Tech Life Tucked away with purpose

Practical Advice for the Obsessive Compulsive Traveler

I’m at peak travel right now. I’ve been elsewhere for three of the past four weeks and that means I’m optimized for travel. I’ve already documented how I optimize moving my crap hither and fro in A Bag of Holding, but it’s during this peak travel that I’ve noticed a handful of helpful behaviors that decrease travel friction. These tips are large and small, but all essential for the traveler who would prefer to be hiding in their Cave, far from all people.

Count the Days. Standing in my closet and staring at collared shirts, pants, shoes, t-shirts, coats and a bevy other other clothing is daunting. I panic. Where do I start?

I start by building around a simple number. How many days will I be traveling? I need at least one outfit for each of these days, and a daily outfit is a shirt, jeans, socks, and underwear. Simple. One outfit. One day. Don’t overthink it, just put each outfit on the floor where you can see it.

Next, there are special events and situations, plus weather, that affect this particular trip. Fancy dinner? Suit. Extreme cold? Long underwear, gloves, a hat, and a scarf. Workout opportunities? T-shirt and shorts. These one-offs are easy to add to the growing pile on the floor. These items can also represent a set of other things that can be helpful on multiple days with multiple outfits: coats, sweaters, collared shirts, shoes, belts, etc.

I finish my daily pile of outfits with a small buffer. To account for random inevitable disasters, I add a pair of extra socks, underwear, and two t-shirts.

Five Days. That’s It. My rule of thumb is to pack for no more than five days. This simple prime number first constrains the number of clothing-related decisions that I need to make, but, more importantly, it reduces complexity.

My current main piece of luggage is a Tumi. Yes, it’s spendy, but having destroyed two similarly-sized pieces of luggage in the last four years, I’m taking the same approach with my luggage that I’m taking with my backpack. Sturdy – like take a bullet sturdy. During a recent long walk in Heathrow, the roller handle on a prior piece of luggage snapped off in my hand as I walked down the stairs. Watching my bag roll and bounce down the stairs reminded me: you get what you pay for.

This particular Tumi model has the usual array of handy, well-placed, and various-sized pockets. The zippers are solid and feel unbreakable. There is also a clever internal sleeve for shirts and coats that does an impressive job of keeping pressed clothing pressed. It’s slightly heavier than my prior bag, but that’s because I’m paying for sturdiness. I don’t want to be chasing my runaway bag down a set of stairs in Heathrow.

The final property of this bag is the most important. While I appreciate Tumi’s sturdiness, I need its size. This Tumi is designed to fit in the overhead bins of most planes, which means I rarely check my bag. I almost always have my luggage at my side. My five-day rule is partly designed around this constraint – I do have limited space. If my trip is longer, there is always a way to get laundry done, but what I’m really avoiding is, again, complexity.

For reasons I don’t understand, when something goes wrong during travel, it is usually accompanied by one or two other similarly-sized disasters. When I’m sitting on the tarmac and they announce “We’re having some mechanical difficulties” I’m both concerned about the aforementioned mechanical difficulties, but also the unpredictable implications of those difficulties.

Travel is complex. When you’re traveling, you’re moving amongst multiple large (and hopefully optimized) systems that are designed to get you from here to there with minimal fuss. When there is a failure in one of these systems, there is a cascading shitstorm effect that travels through all systems. For example: when it rains at JFK, you’re screwed on multiple levels. First, weather-related congestion in the sky, but also the taxis lose their minds as well. Things fall apart.

Every single investment I make in reducing complexity gives me an opportunity to avoid system failures around me. I rarely check my luggage, regardless of where I travel, because it prevents anyone from losing my baggage except me.

Pre-compiled Accessories Another complexity reducing maneuver involves sub-bags. I have a small cord bag that contains everything I need for an average day of technology and convenience. iPhone cable, small headphones, MiFi, nail clippers, a cloth to clean my screen, and that’s it. I use a Tom Bihn Clear Organizer pouches that are transparent on one side so I can see what the hell is in there at a moment’s notice.

Second, I use a Tom Bihn Snake Charmer bag for when I’m either traveling internationally or speaking – or both. This bag contains a power brick, all video connectors necessary to project anywhere on the planet, my presentation clicker, and back-up iPhone cables – just in case.

Lastly, there’s my toiletry bag. Like the bags above, it’s never unpacked and is ready to go at a moment’s notice. Yes, I duplicate everything I need that’s already in my bathroom, but unless I’m traveling without luggage or my backpack, the ready availability of all of these bags means the packing of my gear for any type of trip takes seconds. When you combine this with my superhuman clothing packing skills, packing for a week has turned into a 15-minute stress-free affair.

For this most recent trip, I replaced the toiletry bag I’ve been using for years. I bought one that was 50% smaller than my prior bag, which was already uncomfortably full. This leads me to the next tip.

Constantly Throw Shit Away. A tube of shampoo exploded in my toiletry bag during the most recent trip to Vegas. It wasn’t a disaster, but as I was cleaning the items I realized that 50% of the items in the bag were unnecessary. Let’s stop there for a second.

I’m someone who is allergic to cruft. Ask my wife. Ask my wife what happens when she puts something on my couch in my Cave. What’s that? What’s it doing there? When’s it leaving? I am a maddening jerk when it comes to cruft, yet here I am sitting in the bathroom at the Wynn cleaning shampoo off cruft I simply don’t need.

My travel tip is this: every three months, sit down on the floor of your office, take whatever bags accompany you around the planet, open them, and pour the contents on your floor. From there, you are making two piles: shit you need and shit you think you need. My advice: obvious need is easy, and if there is any question in your mind regarding need, put it in the other pile.

You will be shocked at what this simple selection process will do for the stuff you are dragging around the planet. Bonus tip: try this tidying exercise with desk drawers, crap on your desk, and friendships – your mileage may vary.

Tidiness pays off when you least expect it On recent flight back from Australia, I missed a connecting flight in Sydney because a prior flight was late. It was close enough that I had hope, but when I walked up to the counter and they immediately told me I missed my flight, I lost my shit.

Traveling is work for me. I remain in a constant state of stress because I’m fully expecting these types of system breakdowns where it is painfully obvious I have no control over the situation.

This is why I carefully wrap my cords and cables.

Wait, what?

If you go through my Smart Alec backpack, you’ll notice that each pocket is tidy. There is the pen pocket – 5 pens (Zebra Sarasa .5mm) – all tip down. The passport pocket, an internal easy-to-access pocket, also contains similarly shaped rectangular objects. There’s the side pocket, which contains three Field Notes, one of which is actively in use. I can figure out which one this is with the tips of my fingers because I clip a pen to it.

Inside all of the sub-bags, you will notice delightful tidiness. iPhone cables are carefully wrapped in circles. The power brick in the Snake Charmer bag is carefully ensconced in a well-defined cable. Everything is tucked away with purpose.

All of this obsessive compulsive tidiness serves a valuable point: as with my cruft purge tip, I’m fighting entropy. If I fail to put stuff back in the correct pocket, if I neglect cords and cables and shove them haphazardly in a random bag, I’m letting chaos win. One tangled cord means all cords will be tangled. When things are falling apart, the simple task of not being able to find a pen feels like a disaster. Why not avoid that stress and focus on the actual disaster?

Lines are System Failures. During a recent visit to New York, it was raining. It wasn’t hard rain, but it was enough to drive the taxis crazy. As I walked through baggage claim towards the taxi line, I gasped. The line for taxis criss-crossed through the terminal two or three times. This was easily a two-hour commitment to pay for the privilege of getting to Manhattan. This situation was solved elegantly with Uber, but is a good example of one of my most hated system failures: lines.

It’s an efficiency argument. My time is valuable, and standing in what I consider to be an unreasonable line gives me proportional rage. The irrational story I’m telling myself is that someone somewhere made a poor design decision that has resulted in me standing in this here line. Rage.

My current favorite line avoidance maneuver is Global Entry. This program in the USA allows “low risk” travelers to skip much of the security on USA-based outbound and inbound flights. Leave your shoes on, leave your computer in your bag, and less radiation. Bonus.

Inbound international flights are where Global Entry really shines. There are no forms to fill out; you just walk up to a kiosk, get your picture taken, scan your fingerprints, and you’re bypassing the line the flight crew stands in. When you combine this move with the fact that my luggage is at my side, elapsed time in customs usually decreases from 45 minutes to 5.

Global Entry is $100 for five years. You need to fill out an application and eventually schedule an interview, for which you need to travel to a regional office, which is usually at your local airport. You may have concerns regarding the government knowing more about you via this process, but if this is your concern, I suggest getting off the Internet.

Your Travel Life

I started this piece at the San Francisco airport. I wrote the majority of it in the city of Leicester. I found the ending sitting in the park at Soho Square, and I finished it somewhere over northern Canada at 32,000 feet. That’s five days. That’s 5,654 miles and counting. This might not be your travel life, but these could be your travel tips.

Many of these practices: pre-compiled accessories, purging, and tidiness – they take both up-front and ongoing investment, but all of the work serves a clear purpose. When you travel, you are guaranteed to end up somewhere strange and unfamiliar. But whether you travel for work or pleasure, you are on an adventure, and there will be new faces, strange accents, and unexpected circumstances. The less you have to think about the simple things you should be taking for granted, the more you can enjoy the adventure.