Zaitunay Bay
Back when I was in Zaitunay Bay – Beirut, Lebanon. I always had to be up late so I can sync with Canada’s morning. We had to stop here, camp down for a bit–nay, WHILE–in a Starbucks (for wifi) and then continue with the travels late after. It was challenging since you have to stay up late and then wake up to travel.

Should I Work Remotely: First of the Series


I’ve been travelling since 2012 and I’ve had multiple success with working remotely. At first, travelling is just that 2-3 week adventure you have per year. I’ve really fallen in love with it and I refuse to accept that I only have a 15 (roughly) day window for all of us out of your 365 days. Do you not realize and feel gutted about that? So when I realized that, I’ve made it a mission to bake it as a lifestyle for me, not this optional thing people do. I’ve been through this process and I know what I want. But for you the first question in all of these: “Should I work remotely?”.

A lot of people have asked me before how I do/did it and surprise, surprise! I now have the means, time, and channel to provide those information so here it is. Working remotely is a big topic, so much that I’ll write multiple articles about this. I will probably even create a subcategory just for this so check out the navigation for more articles about working remotely.

Coverage and Assumptions of This Article (or Series)

This article is for you if:

  • You’ve travelled before and you want to travel for longer periods of time; ideally longer than how many vacation days most employers would give you
  • You have a full or part time job / 40 hours of work / 9-5 job; doesn’t have to be just one employer
  • You actually have professional work ethics and you’re not looking to take advantage of any one or any employer
  • Your profession actually allows you to be able to work anywhere (e.g.: You can’t be a surgeon and do your thing without being in the room)

What This Article/Series is NOT

This article is not:

  • a guide for you to become an “influencer” or some social media celebrity.
  • a shortcut to get travelling tomorrow. At best if you play your cards right, ~1 year’s the fastest.
  • a guide to be a begpacker.

En Continue

Point 1: Let It Marinate

So you’re thinking of working remotely. Maybe we have the same motivations, maybe you have your own reasons. Either way, we have the same goal. If this is the first time the thought crossed your mind, let it marinate for a couple of days, even weeks. Just close your laptop now and do something else. If in 10-15 days you’re still thinking about this (the longer the better), then you know you’re a little bit more serious.

There is no shame in abandoning this idea. Maybe you met the love of your life and you guys just want to have a family. Who said one is better than the other right?
(but I still hope you guys still manage to do at least mini trips later on!)

Also, make sure you are running towards something not running away from something? This is big and some people trip on this. This is no bueno. If that’s your case, you will not follow through with the plan, most likely.

It goes without saying, this endeavour will require some money. Are you mentally/physically ready to commit to this? Either you work extra, or you cut down on your weekly gigs. Take this seriously, are you ready to say “no” to certain events? Or are you willing to take on more work/stress for some time?

Consider also that “working remotely” contains the keyword: work. You will definitely work, it just becomes a question of logistics later. But if you want to travel and not work, this article isn’t it. That’s not even called “working remotely”. That’s either called Vacation or Retirement. I definitely want to be at that point too but that won’t be until the latter stages of this series. So if you’re still reading on, prepare to work.

I can advise you however on how to save money to travel.

Point 2: Be Honest and Drill Down Why You Want To Do This

a.k.a: “What is it that you really want?”, not “out of this” but in general, in life. Is working remotely part of it or at least a way to get to what/where it is you really want to be? You want to really get to the kernel of this. There’s a lot of work in this adventure, so the last thing you want is you invest and do things, only to find out that this is not what you want after all (although having travelled to many places is never a bad thing).

You know you’ve arrived at the very core when you get that a-ha moment (vague I know, but I’m getting there), and when you are even ready to ditch part or all of the travelling for that reason.

My Experience

What really inspired me to travel (even before my first ever travel) was partially High School Musical (yup, went there). I was laughing when it came out because it was straight out of my imagination. You have a white guy, black guy with a ‘fro, blonde girl, latina girl. All that’s missing in my imaginary cast is an outgoing asian girl, and for some reason, I think life would be more exciting if you have a talkative gay guy or a black girl that gives you lots of attitude / comments LOL.

I wanted people from different backgrounds, with different cultures, and different upbringing and outlook/perspective in life. Of course I also want to eat their food and experience their culture. I think it’s even impressive to be able to form a gang like that since there will be lots of head butting in all levels, and for everyone to keep it together and live harmoniously…~I think that’s a major achievement.
Today this is called Canada * ba dum tssss *.

And so I travelled and I made it my main objective. I can’t stomach the fact that I will only have very limited chance to do it in my lifetime. I want to do it more hence I focused on the concept of work remotely.

The goal evolves and it will evolve for you too. Now my added goals are: “if I travel and form multiple lives in different places, I don’t want to be like ‘oh, I have to go back. Why? Because my sustenance(job for example) is there’.

“Work to live, not live to work”

as they say

My “a-ha” moment

I travelled so many times after that and I’ve definitely confirmed what I want. It’s the people and the culture. So in essence, I can give up travelling so long as there’s a perpetual stream of people constantly travelling to Toronto and I have continuous access to them.

Maybe you travel and conclude that it’s actually alpine / winter sports that you’re really into. You don’t need to travel a lot for that. You can limit yourself to the Alps, Japan, or North America. Heck even just Canada’s Rockies would satiate all of that. Travelling becomes secondary but maybe you’ll still need to work remotely. Maybe not even; maybe you find a job up at Banff or Zermatt.

Point 3: “How to Fund Yourself”

I think most people can agree that the biggest thing you need to consider (on the material side of things) is how you’re going to fund yourself. Once you figure this out you literally can just wander around the globe and not have to worry about tomorrow.

There are myriads of options here for you here:

If you’re a business owner, then you literally have the most flexibility here (but you also have the most responsibility lol). No one’s policing you to stay anywhere and assuming you can work from anywhere, your laptop and your revenue just follows you. We’ll talk about business ideas you can do later on.

If you’re an employee, ~well I guess this is most likely why you’re here and I’m supposed to tell you how to achieve this. Most employers are not easy with this idea. There’s a higher chance they say no rather than saying yes here. So you have to think first: if your employer ultimately says no, what do you do? Are you mentally and financially prepared to leave if it’s not going to give you what you want? Would you kill the idea of working remotely all in all? What would be your next possible income stream? We’ll talk about the details on how to approach this with your current employer in this series.

Some Financial Literacy Here

A smart alternative is actually being smart with your money. You can get to this option even if you’re either employed or a business owner. You can be in a conservative company and still be able to work remotely and fund yourself in the short, medium, and long term (err, more on the last two). How, you ask? Well here’s how I would do it:

I’d work hard, get money, then invest that money. You can go the trading route, or real estate, or basically anything that involves “money making money” (so long as it’s legal). By doing so, you disconnect your reliance on your employer…~ or any employer actually. The problem with this is it uses the same resource that you would need to actually travel: Time. You need time for your investments to grow, but at the same time the call for travel is “Now, let’s do it now!”. I’ve never heard of anyone say, “I want to travel, but I want to travel 10 years from now”, right? So you have to find and strike that balance.

You can also do a mix and match wherein you have a fulltime job and you have a project/startup in the works. That’s great use of your time. If it takes off, then you’ve transitioned to a business owner and you get to reap the benefits of it. When it gets more money, dump it in investments to grow it even further. This is not even about travel any more, that’s important financial literacy folks!

“Don’t work for money. Make money work for you.”

-something like that by Robert Kiyosaki

Other Alternative Ways

Yes money is important, but remember that money is just a medium. You don’t “need” the money per se but you need what the money affords you: food/water, roof, etc. So if you think outside the box, you can circumvent the money part. If you don’t have to pay for necessities and some of the things you want, then it’s all the same right? So here are some ideas:

  • WWOOFING – Volunteer in a farm in exchange for accommodations and/or food.
  • Working at a Ski Resort (or similar large companies that deal with things you are interested in) – When you work at a ski resort, they also offer housing most of the time. So the accommodation’s accounted for, you get discounts for food, basically most of your income there will be pocket money. I don’t know about other industries but try things like scuba or…ooh I forgot what you call it but you work in somebody’s yacht.
  • Exchanging Services – An example would be Nomador, wherein you house/pet sit for someone. Same logic as above; one or more of your necessities are paid for so less expense for you to worry about. Maybe there are organizations or what not where you cook or render any of your services actually in exchange for necessities and/or compensation.

I hope these out-of-usual-bounds ideas help you in your question of: “Should I work remotely?”. Surely there are other alternatives out there, it’ll just be up to you to dig a little more.

This is the first of the many articles of my ‘Working Remotely’ series. The next article is about “Before You Talk About Working Remotely With Your Employer”. Sign up to our mailing list below or follow us in Facebook or Instagram so you get notified about the next highly-asked topic!

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