the freedom to travel regularly, the minimal working hours, the easy job – it all feels like cheating.

The fears take hold partly because I know that my lifestyle is temporary. I like teaching English, but not enough to turn it into a long-term career. I have no intention of using my degree and revisiting my pre-traveling career path. So then, what will I be doing next year and the year after that?  It’s easy to romanticize living moment by moment but, for me, it also means not building towards a future.

For the past year, Brent and I have talked about moving back to Canada someday to open a Bed & Breakfast. It’s an idea that perfectly melds our different talents, and would allow us to keep travel and tourism in our lives, while having a more permanent home base.

But the thing is, I don’t want to move home and work at a menial job in order to save up for this dream. Do I really have to be unhappy for a few years if I ever want to be as successful as my peers? I believe that hard work is necessary for success, but are struggling and delaying my dreams also required?

travel, careers, uncertain success

Does there have to be a trade-off between money and freedom? It’s certainly a topic that many people have pondered before me, but I have yet to meet anyone who knows the answer.

I feel like there should be some way for us to continue traveling for as long as we want, and then to fluidly transition into a more stable lifestyle in Canada that excites us equally as much as this one does. I want every year to be as good or better than the one before it.

If someone else explained this same dilemma to me, I’d be the first person to tell them that there are countless ways to save money while still continuing to travel. It’s true, but that in itself is part of my problem. There are too many choices, and I don’t know which one is right for me. Should I focus on monetizing this blog? Or maybe on freelance writing? Or teaching extra classes via Skype? Or learning a digital nomad-esque skill like graphic design? These options all seem doable, but none of them fill me genuine enthusiasm. I don’t feel more drawn to one over the others.

But eventually you just have to make a choice and stick with it, right? I’ve met people who chose a job, a career, a life, not because they felt passionate about it, but simply because they thought it was time to choose. They had reached a certain pivotal age, so they sucked it up and applied for medical school, or went after the entry-level sales job because it was the sensible thing to do. There’s no joy, but just a sense that they did what they thought had to be done.

But what if I don’t want to suck it up and settle for a career that seems just alright? What if I want to hold out for something truly fulfilling? Does that make me an admirable idealist or is it an excuse to be plain old lazy and undisciplined?

Should I follow this feeling, and wait for an opportunity to come along that feels right? But, how long am I willing to wait for that? Or maybe should I push myself to make the tough decisions. Because that too would only be temporary, right? I would only have to work in that boring job until we could save up to start the B&B. Yet, I don’t know if I’m willing to endure those dark years – those years when I would suffer through the present and live for a vision of the future.

travel, careers, uncertain success

So I hold on to the fact that in midst of all I don’t know, I do know that I love traveling. And I love sharing it with people, whether it’s through blogging, stories, photos, or hosting other travelers and providing local tourism tips. I have my doubts at times, but I never regret following my instinct to travel. Even when my confidence waivers, I still want to believe that if I just keep doing what I love, then the rest will fall into place…..eventually…..


I want your advice! How did travel influence your career? Do you have any regrets?


  1. Gary Yeates August 7, 2013

    Lovely sentiments but one of the (few) advantages of getting on in years is when you are retired you don't have to worry about quitting jobs. Welcome to http://www.thegreyglobe.com

    • waysofwanderers August 7, 2013

      Very true. But, at the risk of sounding morbid, what if I were to work for all those years and then die at 50? Then I'd never get to enjoy the freedom of my retirement. There's no guarantees about the future, which is why I don't like the idea of wasting away my youth building for it.

  2. Jessica Wray August 7, 2013

    Oh boy, do I know what you mean. Being at home, with nothing to keep me busy I can't stop thinking about all of this. Travel is the only natural thing I know how to do, but sometimes it almost feels like a burden I carry around. I love my home so much, but I know I wouldn't be totally completely satisfied starting the cubicle job hunt tomorrow.

    I want to choose more ways to make more money as well! When it comes to blogging and monetizing I feel so overwhelmed. It seems so hard! I also have all these ideas, but choosing one is impossible!

    Maybe we are all just terrified of having regrets. I think that is better than never trying anything at all though, right? At least we are trying to live the best life we can!
    My recent post Backpacking Southeast Asia, As Told By Memes

    • waysofwanderers August 7, 2013

      Glad to know I'm not alone! You're right though, we're all just trying to live the best life we can – that counts for something, right?

  3. OCDemon August 7, 2013

    This is one of the things that bothers me about the atmosphere around travel blogs; not necessarily the blogs themselves, but the attitude that is sometimes present among the writers and readers, which is to cast off whatever shackles are holding you back from living your dreams and just do it. As if it's just that simple. You see inspirational quotes set against backdrops, telling you to live your dreams, but anyone who's ever managed to live their dreams probably had startup capital to make it happen. They don't seem to discuss that step in the quotation-based viral photography. "Accrue investment capital! Spend years constructing a successful business! Live your dreams!"

    I've noticed friends and family will alternate between saying you should do what you want, or do something you hate for a while in order to get there. But whichever one of those two things I'm doing at any given time, they'll tell me to do the other one. If I'm doing something I don't enjoy, they tell me I'm doing things wrong. If I'm doing something I enjoy, they'll ask me when I'm going to get serious about work or whatever. Not too many people out there understand the drive toward financial independence for the sake of a long-term or frequent travel lifestyle, so they just end up naysaying whatever is happening. It's very odd.

    It's gotten to the point where there's really no reason to tell them what's going on until after it's successful, at which point they simply won't complain anymore. So I can't say I have any particular advice for which path to choose in your particular case, but just to know that if people are giving you dumb or contradictory advice, there's not much reason to let it get to you. And, at the other end of the spectrum, "living your dreams" often requires meticulous planning and effort, not just a head-in-the-clouds daydreaming session. So don't feel bad about serious analysis when you're supposed to be dreaming.
    My recent post 10 cool cities in Russia besides the big two

    • waysofwanderers August 8, 2013

      Well said. I do think the inspirational messages are important because it definitely is possible to create excuses, and stand in your own way when it comes to accomplishment; but, it seems like the people who are truly successful use positive thinking in combination with real practical effort. It's easy for outsiders to throw in their opinion about your choices, but at the end of day, you just have to go with your gut, and do what feels right for you.

  4. Andrea August 7, 2013

    I'm on the cusp of big life changes, so I know what you're talking about! I hope that freedom and money don't have to be mutually exclusive. That's what I'M working towards! Doing what I love for a living and having the means to travel (sort of) whenever I feel like it. I think it's possible, I just think you have to get creative with it!

    • waysofwanderers August 8, 2013

      Agreed! My education made me really good at following the rules, but didn't really help me build and flex my creativity muscles. It's definitely something I'm working towards too because I think that being innovative is the first step towards financial stability as well as freedom. If you figure it out, let me know! 🙂

  5. Delia @ World in Words August 7, 2013

    I too quit my job to travel but realised early on that travel is not enough alone… I need projects, ambitions, a future – which I’m now trying to work on, while travelling. If there’s one thing travel does do it’s give you the time to think about what to do next without all the pressure and outgoings of normal life when it is so hard to take risks. And that’s so liberating.

    • waysofwanderers August 8, 2013

      Totally! Traveling gave me the space and perspective to realize that my former career in Canada wasn't right for me. I don't think I could have ever realized that until I had some separation from it. I don't know what I want to do instead yet, but I'm closer to figuring it out than I was before.

  6. Dale Davies August 7, 2013

    On the build up to leaving my job I didn't have a doubt in the world. I was clinically depressed and annoyed at the state of my life and the direction it was heading.

    It's only now after a year of travel that I'm experiencing some kind of doubt and it's almost the same as yours: What happens after travel?

    Sure, there are the lucky few that might make travel blogging their full-time job, but the the majority it's just not realistic.

    For me personally I'm already starting to sketch a path for where our future lies and it may not be easy when it happens, but I know we'll be happy.
    My recent post The Ease and Pain of the Thai-Laos Border Crossing

    • waysofwanderers August 8, 2013

      "What happens after travel" – it's the question I'm trying most to avoid, and the one that all of my friends and family keep asking me and reminding me of! But it sounds like you guys are headed in the right direction :).

  7. Jessica August 8, 2013

    Great post! Thank you. My husband and I have been traveling for 7 months and one of the best lessons out of all of it was simply the learning around taking the step to quit the jobs and leave. We wrestle with the problem of having too many options all the time, and those are the moments where we really consider what's important to us and what kind of lives we want to lead. But it does push your boundaries and take you out of the sometimes easy answer of having that secure job and lifestyle. A lot of times the difficulty of making those travel choices makes going home and setting up shop enticing, but I have to remember that I've never been happier, even when faced with the tough choices and difficult financial circumstances.

    Thanks for your post.

    • waysofwanderers August 8, 2013

      I'm so happy you enjoyed it! Travel certainly does have this way of showing you what is truly important. I think we have a pretty good idea of what kind of life we want to lead – how to create it is still a bit of a mystery, but it's nice to at least have that clear vision to work towards.

  8. Anna August 8, 2013

    What a great post! I often fantasise about giving it all up and doing exactly the same as you, but not sure I'll ever have the guts. I went on my first o/s trip in 2009, Bali, ten days and have been addicted to travel ever since. However, prior to this experience, we had already made our way in to the property market. Since then, we have gone against the norm of getting married, then having kids to enable our dream of having a solid financial future (hopefully!) with our furry children (two little staffies) and a vege garden! But, now, a few years on, I wonder at what cost has this come, because essentially we are in debt to our employers! It's unfortunate that we when we ask for any more than three weeks off at a time (we travel abroad once a year), it's like asking for a paid full time personal assistant! Yet, so many of us are in the same boat. All I can say, is thankyou! Thanks for having the guts to do it. To quit your job and life as you know it to go on an epic adventure. And, what happens after travel? I'm not sure, but I don't think you will ever look back and have regrets on the experiences you've encountered and become so much richer for it. I absolutely admire you and everyone else who has taken that leap into the unknown. Perhaps one day, we'll make it too!
    My recent post Asian toilets: My first exposure away from the hotel…

    • waysofwanderers August 8, 2013

      Thanks, Anna! I guess we just all want to have everything. Like you, a lot of my friends at home admire our travels, but I look at them (and you!) and envy knowing where your money will be coming from for the next 1 year, and being able to have dinner with friends and family. Whatever happens, though, I can't imagine looking back and regretting the decision to travel. I'm not sure how it's all going to turn out, but I'm think I'll still be glad that we did this.

  9. Jennifer August 8, 2013

    I was very lucky that when we moved to Italy for my husband’s job, I was able to present my employer with a trial of me working location independent. It was accepted and here I am more than 4 years later still working for my employer.

    I think a lot more companies are open to remote workers these days and there are a lot more jobs that can be location independent than people think.

    Hang in there! You’ll figure out a way that works and works toward making your dreams come true.

    • waysofwanderers August 9, 2013

      Very true, Jennifer. I'm always amazed at the range of jobs that can be done remotely. I actually had a short location independent assignment from my former employer when we first left. I knew up front it was going to last for under a year – but it was nice while it lasted. If it can happen once, it can happen again, right?

  10. Emily August 9, 2013

    I think one of the best things to do for yourself (career-wise) while traveling is to constantly hone in marketable and "special" skills – those that will make you a unique job applicant or build you a freelancing niche in the future – this could be graphic design, as you mentioned above, the ability to write well and attract an audience (which you are doing here on the blog), or many other things (such as language skills, web development, etc). This article is incredibly appropriate: http://www.photoshereandthere.com/how-traveling-t
    My recent post Rajasthan “Land of Kings”

    • waysofwanderers August 10, 2013

      That's a good point. Traveling definitely helps you gain new skills and experiences (particularly if you work at it), and that can be career assets. I'm not sure how all of my new skills come together at this point, but I'm sure I'll figure it out!

  11. @TammyOnTheMove August 12, 2013

    Wonderful post Jess. I can really relate to what you have written. I have left London two years ago as well, and people back home keep asking us if we are coming back and when. I am not ready to go back yet. I couldn't imagine living the same 9-5 routine back in the UK. I don't mind doing the 9-5 routine abroad, as I am experiencing a different culture and a new country. I think you shouldn't put pressure on yourself. As long as you don't hate your teaching job and as long as it allows you to experience so many amazing countries, just keep on doing it. When you get fed up with it, just move on. Your gut feeling will tell you what's right for you.
    My recent post The ups and downs of work field trips to rural Cambodia

    • waysofwanderers August 16, 2013

      That's generally my attitude too – just keep doing it as long as it's enjoyable. It makes sense. Sometimes though, it's unnerving to talk to people who have long-term plans for success – it makes me doubt myself, and wonder if we should be thinking about our future too, instead of only focusing on immediate happiness.

  12. Alisha August 20, 2013

    great article! thanks!
    I made the same experience, a lot falls into place if you wait a while, especially when travelling, a lot of good stuff just comes along. still, there is some stuff you have to give up for travelling- especially a stable job and a own home.

    and for me, it was really hard to come home again- nobody warned me of that, but later I heard that a lot of people have problems at that point. I had changed and people expected me to be just the same as I left. and after long-time travelling, you have to start fresh- find a new job and a new home.

    but I guess it is no real harm done to set back your career for a while. there are still a lot of years to work…
    and right, people always say they envy it and make you feel guilty about having so much holidays, but most of them wouldn´t really wanna travel long time.

    • waysofwanderers August 20, 2013

      The idea of going home definitely freaks me out. It's like traveling is its own kind of success, but if I were to move home, I'd be measured on the same success scale as all my friends again – which I think would make me feel pretty behind. At the same time, we wouldn't just be returning to our old life; hopefully we'd be creating something new and better, and one that incorporates our experiences traveling.

  13. ferretingoutthefun August 21, 2013

    Have you thought about finding a job managing someone else's B&B for a while? This could help you save up some cash AND give you real-world experience for eventually setting up your own. We stayed at a lovely B&B in Budapest and chatted with the owner. He was just training someone to run the place so he and his wife didn't have to be there all the time. If you have to work, you might as well try to gain useful skills and knowledge that will help you with your own goals down the road.

    My recent post The Best Meals We Ate in Budapest

    • waysofwanderers August 21, 2013

      We've actually been looking into that! Although I haven't been able to find a reliable website that connects B&B owners and potential new managers. If you hear of anything, definitely let me know!

  14. vegetatingearth August 22, 2013

    This is an excellent article that articulates some of the things that worry me (just a little bit) about long term travel. I know that my career isn't what I want to do forever, and I know that traveling has been a dream for as long as I can remember, but I still worry about the "after" part. I just have to have faith that things will fall into place (as they always seem to, whether I worry or not!).
    Good luck!

    • waysofwanderers August 23, 2013

      Thanks! I guess you just have to trust that you're resourceful to land on your feet during the "after" part. Some days I believe in myself more than others.

  15. Katie August 24, 2013

    Wow, this is a great post. Hilarious that I even came across this because I was sitting here thinking about the exact same type of thing. Settling and doing what's "right" versus going for it but risking not saving for my future. Awesome. Glad to know I'm not the only one.

  16. solowayfarer September 4, 2013

    Great article Jess! I have just made the leap myself – from a full on career which wasn't right for me, to quitting and preparing for some solo travelling in the very near future. I don't know how long I'll be heading out for (depends on whether I like it I suppose) but I am quite cognisant of the fact that I will in all likelihood have to do something after my travelling, and I am therefore trying to develop some alternative skills. The travelling part will be important though, as the time away will at least give me the opportunity to reflect and think about what it is I DO want to do (no real idea at the moment!). Best of luck to you, and look forward to following your travels. 🙂
    My recent post My 5 Week New Zealand Itinerary

    • waysofwanderers September 4, 2013

      Good for you! As terrified as I am sometimes, I think going out into the unknown and trying to figure out what is right for you is still 100X better than playing it safe and sticking with something you know you hate. I'll be sure to follow along with your trip too.

  17. Must For Wanderlust September 4, 2013

    To be honest I don't exactly have a career in mind & I'm not too worried about it either… I'm going to travel until I feel the need to settle down (if I ever do) & if I don't feel the need to… I won't. Simple as that. I won't be worrying about my career as long as I am happy. Our society is so wound up with labels it seems, I kind of shun even the title of 'career.' Just my ramblings! Great post. x
    My recent post Views from Up Top: Eiffel Tower Edition

    • waysofwanderers September 4, 2013

      Awesome! I totally agree – I just wish I could feel equally as confident about it :).

  18. Rhonda January 10, 2014

    Hi Jessica… I just found your site from Steph at Twenty Years Hence. This post so struck home with me. I am older than you, but still struggle with the same problems. After my husband & I our 14mth backpacking RTW in 2007-2008 we knew we absolutely wanted a different life than we had previously. But, in debt, we went back to an almost identical life, buying a house in the same area and with me back at my previous job! We are now planning to become nomadic long term, driving the Pan Am highway, etc but the questions always remain. We absolutely know that, at least short term, our goal is to visit our last undiscovered continent and hopefully make enough $$ blogging, writing, selling photos, doing web design, etc to keep our travels going… but we know at some point even this dream will become staid and we'll want to run a travelers inn in Mexico or Central america or do settle down somewhat and, that takes capital. Capital we most likely won't have. But do we want to return to the cubicle and jobs we don't love to make it happen? It's a quandry for sure, and at this point we are just focusing on more short term goals, trusting the universe to provide the answers somewhere down the road! Good luck in your own quest!
    My recent post Foto Friday

  19. Tom March 11, 2014

    If you can't tell what's more right thing to do, you surely can tell what's worse for you and that's the answer from your true inner-self. You've actually given yourself an answer and your intuition gave it to you. I was totally rational my whole life untill I said: enough, I'm not trully happy with this – I don't regret this time because it gave me some skills and.. courage to leave it all behind – just like you. My close friend's chosen the second way: invest now, have short but frequent journeys and calm future – he's not fully happy with it, just like we are not with our decision, because every decision, even that made out of heart, has its disadvantages in real life.

    No matter how worried we are, as we ACCEPT our decisions, we'll be happy no matter what's gonna happen later. As it's been said here many times in comments: your journey is the path to the solution – it shows you what you like, what you don't – this is the process of finding yourself. Keep thinking of it, but not worrying, as long as you feel you're on your way.

    Whoa, as an ex-rational guy, I didn't know I could write like this 🙂

    P.S. Thank you for writing this blog. Love it.

    • waysofwanderers March 11, 2014

      Thanks for sharing your perspective, Tom. I think the only thing any of us can do is continuously gut check, because on some level, our intuition will always let us know if we're making the right choices.

  20. Megan July 7, 2014

    I'm in the beginning stages of planning a year-long backpacking/HelpX-ing trip with my boyfriend and I'm now starting to entertain the idea of traveling indefinitely, and I'm already having these thoughts! Our plan was for us to work for a couple of years then I would go back to my school for a PhD in Clinical Psych and for him to get his Master's in Accountancy and sit for the CPA to be an accountant. But now I'm not so sure, and even if we were to travel for say 5 years and then move back to the states, how do we pick up with our lives? Relationships with former professors may be too old to jump right in to grad school. And would I even want to go back? What about getting my PhD abroad and all those challenges? I honestly just don't know how to feel about it all. I'm pulled in so many directions right now. Thankfully your blog has been helping me with a lot of my other concerns and questions.

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