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

by Travel & Adventure, Working Remotely60 comments

Quit your job and travel the world? It sure sounds like a pipe dream, but I’m a living example of how it can truly be anyone’s reality.

RELATED READ: How to Quit Your Job & Travel the World

Now don’t get me wrong — I wholly understand the fact that some people are perfectly happy with their office job given that 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.

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

It has been more than 10 years now since I’ve been leading this nomadic life and since then, I’ve been to ALL the 7 continents! The icing to the cake? I even managed to set up an online business during my travels that now lets me lead a sustainable traveling lifestyle indefinitely.

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.

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!

BUT… before you start following MY advice as well as other people’s helpful tips, guides, and hacks on how to quit your job and travel the world, 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.

…Before You Quit Your Job & Travel

1. Determine if a travel lifestyle is truly your desire

Quit Your Job and Travel

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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 these things because 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…).

After all, 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 and travel‘ predicament 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. Of course, it’s an amazing thing; but it’s important to NOT let it sway you too quickly… because the basic truth might actually be that you only need 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 line of work. Think about your interests and the things that you enjoy! So let’s say you are currently working in finance but you have always been interested in marketing or even 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: POSITIVE = If you end up being happy in the new job or position that you’re in, that’s GREAT! There’s really no need for you to quit your job and travel the world — 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.
    • RESULT: NEGATIVE = If you still 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…
  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. For instance, you can 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.)
    • RESULT: NEGATIVE – If you realize that a life of travel AND a corporate job is NOT for you, i might be time for you to examine your other choices. Maybe starting your own business in your home country is where your passion lies…? Honestly, the possibilities for this are endless; 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 minor inconveniences it may bring — then by all means, go ahead and want this lifestyle BAD and 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!

2. Manage your expectations

Manage Expectations: Travel Life

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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.

For starters, it’s not like everyone instantly goes to 5-star hotels once they become a traveling nomad. That’s why as early as now, I highly recommend that you lower any expectations that might be overly romanticized.

To name a few of the top ‘realities’ that you will experience and/or 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 you could 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 for hours in a day. 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 hard at first or maybe even for a longer time until you manage to stabilize everything.
  • It can get lonely and solitary. This is especially true when you’re traveling alone. In fact, no matter the number of people that you meet on the road, there will still be those times that you will get emotionally vulnerable — 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 have to 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 can be moments when you might wish for a permanent home or address to stay in… In fact, 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 set up a home base for a longer time, or you can even 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: “How to Get Free Accommodation
  • There will be ups and downs, but sometimes, more on the ‘down’. Locals might not be that friendly to you, money might start to be an issue, your flights might be delayed or canceled, and a whole lot more of regrettable scenarios can happen! (Heck, a pandemic can crop up anytime!) 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.
    • As an example, I’ve had my first 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 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, 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 — and that of course, I also learned to be more mindful of how I stow away my stuff in a rental car while traveling abroad.

If you want to learn about other travel realities that will help debunk any ‘myths’ of long-term travel that you wrongfully perceive, you can also research and study the way that other traveling nomads live. (If you ever need more information, feel free to ask questions from me, from any other travel blogger that you know of, or from other travelers — you can even converse with them online by joining travel groups).

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.

3. Your plans might not work out

Travel Planning

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It’s always important to have a plan to keep you focused on your goals! 

I have discussed such matters 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 them to… it’s an unavoidable fact.

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. As I managed to kick off my online business several months later, I found myself exploring countries in Europe instead of Asia.

Evidently, not strictly abiding by 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.

No matter the outcome, if alterations should ever happen to your plans, try not to 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, 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.

4. You need to be a LONG-term thinker

Take Online Courses and Learn Remote Work Skills

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Let’s take a look at volunteering — it’s one of the most popular working arrangements that travelers opt to do lately and it can keep you traveling for years… HOWEVER it’s always important to think of your future. As such, you have to find a way of doing a more sustainable profession that can secure your life on the long run.

Besides, 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!

RELATED READ: Best Remote Travel Jobs

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!

5. To quit your job and travel the world is a difficult journey — but it IS possible

Godafoss, Iceland

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

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.

RELATED READ: How I Afford to Travel

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.

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.

RELATED READ: How to Save Money for Travel

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 and 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 in 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 quickly 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

About Aileen : Sidebar

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


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  1. John Mark Isaias

    Great vlog Miss Aileen keep up the good work and continue pursue your dreams!

  2. Alice Carroll

    You made a good point that having a sustainable profession would be the best way to spend a lot of time traveling later in life. My father used to tell me when I was young that I have to be smart with my money when I grow older but I’m not really quite sure what I’m saving up for anyway. Maybe going an a number of luxury family travel vacations someday would be a good way to spend my retirement.

  3. Maya Maceka

    Aileen, this is SO spot-on. I love being an online entrepreneur and having the flexibility to travel full-time. I wouldn’t change it for the world. BUT, it is certainly harder than it looks! It’s awesome that you’re shedding light on this topic and letting people know what to watch out for. Sharing this all over!

    • Aileen

      Thank you Maya! I wrote this at a time when people thought that this lifestyle is easy haha. It always helps to give some real insight.

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