5 Things to Know First Before You Quit Your Job and Travel the World

by Travel & Adventure, Working Remotely59 comments

You all know by now how I am one of those people who quit the 9-to-5 grind in exchange for a life of travel… (Quit your job)

Now please don’t get me wrong, and please don’t start thinking that I’m dissing those who are still working as employees or whatnot, because I DON’T think that at all. I wholly understand the fact that some people are perfectly happy with their office job since it is their passion in life — but unfortunately, such wasn’t the case for me. It turned out to be the kind of career that didn’t fit me, and I even realized that it wasn’t my passion at all.

So when I was 21, I did leave my corporate job to go after my real passion in life: traveling the world while working remotely instead for myself.

I’m 23 now as of this year (2015), which means that it has already been two years that I’ve been leading this nomadic life. Since then, I’ve flown around the French Alps as a paraglider, played around with elephants in Thailand, enjoyed my first winter in Europe, and so much more! The icing to the cake: I have even managed to set up an online business during my travels in order to live a more sustainable traveling lifestyle from here on out.

It has really been a ‘dream come true’ situation for me and I’m immensely thankful that all those months of hard work have paid off, and that all those risky steps I took were worth it!

True enough, creating this way of living can be truly amazing and for those of you who have the SAME aspiration, I bet that you have also been inspired by the stories of other people who have done the same thing as me! (Somehow, this ‘quit your job’ thing is turning into some sort of trend haha.)


Before you start following MY advice as well as other people’s helpful tips, guides, and hacks to starting a travel lifestyle, there are actually some very important things that you should consider FIRST before deciding to take the BIG leap!

You see, I am a big ‘advocate’ of making informed decisions so hopefully this article would cover that aspect perfectly especially since this will be such a big life change for you… (Actually, I have already discussed this topic briefly in my ‘How to Start a Life of Travel‘ article, but for this post, I will expound on it a lot more by grouping them into 5 points.)

So first up, you should…


Know if this is really the kind of life that you want. ASSESS yourself and your situation carefully.

Quit Your Job

Ask yourself these vital questions: “What exactly am I looking for? What makes me happy? Do I really love to travel? Is this my real passion? Is this what I really want?” 

Take time to think about this as I cannot stress this enough! Going by experience and going by the stories that I’ve encountered, it’s absolutely important that you rethink this over (and over and over again…) since you HAVE to make sure that a traveling lifestyle is what you truly want or are passionate about.

Don’t you ever quit your job to travel the world as a way of ‘escaping’. Don’t you ever do this for someone else nor for appearances. Don’t you ever let the allure of this ‘seemingly’ glamorous lifestyle blind you into thinking that it’s your real ambition when… it could be not.

You see, it’s quite common for some people to think of this ‘quit your job to travel‘ thing when they are extremely stressed, and the desire burns even more when they start to see and hear the stories of people who are traveling the world for a living. It’s a GOOD thing for sure, but it’s important to NOT let this sway you too quickly… because the basic truth could be that what you might actually just need is a different kind of job, field, boss, or company!

Therefore, before you decide to flip your life around, experiment first so that you can see what fits you best. You can do this by doing the two actions below:

  1. Try a different area of work. Think about your interests and the things that you enjoy. Let’s say you are currently working in finance but have always been interested in marketing or the arts. As you start to get burned out by your work, consider the idea of transferring to another department. (The same goes if in case you aren’t happy with your team, your boss, or your company: go and switch!)
    RESULT: NEGATIVE –  If you persist to think that the cubicle life really doesn’t suit you at all no matter the different transitions that you’ve tried, then it’s clearly time to move to the #2 step below…
    RESULT: POSITIVE – If you end up being happy in the new job or position that you’re in, then that’s GREAT! There’s really no need for you to quit your job in order to do a travel lifestyle — though… if you remain to be curious, apart from scrutinizing the kind of life that we ‘nomads’ have, you can also try and do the #2 experimental step below to see if it’s something that you’d still want to do…
  2. Do some trips locally and/or internationally; better if you can arrange it in a way that it’s a longer trip than normal! I say this because it can help a LOT in making you see the kind of life that long-term travel can bring: you could discover that you really don’t like traveling at all, or that you hate continuous traveling in general (the whole repetitive cycle of packing and unpacking, the reality of having a non-permanent address, etc. etc.)
    RESULT: NEGATIVE – If you realize that a life of travel AND a corporate job is NOT for you, then it’s time for you to examine your other choices. Maybe starting your own business in your home country is where your passion lies? The possibilities for this are endless really; but at this point, I would have to leave it up to you in researching what else you might want to do with your life as this is something that you have to figure out for yourself…
    RESULT: POSITIVE – If, however, you have truly analyzed and felt that a travel lifestyle is STILL what you really want — no matter the small inconveniences it may bring — then by all means, go ahead and want it BAD, and then start focusing on how you can quit your job. (On the other hand, if you like traveling BUT you don’t want to quit your job at all, please don’t fret! There are ways to keep your career while still enjoying the ‘gifts’ of travel. For instance, some people have succeeded in requesting from their company the possibility to work remotely, while others have been able to arrange extremely long holidays — there are lots of ways and you just need to explore the options that you can do!)

Manage your expectations. Know the REALITY of a traveling lifestyle.

Traveling Lifestyle Reality

Though a traveling nomad’s life is exciting and fulfilling, it’s NOT as glamorous as most of you would think because the start can be really arduous and tricky! (It’s not like everyone instantly goes to 5-star hotels once they become a traveling nomad — even if they do, the adventures, experiences, and stories are the real golden treasures that NO money or 5-star whatever will ever compare.)

That’s why as early as now, I highly recommend that you lower down any expectations that might be overly-romanticized.

To name a few of the top ‘realities’ that you will experience and that you should know of:

  • It’s not always full of traveling, because you still have to work too! Unless you have a huge savings account that would let you travel for years, you have to find a profession that you would earn from while you are on the road. When I started, I chose to be a digital nomad and that took me months in order to develop myself as a ‘professional’ — looking back, a good half of my 1st year was dedicated to working. Therefore, it’s safe to say that not everyone starts having the liberty of working only 4 hours a week (or even less) while traveling! In fact, it took me more than a year before I managed to create a business that would enable me to live like that. So remember: you really HAVE to work VERY hard at first or maybe even for a longer time until you manage to stabilize everything (more so when you opt to do volunteering work… but at least, you will be doing it in a beach for example, so it still works right? *wink*)


  • It can get lonely and solitary. Especially if you’re traveling alone, no matter the number of people that you meet on the road, there will still be those times that you will get vulnerable emotionally — you will start to miss your friends and family, and you might even start to feel depressed. Regrettably, you need to deal with these feelings alone; add the fact that whenever bad things happen (e.g. getting sick, etc.) you also have to tide these over by yourself. This is why I often advice you guys to not only practice being independent, but to also deal with your problems FIRST before setting out to travel the world. Why? Because every issue that you have will be some sort of ‘baggage’ that you will carry around with you as you go. (OTHERWISE, you can always try to find a travel partner that you can get along with for this journey! As for the ‘missing your loved ones’ part, it’s something that I wouldn’t worry about too much because it’s something that technology can fix — I haven’t been back to the Philippines nor to my family for a while now but so far, the internet really does wonders for me in bridging the ‘gap’.)
  • It can get frustrating to be constantly on the move. Apart from the thrill and the excitement of seeing and staying in new places, there are those moments when you would wish that you have a permanent home or address to stay in… When I started, I had to change my residence a LOT of times and there was certainly a point where I got sick of packing and unpacking all the time! (In case you’re more of the backpacker type, there is that fact too that you might start to miss certain luxuries particularly when you spend most of your time in hostels etc.). To counter these scenarios, you can always decide on setting up a home base for a longer time or you can plan on saving up more money in order for you to splurge on luxury stays every once in a while. For more ideas on answering your accommodation woes, check out this article below:
  • .

  • There will be ups and downs, but sometimes, more on the ‘down’. Locals might not be too friendly to you, money might start to be an issue, your flights could get delayed or canceled, and a whole lot more of regrettable scenarios can happen! But then again, this doesn’t come with traveling only because much like life, sh*t just really happens… And when it does, you need to learn as early as now to NOT let it hit you too hard. I’ve had my brand new laptop stolen once while I was on a road trip in France and it really made me sad in a way that I never imagined that I would! But then the good thing about these bad experiences is that it makes you learn valuable lessons and it helps you avoid making the same mistakes again. For this particular experience for example, I have learned the great life skill of detaching one’s self from material possessions — I learned how to let things go, and it really helps to see your physical belongings for what they really are: temporary and replaceable. .
  • If you want to learn more realities in order to debunk any ‘myths’ of long-term travel that you perceive, one of the things that you can do is to research and study the way that other traveling nomads live. (If you ever need more information, feel free to ask questions from me or from any other travel blogger that you know of).

    Fundamentally, just always remember that there are VARIOUS types of us nomads out there and depending on the kind of path that you choose (a digital nomad, a backpacker, a TEFL teacher, etc.) you can either end up leading an easier traveling lifestyle or a tougher one.


    Your plans might NOT work out.

    Travel Plans

    It’s always important to have a plan to keep you focused on your goals! I have discussed extensively in my ‘5 Steps to Starting a Life of Travel‘ post the planning processes that you need to take before you start traveling the world. However, after you finalize everything and set out to go on your adventure, it’s also important to know that certain things might NOT go according to how you want it to…

    …it’s unavoidable.

    When I quit my job, I had this vision of backpacking around Asia while I do online work, but what actually happened was that I ended up just hopping to neighboring countries for occasional trips as I stayed in the Philippines to work online and save up more. Months later, as I managed to kick off my online business, I found myself exploring countries in Europe instead of Asia.

    Evidently, not strictly abiding to a plan turned out to be a good thing for me and it could be a good thing for you too! But then again, it might end up being a bad thing too, and I can imagine how that would suck.

    But no matter the outcome, if alterations should ever happen to your plans, DON’T stress about it. Be flexible and learn to let things go; chances are, you might just end up doing far more interesting things if you open yourself to new ideas and different possibilities. Though if worse comes to worst, like what I have discussed on my ‘5 Steps to Starting a Life of Travel‘ article, you always need a safety net or an exit strategy so make sure that you have those precautions up and ready right from the VERY start.


    You need to think LONG term.

    Long Term Travel

    Volunteering — one of the most popular working arrangements that travelers opt to do lately — can already take you to various countries and it can even keep you going for years… HOWEVER it’s always important to think of your future so you have to find a way of doing a more sustainable profession that can secure your life on the long run.

    You really wouldn’t want to keep on working for farms, bars, or hostels for the rest of your life, would you?

    For starters, I have always promoted the idea of creating one’s ‘own sense of security‘. To achieve this, as you travel or before you travel, you have to identify what you’re good at or at least find what you are interested in doing in order to establish a feasible goal to work on.

    Some people have the objective of being English teachers abroad so they can eventually set up their own school. There are others who make use of their hobbies like surfing, yoga, or dance so they can establish their own company, resort, or studio, as they slowly gain enough capital and reputation for themselves. Then of course, there are those who take advantage of what the internet can bring — people like me who become digital nomads, travel bloggers, or entrepreneurs!

    Overall, this whole idea can be a fast process, though most of the time it can be slow; but like everything else, it’s not a race but a journey, so try take things slow and try to enjoy life as it goes. Besides, as long as you have your action plans and that one big GOAL to work on, you’re bound to get things done in the future!



    A life of travel takes hard work and a lot of sacrifices BUT, still and the same, it IS possible.

    Quit Your Job

    No matter if you’re broke and no matter if you only hold a limited 3rd world passport, there are numerous ways to make a travel lifestyle a reality. You really DON’T need to be rich either, because I’m not rich nor did I come from a rich family.

    With that in mind, how then did I make this happen? Three things: discipline, hard work, and sacrifice.

    Other than the fact that I didn’t want to work for anyone else anymore, I also knew that building my dream comes with a ‘price’. So since I badly want to reach my goal given the challenges that I’ve had in the past, I was more than willing to give up a LOT of things in my life in order to achieve what I absolutely want.

    [Tweet “If you don’t build your dream, someone else will hire you to help them build theirs.”]

    It ranged from strict saving routines to working myself to the bone, and it was vicious… it was a real struggle! But I thankfully made it happen in two months, after which I handed my resignation in. Looking back, I certainly have no regrets whatsoever! Like I’ve mentioned previously, with the way my life is right now, I can say with utter confidence that it was all worth it since I am now able to continually see the beauty of this world as I build up on experiences and myself.

    Ultimately, with all of these and more, you should know by now that if I managed to do this, then YOU can definitely do it too!

    Besides, for as long as you just do what you love to do, not only will you become happy but you will also become a master of it! So don’t ever let fear make you settle — if staying inside an office setting is not an ingredient on your recipe of achieving happiness in life, then by all means, QUIT. It’s never too soon and never too late anyway.

    For sure, it requires a whole lot of courage to turn your life around like this… but I know that YOU are not short of it.

    • • •

    5 Things to Know First Before You Quit Your Job and Travel the World


    Take note that this is NOT a post that wants to dissuade you from planning to quit your job to travel the world — NOT at all. Because if you do decide with conviction to take such a course of action in your life, I wish you nothing but the best!

    So why have I made this article then…? Well, like what I said at the first part of this post, I wrote this because I just simply want you to be WELL-INFORMED about this big decision that you are making. A lot of people take the plunge too quick and I want you to avoid that because it’s essential for you to first handle your plans, strategies, and expectations before you go on.

    As you already know, your effort and your time is valuable; so at the very core, I don’t want you to waste those (it’s better to realize the facts NOW rather than later, right?)

    Anyhow, if you remain to be absolutely sure about what you’re doing even after reading these 5 reminders, I now leave you with these final words: trust in your struggle and I’m sure that I’ll be seeing you out here soon! Good luck!

    • • •

    Have you seen my latest vlog?

    How I Afford to Travel the World (Vlog)

    About Me

    Solo Female Travel Blogger: Aileen Adalid

    Hey there! I am Aileen Adalid.
    At 21, I quit my corporate job in the Philippines to pursue my dreams. Today, I am a successful digital nomad (online entrepreneur, travel writer, & vlogger) living a sustainable travel lifestyle.

    My mission? To show you how it is absolutely possible to create a life of travel no matter the odds — and I will help you achieve that through my detailed travel hacks, guides, resources, tips, and MORE!

    Follow Along

    CURRENTLY BASED IN: The Philippines

    Trending Now

    Best Travel Jobs to Make Money While Traveling the World (Top Tips)

    These are the best travel jobs for people who want to explore the world indefinitely! Find out which is the right one for you in this guide.

    Top 10 FREE Things to Do in Paris: The City of Love & Lights (France)

    Paris is one of the world’s most expensive cities, but your trip does NOT need to be pricey. Here are the top 10 FREE things to do in Paris!

    Chicken Adobo Recipe: Authentic Version (Filipino Food)

    Recreate the Philippines’ famous chicken adobo recipe (the country’s unofficial national dish) and follow this authentic cooking method.

    How to Travel the World on a Third World Passport (It’s Possible With These Tips!)

    A third world passport is definitely NOT a hindrance to your travel dreams. Follow these tips and you can easily travel the world!

    How to Save Money for Travel: Top Money-Saving Tips (You Don’t Need To Be Rich!)

    Wanna learn how to save money for travel and make your travel dreams come true? Here are money-saving tips to get you started!

    Learn Today

    How to Start a Successful Blog

    and Earn Money!


    1 2 3 7

      Hi Aileen,
      Thanks for your new feature article. Have you read my article “Future Human Intelligence” which I hope to present in the 2015 APEC meeting? I hope you can correspond with me via my email albeit I know you are that busy.

      Best regards,


      • Aileen

        Hi Dr Dionisio, I haven’t read your article but I’ll send you an email now. Thank you!

    2. Alyssa

      Thanks for this! I am learning heaps from you. I’m not into travelling a lot though I dream to travel alone someday, too. I’m 24 now, but not as independent as you are! I guess I have to learn the skill first :D You’re aawesome! Just thought I’d let you know. :)

      • Aileen

        Awww, thank you Alyssa for your kind words! I’m even more glad to hear that I am helping you out! Anyhow, I’m sure that you’ll be able to travel alone someday. I wish you all the best, Alyssa!!

    3. Wayne Seto

      Great post Aileen. I’ve been travelling abroad for years, but decided this year to take a year off from work and travel. Like you said a life of travel is hard work. I knew a number of travel bloggers/writers who’d been travelling long term for awhile and knew how hard they worked at it. To know and actually experience it is another thing. I’m about 3 months into my travels and am still figuring out if the nomadic lifestyle is for me. Travel will always be a big part of my life. It’s just in what way. I’m not sure where the year will take me, but that’s the beauty of travel isn’t it? You just don’t know where you may end up. Thanks for the post.

      • Aileen

        Hey Wayne! Thank you so much for taking time to leave your feedback, and I’m glad to hear about your story! Indeed, that’s truly the beauty of travel — it’s hard work, but it’s what we love to do so it all balances out. :) All in all, I wish you all the best in your travels, Wayne. :D If you ever come by Belgium, let me know!

    4. Sarah P.

      Hey Aileen, I’ve been reading an innumerable number of travel blogs for quite some time now, and I had always felt that there was something missing. I wasn’t sure. But now I know it was a similar point of view that I have always been yearning for. (I am a 22 year old Filipina, by the way.) Somehow, it makes the impalpable palpable for me. I relentlessly crave for knowledge and wisdom; therefore, I know that this kind of lifestyle fits me perfectly. Do you have any tips on what courses I should be studying or what helpful sites I should visit that could help me sustain a living on the road? I’ve been unceasingly researching, but it’s so hard for me decipher since there’s too much choices out there. I’ve actually plotted mentally to leave next year, and my ultimate goal really is to see all continents of the world. Wish me luck!

      • Aileen

        Hey Sarah! Thank you for taking the time to leave this message — I really appreciate it! And that’s great to hear that you are a Filipina too and almost the same age as me. Anyhow, I’m happy to hear that you are absolutely sure about what you want. It’s already a great first step that you have the drive to make this life change. As for your question, I personally didn’t take any courses at all in order to start this lifestyle. It was mostly just researching Google. I’m not sure if you’ve already read my articles:
        But it could be possible that your answers will be answered there. Let me know if that helps!

        All in all, I absolutely wish you all the best in your journey, Sarah!!

    5. David Stock

      Good points, People quit their jobs to travel daily and some do find out long term travel is not what it really shapes up to be. (Some also think they will just start a blog) People think it’s just like having that wonderful week trip they had when they traveled but when your a long term traveler you see more and experience more then the week to to week traveler.

      • Aileen

        Hey David, I’m glad that you agree! Indeed, it’s best that others know first what they’re getting into and not be blinded by all the good travel photos, etc. I mean of course our life is great but we continually work hard to achieve it — I guess we make others seem to think that it’s too easy so it’s nice to give them that reminder that it’s not always so. :)

    1 2 3 7

    Submit a Comment

    Your email address will not be published. Required fields are marked *

    Pin It on Pinterest