There is a funny, if overused, Tinder line: “I hope you like bad girls because I’m bad at everything.”
I am bad at almost everything.
In the case of photography, writing, and the wholly underappreciated art of beating the living daylights out of other people’s cars, my badness stems from the ever-receding horizon of brilliance that defines all things when you earnestly try to get good at them.
In the case of small talk, empathy, and basic humility, my badness stems from my badness.
But if there is a single thing that I’m good at--some essential skill that I’ve honed over the past 5 months and 40,000 miles--it is the art of traveling light. When you pack and unpack, check-in and check-out, as often as I have, you get good at it.
I'll tell you how to travel with a single and reasonable bag, but first I'll tell you the infinitely more important part: why you should.
It’s liberating. To travel light is to leave yourself unburdened, to make yourself agile for the inevitable chaos of travel. Something's going to go wrong--or perhaps unexpectedly and extremely right--and the less you're holding when that happens, the faster you can adapt.
Besides, the transcendental aspect of travel is no more evident than when you return after a long trip, look around your home, and think "wow, I didn't need any of this crap."
A Theory of Baggage
Mistakenly, we tend to view baggage as some sort of reservoir for solving the maximum number of eventualities. We pace our through our closets, calculating (and overinflating) the cost of not having a jacket or a swimsuit or a hat. Meanwhile, the mass of our luggage is dictated by airline policy rather than the simple, if unreachable, goal of zero. Shortsightedly, we focus on the leg from home to the airport rather than the vastly more important segment of time that begins and ends at the sliding doors of our origin airport.
We need to view baggage as just that: baggage. It’s a weight that we lug around. It’s a thing that we avoid in potential mates. To overpack is to relegate yourself to the task of, first and foremost, figuring out what to do with your baggage. Avoid it.
Never Check A Bag
Above all else, your goal should be to avoid checking a bag. Even if you check-in online, you’ll wait 10-30-?? minutes just to check a bag. This is commonly referred to as hell.
First, I'll let George Clooney briefly explain in Up in the Air.
Second, because to check a bag is to run a three-legged race with the offspring of a shotgun marriage between a morbidly incompetent bureaucracy and some people who apparently rode to the airport on the motorized set of Jerry Springer. On two continents this year, I’ve watched couples try to convince Delta employees to put double trashbagged blobs of clothing in the hold of a $320 million Boeing 777.
Even after these human dumpster fires are extinguished and you make it through the “maybe Charles Darwin was wrong” experience of post-9/11 domestic security screening, you still have to hope that a delayed departure leaves enough time for your bags to be transferred on the 50 minute--now 27 minute--layover in Chicago.
If you have an international connecting flight (say, a stopover in London on the way to Edinburgh), you’ll have to go through passport control in London, claim your bag, recheck it for the flight to Scotland, and of course wait by the baggage carousel in Edinburgh. Then again, I've never been to Edinburgh, so there's a very real chance that I'm w-r-o-n-g.
Then, having spent an untold amount of time shepherding your bag to your final destination, you have to go and fucking drop it off wherever you’re staying because what’s more embarrassing than hauling a Danny DeVito-sized coffin into an art gallery?
Of course, if it’s too early to check-in to your hotel/hostel/airbnb, you’ll have to kill time in the sort of fluorescently-lit place that welcomes people with baggage and excess time.
But if you pare your baggage down to the essential, you can skip all of this. You’ll save hours per flight, divest yourself from the risk of your bag ending up in the wrong place, and drape yourself in the purple velvet fact of knowing that you can go anywhere you want at a moment’s notice. When the weather in Barcelona goes to shit and impulse shouts at you to book that flight to Vienna, you're packed in 5 minutes. When a stranger suggests that you sleep somewhere other than your own bed tonight, you're ready in 90 seconds.
Skip the four-wheeled, plastic-shelled shitbox. The things that make it mobile on hard, smooth surfaces make it extremely immobile on every other surface--otherwise known as Planet Earth--at which point you have an under-engineered handle and an awkward center of gravity to contend with. Plus, their rigid structure encourages you to fill them up. Double plus, you can't dump your clothes out of them and use them as bag for your stuff during the day... meaning you have to carry another bag.
Get a backpack. Take inspiration from the Department of Defense. If you can find it in a combat zone, that means it’s been boiled down to the essential. It’s not so much patriotic design as it is simple economics: we decide how much money the military gets to spend each year and it’s always less than they’d like--so they’re usually good at spending it effectively. Their standards are exacting, their tests can run for years, and they ultimately give the contract to the lowest bidder. Plus, in avoiding the curse of having to market this stuff to vapid consumers, they can skip all of the superfluous shit.
I use something which goes by the "Wow Just to Be Clear I'm Not With Them" name of an assault pack. It has a number of gloriously useful straps on it that allow you to compress or expand it to whatever size you need. I bought it for $40 on Amazon and I've put 70,000 miles on it already. It also has the distinct advantage of unzipping so far that you can lay it open completely. This is a huge advantage compared to many backpacks--which basically force you to stuff things into a black hole.
What to Put Inside the Bag
Above all else, don’t use other people’s packing lists. Think about what you, very narrowly and very specifically, will need. If you forget to bring it, you can always buy it--but you’ll probably find you didn’t really need it. Furthermore, think about your last trip not in terms of what you brought with you, but what you brought and you didn't truly use. Pursue this to the logical extreme (I'm talking about bringing one pen rather than two) and you'll find that this superfluous stuff adds up fast.
Bring dark colors. They don’t get dirty as quickly, disguise the fact that you may be underdressed for an unexpected formal event, and they don’t attract attention (useful for street photography).
Never bring more than 5 days’ clothing, regardless of trip length. You can rewear things and you can do laundry. Furthermore, most washing machines outside the US are small and dryers are comparatively rare. Bring much more clothing than this and you’ll spend your days doing multiple loads of laundry--and if you’re staying with friends, you’ll become a clothes-hanging pest.
Skip the shampoo and conditioner and soap. When was the last time you went into a bathroom that didn’t already have all of these? Bring toothpaste, though. And if you must bring liquids, downsize them--even beneath that magic 100 ml carry-on threshold that nobody seems to enforce anymore--or pay close attention to the shape of the packaging (a thin, flat, and wide containers are much easier to pack than typical bottles).
Fuck shoes. They’re heavy and bulky. If you require more than two pairs, you probably get your news from Buzzfeed. Bring one casual pair that you can put a lot of miles on and, if you absolutely must, bring a more formal pair. Make sure that the more formal pair fits in your fully packed bag (i.e. if you’re wearing your Big Boy Boots on the plane, you might arrive at your destination, find a long walk ahead of you, and discover that you can’t wear the more comfortable shoes because the Big Boy Boots won’t fit in your bag).
Bring a book--one thin paperback. Leave Ayn Rand at home. If you finish it, immediately conform to the first commandment of consumerism and buy another.
Bring a journal, but skip the buckled leather travesty that you bought while passing through Middle Earth. You’re not John Fucking Adams. Get a very thin notebook instead.
Skip the laptop. It’s 5 more inflexible pounds and you’ll spend most of the time proving it’s not a goddamn bomb. Besides, the whole point of travel is to get off the WiFisland.
Leave your ridiculous battery pack at home. After the drive-through Starbucks (but also every Starbucks), this is the single most offensively American Thing. It’s a Ponzi scheme for batteries. It’s also heavy.
Wool socks. Collectively, they represent the Grand Master’s Secret of Tolerable Existence. They’re better than cotton in cold and hot weather. For all my traveling, these are the only things I've ever wanted more of. Except for tall and caustic brunettes.
The only contingency you should plan for is a financial one. You’re going to Scandinavia, not Syria. Make sure your money is both accessible (many merchants in continental Europe don’t accept American Express) and that you won’t pay hefty merchant fees for using it.
How to Pack It
I've honed this packing system over the past few years. The central idea is to keep your clothes separate from pretty much everything else. By far, the biggest advantage is that you're left with a nice package of clothing that is easily removed from your bag upon arrival--thereby allowing you to convert your backpack into a much smaller pack in the span of 5 seconds.
It involves a bit of geometry, but if you learn the technique, you'll realize that it allows you to pack a lot more stuff into a lot less space than if you packed item by item.
Overview: you'll lay down pants and jackets first, then shirts, and keep going towards smaller items before putting a "football" of socks and oddly shaped things in the center. The football allows you to everything to wrap around something without necessarily folding--which means far fewer wrinkles.
So, uh, travel light. And, for the love of whatever dark humorist is writing this galactic screenplay, travel alone.