Road Warrior

The Minimalist Travel Gear Stack for the Techie Road Warrior in 2017

Posted: August 30, 2017 by sullivg2

My work requires that I travel up to 50% sometimes, so i guess I could be considered some sort of road warrior. While this lifestyle isn’t always as glamorous as it may seem, I’ve spent a lot of time optimizing my “travel stack” to make my time away from home as comfortable as possible. Admittedly, I am a “gear whore” – a trait I acquired from my father who is an avid outdoorsman. As a result, I’ve spent plenty of time researching and lots of dollars on different travel gear configurations looking for the one that suits me best.


ˈtravəl/ stak/


  1. A preplanned, personally optimized packing list of travel essentials that can quickly and easily be packed into one or two bags for regular business travel.

My Road Warrior Scenario & Requirements:

I have based all of my travel gear acquisitions on the following scenarios and requirements:

  • Most of my travel is domestic – either within Canada and sometimes the United States.
  • Most of my trips are between 2-3 nights
  • Most of my flights are < 3 hours
  • I live in Canada… So i’m often traveling in cold, snowy weather
  • I try and stay in Airbnb rentals versus hotels when possible
  • Minimalism is important
  • I strive for well built and durable, yet lightweight and multifunction gear
  • I NEVER check my luggage – unless its a complimentary gate check on a direct flight

My Travel Stack

Road Warrior Travel Stack
My current Road Warrior travel stack



Any techie road warrior needs a go-to day pack to carry around the essentials on the road. I use a Gregory Border 25L day pack ($175.00-ish CAD) as my carry on bag and I absolutely love it. After switching back and forth between various backpacks and messenger bags over the last coupe of years, I’ve finally found the bag that works for me. With a well padded laptop section that fits up to a 15″ laptop, a larger zippered section that can fit all any of my paperwork (which barely exists anymore) and a sweater and/or packable jacket, as well as a front zippered section with plenty of pockets for flash drives, business cards, electronics, pens etc. The best part of this bag is the comfort level – it has a very comfortable, padded back that provides good air flow and also features a very well designed rear slot to fit over your roller-bag handle for making your way through the airport terminal. BONUS: Due to the durable construction of this bag, and Gregory’s track record in manufacturing quality outdoor gear, it also makes a great day hiking bag.

Carry-on Roller Bag

Any road warrior inherently puts a ton of abuse on their luggage. I’ve gone through more carry-on roller bags than I care to admit.

Unless you’re willing to fork out several hundred dollars, you can expect most $100-$200 bags to be disposable in my experience. Most of the bags in this price range just weren’t made for longevity with the harsh punishment they take – especially if you every check your bag. After lots of research I landed on the Eagle Creek No Matter What™ Flatbed Intl Carry-On ($189.99 CAD.) It was the durable finish of the bag that originally caught my attention. The bag is constructed with water repellent “Bi-Tech” fabric which is also very resistant to rips and tears. The two, oversize wheels roll smoothly over bumps and curbs as you pull it through busy city streets. Although the bag contains a rigid, durable frame, the soft front of the bag allows you to jam enough clothes in it for 4-5 nights of travel. This bag also meet the size requirements for a carry on with most of the North American airlines (At least Air Canada, Westjet, Porter, Delta and American Airlines in my experience.)

Packing Cubes

After reading a few reviews about them, I decided to try out some packing cubes for more efficient packing. At about $20 CAD for a 4-piece packing cube set from AmazonBasics, I figured it was a low risk trial. Overall, i’ve been very happy with these – they allow me to neatly pack more clothing than if I packed my carry on without them. Typically I pack my clothes in one of the large and one of the medium size cubes, and pack the two other empty ones for dirty clothes once i’m on the road. 

Cable & Accessories Organizer

Cables and electronic doodads drive me nuts! But for the techie road warrior they are a necessary evil. I searched for a good solution to organize these things for a long time and finally landed on the BAGSMART Small Travel Cable Organizer Universal Electronic Accessories Case ($17.99 CAD.) This case has lots of pockets and elastic straps to hold down all of your small electronics, cables, USB keys and more. 

Passport Wallet

I only bring my passport with me on international trips, but when I do, I keep it in a travel passport wallet for safe keeping. I own an older version of MEC’s Transworld Travel Wallet. It is small and lightweight, and has several card holders for any of my frequent flyer and loyalty program cards for hotels and rental car agencies. It does the trick.


Ear Buds

Ear buds have been another category that I’ve struggled with. I’m still yet to find the perfect pair that provides good sound quality, good call quality and comfort that doesn’t completely break the bank. I finally broke down and bought a pair of BeatsByDre Powerbeats2 Wireless earbuds ($149.00 CAD) when they were on sale, and i’m moderately satisfied with them. They do provide good sound quality, and are comfortable once you are used to them, but they are almost useless for calls. The other drawback, which is the case with all wireless headphones is that you have to remember to charge them… I also had an issue with them while flying. Because they are wireless, they cannot be used with any of the plane entertainment systems. I have found a great workaround for this that i’ll explain in a moment.


I am assigned a laptop from employer – however they do give us choice in what kind of laptop we want. I opted for a Macbook Pro with an i5 processor, 16GB of RAM and 512GB SSD. Plenty of power that I absolutely do not need. In hindsight, I wish I had chosen the Macbook Air which would have been much thinner and lighter.


A year ago, If you would have asked me if I needed a phone, a tablet and a laptop I would have said “no!” Since then I acquired an iPad 2 through work and have found several use cases for it. Firstly – addressing my earlier complaint about in-flight entertainment: Netflix now allows you to download content while connected to wifi. This now allows me to bring my own video content with me on flights. Pair that with my wireless earbuds, and it’s the best in-flight entertainment solution i’ve found to date. Additionally, I’ve found that I am becoming more used to the tablet form factor for everyday things like email, note-taking (with Evernote,) chat/IM, and even blog writing!

Other Essentials


When selecting shoes for travel, I like to try and find a pair that are dressy enough for workdays, casual enough for the evenings and comfortable for travel. To me, those are the characteristics of good road warrior footwear. Believe me, if I could get away with my Birkenstocks everyday, I would. But sometimes you have to look somewhat respectable. In late Spring, Summer and early Fall I wear Cole Haan zerogrand wing Oxfords. These things are expensive ($250.00 + CAD,) but are they ever worth it! I was lucky enough to get my on sale for 40% at an end of season sale. These shoes look great in dress attire, but wear more like running shoes – making them super comfortable. In the winter I opt for chisel toe blundstones (specifically the Blundstone 067 – The Chisel Toe in Stout Brown) I swear by these things. I’m going into my 5th winter with mine and they still have lots of life left in them. I usually get them shined up at the airport before boarding my flight and they are certainly passible for business casual attire.


A few years ago I quit expensive sunglasses. They are just way too susceptible to being broken or lost to warrant spending hundreds of dollars on. At the same time I really like polarized lenses – which is hard to come by in inexpensive sunglasses. This is until I discovered Sunski. Sunski makes stylish, moderately prices, good quality polarized sunglasses and they are perfect for what I need. I wear their Foxtail model ($69.00 CAD) and I highly recommend them.

Leather Card Holder

A few years ago I said goodbye to the traditional wallet forever. Normal wallets give you an excuse to carry around a bunch of stuff that you never need. I use a leather card holder from Frank & Oak ($39.50.) More than three years in and the wallet has held up to the abuse I put it through and I am able to carry with me everything I need while on the road – Debit card, corporate credit card, ID, NEXUS and health card.


I’ve been making an effort to read more books. I try my best to reserve flight time for relaxation and rest, so I try to avoid doing work on the plane if possible. Right now I’m traveling with “The Daily Stoic” by Ryan Holiday. Stoicism is an ancient philosophy that is practiced today by many CEOs, successful entrepreneurs and even NFL coaches. This book provides 366 stoic mediations that I find exercise my mind in ways that my usual business or tech book cannot.

Shopping List

I buy almost everything from Amazon. Most of the gear featured in this post is available on

[amazon_link asins=’B006ZE53H0,B00SEYA0TU,B014VBGRR8,B017SKRWL4,B01MXJNOKJ,B072MH3V2R,B0013FRNKG,B01G36Z2QQ,B00Q7DQU0S,B01788O34U’ template=’ProductCarousel’ store=’geoffsulliv0f-20′ marketplace=’CA’ link_id=’239c844a-8e4f-11e7-96aa-d550621f65be’]

What Does Your Road Warrior Travel Stack Look Like?

I am always looking for upgrades to my travel stack. If you have any tips, tricks or recommendations from your own experience please comment below or shoot me an email.


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