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.

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21 Responses

  1. UP in the air 😀

  2. Spot on!

    I figured out the pre-compiled toiletry bag and cables thing last year and it’s amazing how much easier it is to pack! I bought two razors, two toothbrushes, etc.

    I can travel with just the Tumi suit bag for up to three days…it holds a lot and is easy to carry.

  3. Stephen 10 years ago

    My travel became significantly less stressful when I sat down to make a list of the things that are TRULY irreplaceable on a trip. For normal business travel, there are two items on the list: my laptop and my contact lenses. Those two things would be a real pain to replace; anything else left behind can be solved by a quick trip to a store. I still try not to forget clothes, or nail clippers, but when I’m about to close the door to the house, I only obsess about the two things that really matter.

  4. Solen 10 years ago

    “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 … When things are falling apart, the simple task of not being able to find a pen feels like a disaster.”

    Well said. I’ve been trying to communicate this very point to a friend. You put it so eloquently. I think the relevance of this point goes much further than travel.

    Many great suggestions. The Global Entry program sounds like the best solution right now, especially because the check-in time is being extended beyond reason at some airports. For e.g. 2 hrs for local flights and 2.5 to 3hrs for international flights at MSP.

  5. Karl B 10 years ago

    Have basically the exact same setup but use Goruck gear ( for backpack/sub-bags and a TravelPro suitcase (I noticed that’s what all the pilots were using).

  6. What is the weight of the Tumi trolley? I can’t imagine getting five days of packing plus a trolley within carry-on weight. Here in Europe, though, I think they weigh carry-ons more frequently than in the US, and there’s usually an 8 or 10 kg limit.

  7. Great advice. I would also recommend mesh packing cubes( Great, light weight way to keep clothing organized.

  8. Sxy Links: 44 Interesting Reads for March 27, 2014 | SxySrvy linked to this.
  9. Walter 10 years ago

    I feel bad if I didn’t use every single piece of clothing in my bag. That means that I packed something wasn’t needed. But, then again, if unusual circumstances had occurred, like unexpected cold or wet weather, it would have been used. One has to strike a balance.

    I have to take a CPAP machine with me. The one I use is reasonably compact, but there are smaller ones that aren’t covered by insurance. Is it worth the out of pocket expense to get one that is considerably smaller?

  10. Crucial gear question: how does the Zebra Sarasa pen compare to the Pilot G2? (In other words, I’m pretty happy with the G2 as my ubiquitous, redundantly available utility pen; is there a compelling reason to consider switching?)

  11. “Karl B 2 days ago
    Have basically the exact same setup but use Goruck gear ( for backpack/sub-bags and a TravelPro suitcase (I noticed that’s what all the pilots were using).”

    That’s because TravelPro sponsors bags for most of the airline crews and they get their bags replaced every couple of years. I’ve had a couple TravelPros and both feel apart in about 2 years – granted this is traveling 40 weeks out of the year. For truly unbreakable luggage my recommendation is either Tumi or Briggs & Riley (Tumi is probably the more well known brand; my personal preference is Briggs & Riley based purely on personal aesthetics). As Rands said you will pay a little more but the premium is worth it both from a durability as well as peace of mind perspective.

  12. After 6 cross-country moves in 7 years, this is also my strategy for travel and moving. I have an anxiety disorder and traveling is just the worst thing ever for me. I used to be an over-packer, because I was always worried I’d need something and I wouldn’t have it. Now I pack twice — once with everything I think I’ll need, then I go back later with fresh eyes and get rid of anything I could do without. I actually prefer bags with no internal organization system because I use ziploc bags to keep certain things together (cables, bathroom stuff). I like your explanation about minimizing your own chaos to deal with the chaos of traveling, it’s a classic anxiety coping mechanism with the bonus of actually working.

  13. I’ve been a migrant computer worker / road hog for most of the last 25 years. Two lessons stick out for me: Carry a few simple meds in the shaving kit (Benadryl, Immodium, ibuprofin), because you will eventually sit next to someone with something communicable and you don’t want to have to search for that shit in a strange town. And tape your business card to your laptop, so you don’t have to argue with anyone about whether it’s yours when you get to the far end of airport security.

    Happy trails to you …

  14. I am happy that there are people way more compulsive about travel than I am 🙂

    One thing about “lines”; I don’t even count on ubers or anything anymore – I have a car service take me to and from the airport. A service like Groundlink works in many cities around in the world and are in general about a 30% charge over taxis. In Asia the hotels will have these services as part of their package. Worth every penny.

  15. Rands On “Cruft” linked to this.
  16. The reusable checklist is a godsend for travel. Keep it in Drafts then export it to a Reminders list before you pack.

  17. Gabriel 10 years ago

    “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.”

    I share this rage. Queuing is a unnecessary way of allocating resources, there must be a better way (or maybe a digital solution).