06b - How to Quit Your Job, Travel, and Do Whatever You Want


Travel planning is hard—let’s go shopping!

It’s easy to go overboard when buying travel stuff. Let’s try to keep things under control.

Tips, Zipped Up Just For You

First up, you’ll need luggage. Modern luggage is a complex beast. Roller bags vs. caster bags vs. duffel bags vs. hard shell vs. soft shell vs. backpacks vs. backpacks with wheels vs. backpack luggage vs. sherpas.

My advice: keep it simple.


Use regular roller bag luggage (two wheels, not four) with straps on the sides. The side straps are important—if you don’t have time to properly pack your luggage, you can just cram everything in there, zip it up, then strongly pull down the side straps to keep the bulk under control (and keep your zippers from stressing out).

Now you’ve got luggage narrowed down to something with two wheels and straps. What else should you lookout for?

I prefer luggage that opens in the middle. Each side of the luggage should have a zippered flap separating it from the other side (stay away from luggage with those old elastic V straps inside).

If you get fully split-opening luggage, your luggage now fits in more hideaway places by opening the luggage and sliding it under something (like, under a bed).

Don’t get too picky about design when choosing luggage. You can get a solid set of luggages (one smaller carry-on roller and one large checked roller) for under $250 total for both bags.

Vanity footnote: I bought my luggage from Oakley’s online outlet store in 2010 (they stopped making the luggage in 2009). The luggage was ridiculously on sale at $180 for the matching set. Sadly, Oakley left the non-insane luggage making business. But, if you see any unused 2009 Oakley luggage floating around for sale, be sure to buy it. Their 2009 line of travel luggage had nice metal buckles (which I can’t find on anything else anywhere), a detachable laptop bag, a detachable tablet bag, solid wheels, and rugged materials all around.

Always check online outlet stores or refurb sections for great luggage deals. Luggage goes through yearly fad/hype cycles just like clothes, so sometimes last year’s style will be half off. In the end, luggage is just a bag with wheels and a handle to hold stuff — not exactly rocket surgery.


Make sure your backpack can carry one or two water bottles, your laptop (with sufficient padding), your tablet, your camera and/or camcorder, a book, and all your cables.

Make sure it has pockets in all the right places including one perfectly located on the front for quick access to your travel documents (paper tickets, passport, transit cards for easy switching, …)

Don’t get too picky on style when choosing your backpack either. You can spent hundreds of dollars on branding and colors and style, but a $90 backpack will work just as well and, as a bonus, your $90 backpack won’t look like a flashy prime theft target.

Actual Backpacking

If your trip is going significantly outside of civilization, you’ll want to skip luggage and go with a full traveler’s backpack. These will run you $200 to $300.


Don’t Panic

People get paranoid about their luggage. Calm down. Don’t do dumbs like packing a $1,000 tablet in your checked luggage. Keep your electronics with you at all times in your backpack which, when flying, will go under the seat in front of you. If you check luggage, it should only have clothes and potentially disposable electronics (electric shaver, electric toothbrush, power adapters, etc).

Only Losers Lock Luggage

Luggage locks are worthless. If a lock isn’t “TSA compliant” and your checked luggage gets selected for random screening, they’ll just cut your lock. If your lock is “TSA compliant” then any bad person already has a master key (or a set of nail clippers to break it). If you want to deter people from opening your luggage, the most you should do is buy a few velcro straps and hook them around paired zippers. Don’t even think about doing ultra-inane things like buying luggage shrink wrap service.

Organize Dat

Internal luggage organization is paramount. You should buy a few sets of “packing cubes” to keep your luggage tidy inside. In addition to packing cubes, you should add a few compression bags (“space bags”) to shrink your clothes even more. Adding space bags also helps in case your luggage isn’t completely waterproof and you end up in a downpour during a long walk to or from airport transportation.

Eyes Only

Luggage tends it come in dark colors that all blends together after a while. Identify your luggage from a distance by getting bright handle wraps. They are small, cheap, will hold your identifying information inside, and make it easy to see your luggage immediately drop out of the checked baggage claim (if you ever have to check your bag(s)).

Locker Lock

Hostel rooms have lockers, but it’s up to you to provide your own lock. Find a medium-size lock and take it along for the ride. Hostels also have locks for sale, so if you don’t get one before you leave, you can just pick one up when you need it.

Let’s buy stuff together. You first.

Your Packing Cubes

eBags Slim/Narrow Packing Cubes (3 cubes) plus eBags Assorted Packing Cubes (small, medium, large)

Buy one set of multi-sized packing cubes for each roller luggage. If you’re traveling with only a 60L backpack, make an educated guess as to how much stuff you need to organize.

eBags packing cubes are cheaper than other name brand cubes plus they come in more colors than you should ever need.

Your Backpack

eBags TLS Workstation Laptop Backpack - eBags Product Info Page

Stay with me here. The eBags TLS bag above is ugly. Ugly as a blue vomit colored bag of ugly. It’s the bag they fill with ugly sticks when they’re too lazy to beat you with individual sticks. They just hit you with the entire ugly bag. Sorry. It isn’t pretty. There’s no getting around that. But, it is the best designed backpack I’ve found. It’s sturdy. Nothing on it rips. It has two snug water bottle pockets with well behaved zippers. It has a stealth laptop pocket that fits my MacBook Pro plus my iPad in its Dodo Case just fine. It has a well thought-out pocket layout in addition to a fold away internal shelf, an internal removable floating container, and an additional restraining velcro strap inside the main compartment.

The bag isn’t completely waterproof, but because the guts of the backpack are behind a few layers of outer compartments, nothing inside has gotten wet in my travels. I’ve been caught in a few downpours and everything inside stayed dry even though the bag was soaked.

The mesh back of the bag is separated from the back of the bag itself creating a vertical pocket. This pocket is extremely useful – you can slip the bag down over the handle of your roller carry on luggage. You’ll appreciate putting your backpack on your luggage when you have to walk for 20 minutes in an airport to reach your gate.

The TLS bag’s overt ugliness ends up being a feature though — it doesn’t look like it has a computer or iPad or anything of value inside. Nobody will be looking to steal your shiny bag because, well, this bag doesn’t draw attention to itself. At all.

Your Metal Water Bottle

Klean Kanteen Stainless Steel Bottle with 3.0 Sport Cap - 27 oz

You’ll be walking a lot. Stay hydrated. This bottle also doubles as a blunt instrument if you have to smash someone in the face and run away. The cap has a loop for easy finger holding or carabiner attachment.

Your Plastic Water Bottle

Camelbak Podium Big Chill 25 oz Bottle

Use your plastic bottle when you’re running around a lot and want a bottle that’s easier to hold while running. I travel with the metal suck bottle and the plastic squeeze bottle listed here.

Your Luggage Identifying Handle Wraps

Lewis N. Clark 3-pack Luggage ID Handle Wrap

These bright colors help you quickly see your luggage from a distance whether you’re waiting for your checked baggage on the conveyer belt or whether you’re being detained by the TSA and need to identify your luggage quickly.

Buy one pack of ID tags for each luggage you’re taking and put them on all bag handles (not on the pull up roller handle).

Your International Power Adapter

Universal World Wide Travel Adapter Plug

This is your basic fifty prong adapter with parts that jut out and zip and flip all over the place. It’s also handy for converting from a two prong outlet to a grounded outlet if you need to convert local North American power to itself.

Buy one. Not two, not six, not infinity, just one.

Your Travel Hard Drive

Silicon Power Rugged Armor A80 1 TB Waterproof/Shockproof

Backups are important. You may not have proper Internet access on the road to use remote backup services. Keep your Time Machine backups up to date by plugging in your external hard drive regularly.

Your Travel Nail Clippers

Seki Edge Stainless Steel Fingernail Clipper

Parts of you don’t stop growing just because you aren’t home. Get a solid pair of non-faulty clippers. It’s better to spend $15 on this good pair that works amazingly well instead of buying a $2 pair that breaks (or has a loose handle or the cutting edge isn’t sharp enough) every few months.

Your Sleep Earplugs

Mack’s Ear Care Ultra Soft Foam Earplugs, 50 Count

Simple and cheap earplugs to use when sleeping. You’ll be sharing a room with between three and fifteen other people. Earplugs will help you not get woken up every time a door opens.

Protip: Don’t travel with the plastic container. Save space in luggage: fill up a zipper bag with earplugs, push the air out (compressing the earplugs), then zip the bag shut. You should take enough earplugs to use two to three pairs a month during your trip without running out (though, every drugstore sells them, so you can always replenish if necessary).

Your Concert Earplugs

Etymotic Research ER20XS ETY-Plugs Hearing Protection

If you find yourself going to a concert or play or musical or bar or club, you should really use hearing protection. These earplugs are designed to quiet the sound enough to stop hearing damage while still letting you hear the full soundscape. These aren’t for sleep. These are for noisy life events.

If your ears have ever stayed slightly ringing after an event, you’re accumulating hearing damage. Take care of your ears.

Your Passport Case

Travelon RFID Blocking Passport Case

Simple case to keep your passport clean and flat (and keeps it from being read surreptitiously).

Your Miscellaneous Electronics Case

AmazonBasics Universal Travel Case

The Amazon travel case is a nice medium/hard shell case to hold your external hard drive(s), extra phone(s) (?), and other things you want to keep together and slightly protected more than just flapping around the of your backpack.

Your Camera

Cameras are difficult to recommend these days. Your iPhone can take better pictures than a $5,000 digital camera from ten years ago. But, when traveling it helps to have a real camera. A real camera will be immeasurably faster, have a physical button to rapidly press, and it won’t drain a phone battery you may need to conserve for maps and chats.

Unless you’re already a pro photo person, stay away from getting a big DSLR for traveling. It’s too big and the size will make you hesitant to carry it as much as a smaller camera. I recommend the middle ground of a micro 4/3 compact camera instead. It still has interchangeable lenses, and is about a third of the size of a full DSLR.

I can’t make any specific recommendations here because cameras change about every six months. For my travels, I bought a Panasonic GX1 with two extra lenses and it worked perfectly. It also works as a capable HD camcorder (as everything else does these days too). (As to why I can’t recommend cameras in a book: My GX1 cost $800 new and now, a year later, sells for $250)

How much you spend on a camera is up to you. Gearheads will want to drop $1,000 on the latest 4/3rds system from Panasonic or NEX from Sony with a few lenses. Others may opt just for phones. The choice is yours and yours alone. Good luck.

Your Camera Case

Case Logic SLDC-203 Compact System/Hybrid/Camcorder Kit Bag

The picture for this case is deceptive. The bag is tiny. If you get a small 4/3 Compact system, the camera body and lens will take up the entire bag. It’s a great little bag with plenty of padding.

Your Flashlight

Energizer Pro 7 LED Headlamp

If you get back late, you don’t want to be rude and turn on all the lights when there are multiple people sleeping in your room. Bring your own flashlight to find your stuff in the dark. This light also doubles as a handy helper if you find yourself walking around after dark and need a “please don’t run over me Mr. Car” light attached to yourself.

Your Movement

Your Sandals

Floors are dirty. Find a pair of waterproof sandals (made of plastic/rubber with no velcro) that can compress mostly flat and re-constitute easily for efficient luggage packing.

Your Insoles

Superfeet Green Premium Insoles

You’re going to be walking around. A lot. If you hurt after walking long distances, add these to your shoes. Your knees will thank you.

Next: 07 Queens, Danes, and Leprechauns