How I Vacation

It has taken me a long time to cope with the fact that the way I travel is fundamentally different than the way most of the world does. At the tail end of a two-week solo trip to Taiwan and Thailand, I took some time to write down my idiosyncrasies.

Packing

I have religiously followed the OneBag philosophy since 2008, when I miraculously stumbled upon the greatest travel bag in the world, the Tatonka Flightcase, in a travel shop in Germany. My first Flightcase lasted ten years, and is still in service as an ultimate field bag. It can only be ordered from Europe (I recommend Amazon.de), but at 100 Euros, I can’t recommend it enough.

Because I travel with only one carry-on bag, I don’t need to pay checked baggage fees, wait around in baggage claim, or deal with lost luggage. The one bag philosophy also allows me to be flexible with changes — I always volunteer for flight bumps, which are much more likely for passengers without checked bags.

I keep packing lists in text files in my Dropbox — I have multiple different lists for different types of trips. As I pack, I open the file up in Notepad++ and mark off the items I include with an X.

Flights

My flights are almost always free, as I book award travel with points I’ve amassed from 5+ years of credit card churning.

Flying business class to Asia from my home base of San Francisco is an incredible steal, with the points price at only double the price of economy. With the ability to sleep on the plane, as well as unlimited lounge access and first-class service, it’s a no-brainer.

For US domestic travel, I prefer Southwest Airlines, as they offer flight changes up to ten minutes before a flight with a full credit refund. This allows me to book trips “on spec” to secure dates or pricing, and cancel at any time if I decide not to go. The credit can then be used to book the next spec flight.

I always aim to be the last passenger to board the plane. Often, I’ll post up in a seat right outside the gates and let the gate agents know to give me a heads up when they’re about to close. This serves multiple purposes:

• I don’t have to wait in line with the masses: it’s always absurd to me that the gate agents make a big deal about ushering you through the gates, despite the fact that the line is backed up to the end of the jet bridge
• I can use this time to continue charging my devices before flights that don’t have in-seat power
• Most importantly: I get my pick of any seat in the cabin. Because there’s always passengers that don’t show up, waiting until the last moment allows me to step onto the plane and quickly survey any potential upgrades. I look for, in order:
  • Any completely open rows
  • Rows with two seats open
  • Economy Plus seats
  • Rows towards the front of the plane — it takes 30 seconds per row to deplane, so if I can jump ahead 20 rows, I’ve saved 10 minutes of waiting

Free travel aside, the one amenity I splurge on is in-flight internet, so I can work from the plane. I find I’m actually pretty productive on a flight, as there’s nothing much to do and peer pressure from surrounding passengers makes me feel like I need to be getting something done.

Travel Companions

I always travel alone.

As an only child, I never understood the desire for constant companionship and validation. Not only do so few people share my travel ethos such that it would be near-impossible to find someone that was suitable to travel with, even if they did, our preferences would de facto make each of us better off traveling solo.

In my experience, people who always travel with friends or family can’t fathom this. They imagine solo travel as a lonely, isolating experience. However, as a solo traveler, I actually meet far more people during my travels than I would if I was with someone else, because it forces me to talk to everyone and see where it leads me.

The most amazing example of this was meeting two Mexicans at a torta stand at midnight, an hour after touching down in Mexico City, partying with them and their friends into the late evening, and then the next morning they came and picked me up from my hostel in a car and drove me around to their favorite spots.

As a solo traveler, I am much more likely to engage in these sorts of situations.

The Trip Itself

What I actually do during my trips departs sharply from our society’s expected ideal of “vacation tourism”. I don’t expect anyone to identify with the below and I mean not to demean anyone else’s preferred way to travel — the below simply works best for the authentic experience I desire.

Ethos

The most awkward situation before any trip is when another person hears where I’m going and says “You have to go to [socially acceptable tourist location X] and [socially acceptable tourist location Y]! They’re a must-see!” and I have to pretend like I’m interested in taking their advice. These places are rarely worth the time or price of admission. They’re often packed, expensive, and provide inauthentic experiences that only cater to tourists who want to get the tribe-approved photo for their Instagram profile.

My ethos is “travel like a local”. If a tourist would do it, I wouldn’t do it. I don’t visit tourist sites, museums, or monuments. I don’t take official or unofficial city tours.

I prefer long-term city stays, with a minimum of a week and usually around two weeks. This really allows me to establish a routine and feel like I’ve truly lived in the place.

I avoid any restaurant, café, or shop that looks like it caters to tourists.

I avoid most interactions with other tourists. If I talk to another foreigner, it’s usually someone who lives there and I try to use the local language instead of English.

Language

I prefer destinations where English is not spoken natively, and I learn the local language before arriving, using the methods I outline in the Beginner’s Guide to Language Learning. This is key to how I travel. It means that every conversation is a new adventure to practice my language skills and throw myself into new, unfamiliar situations.

Even if I’m only in the country for a couple days, I’ll learn the then most common basic phrases and abuse the hell out of them. The difference in service you receive when doing this versus only speaking English is immense.

Work

I work during vacation. I find this helps break up the day, gives me a regular routine, and because of the great culture we’ve built at TopScore, I actually enjoy working.

That being said, while in another place, I cut my work hours down from eight to maybe four or five a day. Trying to work full-time while on a trip is a fool’s errand — it’s impossible to be as productive as you are while you’re in your regular routine.

Lodging

I always book an AirBnB, never a hotel. I want to feel like I have a home. I actually do like hostels, but I can almost never stay in them anymore because I need a space to work.

I look for an “entire place” AirBnB with a workspace, a high-speed internet connection, and lots of natural light. I find that asking the host to run a speedtest in advance of booking is a useful filter for developing countries where internet quality varies.

I try to book in the “hipster” area of town, but avoid tourist-heavy areas. Zona 4 in Guatemala City and Xinyi Anhe in Taipei have been great picks.

Gym

The first thing I do when touching down in a country is find a local gym. I then proceed to go every single day. I go to the gym probably twice as often on vacation as I do at home.

The gym is my home base while traveling. It’s where I meet people, it’s where I get in contact with the local culture, and it’s where I catch up on some phone time. There’s nothing like getting swole in a new culture to truly learn its idiosyncrasies.

Quests

I’m sure the obvious question is: “So if you’re not doing tourist stuff, what are you doing?”

This is actually something I’ve never codified until now, but in thinking about how I spend my time, it represents the majority of my travel goals while on vacation. As a throwback to many childhood hours playing RPGs, I’m going to call them “Quests”.

A quests is simply a goal or errand, usually trivial, I need to accomplish while on vacation. This is a simple way to turn any problems that might arise on my trip into a fun solution.

Here’s an example: yesterday, in Taipei, my only pair of jeans ripped. So in the morning, I mapped out some shops where I’d have a high probability of finding some raw jawnz and set out on my way.

On the way, I realized I was hungry, so I stopped at a corner dan bing stand. The family running it was very interested in why I was learning Chinese, and their energy was awesome, so I stood there for half an hour, slowly eating my dan bing and chatting with them. A Taiwanese guy and girl, noticing I was standing, waved me over to their table. The girl was interested in going to America to work and was excited that I worked for a tech company, so we talked about American startup culture and everything under the sun for an hour and a half. After they took off and LINE IDs were exchanged, I walked over to Zhongxiao Dunhua’s boutique district. I soon found myself in the Taipei Levi’s boutique, talking with the shopworker in broken Mandarin and learning a ton of Chinese jeans-related vocabulary. I spent a couple hours walking through the rest of the district, checking out all the cool shops.

I ended up not finding anything I liked — but it didn’t matter. There’s a great German saying I quote often: Der Weg ist das Ziel. (“The journey is the destination.”) The quest to buy new jeans was just a proxy for another awesome day exploring a new city.

Miscellaneous

Other travel thoughts:

Traveling without an itinerary means I can never be disappointed. I treat every setback as another part of the adventure. Miss the train? Guess I’m having more fun in the same city I’ve been in. Bumped from the plane? Perfect, now I get to spend the night in a new city!

I’ve found Couchsurfing events, Meetup.com, and Tinder are a good substitute for meeting locals if I’m not so much in a “randomly talking to people on the street” mood. Also, I try to find activity-based events for activities you do I home: I always bring my cleats and a disc and find the local ultimate pickup game, and I’ve also taken krav maga classes while in another city.

I always travel with a quart ziploc bag of Optimum Nutrition Gold Standard 100% Whey Protein Powder. Getting adequate protein on vacation can be tough, especially post-workout, and this powder can be mixed into any store-bought water bottle and shaken up, if I can’t find a shaker bottle. On many days, it doubles as breakfast or a snack.