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13 FAQs From First-Time Nomads (Long-Term Travellers)

By Jennifer Chang

· Advice,Digital Nomads

I recently returned from an around-the-world trip, and I've had a lot of people reach out to ask about tips and advice. For efficiency, I've asked friends to send me their questions, and I've compiled the answers below. If you have any additional questions to add to this list, please contact me on Facebook.

This blog covers a lot of the logistics of being a nomad, but if you'd like to hear more about my personal experiences and adventures, please join me for my talk "Eat Pray Startup: One Entrepreneur's Search for Innovation and Creativity Around the World" on Wednesday, April 24, 2019, from 6-9PM at Cross Campus Santa Monica. RSVP here and use promo code *TRIBETHEORY* for a free ticket:


1. Did you buy an around-the-world ticket?
I didn’t for my 2019 around-the-world trip, but when I did my 2007 around-the-world trip, I did purchase the One World RTW ticket. In 2007, I think the RTW ticket made things much more convenient, but I found it unnecessary in 2019 now that nearly all of the airlines have become digitized and a bunch of local budget airlines have emerged. I spent about $4500 in 2007 dollars (so it should be more now) for a 4 continent, 20 flight RTW ticket, whereas I only spent less than $4,000 in 2019 dollars for 31 flights across 3 continents traveling a bunch of budget airlines and getting last-minute tickets. Note that when you’re traveling budget airlines, you can end up in some really ghetto airports on uncomfortable layovers (that dreaded 2 to 6-hour layover where you don’t have enough time to leave the airport). I recommend getting Priority Pass so you have lounge access while you wait it out.

I would recommend a RTW ticket if you have an airline group that you have loyalty on and want to maximize the benefit of miles traveled on your trip. Also, if you have any fear of budget airlines, a RTW ticket may save you money when flying only premium airlines. My 2019 trip involved airlines who have had some notorious crashes like Air Asia, Malaysian Air, and Thai Lion. (No Boeing 737 MAX flights though!) Buying tickets as you go gives you more flexibility in your trip, however.

2. Did you book/plan your flights in advance?
I booked most of my flights as I went, but a few notes on this:

  • Some countries require you to have an exit ticket when entering the country. You can get around this by buying a refundable ticket before you enter the country and cancelling once you get in the country or by buying a cheap bus, train or air ticket that you’re willing to toss if you don’t want to leave at that time. Be prepared for this to happen though. If I didn’t purchase an exit ticket in advance, I usually have a plan in case the country or airline requires this when I check in or arrive.
  • Be aware of holidays. I traveled from October 2018 to March 2019, so I was aware that I had a few major holidays coming up that could impact flight inventory and prices. I did book my flights around Christmas in advance so that I could get better prices. I was out of Asia by Lunar New Year, so that not a concern, but I would advise you to not only think about Western holidays like Christmas, but also about the ways that local holidays may impact your travels.

3. What about visas?
I didn’t run into any problems with visas. All the ones I needed, I was able to do online so I didn’t have to go to an embassy or anything. However, I am a US citizen, and visa issues will vary depending on your citizenship.

One of the more difficult and expensive visas for Americans is PRC China. Getting a Chinese visa usually requires a visit to the embassy (but you can go to any of them) and can take awhile to get processed. I entered China three times during this trip, but I was able to avoid paying for a visa by taking advantage of the Free Transit Visa. The way it works is that most of the major Chinese ports of entry will allow citizens of certain countries to enter the country without a visa if you are going from Country A to China to Country B. This does not work for round-trips, but works well for nomads like me. Depending on your port of entry, you can stay 3 to 6 days. More info about this visa is here. I've used this visa about 7 times successfully in the past few years, but I have also seen people in line with me get denied entry. The key seems to be having your hotel reservations and exit ticket printed and to be able to explain your plans for the "layover." Go on Tripadvisor and look up a few of the tourist attractions in the city you're going to so when the immigration officer asks what you're doing, just mention a few of these.


4. What luggage did you get? Did you get a backpack or suitcase? Carry-on only?
I am 5’3 (160cm) and I’ve just never been into backpacks. It’s just too much weight considering my little frame, and I’m paranoid that carrying all that weight will make me shrink! However, after all my travel experience, I’ve also learned that you should never take more than what you can physically lift yourself.

Traveling carry-on only is appealing, but most of the budget airlines have really low weight requirements for carry-on, like 7 kg, which is basically the weight of a carry on suitcase or heavy-duty backpack, so it makes carry-on only really difficult. A lot of the low-cost airlines also tend to check your bags at the gate anyhow, so I gave up on that dream.

I opted for a medium sized 25” suitcase for my trip which weighed about 20 kilos (44 lbs). I also had a pretty large laptop backpack. On parts of my journey where a suitcase would be too difficult to travel with, I would pack a couple of days worth of essentials into my backpack and then leave the suitcase at airport left luggage (most airports have this, but at varying costs so research ahead) or at a hotel I’d be staying at during some point of the trip.

5. What did you pack?
I had to pack for all 4 seasons, which made it challenging, but some of my must-haves on long trips:

  • Winter jacket - I had a North Face jacket with me for cold climates.
  • Fall jacket - I also had a lighter pleather jacket for temperate climates.
  • Thin layers - I try to find light clothes that can be layered on top of each other. Sweaters are too bulky and take up too much space. Rather, I can wear a t-shirt over a thin hoodie and one of my jackets on top. I buy everything in black and grey so I never need to think about color or whether something matches.
  • Travel yoga mat - I found this one on Amazon which fits neatly in my suitcase.
  • Compartments and bags - Put everything in smaller bags to compartmentalize your suitcase. This makes it easier to find things as well as to pack quickly. I love these Flight 001 packs. I usually have 2 bags for clothes - one for clothes I’ll need at current destination and a second for clothes I don’t need at current destination and can stay in the bottom of the suitcase for this destination.

6. What packing advice do you have for women?
Women particularly have a hard time traveling because the fashion industry has set ridiculous standards on what we need to survive and is constantly marketing us crap we don’t need. Here’s some of the changes I’ve made to accommodate travel:

  • Jeans are too heavy - go for jeggings instead.
  • Give up heels. They take up way too much space considering how little you’ll actually wear them. As someone who’s 5’3 and has always loved seeing the world from a few inches higher, this was difficult for me to give up, but I take solace in the fact that even Victoria Beckham gave up heels for travel. Instead, I now pack one pair of sneakers (I personally love the Nike Terras because of the traction. Mine have held up on city streets, mountain trails, and beaches), one pair of comfortable booties (for less casual occasions and business), and sandals.
  • Bye, bye handbags! My designer leather handbags have also been sacrificed. My travel favorites are Longchamp’s Le Pilage line - an easy find at most duty frees! Note that it’s cheapest to buy in EU countries.
  • Black and grey EVERYTHING. I find that just buying everything in black and grey makes things easier. Almost everything is available in black or grey, and while it means you’re devoid of color, it also means nothing can clash.
  • Skincare is necessary, but makeup is not. I am Korean, so I am a big believer in skincare. I took my full 7-step skincare regime with me, but I minimized the makeup down to just a handful of items. You can totally survive on one shade of eyeshadow and one lipstick.

Moral of the story: I loved Fashion, but I love Travel more, and therefore I’ve made the decisions to sacrifice Fashion for the sake of Travel. It’s a very personal decision, which I leave to each traveler to determine on their own, but I will say that my travels have been much easier since I ditched Fashion.


7. Where did you stay?
Where you stay is probably the most important decision you’ll make in any of your travels. The good news is there’s a lot of options. During my trip, I stayed at a wide variety of places and types of accommodation. Here’s how I think about it:

  • Am I visiting someone specific? If I’m in town to visit someone specific, I’ll usually stay with them. However, I generally feel that if I’m staying with a friend, I should accommodate their schedule and lifestyle. Being a good guest is just as important as being a good host.
  • Do I have lots of friends there? If I have lots of different friends somewhere, I usually will get an AirBNB or budget hotel room. My rationale being that I need to accommodate a lot of different people’s schedules so I need some autonomy of my own schedule. I also find that if I have a lot of friends somewhere, I’m rarely in the room so I don’t see the point of paying for an expensive place to stay.
  • Do I want to rest? Usually at some point in my trip I find myself in need of an introvert day or two. That’s when I’ll find a cheap city and book myself a luxury hotel for a couple of days. I find luxury hotels to be anti-social, but they are good when you want to cut yourself off from the world. Ideally, I like to find cheap, boring cities for my introvert hibernation days. Because there’s nothing to do there, I don’t feel the FOMO of staying in and hibernating. For example, this last trip I did 4 days of hibernating at the Westin in Chennai. I had no friends, business, or any interest in Chennai, but it’s a really cheap city so I used points to book the Westin. Westin has the best beds, but I don’t think it’s worth Westin prices unless I’m going to sleep the whole time. (Which in the case of Chennai, I did!)
  • Is it my first time or somewhere I don’t have a friend? Then definitely stay at a hostel. If I’m going somewhere for the first time and/or don’t have friends there, I find it to be most convenient to stay at a hostel. Hostels allow you to find other travelers and “crowdsource” your travels. There’s so much travel data out there, but it’s become an entire clusterfuck of its own to navigate, especially if you don’t want the cookie-cutter “Tripadvisor stickers everywhere” experience. Also, while hotels have concierges, they’re just making recommendations off Tripadvisor. The fact is, the concierge people haven’t actually been to these high-end places they’re recommending, nor are they necessarily avid travelers themselves. At hostels, you find other like-minded travelers who can give you relevant info based on what they just did yesterday. Also, you find travel partners, which means better travel photos and ability to split costs.


8. How did you find people to hang out with?
I love traveling alone, but I hate eating alone. Some ways to avoid eating alone (in order of effectiveness):

  • Staying at hostels is the easiest way to find travel buddies. Social is basically built into the business model.
  • Dating apps like Tinder and Bumble work everywhere. I love dating when I’m on the road. I find dates to be better than any tour guide I could pay.
  • Check in with your location on Facebook so your friends see where you are. I’ve had many cases where this resulted in friends introducing me to their friends in the location. I’ve also had a few situations where this resulted in me discovering I had a friend who just moved to the area or was also there at the same time.
  • Meetup and Eventbrite can be a great way to find events in the area, and maybe meet some people with common interests. Beware of language barriers though since depending on where you are, the Meetup may not be in English.
  • Workout classes can also be a way to find friends. Classes like aerial yoga and Crossfit are great ways to interact with others and possibly make new friends. Another tip on this would be to check out ClassPass and GuavaPass (which was acquired by ClassPass). These apps now cover multiple cities around the world, so you can go from city to city discovering new gyms and studios.

9. Which co-working spaces/companies did you use? Which would you recommend and why?
I did some coworking as I traveled. WeWork does offer a membership that allows you to access their worldwide locations, but I’d have to continuously pay even when I was in places without WeWork, so I opted not to do this. This would make more sense for a consistent digital nomad that plans to work through the entire trip. I did find a lot of great local coworking spaces. It’s pretty easy to find them on Google Maps (just search for “coworking”) or NomadList also was a good way to find the best spots.

10. How do you address safety?
It makes you very vulnerable to be in a new place, but over the years, I’m finding that apps and technology are making it A LOT safer for nomads. Some of my recommendations:

  • Always know where your phone is. Make sure you have a roaming plan or buy a local SIM. If your phone is working, you’re able to access information to help you navigate out of bad situations.
  • Use the ride-share apps whenever possible. Uber works in a lot of countries or there is usually a local alternative. (Grab, GO-JEK, Ghett, Ola, etc.) Say what you want about these apps and their business models, but the technology makes your travels a lot safer.
  • If you’re following my advice to try online dating on the road, then make sure you meet people in public places and/or get their social media info prior to meeting. I check their LinkedIn or Facebook to make sure that they have at least a few hundred friends, that people are liking and commenting (and that the comments sound like things an IRL friend would say), and to be safe, add them and then message them via the app so you know you’re not dealing with catfish.


11. How did you maintain phone connectivity throughout your trip?
I travel a lot, so I have the T-Mobile plan that lets me roam for free in 200+ countries. The plan gives free roaming because in every country, they’ve negotiated to have their customers roam free on a lower service tier. This means that my data service was crap in a lot of countries where the lower service tier may be 2G or worse. However, it worked well enough considering it didn’t cost anything. The only issue was that I found out during the trip that T-Mobile doesn’t allow you to use this for more than 5 months in a year. As such, I had to buy local SIM cards in a couple of the countries, but T-Mobile unlocked my phone for free and remotely via email.


12. How did you deal with money? Did you use your credit card, ATM or travellers’ checks?
I have an account with a bank that refunds all my ATM fees, so I used that ATM card to withdraw cash. The banks that tend to offer this are the ones that don’t have as many physical locations.


As for credit cards, I got the Chase Sapphire Reserve card specifically for this trip. It costs like $450 for the annual fee, but it comes with $300 in travel credit - so it essentially becomes $150. The fee is totally worth it though, because it also comes with Priority Pass, which is a membership card that allows you access into premium lounges in almost every airport in the world. I find this to be particularly important when you’re flying budget airlines like me since you end up in some really ghetto airports. If not this card, just make sure you have a credit card that has no foreign transaction fees, and you’ll be good.


Travellers’ checks are completely unnecessary in 2019, but I would recommend that you carry some US currency with you on the trip. There are some countries where the infrastructure may be an issue so your ATM or credit cards don’t work for some reason. (Although don’t stress too much about it because you can always just pull the currency from your prior stop and exchange it at the next stop.) Make sure that you get the money in $100 and $1 denominations. Some currency exchanges will give you a better rate if you’re exchanging $100 bills. Also carry about 100 $1 bills in case you end up in countries where vendors prefer to accept USD over their own currency (i.e. Cambodia). Having $1 bills allows you to negotiate prices.


13. Should I purchase travel or health insurance? What if I get really sick when travelling? Did you carry any medications?

I did not get travel and/or travel health insurance, but a lot of people will probably yell at me about this. I did, however, manage to get through the entire trip around the world without getting beyond a couple of mild colds. This is miraculous if you think about how many flights I was taking. A few tips for maintaining your health while traveling for a long period of time:

  • Yoga! I was practicing yoga throughout my trip, and I could feel its impact on my immune system.
  • Vitamins. Make sure you stock up on Airborne and other vitamin supplements. When you feel something coming out, nip it in the bud!
  • Eat with locals. I had one bout of food poisoning - in Singapore of all places, if it was food poisoning. However, I made it through some really disgusting places without getting sick. The key is to eat with locals!
  • Also pack the usual first aid stuff - bandaids, antiseptic ointments, charcoal, painkillers, antihistamine, etc. - but also don’t worry because you can find these anywhere.
  • I think Westerners particularly have this idea that the non-Western world is full of diseases, but it’s really not true. I didn’t get any additional vaccinations for this trip. (I did consult my doctor, who told me I had everything I needed for the types of countries I was going to.)
If you do get sick, you'll discover that healthcare around the world is better than you'd think, especially if you are an American. The US has one of the worst, most expensive healthcare systems in the world, so I feel better off being abroad. For example, in Singapore, you will find doctors in every shopping mall. I got sick in Singapore and walked into a clinic that saw me within 45 minutes and charged me only $40 for everything, including medication - and this was without insurance! There are poorer countries where the standard of care is low, but for minor health issues, you should be fine. Some places I've been had "expat hospitals" for foreigners. You'll usually see ads for these at the airports. Another option I've seen nomads use for healthcare is virtual doctors over the Internet.
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