I spend a fair bit of time traveling. Like many of you, this involves catching planes, trains, and automobiles, schlepping around between airports and hotels, figuring out conference centers, and more.

Some years back I shared a room with my friend Pete Graner and was amused by how much crap he packed into his bag. Despite my mild mockery, whenever anyone needed something, Pete got pinged.

Over the years I too have learned how to tame the road, and as we get into the busy holiday travel season, I want to share some lessons learned from how to pack the right items, book your travel wisely, stay connected, and more so you can enjoy getting to the destination stress-free:

Build a Backpack

Your backpack is your travel buddy. You will carry it everywhere and it will contain the most critical things you need on your journey. You want it to be comfortable, contain the essentials, and be ready for action whether in your hotel room, at the office, at an airport, or elsewhere.

The Bag

First, you need to get the bag itself. Don’t skimp on cost here, this thing is going to get thrown around and trust me, you don’t want it to drop apart in an airport. Some essential features I look for in the bag:

  • Handles that can wrap around the handle on your suitcase. This means you can then attach it to the suitcase and not have to carry the bag when rolling your suitcase along.
  • Includes at least 4 different compartments, which I would use for:
    1. Your laptop/tablet. Some bags can open up to make it easier for scanning laptops in X-Ray machines. Not essential, but nice to have.
    2. Travel documents and important things (e.g. cash).
    3. Your cables, chargers, and other peripherals/devices.
    4. Medicines and other consumables.
  • A means to attach a water bottle (e.g. an included hook) or pocket to strap it into.
  • Bonus side pockets for sunglasses, tissues, and other items are always nice.

More than anything, ensure the bag is comfortable to wear. This thing is going to strapped to your back a lot, so make sure it feels comfortable to carry and doesn’t rub up against your shoulders.

Filling It

OK, so we have a nice shiny bag. What do we put in it?

You want to ensure you carry items not just for your common tasks, but also for a few outliers too. Also, I recommend many of these items always live in your bag (even if you buy duplicate items for your home.) This then ensures that you don’t forget to pack them when you travel.

Here is a shopping list of what I carry with me, which could be inspiration for your own bag:


  • Laptop – the jewel in the crown. This always comes with me.
  • Other gadgets – I often also carry:
    • Tablet.
    • Kindle.
  • Laptop charger – obviously this is pretty essential if you want some juice in your laptop.
  • Cables – I carry a bunch of cables, including:
    • 2 x Micro-USB for phones and devices.
    • 1 x Lightning for Apple devices.
    • Fitbit charging cable.
  • Multi-outlet adapter – a handy travel multi-outlet adapter where I can plug in 4 devices into a single outlet.
  • USB outlets – these are those little gadgets with a USB socket that you plug into the wall. I carry at least two and they are used to juice my devices.
  • Outlet adapters – these are the devices that convert between different power outlet types for different countries. I have been through dozens of these, so spend your money on quality. Be sure to buy one that supports every socket in the world. I always carry 2.
  • Battery pack – this is one of those battery packs that you can use for charging your devices when out and about. Get a decent one (at least 12000mAh) with both the 1A and 2.1A ports so you can get a fast charge.
  • USB sticks – I carry a couple of USB sticks around in case I need to transfer data between machines. I often have one as a bootable Ubuntu stick just in case I need to boot into Linux on another machine.
  • Headphones – get some decent headphones (with a built in mic), you will be using them a lot. I use Bose headphones and love them. They may be more expensive, but totally worth it.
  • Notebook and pen – always handy for scribbling down ideas, notes, and other musings. Also critical if you working with a company that doesn’t let you take a laptop into their office due to security measures – you will use this to take notes.

Personal Care

  • First aid kit – always have this just in case.
  • Tissues – get a couple of pocket packs, useful for when you have the sniffles.
  • Mints – no one likes travel breath, so this is a handy way of combating it when you have to run straight into a meeting after a flight.
  • Hand sanitizer – other people are icky, wipe them off you.
  • Headache tablets – get tablets your doctor recommends. I carry Aleve, but make sure the ones you get are safe for you (that you are not allergic to).
  • Diarrhea medicine – always handy to have and critical for some further flung destinations. I carry Pepto-Bismol tablets.
  • Cologne/Perfume – I always like to smell good and usually carry two colognes with me. You can buy an atomizer that you can pre-fill with your cologne before you travel. Or, buy a travel size cologne.
  • Deodorant – essential. You never know when you are going to be stuck in a hot place and you don’t want to get sweaty. I usually carry a roll on.
  • Band-aids/plasters – I carry a few of these, not just in case I cut myself but also in case I get blisters on my feet when I have bought new shoes.
  • Gas/heartburn medicine – always handy to have, particularly for some destinations with richer food.
  • Hangover medicine – it has been known that I have the odd beer here or there on the road. Some scientific research has resulted in me carrying some Blowfish. Be sure to check what you carry is safe (some medicines have ingredients you may be allergic to).
  • Sunscreen – as a pasty white chap, the sun can be my enemy. I carry a small spray can that I can lacquer myself with if I am going to be outside for a while.
  • Water bottle – I always carry a quality water bottle. When traveling you should stay hydrated. Be sure to get a bottle that can strap to your backpack. If there is no means to strap it, buy a carabiner hook. Also, get a bottle where the spout is covered and the cover is lockable. This will ensure you don’t get germs on the spout and that water doesn’t spray out while walking.


  • Cash – I always carry a small amount of bills and coins in my bag. The bills are handy for tipping and purchasing small items when you have run out of cash in your wallet. The coins are helpful for parking meters.
  • Sunglasses – always handy in sunny climbs. I have a dedicated travel pair of sunnies that always lives in my bag so I never forget them.

Get Expedited Customs Entry

If you are traveling regularly, you should strive to make your overall journey as simple and effortless as possible. One easy way to do this is with expedited customs entry.

This varies from country to country but here in the USA there are two programs that are essential – TSA Pre and Global Entry.

The latter, Global Entry, means you can skip the lines when you arrive from an international trip and simply go to a machine where your documents are checked. It can literally save you hours stood in line after a long trip.

TSA Pre is a program in which you can get expedited screening in American airports. It means you can join a shorter line and you don’t have to take off your shoes or belt, or take your laptop out of your bag. TSA Pre is awesome.

If you apply for Global Entry you also get TSA Pre, so that is the way to do. Sure, it involves you filling in a large form and taking a trip out to the airport for a meeting, but given the amount of time an frustration it saves, it is critical.

Tip: When booking your flights be sure to specify your Known Traveler number (which you get with Global Entry) when booking. If you don’t specify it you won’t be able to use Global Entry or TSA Pre on your itinerary, which is rather annoying.

Book Your Travel Wisely

For the majority of trips you take there will be a mode of transportation (e.g. plane, train, car) and a hotel. When booking either of these you should always (a) choose the wisest providers, (b) book the best trips, and (c) always work towards to status/rewards.

Pick good providers

For picking the best providers, do your research. Ask your friends what their favorite airlines are, which hotels they like, and other opinions. Also do some online research.

As an example, a couple of current viewpoints from me currently about airlines:

  • United – pretty average service but cost effective and have a great rewards program. Also easy to spend your miles (few blackout dates).
  • Virgin Atlantic – awesome airline, but more expensive. OK rewards program but I have found it difficult to spend miles (lots of blackout dates).
  • Southwest – great airline, services a lot of the USA. Really nice staff, but their rewards only really gets you on the plane earlier.

Do your research and find the right balance of service and value.

Book the trip that works for you

For booking the best trips, be sure to check out some of the modern providers such as Hipmunk, Kayak, and others. This can make putting together an itinerary much easier.

A few tips for booking flights;

  • When picking seats check SeatGuru to see if it works well for you. Always pick your preferred seat when you book your flight.
  • Always check the layover time – I never layover for less than an hour. Too risky of you have a late takeoff time.
  • Sometimes I also check the cancellation/delay record of an airport. For example, Shenzhen has a pretty poor record and so I have taken a train to reduce the risk of a canceled flight.
  • Remember that bulkhead seats don’t have movable arms so if you get a row to yourself you won’t be able to stretch out.

Work towards rewards

Most airlines and hotels offer rewards programs for regular business. Where possible, you should try to book with the same providers to build up your status. This will the open up perks such as free flights, lounge access, free bags, complimentary upgrades, and more.

When evaluating which rewards plans to use, consider the following:

  • Assess how the rewards program works. Some can be a fairly complex and some are simple. Make sure you understand how you can get the most out of it.
  • Choose airlines that have lots of flights from your nearest airports. This will make it easier to ensure you pick the same airline for most flights.
  • Review how easy it is to book free flights. Do they have lots of blackout dates that make it difficult?
  • Review the perks of the airline. Is it worth it and can you accomplish the different status levels with your typical travel?

Load Up Your Phone

When you are on the road your phone is your trusty companion. It will keep you entertained, informed, and connected.

Aside from ensuring it is always charged, we want to ensure it is connected and has the right apps on to make our trip easier.

Choosing a Plan

Be sure to check what your carrier’s travel/roaming rates are. This varies tremendously between carriers and getting this wrong can cost you a fortune.

Where possible, I always recommend that you are able to have roaming and data when you travel. While it is often slow, it can be essential as part of your trip for contacting colleagues/customers, coordinating travel, finding places to eat, learning the local culture and more.

As an example, T-Mobile has phenomenal unlimited international roaming. Ever since they switched this on it has made travel infinitely better and more reassuring.

Be sure to check the parameters of how this works though. As an example, with T-Mobile, for me to have a call with my wife in America it is better if I call her (the rate is much lower) than if she calls me. Be sure to know these specifics so you can make the most out of your service.

Install Essential Apps

Everyone will have different requirements here, but I recommend you install the following types of apps:

  • Itinerary – I love TripIt. It is a simple app you can forward your email itinerary confirmations to and it provides a simple way of viewing them and providing additional information.
  • Airline – be sure to install the apps for the airlines you fly. Often you can check-in with the app as well as use an electronic boarding pass so you don’t have to print your boarding pass at the airport.
  • Carsharing – be sure to get Uber / Lyft and any regional travel apps (e.g. taxi apps for towns that have banned ridesharing).
  • Business discovery – be sure to install Yelp and TripAdvisor which is hugely helpful for finding decent places to eat, fun bars, and more.
  • Translation – I also recommend you install the Google Translate app. It can not just translate text but also translate text in photos and via the camera too.
  • Entertainment – be sure to install the video, music, reading, and games apps you love. This is always handy for evenings when you just want to relax in your hotel room or for the long trips.

So, there we have it. I hope some of these recommendations are helpful.

Travel Tips

Outside of getting prepped for your trip, here are some random tips that might be handy for while you are on your trip:

At the Airport

  • Check in as soon as your flight opens. When you make the booking, add a cell-phone number so you get texted when check-in opens. This will ensure you get a decent seat choice.
  • Before you fly, buy some essentials in case you need them in the air:
    • A few bottles of water.
    • A few snacks (e.g. protein bars).
  • I always like to eat a big meal before a big flight. Plane food is usually not great and they may have run out of the option you want.
  • Explore off-site parking options. Often it can be way cheaper for parking. Also, check for coupons, there are usually decent discounts available online.

On the Plane

  • Wipe down your tray table and arm-rest with a sanitation wipe. This can prevent getting sick while traveling (which is never fun).
  • When you get to your seat, take your headphones, e-book reader, and tissues out of your bag. This means you don’t have to wait for the seat-belt lights to go out before you can grab them.
  • Track your flight time and be sure to hit the restroom around 45 minutes before landing. When they announce the plane is descending there is often a bum rush for the loo.
  • When they offer drinks and they pour you a little cup, ask for the full can. They usually give it to you.

At the Hotel

  • If you wear shirts/blouses, be sure to check if an ironing board and iron is in your room when you arrive. If not, ask for it to be brought up before you go to bed so you are not rushed in the morning.
  • Don’t have an ironing board and have creases in your clothes? Use a hairdryer on your clothes while you wear them. It often gets most of the creases out.
  • When you got to bed, plug everything into charge, including your portable battery pack. This will ensure you are powered up the following day.
  • You can call reception for a wake up call, but always set a wake-up call on your phone/tablet. Too many hotels forget to actually wake you up.
  • As soon as you wake up, switch the shower on and see if there is hot water. Some hotels take a while to warm up and this prevents you getting delayed.
  • Have one of those rooms where you need to enter your room card to keep the lights on? Just put any other card in there (e.g. an old subway pass) and it usually works.

I would love to hear your tips though. What travel secrets have you unlocked? Be sure to let everyone know in the comments…