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Once upon a time, I proudly toted everything I owned around the world in a carry-on bag. (Here was my carry-on packing list). Since then, I’ve reverted back to checked luggage for a variety of reasons, which I’ll outline here.

I’m not the only one either; while traveling with carry-on luggage was a huge trend over the last decade or so, it’s shifting again. Here are the pros and cons of checked vs. carry-on luggage, along with some criteria to help you make the best decision for your own travel needs.


Oh, to gallivant around the world without a care, and just a light bag that never leaves your side. To enjoy the freedom of being able to handle anything your travels throw at you, without the weight of the world (or at least, a checked bag) holding you back.

Here are some of the benefits of traveling with carry-on luggage:

It’s Stress Free. No more worries about whether your checked bag made it on the same plane as you; it’s a sure thing.

Faster Airport Arrivals. You’re golden once you’ve cleared customs and immigration. I once clocked 15 minutes from the plane landing in a new country to my walking out of the terminal.

Moving Around Isn’t a Hassle. Changing accommodation/location frequently? Walking your stuff a little further than you thought? Navigating a cobblestone street? No problemo. Packing up is easy (since there’s not much to pack, after-all), and your carry-on luggage is light enough that you can carry it over rough terrain/stairs/etc with ease, even if it doesn’t have backpack straps.

I did two standalone trips with carry-on luggage only, before ditching my checked luggage for good: I spent three months sailing the Caribbean, living on five boats spanning three countries. To do so with a 20kg checked bag would have been a nightmare. The other was a sponsored trip through Europe where I traipsed through eight countries in three weeks; traveling at that pace would have been miserable with a lot of stuff in tow.

Packing is Simple. Even if your carry-on luggage is chock-a-block, there’s still just not that much to pack. Hence, the process is quicker and easier.

You’ll Save on Checked Luggage Fees. With airlines separating out more and more fees (like meals, seat selections, and bags), you can save a few bucks by not having to pay for a checked bag.

Best Scenarios for Carry-On Luggage

You’re Going Somewhere Warm. Hot, preferably. The lighter your clothing requirements, the more packing options you have.

Fixed-Length (Short) Trips. I’ve packed for trips as long as three months with carry-on luggage only. Having said that, I’d suggest the ideal carry-on trip length would be one month or less.

It’s a Busy Trip. The more you have to pack up and move from one destination to another, the better you’ll appreciate traveling light.

Best Carry-On Luggage Types

With increasingly stringent airline carry-on luggage restrictions, the lighter your bags, the better. Here are some specific luggage types and suggestions:

Wheeled Luggage

I prefer wheeled luggage in general; I’m spared of back pain, wear-and-tear on my clothing (from hauling on and off a backpack all the time), and call me vain, but I simply prefer the image of rolling luggage vs. backpacks. While some people might argue that wheeled luggage is impractical over rough terrain (like cobblestone or dirt roads), being carry-on sized, it’s light enough to carry by the side handles when necessary.

Wheeled Carry-On Luggage Suggestions

NOTE: My luggage suggestions in this post have not been influenced in any way; I have purchased all luggage on my own, and any luggage suggestions that I have not owned personally have been road-tested and endorsed by friends and colleagues.

If you click any of the luggage links in this post, I will earn a small commission for your subsequent purchase; your own price is not affected, and I thank you in advance for supporting The Professional Hobo this way.

My own carry-on travels have been made pleasurable by the Pacsafe Toursafe AT21 Anti-Theft Wheeled Carry-On, which I absolutely adore to this day. It’s lightweight, has all kinds of awesome security features, and has super sturdy wheels for rolling all over the place. Although I no longer travel full-time with carry-on luggage only, my Pacsafe is safely stashed away somewhere I can pick it up should I have the occasion to leave my checked bag behind for a spell.


I’m not a backpack girl for many reasons (which I outline here). But if you’re going to travel with a backpack, a carry-on backpack makes the most sense. They’re generally the most lightweight form of luggage you can find, allowing you to allocate the most weight and space for your stuff. Aim for a 40 litre (or so) backpack, which will give you the most space while adhering to (most) carry-on luggage rules.

Carry-On Backpack Suggestions

The Osprey Porter 46 is the largest carry-on backpack you’ll likely find at 46L. Osprey makes solid luggage and is particularly adept in the backpack department.

For something a little smaller, and massively popular amongst my carry-on travel colleagues, check out the Osprey Farpoint 40 Travel Backpack. People love it for its versatility, organizational features, and harness comfort (with multiple sizes to choose from, depending on your own size/stature).

Personally, I love Pacsafe, and would consider the Pacsafe Venturesafe EXP45 Anti-Theft Carry-On Travel Backpack for its security features (like slashproof material and tamperproof lockable zips), its light weight, and great amount of space. It also has a front pocket with lots of organization power, and Pacsafe’s signature locking cord so you can lock the bag to a secure fixture.

Lastly, Tortuga is a popular name in travel bags, and their Tortuga Travel Backpack is 44L and host to about a gazillion organizational features.

Carry-On Wheeled Backpack Suggestions

I adore wheeled backpacks and have traveled with a few different ones over the years. (See also: Wheeled Backpacks: Why They’re the Best, and Tips for Buying One).

But I would generally shy away from wheeled backpacks of the carry-on ilk, simply because the combination of both wheels and straps comes at a cost of weight and space, which is vital when traveling ultralight.

Having said that, Osprey has (in my opinion) the best carry-on wheeled backpack on the market with the Osprey Packs Meridian 60L/22″ Wheeled Luggage; it’s 60L in total because it features a detachable daypack. You can stow the main pack in the overhead compartment while flying, and keep the daypack (with items like your electronics) at your feet. While in transit, your daypack attaches smartly to the main bag so you don’t have to look like a dork walking around with one pack on your front and one on your back!


While carry-on travelers sing the praises of ultralight travel (almost evangelically so – I know, I used to be one of them), it also has many drawbacks, some of which might be insurmountable depending on your travel style or trip at hand.

Your Wardrobe Will be Extremely Limited. You won’t have an outfit for any occasion; and will likely be perpetually over-dressed or under-dressed. Buying clothes at each destination to suit the circumstances/climate (and getting rid of them before you leave) can be expensive and impractical.

Winter? Forget It. My carry-on packing list got me through three seasons (barely); the sheer bulk of my very limited selection of cool weather clothing made it difficult. Packing for winter climates as well would have been impossible.

Constant Hand Washing. With a limited wardrobe, be prepared to wash your clothes in the bathroom sink all the time. This can get tricky if you’re moving around often and your stuff doesn’t dry easily overnight. If you’re staying in communal quarters, good luck finding somewhere to modestly dry your undies.

You Might Have to Check it Anyway. General airline carry-on luggage dimensions are 22 x 14 x 9 inches (roughly 55 x 35 x 23 cm), but some airlines are much smaller (for example, Spirit Airlines limits you to 16 x 14 x 12). Other airlines are stingy on weight, some allowing carry-on luggage to be only 5 kg (11 lbs)!

And don’t think the airlines will let it slip if you’re a hair over in weight or size. I recently took a flight where the check-in agents didn’t check the size or weight of anybody’s carry-on luggage if they were checking a bag, but they meticulously weighed and sized up all the bags for people flying with carry-on luggage only. I watched a couple forced to check their carry-on luggage, frantically pulling out their laptops and other items inappropriate for the cargo hold, and having to carry it all in a plastic shopping bag for the rest of their trip. And for this inconvenience, they also had to pay (top price no less) to check their bags at the last minute.

There May Not be Room in the Overhead Bins. Depending on when you board, and how many other people have bulky carry-on luggage, you might be out of luck. Sometimes the gate attendants will nail you before you even board; if too many people have carry-on luggage only (which is common on domestic flights), they’ll go around the waiting room and tag your bag to be checked at the gate, whether you like it or not.

You Might Still Have to Pay. Some airlines are getting cheeky and not only charging for carry-on luggage, but charging even more than for checked luggage. They’re doing a great job of capitalizing on the popularity of carry-on travel.

Long Layovers Suck. Although carry-on luggage is a delight compared to schlepping checked luggage around outside of the airport, toting your carry-on bags around the airport before your flight and during long layovers is not fun. One ill-fated nine hour layover in a poorly laid out airport gave me back pain for a week.

Souvenirs? Think Again. While limiting the things you can buy might be great for tight budgets, sometimes you really want that special something to commemorate your travels. You’ll be outta luck unless you’re prepared to throw something out to make room. Which, to be honest, is also a bit wasteful.


Taking into account the dark side of carry-on travel as outlined above already creates most of my case for traveling with checked luggage. It ultimately depends on you, your travel style, and trip requirements. Here are some general benefits of checked luggage:

No Stress at Check-In. When I traveled with carry-on luggage, I always worried that the check-in agent would deem my bag too big or too heavy. Once, when flying with Ryan Air in Europe, in the middle of a horrendous heat wave no less, I had to wear all my heaviest clothes and hiking shoes for an agonizing flight, and without a reliable scale I still wasn’t sure I was within the weight limit. With increasingly stringent carry-on restrictions, stress at check-in will only increase with time.

Bring What You Want. You don’t have to pack your checked bag to the seams; simply having the option to pack whatever you want and/or to get a few extras along the way makes your trip more civilized, and less an exercise in stingy discipline.

As a full-time traveler, this is the biggest reason I’ve reverted to checked luggage from my former carry-on days. While I was in Asia renting apartments with kitchenettes, I carried a small espresso maker with me to make my morning routine a delight. When I was in South America doing shaman-things, I had space for all my shamanic accoutrements. I also like to have specialized nutritional supplements, which take up space. So no matter where I go, I have room in my luggage for a few extras (adding either comfort or aesthetic value) that make each place I visit feel a bit more like home. (And for a professionally homeless person, this has great value over the long run).

Packing is Easier. Although heaving my 18kg checked luggage up a flight of stairs isn’t exactly pleasurable, at least I don’t have to worry about playing tetris while packing a maxed out carry-on bag. I can use all the organizational packing tools I wish without worrying about the extra bit of space or weight they take up. This makes packing and unpacking (something you do a lot on the road) a dream.

Lost Luggage is on the Decrease. While it only takes one incident to make you reconsider ever checking your bag again, stats indicate that the chances your bag will be misplaced have drastically reduced. According to SITA Baggage Reports, cases of lost luggage are down 70% over the last 10 years, despite global passenger volumes being at record highs.

Best Scenarios for Travel With Checked Luggage

You Travel Full-Time. If everything you own has to fit into your luggage, going with carry-on will involve sacrificing either comfort, style, or versatility (or a bit of all three). Why bother? If travel is your lifestyle, consider just that: it’s your life.

You’re Traveling Through Multiple Climates, Including/Especially Winter. Taking a winter trip alone practically necessitates checked luggage; going from snow to beaches requires even more luggage space.

You Want to Get Souvenirs. If you’re taking a trip of fixed duration and want to bring back some gifts or souvenirs, you’ll have the space with checked luggage. Alternately, you can bring an extra bag to check full of goodies on the way home.

You Travel With a Lot of Electronics. Would you check your laptop or expensive camera? Probably not. Digital nomads in particular are renowned for their electronic requirements; photographers have it the worst with multiple cameras and lenses, and even drones. In these cases, traveling with just carry-on is near to impossible. (See also: Electronic Travel Gear – Travel Experts Reveal What’s in Their Bags)

You’re a Gear Head. If you participate in any kind of specialized sport or activity requiring “gear”, you’d better bring along a checked bag. Some types of gear aren’t even allowable on-board.

Best Types of Checked Bags

While some travelers swear by their giant backpacks, I don’t. So by the process of elimination, I won’t recommend any here. (I speak from experience; click here to see the various backpacks I initially started traveling full-time with, and why I don’t think they make sense).

Okay, then. On with the various checked luggage types I do recommend:

Wheeled Backpack

The wheeled backpack is the best of both worlds, and was the first form of luggage I actually enjoyed traveling with. However beware: you won’t want to take it hiking in the countryside. Think of a wheeled backpack as rolling luggage that you can put on your back when you need to. You can reduce the discomfort of using straps by getting a model with a padded hip belt, and pay attention to the construction of the bottom part of the pack, so it doesn’t dig into your back/hips.

Checked Wheeled Backpack Suggestions

If you’re on a budget, check out the High Sierra AT7 Wheeled Duffel with Backpack Straps. This is the newest generation of the wheeled backpack I first started out with, and for the price I loved it. However on this particular model, the straps are pretty flimsy and there’s no hip belt so you won’t want to take it far on your back. You can choose between the 22, 26, or 32-inch models; I recommend the 26”.

For something considerably more solid, check out the Osprey Sojourn Wheeled Luggage (25-Inch/60L). I also owned this model and loved it. It’s really spacious, lightweight, and well-made. It has zip away backpack straps and a proper waist belt, and very sturdy wheels. It’s a great lightweight wheeled backpack, but you get what you pay for: it’s pricey.

What I loved most about the wheeled backpack I started traveling with (that has since been discontinued by High Sierra) was that it had a detachable daypack. Most of the time I rolled the bag and wore the daypack, but I always had the option of rolling the whole thing; and when I needed to strap it all to my back, the ability to attach the daypack was invaluable.

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Susi Kaeufer is a Visibility and Mindset Coach for female entrepreneurs who desire the freedom and flexibility to travel with an online business. Susi’s on her second tour around the world and has been a nomad for four years now. In the last year, she’s moved 75 times. Through Susi’s work at Dream Life Deluxe, Susi creates multiple five-figure months from her laptop while she’s at the beach, living in luxury accommodations, or adventuring.

She’s helped female entrepreneurs create high-ticket offers allowing them the freedom lifestyle they crave, create consistent income in their soul-based business, take their offline business online to be fully location independent, and get fully booked in their service-based business. Read on to learn  more about Susi’s awesome lifestyle and career! 

How long have you been living/working on the road, and where have you traveled to?

I left Germany in January 2014 to volunteer and work my way around the globe for one year. I volunteered at a cheetah rehabilitation project in South Africa, with koalas in Australia and at a cat sanctuary on Bali. When my savings got low I took a job in Sydney, Australia where I lived for 2.5 years.

This is when I started my own online business, as I was craving the freedom to travel full-time and be fully location independent.

After seven months in business, I quit my job in Sydney and am on my second round the world trip since May 2017.

I discovered housesitting as an amazing opportunity and have been all over the globe this year: Bali, Europe, Las Vegas, Canada, New York, Saint Lucia, Martinique, Barbados, England, Vietnam… to be continued.

Please describe what you do for income.

I work as a Business and Mindset Coach for female entrepreneurs.

My income comes from several income streams: 1:1 Coaching, Group Coaching programs, self-study courses, a membership tribe, and affiliate commission.

When I started my own online business as a certified life coach I mastered the art of finding clients on Facebook and Instagram quickly.

Today I have a large following and Facebook group and my coaching has shifted more and more towards Visibility Strategy and Mindset Coaching, as those are the areas that helped me the most to establish my own business.

I help other service-based Biz Babes (aka female entrepreneurs) to create content that converts and overcome their own limitations when it comes to aiming for a higher income than just the bare minimum.

How many hours per week do you work on average?

It depends how much I’m traveling and if I’m launching any new programs, but I’d say anywhere between 20 and 40 hours per week.

I show up in my business every single day (content creation, sharing my message, selling) and I love it, so sometimes I’m glued to my laptop for longer than I even notice.

But that’s the magic of being your own boss: You get to decide.

How much money do you make?

I make consistent five-figures per month, with ups and downs depending on the current group programs or courses I’m running.

My main income streams are my 1:1 coaching clients and group coaching clients.

On top of that I make around $1,500 per month with a membership tribe for mindset journaling, $1,500 passive income with the courses in my online shop about mindset and online visibility, and around $400 per month from affiliate commissions for tools like Convertkit and for referring new coaches to the life coaching school that I got certified with.

Do you make enough money to support your lifestyle?

I make enough money to support my lifestyle and shifted my travel standards to the next level several times during the last four years.

Starting out as a classic “backpacker” I turned more and more into a “flashpacker”.

Today I love to stay at five-star hotels, life-changing retreats and I love to pay for comfort whilst being on the road.

When I was starting out with the lifestyle, all I saw within the Digital Nomads world was the philosophy “to get by as cheap as possible in Chang Mai”, which is definitely not what I’m aiming for.

I love to surround myself with successful seven-figure business owners and inspiring role models to learn from them and grow and create and live the lifestyle I TRULY desire.

What do you like most about your career and lifestyle?

The freedom to be fully location independent and go with the flow, whilst doing what I love.

When I got into coaching I didn’t even know something like “Online Coaching” existed. I was simply very good with encouraging people to believe in themselves and simplifying complicated processes so they’re easy to understand and implement.

Only later did I discover the crowds of online coaches out there, and I honestly think some people might get into coaching for the wrong reasons.

I love seeing female entrepreneurs grow and step into the next level version of themselves.

At the same time I am blessed to travel the world, work with the most inspiring mentors, attend life-changing seminars and work with my laptop at a beach bar.

If someone would have told me this was possible a couple of years ago, I wouldn’t even have believed them in my wildest dreams.

What are some of the challenges you have with this career and lifestyle?

Not having a fixed address makes it harder to get equipment from places like Amazon. (See also: Everything You Need to Know about Virtual Mailboxes – which can help solve this problem) 

Investing money without a local phone number connected to your bank account is a challenge as well.

I’m a German citizen with a business registered in Australia, traveling around the world full-time – and sometimes that doesn’t seem to fit into the boxes and forms of governments and banks.

(See also: Everything You Need to Know About Filing Taxes as a Digital Nomad)

What is your vision for the future of your lifestyle on the road?

I’m currently madly in love with house-sitting and petsitting in between travel adventures. Having a temporary (rent free) home for a couple of months is amazing to settle for a while, before hitting the road again. Plus I love pets, which makes petsitting the ultra combination of traveling and being surrounded by animals. (Learn more about house-sitting and where to get gigs here.)

I think having a freedom lifestyle on my own terms is something I’ll always crave, however I can imagine investing in property on several continents and building a home base in some countries.

Any advice for the aspiring traveler about living and working on the road and managing finances?

There are NO excuses. If this is what you truly want, there WILL be a way.

“No money”? Look into housesitting or volunteer websites like workaway and helpx. I loved volunteering and working my way around the globe before I had my own business. (Nora’s Note: Amen to this! When I was building my own online business and wasn’t making much money in the early years, I stretched my travel budget 10-fold by getting free accommodation using these and other methods. Learn more: How to Get Free Accommodation Around the World).

Done with playing small and working for $10 per hour? Get help and hire a mentor who can help you build and scale your location independent business. Learning from others has been life-changing for me and surrounding myself with people that inspire me has been very helpful when it comes to “questioning my own limits”. The only limits you have are in your head.

Is there anything else you’d like to add?

I’ve been following the Professional Hobo for years, when I was still stuck in my 9-5 in Germany, browsing travel adventures in a secret window at the office. Follow inspiring people to expand on what’s possible for you! They all started somewhere, I did too! It took me no longer than two years to create an amazing Dreamlife Deluxe that’s wilder than my wildest dreams!

I’d love to connect with you! Send me a Facebook friend request.

Want to know more about how to design your life so you can earn money while traveling the world? Check out Working on the Road: The Unconventional Guide to Full-Time Freedom.

The post Financial Case Study: Susi Kaeufer, Coaching Female Entrepreneurs appeared first on The Professional Hobo.

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“All life is suffering,” murmured my friend Dustin through mouthfuls of ice cream, in Chiang Mai. It was a catch phrase he liked to use when enjoying something delightful (like ice cream); the irony and timing in reminding himself (and others) of this first noble truth of buddhism always drew a laugh.

If only I knew at that time the degree to which I would suffer – truly suffer, even optionally and at great expense – in Koh Phangan Thailand, just a few months later.

Phase One: The Irony

As if the irony of observing that all life is suffering while eating ice cream wasn’t poignant enough, the irony of being depressed on arrival to a place like Koh Phangan was ludicrous.

I mean, it’s a tropical island in the south of Thailand. In fact, it’s the tropical island of tropical islands in the south of Thailand; one of the more hedonistic places you can visit, as is evidenced by the full moon party culture of travelers drinking buckets (literally, buckets) full of alcohol and ingesting all kinds of other “stuff” on offer while dancing the night away on the beach.

Not that there’s anything wrong with that, but that’s not why I was in Koh Phangan. There is another side to the island; literally, the opposite side of the island, in a place called Srithanu where the pace is quiet and the focus is on another kind of hedonism; that of spirituality, healing, and general well-being. Throw a stone and you’ll either hit a yoga shala, tribal clothing store, or vegan restaurant. Visit Zen Beach at sunset and you’ll find drum circles and poi dancers; walk a little further up the beach and strip down to enjoy some (illegal) nudism. Sit long enough at Cookies Cafe with a coffee and you’ll surely overhear somebody sharing their thoughts on enlightenment.

Not that there’s anything wrong with that, but that’s not why I was in Koh Phangan either. Hell, I don’t really know why I was in Koh Phangan. I’d heard through the grapevine a few times that Srithanu was the place to be, and after the relatively dismal weather I experienced in Hoi An, I needed some sun and fun. Koh Phangan is also informally known as “sticky island”; it’s another one of those places that people come to visit for weeks, and end up staying for years.

So there I was, enjoying the idyllic sunsets, delicious Thai food, cheap cost of living, and even fast internet. All life is suffering. And I was. Suffering, that is. Suffering from a continued depression that inspired a total life crisis, all of which came to a head somewhere in India when butter was being poured into my eyes. (That’s another story).

Ah, the irony. To actually be suffering, in paradise. Little did I know, the suffering hadn’t even begun.

Phase Two: The Agony

A friend who (like me) had spent extensive time in countries where the water isn’t potable told me she had also been feeling depressed, along with a host of other physical symptoms we shared in common. In a series of colonic hydrotherapy sessions, she discovered she had an enormous population of parasites, bacterias, and other unwelcome hitchhikers that were wreaking havoc in her gut and causing many of her seemingly unrelated health issues.

This inspired me to research what forms of similar healing I could experience in Koh Phangan. As a mecca for just about any modality of healing you can imagine, I wasn’t disappointed to discover a few places offering intensive detox programs that promised to cure me of just about anything. These detox programs involved many days of fasting, combined with colemas twice per day. (A colema – if you are currently scratching your head, as I was – is best described as a hybrid between an enema and colonic hydrotherapy).

Now. You may recall I had a slightly traumatic enema experience in India. (It’s an amusing read). So perhaps you’re wondering why I might be prepared to do something like that again. But, desperate times call for desperate measures, and I was tired of feeling like shit. Perhaps if I cleared some of it out of me, I’d feel better.

And that’s how I found myself suffering – really suffering – for 11 days of detox hell.

Actually, the first two and last two days of the detox didn’t count towards the agony; they were my days to ease in and out of the program, while drinking liver cleansing juices and eating delicious fruit and vegetable salads. The seven days of fasting (and colemas) in between were the meat of this shit sandwich.

I’ll spare you the gory details of the minutia of my daily routine, save for a few surprising occurrences.

First of all, I wasn’t hungry. As somebody who believes wholeheartedly in eating regularly, this came as a huge surprise to me. But it was probably the constant ingestion of detox “shakes” (prior to arriving I had envisioned these being lovely fruity refreshing drinks; if water with bentonite clay and psyllium husk is fruity to you then you’ll be in heaven) five times per day, with supplements and herbal detox pills in between. Given an additional five capsules/day I also swallowed as an optional anti-parasite treatment, I had no chance to be hungry; I was full of water (and clay, and psyllium husk, and supplements). Once a day I was given coconut water, and the highlight of each day was the “detox soup”: vegetable broth.

Instead of actual hunger, I discovered (as many detox retreat participants do) another type of hunger: mental hunger. I missed chewing. I missed smelling my food. And I missed the bonds created by people, the transcendence of culture and language around the world, all facilitated by food. One of the reasons I started traveling full-time was to “break bread around dinner tables around the world”. And now, all I could do was dream about cheesy garlic bread.

Ah, cheesy garlic bread. I can’t even remember the last time I ate cheesy garlic bread, but for the duration of the detox program, it beckoned. Somewhere around day three, I was having a particularly tough time. I laid in a hammock feeling sorry for myself, outside the main hub of the retreat centre, which also served as a restaurant. I watched a guy sipping coffee (oh god, coffee), and eating fruit with yogurt and granola on top: my favourite go-to breakfast for years. I started obsessing about the granola. Knowing this would do me no good, I closed my eyes and tried to ignore the fluffy clouds of granola floating through my mind.

And then I heard it, wafting to me from a conversation at another table: “garlic with bubbling melted cheese on top”. I have no idea what they were talking about, and all further conversation faded into oblivion. The seed had been planted, and out of it grew a complete infatuation with the idea of cheesy garlic bread, which stuck with me through the rest of the agonizing detox retreat.

No, hunger wasn’t an issue. And even more surprisingly, neither were the colemas. In fact, I came to quite enjoy the feeling of clearing myself out, complete with a slightly morbid fascination with what was coming out of me.

But everything else was an issue. I was weak. Lightheaded all the time. My muscles atrophied. My flexibility stopped; it didn’t just get worse – it stopped altogether. I could barely fold forward to touch my knees, much less my toes or put my palms on the floor, as I typically can. I was irritable. Emotional. I was in agony.

I kept waiting for the tipping point. In the daily check-in meetings with other participants, it seemed that everybody eventually hit a point where everything got better. Where energy levels actually increased, and people started talking about extending their fast because they felt so fantastic and light and energetic. For some people it was after day three. For others, day five. My boyfriend, who was participating alongside me, barely had any trouble. He even said one day “if I could continue feeling this good, I wouldn’t eat food again.” For me, it never happened. It was a slugfest every single step of the way.

“Are you resisting something?” my boyfriend said one day in the gentlest sweetest voice he could manage, before backing away quickly expecting some sort of physical repercussion for his astute observation. Of course I was. But I had no idea what I was resisting. I had paid (a lot of money) to do this program, and I was committed wholeheartedly to achieving better health and wellness; I saw this detox as a way to hit “reset” on my body and eliminate any possibility that my depression and other symptoms could be related to my gut health.

So, I continued as best I could to surrender to the process. I gave myself permission to hate it. I mentally burst into flames a few times. I cried a lot. And I honoured every step of it as the release of some sort of pent-up emotional shit that needed releasing. While most of the time I like to analyze what I’m letting go of (childhood trauma? Adolescent body issues? Bad relationships?), I gave up. It was too much work. And so I just felt the agony for what it was.

All life is suffering.

Phase Three: The Ecstasy The Massage

I don’t even like papaya. But seconds after I put that piece of papaya into my mouth to break the fast, my world changed. The improvement was marked, sudden, and frankly unbelievable. By midday on the day I broke the fast, I was a new woman. My energy had returned, and then some. I was smiling and laughing. Other detox retreat participants, many of whom had never seen this side of me, didn’t even recognize me.

What was most shocking to me, was the immediate change in my outlook on life. I noticed it reflected in a few emails I composed. Instead of resorting to a stock phrase I’d come to rely on to describe a certain situation – a phrase with both a negative outlook and language – I wrote a different phrase. One more positive and grateful. And then I did it again. And later in the day, again. Without even consciously trying, I had changed my negative paradigm into a positive one.

Was is possible? Could I have kicked my depression by fasting for seven days and (quite literally) clearing out all my shit? I wasn’t ready to drink the evangelical koolaid of detox retreats quite yet, but as the days progressed, it seemed that indeed, the steely grip of depression had loosened.

So it was time to reward myself with a massage.

Massage parlours are everywhere in Thailand – especially anywhere tourists roam. Most of them look the same, with a signboard featuring a long garish menu of prices and services that vary minimally from place to place. But the joint that came recommended to me wasn’t one of these massage parlours. It was a relatively nondescript house at the side of the road. No prices, no billboard-style list of services. Nobody outside beckoning you in for a massage. There were always multiple pairs of shoes out front (indicating customers inside). All good signs.

Words like “divine” and “sublime” had been used to describe these massages, with the quiet caveat that you need to like deep massages. One fellow participant of the detox retreat said he went and was sore for days afterwards, but I discounted his review on account of my assessment that he was a bit “soft”.

Little did I have any idea what I was in for.

I should have known when I walked inside and saw a guy on fire.

He was lying on a bed in the informal waiting room where I was seated, surrounded by three Thai therapists, casually talking as if there wasn’t a guy on fire in front of them. They – patient included – were all chatting away in Thai, while a washcloth doused in some sort of fuel was in flames on the patient’s leg. I watched with wide eyes.

“It’s great for inflammation,” said a Dutch fellow sitting beside me, waiting for his massage. “I got it last week for my foot. Amazing results! But the swelling was back the next day.”

While a quiet inner voice whispered that perhaps the guy on a fire was an omen that I should find another place to get a massage, I was encouraged to stay by the idea that the fellow next to me was a repeat customer (they must be doing something right), and that the guy on fire was Thai (if the locals go, it’s gotta be a good place).

So I peered past the waiting room into the main massage room, from where I could hear various exclamations of pain or pleasure – I couldn’t discern which. It was a long, dark room with one wall lined with Thai massage pads, about ten in all, each a foot apart. Every bed had somebody in some kind of contortion with a look of agony on their face. Though this concerned me, I watched two people as their massages finished, bow with such overwhelming gratitude to their therapists, that I was taken aback. Looking past the agony, I noticed that a large percentage of the patients were also Thai – another great sign I’d come somewhere for “the real deal”.

As a minuscule smiling Thai woman in a pink shirt beckoned to me to come in for my massage, I stepped through the threshold and past the point of no return.

When her opening move was to press on the backs of my legs with the sort of pressure that I thought could only come with the assistance of heavy machinery, I asked her to lighten up the pressure a bit. She laughed. This was not that kind of place.

And so commenced an hour of a kind of agony I’d not before experienced. She walked on me; this woman who couldn’t have weighed more than 90 pounds soaking wet, exhibited the force of an elephant. She poked and pressed and prodded all the “right” spots with hands, fists, elbows, knees, and feet while flattening, stretching, and twisting me. When she wasn’t crushing the air out of me completely, I breathed deeply into the discomfort, while she held the pressure long enough for me to “relax” into it.

Once she and I got into some sort of rhythm, I expanded my awareness into the room. It was chaos. People on either side of me were moaning, some even screaming; mostly in agony, but with just a hint pleasure mixed in there so I couldn’t be sure.

“It sounds like a torture chamber in here, except everybody seems to be enjoying it,” exclaimed a guy a few beds down who was as surprised as I was at what was happening, to his own body and the bodies around him. At this, everybody laughed. Pain or not, the mood in the room was lighthearted on the whole, and we often collectively chuckled at the ridiculousness of others’ (and our own) cries of misery. The therapists had their own schticks too; it seemed like a running joke to them that people would come in such droves to be manipulated so violently, and would even keep coming back for more.

“Why do I do this to myself?” exclaimed one particularly vocal woman who was getting an oil massage next to me and sounded in inordinate amounts of pain. “Over and over again?”

Coming out the other side of the massage experience, I felt like I’d escaped with my life. Although I experienced moments of excruciating pain, I’d had worse in certain shiatsu sessions. In fact, a part of me kept waiting for it to worsen; to feel the sort of pain the screaming girl next to me apparently was. Instead it didn’t happen, and I felt grateful for my “elephant weakling” of a therapist. So grateful, that I too, like many before me, bowed deeply in gratitude for having survived. I even felt better for having gone.  All life is suffering.

All Life is Suffering: The Final Chapter

My last week in Koh Phangan was spent slowly and sweetly introducing my digestive system to different foods again; at the same time a sort of crash course to prepare my body for the onslaught of travel ahead, where I couldn’t guarantee what kind of food I’d be eating, nor when, nor where. Travel can be tough on the body, and I felt like the detox retreat was like hitting “reset” on everything. I hoped not to lose the benefits of all I’d achieved in those agonizing seven days.

But I also had to have another green curry before leaving Thailand, and Asia. I’d been bouncing around Asia for ten months, and almost as many countries of agony and ecstasy:

And I embraced, even embodied, the irony of my own suffering on the idyllic palm-tree lined hedonistic island of Koh Phangan. Perhaps I even let go of my suffering, just a little.

But you’d better believe, every time I have a mouthful of delicious ice cream, the first words out of my mouth will always be “all life is suffering.”

The post All Life is Suffering: A Month in Koh Phangan, Thailand appeared first on The Professional Hobo.

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I’m often asked: are there any mail services for travelers? Great news: yes, there are, all over the world! If you travel full-time, long-term, or even just find yourself moving a lot and hate changing your mailing address, you may benefit from using a virtual mailing service.

Updated For 2018: Latest rates and details below! 

What is a Virtual Mailing Service?

A virtual mailing service gives you a physical address, that you can set as your permanent address, and to which you can direct all your mail. In many cases there is even a physical person there who can sign for packages.

When you receive mail, the virtual mailing service will alert you to its arrival by emailing you a scan of the envelope. You can then direct them to do any of the following:

  • Open the letter, scan the contents, and email them to you
  • Forward the letter to your current address
  • Recycle or shred the letter

Most also offer the option to then forward the mail to you, which is handy when you’re receiving packages, a new credit card, or important government correspondence.

Many virtual mailing services offer a series of extra perks (usually for extra fees), such as depositing cheques to your bank account, fax services, and more.

While it used to be common for virtual mailing services to assign PO boxes to their customers, many financial institutions, government bodies, and even courier services won’t deliver to a PO box, which rendered it impractical to use as an official address. So these days, the vast majority of virtual mailing services give you a physical address.

There are many services offered in different countries. Obviously it’s probably easiest and best for you to choose a service based in your country of origin.

Some services offer you a choice of cities (or countries!) for your address to be based in (these are often slightly pricier), while others only offer one city option.

Why Use a Virtual Mailing Service?

If you’re living or traveling abroad, you might have a home base at a friend or family member’s home. You might be sending your mail there and having them sort it for you, but if you don’t want to burden them with that anymore, or if said friend/family member moves too often for it to be convenient, a virtual mailbox might be your answer.

Perhaps you’re not abroad, but instead are running an online business and want to convey the appearance of having a physical office (perhaps even one with a prestigious address); in this case, you can use a virtual mailing service that also has full office services like dedicated phone numbers answered by a receptionist, meeting spaces, and more.

Virtual Mailbox Fees

Fees for using a virtual mailing service vary greatly. Part of that is dependent on the amount of mail you receive and the number of perks you get.

Some virtual mailing services cater more to businesses rather than individuals. This means that they have higher standards of security and a larger repertoire of office-related services on offer, and therefore will cost more per month.

In most cases there is a monthly fee, with additional charges to forward mail/packages, deposit cheques, and receive/scan letters above the monthly quota.

You’ll find quite some variety in the fees listed below; remember that some monthly fees include a monthly quota of services (like forwarding x letters per month, above which you’ll pay extra per your usage), while other monthly fees are only for the address, and you pay for all additional services as you use them.

Authorizing Your Virtual Mail Service (U.S.)

As you might know, opening someone else’s mail is a federal offence in the U.S.; because of this, it’s important to authorize your virtual mailing service to legally open your mail for you.

That means filling out a USPS Form 1583, and also having it notarized.

Now, you may remember from getting your passport, that having something notarized means signing it in front of a legal notary, and usually involves a trip to the U.S. Post Office.

But what if you’re already on the road in another country and can’t get there? Or maybe you’re still in the U.S. but don’t have time to make it all the way to the post office.

Thankfully, there’s such a thing as online notarization now!

By using an online notary service, you can have your documents legally notarized by an official notary via webcam.

The service for individuals usually starts at $25, and for the convenience of being able to get your mail sent to you directly, it’s an extremely worthwhile investment.

Some online notary services include:





Virtual Mailbox Comparison

There are a lot of virtual mailing services out there; more by the day. One way to find the best virtual mailbox service for your needs is to search for “virtual mailing service + [your country]”. Below is a selection of companies that I found through the grapevine and with a few basic searches.

(Note that some of these links are affiliate links; making a purchase through these links won’t affect your own price but will earn me a small commission. Thank you in advance for helping to support The Professional Hobo). 

Virtual Mailing in the USA

Earth Class Mail

Earth Class Mail is arguably an industry leader, and they strive to be best virtual mailbox service for business, with a full suite of services. Most people I know who use them also complain about the cost (but continue to use them).

Fees: $99-$179/month


  • Integration with Dropbox and other software
  • Option to use them as your business’s “registered agent” in the U.S.
  • Higher standards of security
  • Multiple user logins
  • High variety of addresses available


  • Pricier than many travelers are willing to pay

US Global Mail

Fees: From $10/month


  • No hidden fees
  • Originally designed specifically for travelers


  • Only address is in Houston, TX
  • Page scans of letters not included

Traveling Mailbox 

Fees: $15-$55/month


  • Integrates with Evernote
  • Multiple mail recipients
  • Easy to use interface and app
  • Limited number of page scans included in monthly fee


  • Additional fee for some addresses

Virtual Post Mail

Fees: $10-$60/month

Post Scan Mail

Fees: $15-50/month

PO Box Zone

Contrary to its name, users get physical addresses, not PO boxes.

Fees: $8-21/month

Virtual Mailing Services in CANADA

Canadian Address

This is the only virtual mailing service I found with no monthly fee; they give you a free virtual mailing address and simply charge you for what comes in and what you want to do with it. And the prices seem quite reasonable.


Fees: $25-$55/month


  • Discount on the annual plan
  • Can scan magazines
  • Limited number of mail and page scans included in monthly fee
  • Multiple users


  • No check deposit
  • No junkmail filter
Virtual Mailing in the UK

UK Post Box 

Fees: Pay-as-you-go – 60 GBP/month

INTERNATIONAL Virtual Mailing Companies


Regus offers full virtual office services around the world, of which virtual mail handling is just one service.

Fees: From $37/month

Anytime Mailbox

These guys are taking over the world, slowly! As of the latest update of this post, they’re in nine countries, and strive to be the best virtual mailbox service for travelers.

Fees: $6-40/month

Determining What You Need

Once you’ve window-shopped a few virtual mailing services, you’ll become familiar with the terminology and pricing options. With a large range of monthly packages, it’s now time to determine the best option.

Here are some questions to ask:

  • How much mail do you receive on average monthly? (This will determine the package you choose; the less mail you get, the cheaper it is)
  • Can you reduce the physical mail you get by signing up for online statements?
  • How often do you need your mail forwarded?
  • Do you get cheques that need depositing? (Not all virtual mailing services can do this, but many can).
  • Can your address be a PO box? (Some virtual mailing services show your address as a PO box, which some organizations won’t accept or ship to).
  • Is having your address in a certain city or state important to you? (For example, for U.S. taxpayers, the state you “reside” in makes a huge difference to the amount of tax you pay; learn more about this and other tax issues in the Ultimate Guide to Filing Tax as a Digital Nomad)
  • How about what country?
  • Would you like it to integrate with software you already use?

Have you ever used a virtual mailing service? Which service was it, and how was your experience? 

The post Virtual Mailbox: The Easy Way to Get Mail When You Travel appeared first on The Professional Hobo.

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In March of 2015, Robyn (known as Robyn Around the World) left Seattle to go on an epic trip round the world to explore everything the world has to offer. What started out as a 12-month career break turned into over two years of world travel. Her style of traveling was slow. She’d stay in each city for 2-10 weeks to really immerse herself in the country and culture of each place she visited. During her travels, she picked up scuba diving and became a PADI Divemaster then a PADI Open Water Scuba Instructor. She worked as a divemaster in Indonesia and Thailand, and as a scuba diving instructor in Vietnam, Egypt and Mexico.

Although Robyn has since returned to a home base in the U.S., I wanted to feature her in a financial case study, since many readers have asked me about the possibilities of earning a living scuba diving while living on the road, and Robyn shows that it’s possible, and more so, how it’s done. Read on!

How long did you live/work on the road, and where have you traveled to?

I traveled for 32 months and visited 22 countries. Most of my time was spent jumping around Southeast Asia working as a scuba diving divemaster and instructor, but I also visited quite a few countries outside the Southeast Asia area.

  • Southeast Asia: Thailand, Laos, Indonesia, Vietnam, Cambodia, Myanmar, Philippines, Singapore, and Malaysia
  • South Asia: India, Sri Lanka, and Maldives
  • Oceania: Australia, New Zealand, and Cook Islands
  • Middle East: Abu Dhabi
  • Africa: Egypt
  • Europe: Greece, Spain, and Portugal
  • North America: Cuba, Mexico

Please describe what you did for income.

Most of my income was from working as a divemaster and scuba diving instructor. I also did a little freelance writing and brochure editing for a Thai tourism company.

How many hours per week did you work on average?

As a scuba diving instructor I worked six days a week. Industry standard is four days off a month. The brochure took me ~18 hours and articles under 90 minutes each.

How much money did you make?

Freelancing as a Divemaster in Thailand was a flat 900 baht (~$28) a day.

Scuba diving instructor varied from country to country.

In Vietnam, I made $500 a month plus tips and the dive shop offered free shared (two beds in a room with private shower) accommodation and lunch on the boat.

In Mexico, scuba diving instructors made $900 a month plus tips with resort lunch included, but no accommodation.

I made $350 for editing eight brochures for the Thai tourism company.

I wrote ~20 articles for a couple of companies during my time abroad where I made anywhere from $20-50 for short (500 words and less) articles.

I also volunteered for SEVENSEAS magazine where I wrote five articles (two were feature articles) for the magazine and had many of my photos published in the magazine. This is the only time I took on work that was unpaid, as I don’t support free work in exchange for promotion. This magazine is different in that it is 100% volunteer run and is a magazine that I believe in and their values align with mine.

Did you make enough money to support your lifestyle?

I made enough as a scuba diving instructor to support myself, as I wasn’t spending much money outside of diving. I saved $50,000 before I left to travel as I wasn’t really planning to blog for money. I started my blog more to keep a journal and have a place where my friends and family could go to read about my travels.

I also did one Workaway. I was planning to do a bunch, but then fell in love with scuba diving and went that route, but have met a few people who had been doing them for six months to a year and loved doing them. Workaway is the same concept of WWOOFing in that you work 20 hours in exchange for accommodation and some meals, but Workaway isn’t just farming. The Workaway I did, I exchanged setting up a CRM (Customer Relationship Management) system for them in exchange for a private room and a few meals. I did it for three months, in Chaing Mai, Thailand. Some of my friends did Workaways as teachers, nannies, working on butterfly farms, and household help.

(See also: Volunteering in Trade for Free Accommodation)

What did you like most about your career and lifestyle?

I loved meeting the locals and learning about local cultures and eating the food! I took cooking classes in almost every country I visited. I stayed mostly at Airbnb’s with locals and made lifelong friends from staying at local homes. Airbnb winded up being cheaper than dorms sometimes, so I rarely stayed in hostels and opted to live with local families.

I also loved teaching people how to breathe underwater and helping my students overcoming their fears. As a scuba diving instructor I have the power to change peoples relationship with the water and it’s such a great feeling when you see fear turn into passion.

What are some of the challenges you had with this career and lifestyle?

VISA’s! I was constantly playing the visa game. There were only a few countries where you could stay for 90 days; most were only 30 days. Some you had to get a full-page visa before entering, which meant I needed to go to an embassy (usually Bangkok) to get the proper visa. I also ran out of space on my fairly new passport and had to renew it in Chiang Mai, which was easy to get, but a pain to transfer the visa to the new passport.

What are you up to now?

I am no longer on the road. I’ve been back in the states for six months. My plan to travel was never long-term. I had only planned 12-15 months, doing mostly Workaways (I only did the one in Chiang Mai) but I was also open to doing anything that came my way. I started meeting people the second I arrived at my first Airbnb and my adventures just kept going for over two years. I didn’t have anywhere to be so I kept traveling until I felt ready to come home. 32 months is a long time on the road.

Even though it was only six months ago that I was still backpacking and working as a scuba diving instructor, it feels like it was a lifetime ago. Hands down, it was the best decision I ever made.

Any advice for the aspiring traveler about living and working on the road and managing finances?

I saved $50,000 before I left because I thought I wouldn’t be working that much. You don’t need to have this much saved to travel though, especially if you plan is to make money from other sources while on the road. Although, if possible, try to have a stash of money and an idea of what you plan to do for income before you leave. Additional reading from Robyn Around the World: What Does One Year of Travel Cost and Cost of One Year of Travel in Southeast Asia.

(See also: How Much Money You Need to Start Traveling)

Some of the ways to make money is freelancing, income from your website, and taking on side jobs in the countries you plan to visit. If you can have your loose plan mapped out before you leave, you’ll be in good shape to stay on track to find ways to make income once you get on the road.

I used Expensify to manage all my expenses. It’s a free app where you can log transportation, meals, lodging, and other. I exported all my data for each country and wrote a post yearly to show my readers how much I spent. It’s one of the best apps I’ve used abroad. (Nora’s Note: I’m not familiar with Expensify, but Trail Wallet is my own fav app for these tasks).

Is there anything else you’d like to add?

Enjoy your time abroad! It’s a privilege that you get to travel. Most of the people you will meet abroad (especially in SEA) have never traveled outside their home city. Take the time to really enjoy the country you’re in. Having income to travel is important, but try to take enough breaks during the week to really get out and immerse yourself in your surroundings and the culture of the city you’re staying in. (Nora’s Note: Great point! Work-Life balance on the road requires flexibility).

Want to know more about how to design your life so you can earn money while traveling the world? Check out Working on the Road: The Unconventional Guide to Full-Time Freedom.

The post Financial Case Study: Robyn Hartzell, Scuba Diving Instructor appeared first on The Professional Hobo.

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How do you go about filing taxes as a digital nomad? With an ever-increasing population of digital nomads taking to the road, this is becoming an increasingly prevalent issue. And it’s not easy to figure out on your own.

Good news! You don’t have to. Learn from experienced digital nomads in this GIANT guide with everything you need to know about filing taxes as a digital nomad.

BIG IMPORTANT NOTE: I am not a tax expert. Although I’ve researched this information as best I can, it is not gospel! No part of this article constitutes legal and/or tax advice. Also, tax regulations vary greatly from country to country, and this information is a general guide only. I highly advise you seek professional counsel with an accountant or tax preparer familiar with the tax regulations in your country of residence.

There. I am absolved. Now enjoy the following guide!


Most digital nomads are entrepreneurs or freelancers. Even if you have a telecommuting job, if your employer has hired you as a “contract” employee (ie: without benefits, pension, or other employment standards act requirements), then you’ll be filing taxes as if you’re self-employed.

Although this might seem daunting if you’re new to the self-employment game, the good news is that operating as a self-employed/freelancer means you are able to take advantage of way more tax deductions than you can as a salaried employee.

Tax Deductions for Digital Nomads

Any expense you incur in the name of earning your living is deductible. For most digital nomads, this will include things like:

  • Laptop, and all computer-related equipment, including laptop bags and accessories
  • “Office Expenses”, like notebooks, pens, and other supplies used in your work
  • Internet service
  • Phone expenses, including your cell phone, as well as SIM cards and service
  • Co-working space membership
  • PayPal fees and other banking fees incurred in the process of getting paid
  • Legal and accounting expenses
  • Professional fees, including licenses or insurance you need to operate in your line of work
  • Memberships and subscriptions, including association fees
  • Courses or education expenses related to your field

If you have a blog or website as part of your digital nomad career, even more expenses are deductible, such as:

  • Website hosting and domain fees (such as Host Gator or for larger websites, managed hosting like Performance Foundry)
  • Newsletter programs (like Aweber, click funnels, operating platforms (for selling digital products) and other marketing expenses
  • Advertising expenses, including boosting posts on Facebook
  • Blogging courses, or any educational expense incurred to help you run your business effectively
  • Affiliates you pay to help you sell your products
  • Employees or virtual assistants

And if you’re a travel blogger, great news! All your travel expenses are (generally) also tax deductible!

Note: All links in the above section are to services that I have personally used and thus endorse. If you click through these links and make any purchase, I will receive a small commission, which doesn’t affect your purchase price. Thank you in advance for supporting The Professional Hobo in this way!

Tracking Expenses, Managing Receipts

Before you can even consider filing taxes as a digital nomad, it’s important to keep records of everything. This requires organization and attention to detail, as you go. Don’t shove everything in a folder or proverbial shoebox to be dealt with at the end of the year. It will take you exponentially longer to prepare your finances, and filing taxes as a digital nomad will become a much bigger pain in the butt than it needs to be.

Here are a few different ways to manage receipts and expenses:

The Expense Spreadsheet

Me? I’m a dinosaur. Although I could rely a bit more on technology to manage my expenses and receipts, I’m really happy with my little system, and perhaps you will be too. Here’s my process – which you can customize (with as much or as little technology as you wish) to suit your own needs and preferences.

STEP 1: Stuff Tax-Deductible Receipts in Your Wallet

Every time you buy something on the fly that’s tax-deductible, just put that receipt in your wallet. When you’ve collected a few receipts in there, or at whatever pre-ordained juncture you determine (eg: weekly or monthly), pull the receipts out, and….

STEP 2: Log Your Receipts

I open my trusty expense spreadsheet and log my receipts. I log the date of the expense, store/vendor, expense category, amount, and relevant details.

As a digital nomad, it’s also important to log the currency you incurred your expense in; if you’re living the nomadic life, you’ll likely rack up expenses in a variety of different currencies. I also convert these expenses to my home currency to have a base-line understanding of my expenses.

The image below is the template I personally use to log my receipts and track my tax-deductible expenses throughout the year:

You may also incur expenses that don’t have a physical receipt (such as online expenses). In these cases, log the information accordingly in the spreadsheet, and create a folder on your computer to store online receipts.

STEP 3: Store Your Receipts

If you are ever audited, you’ll need to produce original receipts of your expenses. While some countries and tax authorities may accept digital images of paper receipts, I don’t leave anything to chance. Thus, I store all my original receipts as I go, by clipping them together and storing them in a plastic sleeve. At the end of the tax year, I seal my receipts in an envelope, for eventual storage with my previous years’ tax returns in Canada. (I either mail it back to Canada, or if I know I’ll be returning to Canada for a visit, I hang on to it until then).

Some receipts are only ever issued electronically (with online purchases for example); in this case I store these receipts in a folder on my computer.

STEP 4: Organize the Spreadsheet

When the time comes for filing taxes as a digital nomad, I prepare my expense spreadsheet by organizing all the data by category and sub-category. I tend to break the information down quite extensively, so my tax preparer can then massage the data as they wish and input various expenses in whatever tax category works best for my situation.

As you’ll see in the below image, I also break down each expense by currency. Depending on the currency you pay for things in, fluctuations over the course of the year can make a difference. Some tax preparers prefer to record/file expenses in the currency incurred and use an overall conversion rate designated by the tax authorities for that tax year, while others prefer to use the pre-converted figures. I allow my tax preparer to choose by breaking it all down for them.

Alternate Expense-Tracking Methods

You don’t necessarily have to manually log all your tax-deductible expenses into a spreadsheet throughout the year. Lots of digital nomads prefer to track expenses and manage receipts digitally.

There are a variety of mobile scanning apps that utilize your smartphone camera. Other people use programs/apps like Freshbooks, Quicken, Quickbooks, or financial management software. Some sophisticated apps even identify the relevant information from the receipts and convert it to spreadsheet format. However I’m not sure how effective this function would be with foreign receipts, in other languages and currencies.

My favourite expense-tracking app, Trail Wallet, just incorporated the ability to add images to recorded expenses. So, using this app, you can now record every expense in whatever custom categories (and currencies!) you wish on the go with the app, take a photo of the receipt, and later export all your data to a spreadsheet for final preparation and tax filing. (I actually use Trail Wallet to record all my expenses – tax-deductible and otherwise – for my annual expense reports, which is why I keep a separate (manual) log of my tax-deductible expenses).

Note: Although some digital nomads simply throw away their original receipts once they have a digital record of it, you may want to check with your tax preparer to see if the tax authorities in your country would allow digital records in the case of an audit. If they don’t, and if you can’t produce original receipts, you’ll be liable for a whole lot of extra tax payable.

Also: If you choose to store your receipts only digitally, then be sure to back everything up.

Tracking Income

Filing taxes as a digital nomad involves more than tracking and managing tax-deductible expenses; you’ve got to track and organize your income as well!

As a self-employed digital nomad blogger and freelance writer, I have income from dozens of different sources, from multiple countries and currencies, organized into about 10 different categories. Most of these income sources don’t send me tax slips, and none withhold taxes. So the responsibility is mine to claim all these worldwide income sources on my tax return.

Caution! Just in case you wanted to get sneaky and omit an income source (or three), remember that some of your clients/income sources file their payments to you as deductions on their own tax returns, and if you filled out a tax form for them at any point (such as a W9 or W8-BEN for U.S. payors), this income can be tracked to you, and you’ll be in trouble if audited.

I manually record the following income information in a spreadsheet:

  • Income Category (eg: affiliate payment, website advertising, book sales, freelance writing)
  • Payor
  • Date of Payment
  • Currency of Payment
  • Amount

I also convert payments to Canadian dollars for ease of understanding how much money I’ve earned.

At the end of the year, I organize all this information in a way that will be easily digestible for my tax preparer. It looks something like this:


If you’re a digital nomad, chances are you won’t be in your home country come tax time. Just in case you thought you could delay filing, learn from my experience:

Don’t Procrastinate

When I first started traveling full-time, I was away from Canada for two years. With very little income to speak of (and more than enough deductions), I knew I wouldn’t owe any taxes in those years so I planned to wait and file both years’ taxes when I returned to Canada for a visit.

CRA (Canada’s Revenue Agency) didn’t see it this way. 1.5 years in, they sent me a letter demanding I file the prior year’s taxes. I ignored it (knowing I’d file on my return), so they sent me another letter with a filing deadline.

I emailed my tax preparer for advice, saying I’d be back in a few months to file both years’ taxes anyway, and asked if I could ignore the letter. He said that if I didn’t file by their deadline, CRA could seize my bank accounts until I filed, since they were expecting that I owed them money and they wanted it.

Ironically when I did file (using the method below), I ended up getting thousands of dollars back. I figured that would be the end of CRA’s demanding letters so I was late in filing the following year’s tax return, only to get another demanding letter – and another tax refund of thousands when I filed. Now I just file my taxes from abroad anyway, but I’m sure if I delayed I would discover that they still haven’t learned.

Step 1: Find an Accountant/Tax Preparer in Your Home Country

This is best accomplished before you embark on your life and career as a digital nomad, but just in case you didn’t do this, not to worry. With digital nomads and expats forming an ever-growing demographic all their own, more and more tax preparers and accountants are becoming experts in tax planning for digital nomads and expats.

Further down in this guide, you’ll find a few suggestions depending on your country of residency, but if you want to find one yourself, simply search for something like accountant+ digital nomad + [your country of residence]. This will likely result in a list of tax firms, accountants, resource articles, and forum results where you can find recommendations.

I have a tax preparer that I’ve worked with for many years, so we have a good system going. I simply email him my spreadsheet (from wherever I am in the world at that moment), and he goes to town with it. To reach this level of understanding, we had an initial consultation where he told me how best to organize my information to enable him to do the most effective job on my taxes. I highly recommend you do the same. In the consultation, you may also need to sign paperwork in advance to give them the ability to communicate with your country’s revenue agency on your behalf (for example, to access income slips or in the event of an audit).

What is the Difference Between a Tax Preparer and an Accountant?

I’m generally avoiding the use of the world “accountant” in this guide because you may not need a formal qualified accountant to satisfy your tax preparation needs. Accountants offer a higher level of expertise, along with much higher fees. If your taxes are relatively simple, perhaps you can get away with using a tax preparer who still has sufficient expertise in filing taxes as a digital nomad, without being a fully-qualified accountant. My guy has been filing taxes his entire career and is awesome at what he does; but he’s not an official accountant.

Step 2A: Send Your Tax Preparer Your Income Information

Some accountants and tax preparers can (with your permission) access your income slips automatically through your country’s online tax system. These slips include not only certain employment income and payments from clients/employers in your home country, but also investment income like interest and capital gains.

If your tax preparer doesn’t have automatic access to all these slips, then you’ll need to collect and forward them. Most institutions are able to generate these forms electronically, so you can likely accomplish this from abroad.

You’ll also need to send along the spreadsheet of other non-reported income and sources, as per “Tracking Income” above.

Step 2B: Send Your Tax Preparer your Expense Records

Remember that spreadsheet you laboured over all year, and then further organized in preparation for filing your taxes? Time to send that along as well. The cleaner the records you keep, and the more clearly you itemize and break down your information, the better the chance your tax preparer will be able to kick some butt on your tax return.

Step 3: Pay Tax / Receive Your Refund

Once your tax preparer has your return ready for filing, they’ll advise you of the refund you’ll be receiving (which can be direct deposited to your bank account), or the amount of tax you’ll owe. Most banking institutions allow you to make your tax payments online.

To Incorporate or Not to Incorporate?

Lots of digital nomads choose to incorporate their online businesses, depending on the type of business they have and income it generates. Reasons for incorporation can include limitation of liability, sheltering of income from personal taxation, types/number of customers and employees, location of the business, and even company image.

Incorporating is costly and complicated to both establish and maintain; you’ll likely need the services of an accountant and a lawyer. To determine if incorporation is a good move for you and your business, consult with a qualified accountant with expertise in your field as well as expat/digital nomad tax legislation.


As a former Certified Financial Planner, I get a lot of questions about filing taxes as a digital nomad. Unfortunately for many of my readers (specifically those who are based in the U.S.), I’m not familiar enough with tax legislation to advise on anything beyond the most basic of details.

So I’ve asked Ines Zemelman to fill in the blanks. She’s the founder of Taxes for Expats (TFX), a specialty tax firm that helps overseas Americans file their taxes.

When I saw that she had published a variety of easy-to-understand tax guides such as the U.S. Tax Guide for Digital Nomads and the U.S. Tax Guide for Retirees, I knew she’d be able to help out. Here’s what Ines had to say.

Ines, do American Digital Nomads need to file tax returns, even if they’re not located in the U.S.?

As a U.S. citizen or Green Card holder, residing anywhere in the world, you still have to file U.S. tax returns declaring your worldwide income.

What kind of taxes do Digital Nomads need to pay if they’re living and working abroad?

If you work for a foreign employer you are not required to pay U.S. self-employment taxes (Social security and Medicare). If you work for a U.S. employer, they will automatically deduct this from your salary.

However, many digital nomads are self-employed, and may be liable for SECA (Self-Employed Contributions Act) tax. Choose your destination country wisely — some countries have signed a ‘Totalization Agreement’. If you reside in a country that has signed this agreement, you are exempt from SECA tax and instead pay Social Security taxes in the country where you live.

Here is a current list of the countries that have a Totalization Agreement with the United States:

Europe: Italy, Germany, Switzerland, Belgium, UK, Sweden, Spain, France, Austria, Finland, Ireland, Luxembourg, Denmark, Slovak Republic, Norway, Greece, Czech Republic, Portugal, Netherlands, Poland

North/Central/South America: Chile, Canada

Asia/Australasia: Japan, South Korea, Australia

If the only source of income is self-employment in a country with a Totalization Agreement, please be aware that the IRS may request a Certificate of Coverage from the resident country Social Security administration.

If you are not covered in the resident country then U.S. SECA tax cannot be exempt. If you are self-employed and live in a country without a Totalization Agreement, then U.S. SECA tax must be paid, even if you paid into the Social Security system of the non-U.S. country. However, you may still utilize this amount as ‘Foreign Tax Paid’ and use it for calculation of the foreign tax credit. If you choose to reside in a low-tax country like Hong Kong or Singapore, this is especially important.

What is the Foreign Earned Income Exclusion (FEIE)? Does it mean Digital Nomads who earn under $100k while abroad don’t need to file taxes?

This is often misunderstood. The Foreign Earned Income Exclusion (FEIE) is the amount you can deduct from your taxable income, during the course of filing your tax return, to reduce the tax you may owe. I.e. – if you make $75k USD, you likely don’t owe tax, but you still have to file. Until you file and properly utilize the FEIE, it is not granted to you.

If I set up a virtual address through a Virtual Mailing Service, does it make a difference which state I create my address in?

Yes! It makes a difference. You can avoid huge potential problems with the IRS and State tax authorities by choosing your state address carefully. You’ll find extensive information about this in our post: Virtual Mailbox and Why You Should Have One.

How do the Recent Tax Reform Changes Affect Digital Nomads?

The biggest changes particular to digital nomads are the corporate tax changes, which inadvertently also require individuals, who own foreign corporations, to repatriate deferred untaxed income.

We’ve written quite a bit about the recent tax reform here: Tax Reform & Expats – Winners and Losers.

One of your specialties is helping Digital Nomads and expats file their taxes from abroad. What happens if they want to use your services?

Step 1: Create an account here.

Step 2: Once you sign up you will receive access to your personal documents as well as our Tax Questionnaire. Your answers to the questionnaire will provide us with an overview of your situation and be used to prepare your return.

Step 3: You can schedule your Free Intro 30-min Consultation!

And as a special offer to readers of The Professional Hobo, Taxes For Expats is giving new signups a $25 credit! Simply enter the code Prof_hobo when signing up.


I’m a big fan of using the services of an expert tax preparer. One year I decided to test my ability to file a decent return (I was a Certified Financial Planner after all….it should have been easy); when my tax preparer got me an extra $3,000 back compared to my own return, I gave up ever preparing my tax return alone again.

But, for U.S. Digital Nomads who are keen to DIY their tax returns, here are some tips:

Foreign Earned Income Exclusion (FEIE) – As Ines said above, this income exclusion doesn’t preclude you from filing your taxes if your income is under $100k, but it does provide a lovely tax credit which will reduce/eliminate the federal tax you owe. File Form 2555 with your federal return.

Physical Presence Test / Bona Fide..

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Elaine Mercedes Mendoza is a global citizen and world traveler. She is a free spirit documenting her inspirational articles and trips around the world on FinallyElaine.com. Elaine also provides valuable budget travel tips and articles to bring out your wanderlust. She has been working as a freelance writer and teacher for those that benefit from her travel writing and experiences. Learn more about Elaine’s varied career that has taken her around the world (a few times over)!

How long have you been living/working on the road, and where have you traveled to?

I have been traveling as a choice since 2015 but I was always a traveler since I was in college. My travels (in general) have taken me to Czech Republic, Germany, Austria, Italy, Hungary, Poland, Thailand, Grand Cayman, Jamaica, Bermuda, Bahamas, Spain, the Spanish island Ibiza, Puerto Rico, Venezuela, France, Belgium, and numerous small towns and cities in various places. In The United States I have been to Los Angeles, San Francisco, Seattle, Portland, Las Vegas, and all the states from Massachusetts to Florida on the east coast. I have also stepped into Canada but there’s a lot more to explore.

However, Mexico is becoming more of my home base.

Please describe what you do for income, and how much money you make.

I teach languages online to executives in other areas. My school is European. 80% of them need Business English lessons and about 20% need Spanish lessons. Luckily I am native in both so am able to teach both. I can teach locally to Expats living in Mexico while securing 15 to 25 online hours. I make anywhere between 17 Euros to 34 Euros per class depending on the length and number of people.

However, this is just ONE of my ways I make money. Recently my teaching is bringing about 1500 Euros online per month. That may not seem like a lot to someone living in the USA, but when you consider that the average Mexican family makes somewhere around 10,000 MXN per month or 500 USD, I am considered to be doing excellent in this country. Most of the world would welcome me on this income alone.

In addition, I am a freelance writer. My articles have gone from $50 to $200 USD for one article alone. I have written for Microsoft, Atlanta Bread Company, and International Living to name a few of my clients. I also did some ghost-writing but did not enjoy that route. I felt there was a lack of integrity to it. I stopped doing it. Some months I have no writing work while other months I have more than I can handle. It varies and is very unpredictable.

In addition, I have recently been published as Co-Author in Time To Rise as one of 29 inspiring stories. All the profits go to The Gandhi Foundation to create a more peaceful world for all of us. My writing career is “just” taking off on a more global scale.

Finally, I do foodie tours in Playa del Carmen and design retreats. The retreats are designed around low season so that I can offer competitive prices for my escorted private trips. You get to have me as your host as I take you to some of my favorite destinations. While I do profit off of these trips, my most affordable retreat goes from $599 USD. I negotiate very well with vendors so that my travelers get an experience they will remember at a fraction of the cost. My foodie tours are a free walking tour and depending on the group, I get cash tips for my services. It is not unusual for me to make a decent amount in two to four hours of my time.

When you do not live a routine life, it leaves you open to all of these opportunities that present themselves effortlessly. I have even be asked to sing professionally. There are limitless ways to make an income. Find one or five that you love.

How many hours per week do you work on average?

Anywhere between 20 and 30 hours per week.

Do you make enough money to support your lifestyle?

Knock on wood, yes. The worst thing that has happened to me is suddenly losing a contract due to poor internet at that particular location. I was unemployed for four months and had to scout around for a new contract.

What do you like most about your career and lifestyle?

I love being my own boss. I do not have to ask HR for days off and wait for an approval process. There is no such thing as a commute for me or even work clothes (I do look decent from the waist up for my online classes). I do what I want for as long as I want or as little as I want. I am in charge of my own schedule.

Although I make less money than I use to when I lived in the Washington D.C. area, I do not have the expenses that I use to have. Life is just about my rent and having more awesome travel experiences. With no parking, work clothes, expensive cell phone bills, car expenses, and so on……..I learned to see abundance as freedom instead of material belongings. What price can we put on our freedom?

What are some of the challenges you have with this career and lifestyle?

While shifting from my “old” life to my “new” one, the mental obstacles have been my toughest challenges. At first I thought, “OMG, I was in a six figure income position and now I make less than half of that” but it is all an illusion. I have significantly more time NOW than I use to have. I discovered that time was our most valuable belonging. Also, at times I cannot predict how much money I will make per month. It varies all of the time. However, I am still paying my rent, enjoying many lovely meals wherever I go, and traveling to places I have never been to before. The ball is still rolling.

See also: Lifestyle Inflation: Why Earning More Money Sucks (the Life Outta You).

What is your vision for the future of your lifestyle on the road?

Most recently, I have decided to have a home base. I will schedule my travels in the late Summer and Fall. I guess you could say I have gone from being nomadic to being more location independent with a longer term home base in Playa del Carmen. I will be focusing more on my writing career and publishing more books. My goal is now to attract more speaking engagements and be able to share with others four retreats a year to awesome destinations.

Any advice for the aspiring traveler about living and working on the road and managing finances?

Yes, make a plan. My biggest advice is to save as much money as possible to carry you through the first year. It is a lot like saving for a down payment on a home. During that year, see it as the best investment you will ever make that may not be tangible. You are making a life change internally and externally. You are giving yourself the time to discover what you want to do and how you want to live. During this year, you will be guided on what to do next. It is a lot like the book The Alchemist. It does not matter what you do or where you go. Life is always happening right now in THIS moment.

Is there anything else you’d like to add?

Anything that gives you great joy also takes risk, strength, and a leap of faith. My lifestyle has not been easy to build and I sacrificed some aspects of my former life to create this one. However, it came down to “Do I work hard to make someone else money?” OR “Do I work hard to build the life I want?” Once I started seeing things as they really are instead of living off of expectations and illusions, the choice became obvious.

Want to know more about how to design your life so you can earn money while traveling the world? Check out Working on the Road: The Unconventional Guide to Full-Time Freedom.

The post Financial Case Study: Elaine Mendoza, Online Teacher, Writer, Tour Guide appeared first on The Professional Hobo.

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I recently spent six weeks in Hoi An, Vietnam; my eighth Asian country in as many months. (See Also: 10 Countries and 29,254 miles: This Was 2017). While the experience wasn’t necessarily everything I had hoped it to be (more on that here), on reviewing my photos I realized that Hoi An has a few stories to tell. I’m here to tell those stories, through pictures.

Hoi An Old Town

Hoi An’s old town (also known as Hoi An ancient town) is the main attraction, which is located halfway down the coast of Vietnam, a 45-minute drive from Da Nang (where the airport and train station are). With a blend of cultures and time periods, this well-preserved largely pedestrian area is full of restaurants and shops lining both sides of a river.

It’s usually pretty crowded, so if you want the place to yourself, it’s best to go early in the morning. Hoi An old town also takes on a new life at night, with colourful lanterns everywhere, and wooden boats to take you down or across the river to release floating offerings with candle lanterns.

Hoi An Cuisine Banh Mi Phuong – one of the best places for these traditional Vietnamese sandwiches in Hoi An

Hoi An reputedly has some of the best food in Vietnam – a country with amazing food no matter where you go. Anthony Bourdain helped put Hoi An on the culinary map, and the handful of eateries he frequented and mentioned on his television shows are not only worthy of their reputation, but also usually have a crowd to match.

Banh Mi Phuong is one such place; ironically I went because a Hoi An local told me it was his favourite place to get a traditional banh mi sandwich, only on actually going did I discover its popularity and realize why.

(Speaking of Anthony Bourdain, on his (sort of) recommendation, I saw “The Greatest Show in the History of Entertainment” in Tokyo – and I wasn’t disappointed!) 

Hoi An is also home to some special dishes you can’t get elsewhere, such as cau lau and white rose dumplings. While vegetarians may have some trouble eating on the streets of Hoi An (given the Vietnamese general love of meat, especially pork), if you have an adventurous palate and no dietary restrictions, I highly recommend trying anything and everything you see.

Vietnamese spring rolls are a staple Banana flower salad is delicious, and although it often comes with shrimp and pork, you can find vegetarian versions. Banh xeo is a Vietnamese crispy pancake (savoury, with bean sprouts, shrimp, and pork), which you then roll into rice paper. It’s a bit oily, but delicious.

Because of Hoi An’s culinary leadership, cooking classes are available everywhere, and they’re great fun. I found one on Get Your Guide that involved a short market tour, followed by a boat ride down the river where we anchored and prepared the above foods and a couple of other dishes. Learning to cut vegetables as garnish (tomatoes into swans, cucumbers into hearts, and carrots into flowers) was especially fun as we all made butchered attempts.

(Get Your Guide subsidized my tour, and the link above as well as in the image below will earn me a small commission if you book any tour on their site. These links help keep my site running, so I thank you in advance).

Hoi An Markets

As part of the cooking class, I got a tour of Hoi An’s large fresh market, which shed light on dozens of otherwise unidentifiable foods had it not been for our bilingual guide.

Making fresh rice noodles, a staple in most Vietnamese soups and other dishes, and a personal favourite National Pride

During my six weeks in Hoi An, a number of international soccer games were held. The air was palpable on the days Vietnam played; coffee shops and restaurants were packed beyond capacity with people crowded around televisions. When the Vietnamese team scored a goal, the cheers resonated throughout the entire town.

A few times during my stay, Vietnam won a game, and it turned into a huge event. The sidewalks were lined with people cheering on an impromptu “parade” of vehicles (mostly bikes) waving Vietnamese flags. Anybody (and everybody) with a vehicle could join this parade, which roamed around and around and around all of Hoi An, honking continuously.

This outpouring of national pride was an uncharacteristically gregarious display, given that to a larger extent in my experience, the Vietnamese people are relatively reserved. And the enthusiasm was contagious; it was hard not to get caught up in the energy of the game and after-game festivities.

Tet in Hoi An

Speaking of festivities, the Vietnamese celebrate lunar new year, known as Tet, which coincided with my time there. It’s both a good and bad time to visit Hoi An; because it’s Vietnam’s biggest holiday of the year, many restaurants and markets shut down for up to 10 days – which limits the things you can do if your time in Hoi An is short. Its also worth noting that the banks all close for about 10 days, which means that many ATMs end up running out of money. So if you’re visiting Vietnam during Tet, make sure you have enough cash before it begins.

If you’re around for a while and have made a few Vietnamese friends, you might be invited to some parties and dinners, which are beautiful displays of Vietnamese hospitality. My landlord and his family hosted a dinner for the tenants in the family compound where we all lived, and it was one of those quintessential “off the beaten path” experiences you can’t possibly plan for, but that every traveler aspires towards.

I found the build-up to Tet fascinating, with the change in pulse at local marketplaces (including the regretful disappearance of my two favourite food vendors weeks in advance), the increasing sound of karaoke parties wafting through the streets, and flowers. Oh, so many flowers. Pots and pots of flowers for sale. So many flowers, in fact, that they occupied space on entire sidewalks – a form of public decoration as much as items for sale.

The sun didn’t shine much for me during my time sampling Hoi An as an expat; the first proper day of it coincided with the appearance of these flowers, and the experience was magical, if not comical.

More on Vietnam, From my First Visit

How to Cross the Street in Saigon – and other Bike-Centric Observations

Vietnam Food Culture: Coffee, Street Food, and Hygiene

Back of the Bike in Saigon

Random Saigon: Little Stools, Big Wires, and Lots of Smiles

The post 6 Weeks in Hoi An, Vietnam appeared first on The Professional Hobo.

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Will Hatton has been travelling the world for nearly a decade now and he started his travel blog – The Broke Backpacker – three years ago to document his adventures on the cheap. His style of travel changed big time when he met his partner whilst hitchhiking across Iran. They fell in love, got a temporary Islamic marriage and headed off on a whirlwind journey across Iran, Pakistan, India, Nepal and Bhutan. Faced with mounting debt, they’ve been working hard on taking the first steps towards a life of financial freedom and earning a reliable income online. They’ve experimented with many different ways to make money and have had some wild successes and some dismal failures along the way.

Will was featured in a financial case study in late 2016 as a “jack-of-all-trades turned blogger”, and since then has changed tack (and income) dramatically through his revised efforts with his new wife. I decided to feature him again to demonstrate how much can change in as little as a year. Please enjoy this captivating interview!

How long have you been living/working on the road, and where have you traveled to?

I’ve been on the road almost my entire life and have travelled all over, however I’m not a passport stamp-collector and have no desire to visit every country in the world – I would far rather get to know a place properly. I spent two years living and travelling in India when I was 19 and that was a real game-changer for me; I learnt a lot about myself and what I could handle. (Nora’s Note: my own recent travels through India were also a game-changer for me!)

More recently, I’ve been travelling in Iran, Pakistan, Nepal, Bhutan, Myanmar and Indonesia. For about a year now, myself and my girl have been based in Chiang Mai in between adventures and it has been a really amazing experience to hunker down and actually get into a decent routine. It has been a different kind of adventure, and one I have thoroughly enjoyed. (See also: How to Find an Apartment in Chiang Mai)

Please describe what you do for income.

Over the last year, I’ve been involved in a lot of different ventures aimed at diversifying my income. In early 2017, I was facing mounting credit card debt and was in an extremely tight situation. My lovely wife, Esme, is just as broke as I am and on account of her expensive visas (she is Iranian and visas are expensive for Iranians) it looked like we were going to be split apart due to a lack of money. We settled down and focussed on working our asses off, jumping into as many opportunities as possible. As we grew and jumped on new trends, I invested more and more money, eventually racking up a credit card debt in the five figure range. 2017 was a scary and difficult year for us financially but we turned it around and by the end of the year we were making seriously good money.

Right now, we make about $5000 a month from The Broke Backpacker – this is mostly through affiliate sales on hostels, travel insurance, and adventure gear as well as sales of my ebook on how to travel the world on $10 a day.

A year ago, I launched Broke Backpacker Adventure Tours and in September 2017, I led the first tour of 11 backpackers on a 17 day expedition around Pakistan. We plan to run four more of these tours in 2018 and so far the trips sell out within a few days of us launching them. I won’t be running all these tours myself and have a close buddy to fill in for me as the lead guide where necessary. The tours make me a profit of about $12,000 a pop and provide me with valuable cash injections which I can roll over into other ventures.

I also run an SEO agency with another business partner; we launched this about a year ago and it’s on autopilot in the background – overall, it probably takes me less than an hour a week to keep this ticking over and it makes me a solid $1000 – $3000 profit a month.

I recently launched Active Roots – an adventure gear company – with a business partner and although we are currently about $10,000 in the hole, I am confident that this will be a very profitable business soon as well. Launching Active Roots was a really useful exercise as it taught me how to design products, liaise with China, organize warehousing space for our Amazon store, and handle the logistics of international shipping – I intend on capitalizing on this later this year by launching a truly innovative adventure product – watch this space!

Perhaps the biggest game changer for us financially was when I took the plunge and scraped together the very last of my credit… I put it all into Bitcoin and taught myself how to trade cryptocurrency. I diversified my portfolio and turned a $9000 stake into $350,000 in a year and I recently took out $50,000 which has enabled me to wipe out my remaining debt, treat my parents, buy plenty of cocaine and invest heavily into my (currently top-secret) master project for 2018.

How many hours per week do you work on average?

Right now, I work about sixty hours a week. I like to be busy and productive so sometimes I’ll work 100 hours a week. I do however have the option to take time off whenever I want but, honestly, that ain’t for me. I spent a lot of my younger years not working, living rough and struggling to understand why people would want to work – I now get it, it’s fun if you’re working for yourself and focussing on building your own dreams rather than somebody else’s.

How much money do you make?

Over the last twelve months, our income has exploded.

We have been driving a ton of traffic to Amazon and December was, obviously, our best month ever…

In December 2017, we made approximately…

  • $2560 from Amazon affiliates
  • $1600 from booking affiliates
  • $800 from insurance affiliates
  • $600 from digital product sales
  • $1150 from pay per view advertising on the blog
  • $3000 + from sponsored content on the blog

I was beyond stoked with this but I face an uphill battle to replicate these numbers in January now that the Christmas buying frenzy has ended.

I am however very confident that I can hit 20k a month by the end of this year – not including cash injections from the tour side of the business or cryptocurrency. Technically, I can only count cryptocurrency profit as in the bank when I actually take it off the exchanges and put it in the bank! So whilst I do have a portfolio worth about $350,000, I am going to only count the $50,000 that I have already taken out of crypto…

Do you make enough money to support your lifestyle?

I’ve lived on the cheap for years so my lifestyle is pretty spartan. I do spend a lot on nutrition now that I can afford to, and if I can solve a problem with money, I’ll do it. My time and stress levels are the most important things to me and I know that making money is pretty easy if you can just commit to the grind so I have no problem with spending money, I’m not interested in a savings account or retirement fund – my cryptocurrency portfolio is my retirement fund. I do intend on taking more money out in the future to invest in a string of epic hostels…

What do you like most about your career and lifestyle?

The total freedom to do whatever I want and the knowledge that the sky is the limit to what I can achieve. Having the freedom to live life on your own terms is intoxicating but it’s a life that is certainly romanticized by many influencers out there – in my opinion, everybody should try being broke; it’s a character building exercise.

What are some of the challenges you have with this career and lifestyle?

Right now, I’m more pumped about my lifestyle than I have ever been. It took some serious time – two years and counting – of blood, sweat and tears to get where we are now but I now know that I will never have to be worried about whether or not I can afford basic food or bills ever again. That is an incredible feeling.

What is your vision for the future of your lifestyle on the road?

I love to experiment and tinker with new business ventures – frankly, it’s just really exciting to me and I enjoy the learning curve. My dream is to unleash my master project, Ditch Your Desk in the next four months – I’ve been working on this for over a year already with my business partner, close friend and comrade in arms, Aaron. Ditch Your Desk will be the ultimate resource to show others the different paths to financial freedom through making money online – I want to lay out everything I’ve learnt; what works, what doesn’t work, how to invest wisely and how to motivate yourself when nobody else believes in you. The fact of the matter is that anybody can live this kind of lifestyle; you just need to want it enough, and hell – having access to the right resources certainly helps. Both me and Aaron are long-term backpackers and we want to give back to the backpacker community by arming our brothers and sisters with the intel they need to start their own online ventures.

Any advice for the aspiring traveler about living and working on the road and managing finances?

This lifestyle isn’t easy… Don’t even think about it if you’re scared to work hard. A strong work ethic is the most important part of being your own boss and running your own businesses but do not fall into the trap of trying to do everything yourself – learn how and when to outsource.

Want to know more about how to design your life so you can earn money while traveling the world? Check out Working on the Road: The Unconventional Guide to Full-Time Freedom.

The post Financial Case Study: Will Hatton, Crypto, Adventure Gear, SEO, and More appeared first on The Professional Hobo.

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I was attracted to Hoi An after reading a few articles about this charming, well-preserved historic town halfway down the coast of Vietnam. I last visited Vietnam in 2011 and fell hopelessly in love with the cuisine, so when I heard that Hoi An is considered to have the best food in Vietnam, the decision was made. My idea to visit Hoi An was further supported by a few digitally nomadic colleagues who generally had great experiences there. (See also: Digital Nomad Life in Chiang Mai)

Unfortunately it wasn’t until almost the end of my time in Hoi An that I got into a groove and began to understand more about expat life in Hoi An, and why (and how) people who come, often stay for many years. Instead, I wrestled with the place, eventually truncating my stay and leaving (earlier than intended) after six weeks.

Here’s what happened, and what I learned about expat life in Hoi An.


I had no idea just how dramatically the weather in Hoi An was impacting my mood until it improved (after I’d already made onward plans of course).

“Hoi An really is a different place when the sun shines,” said my expat neighbours when I was lamenting one day. A solid month of grey skies and chilly(ish) temperatures had severely affected my mood. (Silver lining: it confirmed that I have no business ever living in a place where the sun doesn’t shine regularly).

But I didn’t really believe them until the sun eventually showed itself. Not only did my own mood improve, but so too did the dispositions of everybody else. The energy of Hoi An literally changed in a day, as did the scenery; a formerly drab townscape took on a new personality and colour.

My neighbours told me so. “Hoi An is three months of misery, and nine months of sunshine,” they said. Lucky for me I was there in January/February, at the tail end of the miserable season, so the constant rain and floods already had their way with the place. That, I wouldn’t have survived.

So if I can recommend a time of year to go, it would be between March and July, before the suffocating heat of summer sets in, followed by the onset of the rainy season. “Three months of misery, eight months of sunshine, and one month of ridiculous heat,” is how another expat explained Hoi An’s humid climate, further describing the hottest time of year as pretty unbearable, which happens around July/August.

Choice of Neighbourhood/Transportation

Finding a place to rent in Hoi An was relatively easy. There are a few Hoi An Expats Facebook groups, one of which is dedicated solely to properties for rent and sale. In a day, my boyfriend and I had toured two self-contained apartments that fit our needs and budget.

One was brand new (like the many places being built for short/medium term rental purposes in Hoi An at the moment), on a busy street, and about a 10-minute walk from the historic old town of Hoi An (for $350 U.S./month all-inclusive). The other was part of a family compound in the quiet neighbourhood of Cam Thanh (on a rice paddy!) a 50-minute walk from the old town (for $300/month + utilities). The neighbourhood had a local fresh food market with a number of vendors selling hot/prepared foods, which at first glance appeared to have plenty of variety.

Given that we had just spent two months in a busy area of Chiang Mai, we chose the quiet more rural location of Cam Thanh.

(See also: How to Find an Apartment in Chiang Mai)

Life in “the burbs” of Hoi An: our street The calming allure of living next to a rice paddy!

Problem was, in keeping with my pattern of counter-intuitive living in Ubud and Chiang Mai, we also didn’t rent scooters, which is how everybody in this part of the world gets around. Given my own experience in a near-fatal accident in Grenada, and my boyfriend’s total lack of experience on two wheels, it just didn’t seem like a good idea. Besides which, we like to walk, we didn’t figure we’d need to visit the hustle and bustle of central Hoi An that much, and we could always Uber for about $2 each way.

Given our lack of scooters, our choice of rural neighbourhood was a mistake. We found ourselves isolated – logistically, culturally, and gastronomically.

Taking a yoga class or doing much of anything in the centre of town became too much of a “trek” to bother with on a regular basis.

Because we were living rurally and very locally, almost nobody spoke English, and we discovered Vietnamese to be a horrendously difficult language to learn and understand.

And the local selection of prepared foods at market vendors (which we had largely planned to subsist on) turned out to be quite limited.

Despite looking quite busy at first, our local market place left a bit to be desired over time.

And after my boyfriend suffered a rough bout of intestinal illness requiring antibiotics, western food was all he craved, which wasn’t particularly available in our hood. Except for one place……

The Dingo Deli Bubble

I read about Dingo Deli before arriving to Hoi An, as being a deli/restaurant/market with a selection of groceries you can’t generally get elsewhere (like imported cheese and meat and high-quality breads baked on-premises), and a very location independent-friendly atmosphere with great WiFi, lots of outlets, and even a “co-working” quiet room. (For digital nomads, it’s also worth noting that Hoi An has an official coworking space called Hub Hoi An. I didn’t go because it was a bit out of the way for me, with Dingo Deli so close).

It’s a foreigner joint through and through, featuring a western menu with western prices. You’d think the prices would keep people away (when a local Vietnamese banh mi sandwich costs less than $1, why would you pay $7 for a deli sandwich?); instead, the place is packed, all the time. I would know; I was among the ranks who made it a regular hangout and informal office space, often camping out for hours at a time. Why? Because it was the only place in walking distance of where I lived that was truly comfortable, well-equipped, and welcoming of people wanting to work and hang out.

And I learned over time, it was also a hub of expat life in Hoi An.

Learning About Expat Life in Hoi An

On my last full day I was seated at Dingo Deli when a man (who I’d seen there many times prior) approached me. “Do you live in Hoi An? I’ve seen you here a few times. I’m Syd.” (I’ve changed his name here just in case he wasn’t interested in eternal fame on my website).

“I’ve been here for the last six weeks (if you can call that living here), but I’m leaving tomorrow,” I replied.

After remarking on the unfortunate timing of our introduction, we chatted about our respective paths to and from Vietnam. He has been living in Hoi An off and on for 15 years, working the odd contract abroad (as a consultant), but always returning to Hoi An.

For Syd, life is easy in Vietnam. “I keep thinking ‘maybe I’ll try another place’, but Hoi An is where I always end up. You can live comfortably for $1,000/month. The weather is hot at times, and the rainy season is a drag, but on the whole the climate is a lot nicer than many other places. And you can really get stuff done here.” By ‘getting stuff done’, Syd was referring to Hoi An as a relatively untouched marketplace. He recently helped a local restauranteur launch a book which ultimately made a bigger splash than it could have in other more saturated markets abroad.

Gordon, the owner of Dingo Deli (a smart man who does the rounds daily and gets to know all his patrons, making the place a community rather than just a restaurant) is testament to the untouched markets of Hoi An. Eight years ago he brought his wife and two daughters to Hoi An from Australia, in an attempt to raise their girls in a non-suburban environment, away from a traditional school system and consumeristic lifestyle. His daughters are now almost grown and he feels he has succeeded in his mission. (On that note, I was surprised at the number of expat families with children I saw whilst in Hoi An).

In the last eight years, Gordon has dabbled in numerous businesses, and although he said it isn’t easy to run a businesses as a foreigner in Vietnam, it can be done (and judging by the constant stream of expats in and out of Dingo Deli every day, it can also be quite lucrative).

Syd and Gordon are both among the many ranks of expats who have made lives for themselves in Hoi An (and to a larger degree for other expats, Vietnam on the whole). The expat community in Hoi An is extensive, but feels small. With places like Dingo Deli (and other similar establishments, which you’ll discover after lurking the Hoi An Expat Facebook group), expats congregate and mingle to form a tight-knit community. When Syd and I finished our conversation, I watched him go on to greet and chat with half a dozen other expats, all of whom knew him by name.

The Visa Situation

While Gordon operates on business visas, almost all the other expats I met lived in Vietnam on tourist visas, skipping the border every three months to renew. When I asked Syd if he’s ever had trouble at immigration after 15 years of visa stamps in his passport, he shook his head. “No problem at all,” he said. This surprised me, given that many countries start to question your activities after a few visa runs.

What fascinated me was the number of expats who were able to find under-the-table work in Hoi An. Working online is one thing; waiting tables or teaching English is quite another; in a country like Vietnam, there’s no mistaking who is a foreigner and who isn’t. And my assumption that Vietnam would be strict about this (being a communist country and all) seemed to be misplaced.

I met travelers who were waiting tables to supplement their travel budget for anything from weeks to months. And I met full-on expats who had homes and roots in Hoi An, earning a full-time living at English schools.

So, if you’re interested in sampling expat life in Hoi An yourself, no problemo. Give it a whirl.

Cultural Integration in Hoi An

Cultural integration is a touchy topic among travelers and expats, and something deserving of a more in-depth exploration (coming soon). After almost a solid year of bouncing around Asia (Japan, Indonesia, Hong Kong, Macau, Sri Lanka, India, Thailand, and Vietnam), I can say that local cultural integration in Asia in general is incredibly difficult. With language and cultural barriers that are difficult to understand and transcend, you have to stay a long time and work very hard to be accepted. Although on the surface I found Vietnamese people to be hospitable and friendly, it was also somewhat superficial. I doubt that people with western backgrounds could ever truly be considered “local”. My own experience of living “off the beaten track” in a local community was more isolating than rewarding.

That’s where expat life in Hoi An comes in, providing a greater sense of community that’s lacking for foreigners. It’s not for lack of respect of the local culture by any means; rather, I see the bonding of expats as an outlet for connection – often, a deeper connection than the bonds we create in our home countries where we tend to take connection for granted. And frankly, in a greater world where connection is suffering everywhere we go due to our digital afflictions, perhaps a little in-person expat connection isn’t such a bad thing.

Given that my attempts to integrate by living locally were a bit of a flop, ironically, the most connected I felt in Hoi An was when I did a tour. Although hardcore “travelers” eschew tours as pre-fab non-local experiences, I learned more in one morning of touring Hoi An’s fresh market with a bilingual local and later cooking a meal with her, than I did in the rest of my six weeks.

I found my tour of choice through Get Your Guide; a site I recently discovered that aggregates travel experiences of all kinds with both locals and tour companies.

(Get Your Guide subsidized my tour, and the link above as well as in the image below will earn me a small commission if you book any tour on their site. These links help keep my site running, so I thank you in advance).

My Take on Expat Life in Hoi An

I’ll be ruminating in a future post about expat life in general (pros and cons) given my experiences around the world, and the intersections between “travelers” and “expats” therein.

With regards to expat life in Hoi An, I can say that by the end of my six weeks there, I had discovered a small but thriving community of expats from around the world who were living an inexpensive and socially fulfilling life – though not particularly a life of true cultural integration; something that I believe is difficult – if not impossible – in Asia.

If you want to give expat life in Hoi An a whirl, (learn from my mistakes and) give yourself the best chance of evaluating the place fairly by arriving at a climatically favourable time of year, and getting a scooter. The rest, is up to you.

The post Expat Life in Hoi An, Vietnam appeared first on The Professional Hobo.

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