Packing the personal item

Barring specific gear recommendations or small tactical tips (like buying an international SIM card), I don’t actually think there’s that much that needs to be said about packing for a business trip.

My entire List Of Extremely Important Things To Know About Packing is as follows:

That blissfully short list and its linked articles should help you cover virtually almost all of your bases except one: packing the personal item. The “personal item,” in case you’ve never flown before,1If this is actually the case, either you must be about to embark on your first-ever business trip (in which case, congratulations and welcome to the club!) or I’m not really sure what you’re doing here. Either way, I might consider watching Up In The Air for what may be the most accurate portrayal of this strange, strange world ever committed to film. is the bag that has to fit under your seat, full of things that you want to be more readily accessible than things in your suitcase.

There are two main components to the personal item: the bag itself, and what goes in it.

Choosing the bag

The size requirements for a personal item are basically just “will fit under a seat,” which could plausibly mean everything from a 40L hiking pack to a clutch purse.

Because of this leeway, it’s tempting to bring the biggest bag physically possible, just in case you need a little extra room to fit an unexpected item or two. Resist this urge, and instead choose a medium-sized briefcase, backpack, satchel, or tote; something that can hold a computer (or two, if you regularly work for clients with intense information security policies2Or as I normally refer to them, good infosec policies), a book or kindle, a pair of good headphones, a modest amount of cords, cables, and papers, and not much else.

Why a smaller bag? Because you will always fill the bag.

Even if you try to always leave it half-empty or with extra room, it will become full again, quickly. Personal accoutrements will always accumulate to fill the available space in the bag, whether it’s a huge roll-top backpack or a modest briefcase. Even if you have a tendency to need a lot of things, try a smaller bag for a while and see how much pain it really causes..

If you don’t believe me, feel free to try this experiment next time you go on an extended trip: if you decide to bring a checked bag, you will magically find that you need almost exactly a checked bag’s worth of stuff. If you force yourself to fit everything in a carry-on, you will find that you need almost exactly a carry-on bag’s worth.

With a smaller bag, you’ll bring — and therefore have to schlep, deal with, lose, and replace — less stuff overall. Don’t ask me why our brains work this way, but they do, and we might as well take advantage of it.

The bag should be durable and functional, but should still look professional.

if you work in a client-facing role and don’t pay careful attention to the subtle messages your clothing and accessory choices say about you, you are leaving simple intrapersonal wins on the table. With a few exceptions, tech CEOs and investors do not wear hoodies and Allbirds because they can’t afford to or don’t like wearing suits; they wear them because of the image they want to project.

Function is ultimately more important than style, but that doesn’t mean you need to be carrying around something that looks like you just got done climbing a mountain. Many manufacturers make smart and functional bags that have built-in computer protection and wouldn’t look out of place in a boardroom, options that provide all the carrying capacity (and even comfort) of one of those big SwissGear nylon backpacks without sending the same incoherent, delegitimizing visual message about the wearer to clients.3Can you tell that my undergrad degree was in visual communication?

I am generally not a fan of backpacks at all, but this is more an aesthetic choice than a practical one — TUMI and others make smart two-strap models that don’t make you look like you’re an intern that has to lug around their textbooks so they can make it to class later.

Assuming you’re with me on this no-backpacks argument, this rule also becomes a secondary argument for a smallish bag. Any non-backpack bag needs to be small (and therefore light) enough that it’s not going to break your spine when you carry it around in your hand or on your shoulder, both in an airport and during the workweek. Bags with cross-body straps (messengers, satchels) are better in terms of shoulder and neck strain than single-arm totes, but either can work if you don’t overstuff them. Also, try to find something that can be somehow attached to your suitcase (or at least set on top of your suitcase and held in the same hand as its handle) so you can have a free arm while moving through an airport.

Women’s ‘work totes’ and briefcases naturally trend towards these criteria, but there are a number of smart options for men too, including the classic Filson briefcase and a number of offerings from Tumi, Saddleback, Jack Spade and other smaller (and larger) manufacturers.

A bunch of compartments are not actually a good thing

My preferred style of bag in almost all contexts is one or two big compartments and that’s it. I dislike bags with a bunch of internal or external compartments, because these compartments are normally poorly designed (how many pens have you ever put in those weird backpack pen loops), poorly sized, hard to get to, and make it hard to remember what got put where. Most critically, they cannot be removed from the bag, meaning I can’t dig around for something without also hoisting my bag to face level to dig around in a tiny pocket.

Instead, I use a trick that I picked up from my fellow traveler Nick Disabato: I combine a bag that is mostly or entirely one big pocket with a small collection of 12.5″x7″ Klein Tool Bags. (Any medium-sized zippered canvas bag will do; Klein’s are just well-made, extremely durable, machine-washable, and produced in the USA.)

Buy a few zippered bags in different colors, and designate each one for a specific small thing that you regularly carry with you — I have a brown “electronics” bag (for my standard chargers and adapters, a couple of flash drives, a rechargeable battery pack, and backup headphones) a black “stationary” bag (square and tab-style post-its, index cards, pens, pencils, markers), and a gray bag for the mobility/self-massage tools I normally travel with (lacrosse ball, light and heavy stretch bands, and a small trigger point tool; this one normally goes in my carry on). The small bags go in the bigger bag, and when you need something, you just pull the appropriately colored one and look inside. I haven’t had to rummage in the bottom of a bag for a pen in years.

On top of these ‘standard’ kits, you can also create pre-packed bags for special purposes, like a conferences bag (business cards, rarer but potentially necessary dongles, presentation remote, hand sanitizer), a running-a-workshop bag (sharpies and post-its, flipchart and whiteboard markers, USB drive for the inevitable run to a print shop) , an international travel bag (sleep mask, international plug adapter, passport, pills to help you sleep on the plane and be awake after the flight). These can live in your house and be grabbed as you’re packing, eliminating the scramble to remember and find everything at the last minute.

What goes in the bag

We’ve touched on this already by talking about the Klein-based organization system, so might as well get into it wholesale.

There are three main things to consider when packing a personal bag:

  1. It should contain your computer, charger(s), notes, notebooks, documents, pens, and anything else you might need for doing your job.
  2. It should contain everything you need to help you productively occupy your time during travel.
  3. It should contain nothing that you wouldn’t actually use in a week of work.

Things you need to do your job

This one is pretty straightforward — if you need it for your job, bring it. Make a checklist so you don’t forget things. I find it handy to actually write down a physical checklist until I use and revise it enough to see it’s not changing much, then I try to memorize it.

Things you need to productively occupy your time

30,000 feet in the air is one of the few remaining truly distraction-free environments, assuming you don’t buy the WiFi.4and I encourage you not to; it’s an overpriced distraction that’s rarely necessary for work. There’s no Twitter, no Facebook, no article to read about the latest Game of Thrones fan theories. Just you and your book, work, or thoughts. Don’t squander this undistracted time.

Practically, this means that remaining space in your personal bag should be devoted to things that support this mission of keeping you happy and occupied during travel. I like to think about this in terms of identifying activities and then identifying the stuff I need to support those activities, rather than jumping directly the things themselves.

Working on a plane

I personally find a plane a bad place to do anything that requires extended deep focus, like long-form writing, from-scratch presentations, design, or non-trivial coding — there are too many interruptions, distractions, and opportunities to get up and walk around. I try not to save mission-critical work for the plane, and prefer to see it it as bonus ‘alone work time’ to tackle non-critical and overlooked tasks.

This still leaves a lot of options: you can read material, respond to emails, edit, clean up or punch up a presentation, clean up your folders, clean out your inbox, plan your week, recap and reflect on your week, type up notes, or (my personal favorite) review notes and think about larger-scale strategic questions about an account, relationships, team, and objectives that are easy to ignore when you’re stuck in the tactical hell of boots-on-the-ground work.

You can also learn on a plane

Reading, screencasts, podcasts, webinars, and other learning activities are ideal for plane time — whether you’re learning a work-related skill, a hobby, keeping abreast of the news or industry trends, or even reading an article from this blog and sketching out a plan of action for implementing some of its strategies (nudge nudge).

Time you enjoy spending is productive time

Just because I strongly encourage you to spend your plane time productively doesn’t mean I’m discouraging you from enjoying yourself. Watching a movie or a TV show you’ve been meaning to see, listening to a comedy podcast, knitting, taking a nap, or otherwise spending your time exactly how you want to be spending it is a worthwhile use of time.

The kind of ‘wasted time’ I want to warn you against is time wasted because of poor preparation — it’s getting expensively drunk and watching Duck Dynasty on the inflight entertainment TVs because you didn’t bring anything better to do, not having a nice evening catching up on your favorite show.

If it makes you happy, it’s encouraged.

Whatever you bring, prefer digital

Digital content is especially nice for travel because it takes up no physical space and has no weight — as much as I like physical books, they take up bag space, and weigh literal pounds, and I normally jump between two or three books, plus a trove of stored short- and long- form articles from around the web as my attention ebbs and flows.

I suspect this goes back to a teenage feeling of procrastination pressure — without multiple options, my one option feels like a chore, and it’s harder for my brain to dig into it. The solution? Give my brain another thing to “procrastinate” on reading the first thing with.

Allowing for this optionality makes digital content basically a necessity. I normally have one paper book and a small amount of printed work-related reading as a fallback for dead batteries and device failures, but everything else goes on my Kindle (an old Paperwhite), in my Instapaper queue, or on my phone as an audiobook.

Be sure to make the time to load all of your webcasts, podcasts, ebooks, audiobooks, articles, work, learning content and so-on beforehand, and test that they work while in airplane or offline mode — some apps use the internet to check that you have the rights to listen to or watch something, even if it’s already on your machine.

Above digital, prefer audio

Devices that can painlessly store hundreds of hours of audio content are the single best thing that has happened to travelers since electronic ticketing.

The distinct advantage of audio over readable or watchable material is a practical one: you don’t need your eyes for it. This means you can continuously listen to the same audiobook (or an uninterrupted string of podcasts) while you’re packing, while you’re in a cab, while you go through security, while you wait in line to board, while on your flight, while deplaning, while in the cab to your hotel, and while you unpack, without all of the nasty bumping into things and missing important information that would come with having your nose buried in a book for all that time.

Two plane journeys a week of audiobooks adds up fast, and can add up even faster if you also get into the habit of plugging away at the book while getting ready in the morning, exercising, and commuting during the week — this habit is the reason I was able to read (and mostly retain!) something like a book a week from ~2013 to 2017.5Why not this pace in 2018? Fewer flights, a busier life, aggressively optimizing my choices to minimize commute times as much as possible, and a growing obsession with podcasts.

Invest in a good pair of headphones

Even if you don’t take my glowing recommendation of audio content to heart, a pair of good headphones (ideally noise-cancelling) is a must-have for plane journeys. Even if you listen to nothing at all, wearing them can reduce the annoying whine of aircraft engines, and send an obvious “I’m not interested in hearing about your essential oil business” message to fellow passengers.

I prefer passive noise cancelling earbuds to the more common active noise cancelling headphones, because they more reliably reduce all kinds of sounds. Active noise cancellation works by producing an “anti-noise,” a second noise that cancels out the first, and really only works best for consistent, low-frequency sounds like engine noise.

By contrast, passive noise cancellation works by creating a sound-tight barrier between you and the world —basically, they’re headphones that are also earplugs. This means that while both will block out the sound of the engines, only passive cancellation will also block out the crying baby two rows behind you. The better headphones that do strong passive cancellation sometimes also have a mode that lets you use their microphone as a ‘pass-through’ mic and hear the outside world without removing them. Win-win.

You can buy passive and active noise cancellation headphones in both over-ear and earbud styles; I prefer earbuds because they’re lighter, easier to pack, and normally do a better job.

Pack now, revise later

Even though I’ve just spent a lot of time explaining exactly how and why to pack a bag, the best advice I can give you on the subject is to not overthink it. Don’t obsess about everything that goes into the bag, just do your best approximation of a pretty good job and get on with your Sunday.

At least, don’t obsess yet.

Like most things, the way to perfect your pack list isn’t to read a bunch of tips, pore over what you might or might not need, make lists, remake lists, and then do it once, in a single monumental act. It’s to just do a pretty good job the first time, knowing you won’t nail it, and then pay attention throughout your week to what you were missing, what you never touched, and what you could find a smaller, lighter, more travel-friendly version of. And then the next Sunday (or whenever you fly), trying a new organizational system, or just finding a couple of things to add or remove..

You aren’t going to get this right on your first go, and that’s fine. Just get it pretty right, and then next time, make it a little better, and so-on. You’ll be an old hand in no time.

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