(I’m in Haifa this week at Wikimania, which is what prompted this post.)

There are two kinds of travellers — people who wing it, and compulsive hyper-rational utilitarian minimalists, like me. This blog post will bore or horrify the former group, but I hope it’ll be useful for the latter :-)

I travel with a small carry-on rollerboard, and yet I have what I need for pretty much any situation. That’s because I iterate — every time I have a problem on a trip, I refine how I pack so it never happens again.

And I have made a lot of mistakes. Running out of Sudafed once cost me half an afternoon in Amsterdam, where only one pharmacy is open on Sundays, and, by the way, pseudoephedrine is illegal anyway. Over the years I have forgotten and needed to hunt down all kinds of things, often in countries where I don’t speak the language. Out of sheer absent-mindedness, I have bought laptop power cables and phone batteries on no fewer than five continents.

But now I am pretty much optimized. Here’s what I do.

Use case #1: On the plane

On the plane, I’m space-constrained and weight-constrained, I’m either working or killing time, and my needs are totally predictable.

I always wear the same jacket with zippered pockets, with my passport and boarding pass in the left and my phone on the right. I never think about them because I know where they are.

My laptop and e-reader live in brightly-coloured neoprene sleeves, so I don’t leave them behind. A zippered pouch holds my earphones, plus a travel-sized power cable for my laptop, plus a phone charger. On night flights, I bring a tiny flexible-neck USB-powered light so I don’t irritate the people beside me by using the overheads.

I carry a ziploc bag that holds alcohol wipes, hand sanitizer, antiseptic ointment, paper napkins, pseudoephedrine, benedryl, ibuprofen, lip balm, a toothbrush and paste, mouthwash and a plastic spork. Most of that was recommended by Dan Pink, who gives excellent advice about how to keep from getting sick and jet-lagged on long flights.

The one thing I will never fly without is pseudoephedrine, because it’s illegal or restricted in many countries. If I get sick travelling and don’t have pseudoephrenine for my flights, I end up deaf and miserable for days afterwards. (Hello Lima, Nijmegen, Buenos Aires and Bangalore!) I’ve tried plenty of substitutes, and pseudoephedrine is the only thing that actually works.

If the box says PE, you know it does not work

Use case #2: Charging stuff

The first thing I do when I get settled in a hotel is plug everything in.

I carry this style of travel adaptor, because it’s self-contained with no parts to break or lose. The ones I own are black but I’d rather have them in a bright colour so I would notice when I am leaving them behind.

I carry the Monster outlets-to-go powerstrip, which is recommended by Larry Brilliant on Kevin Kelly’s wonderful Cool Tools blog. I have the four-outlet version as well as the three-outlet version: the latter is smaller and I’ve never missed having a fourth outlet. And I use these converters to connect the powerstrip to the travel adaptor. This set-up gives me the ability to simultaneously charge three devices from one outlet, which is useful in hotel rooms and has made me lots of friends in conference centres and airports.

All my mobile devices are micro-USB, but I carry a bunch of adaptors anyway: they don’t take up much space and have been useful when I’ve accidentally brought an old mini-USB charger or needed to charge my phone from my laptop.

All my electronic accessories. Neatly bound because cable mess sucks :-)

Use case #3: In the hotel, getting washed and dressed

Clothing: I don’t pack anything that’s bulky or needs ironing or dry-cleaning — I mainly pack unstructured clothes (like knits) in solid neutral colours, and I roll them so they’re compact and don’t wrinkle. I don’t pack like things together –all socks or all T-shirts– instead, I put complete outfits into ziploc bags sorted by date.

Toiletries: I carry a lot of different items, so I aim to keep the amount of each super-small. I buy micro-travel-size items from places like Minimus, and when I can’t get something in a small size, I decant from bigger containers into small leakproof plastic bottles like these from The Container Store. And because leakproof is more aspirational than actual, I pack those bottles into self-sealing waterproof bags. And then I pack those bags, perhaps somewhat freakishly, into a single zippered mesh pouch.

Leakproof bottles in leakproof bags :-)

Use case #4: Out of the hotel, working

I normally just need my laptop and phone, plus chargers. But because my Droid Pro only gets about eight hours out of its extended battery, I also carry an external battery pack which can fully charge my phone at least two or three times before needing a charge itself. It’s a little bulky to carry around, but better than not having connectivity.

Use case #5: Something goes wrong

I’ve got scans of my passport and credit/debit/ID cards online, plus the helpline numbers. I haven’t needed any of this yet, but when I do it’ll be there.

And, I keep a pouch tucked in a corner of my suitcase that holds stuff I won’t normally need, but will be grateful to have if I do. It includes a mini first-aid kit, laundry soap, tiny amounts of painkillers and other medications, a couple of granola bars, a manicure kit, some pressure point tools for stiffness and pain following long flights or long sessions on my laptop, miniature basics –mostly from Muji– like glue and tape and pens, plus a multitool and a few duplicate essentials like phone batteries and chargers. I add something new every now and then, but mostly I don’t touch it or think about it: it just lives in my suitcase.

That’s what I do. If you’ve got more or better hacks for ridiculously-efficient travel, please share them in the comments :-)