Mark Loveless, aka Simple Nomad, is a researcher and hacker. He frequently speaks at security conferences around the globe, gets quoted in the press, and has a somewhat odd perspective on security in general.

A Hacker's Laptop Bag

A Hacker's Laptop Bag

Photo courtesy of Tom Bihn.

Photo courtesy of Tom Bihn.

The laptop is the mainstay of the hacker, on the go doing hacker things. But the bag you put it in, and the rest of the gadgets and toys you carry with you, well they have to meet certain standards. We are going to discuss all of this in time, but first we need to discuss the bag itself.

I’ve talked about my main laptop before, the System 76 Galago Pro. In summary, it has tons of RAM, it is sort of light, plenty of drive space, and it runs Ubuntu Linux with a smattering of security and hacker tools I loaded onto it.

I wanted a messenger-style bag for the laptop - not a backpack. I've done both, and while I am going against the hooded basement lurker stereotype, the idea of having a messenger bag that I can easily shift to the front of me during urban excursions is quite appealing. I hate the idea of zippers to my bag contents being completely out of my line of sight, especially in crowded urban settings.

So here is my process, as well as why I made the choices I made. They may not be your choices, but in seeing why I made the decisions I made could possibly give you some insight to help you make your own decision. My basic steps were as follows:

  • Make a list of “must have” features.

  • Make a list of “nice to have” features.

  • Ask friends, read reviews, and refine your lists.

  • Watch review videos on YouTube.

  • Note any extra features you didn’t look for that make the bag more appealing.

  • Break any ties with the “nice to have” and extra features.

  • Buy it via a method that allows for it to be returned for a refund (just in case).

Now let’s delve down into some details.

Make Your Lists

Make a list of everything you want out of a bag including physical size, color, storage space, and so on. My “must have” list included a variety of important-to-me details.

  • Messenger bag only, no backpack.

  • Black with minimal branding. Not a fan of easy-to-read large logos, these tend to draw attention, and I wanted it to be less conspicuous.

  • Able to hold a 13” MacBook Pro. My laptop of choice is my Galago Pro, but messenger bag vendors don’t advertise what size of System 76 laptops they hold. I did know that if it could hold a 13” MacBook Pro, it could hold my Galago Pro. Also, the job had issued me a MacBook Pro so I wanted to have the option to take either with me.

  • A strong and well-made bag that is weather resistant with YKK zippers, which are generally considered some of the best zippers around. I have had them on other products and prefer them.

  • Organizational pockets that will allow me to sort and organization my EDC, with enough room for the messenger bag to be used as a day bag (like while at a conference).

My “nice to have” list was just that, but it consisted of the following:

  • Security features. This could be anything from zippers that allow for locks, slash-resistant material, RFID pockets, and so on.

  • Weather-resistance bag. Weather-proof would be real nice, but I’d really like some type of basic weather resistance.

  • Center-of-bag strap connections. If I was going to go for a messenger bag, I was hoping that the connectors for the strap were at roughly the center of the bag as you looked at it from the side. This is mainly for balance, and as I’d tried a couple of messenger bags already that didn’t have this, I thought this might work pretty good.

Mass Eliminations

It became readily apparent that none of the free bags given to me at conferences or employer “holiday gifts” were going to cut it. Most had either some large logo on them to commemorate some conference sponsor or employer, were some god-awful color, or didn’t meet but maybe one “must-have”. This also eliminated dozens and dozens of choices by simply looking down the must-have’s as I’d look at choices online.

Ask your friends what they are using and why. Listen to their complaints and the things they really like about the bags. Sure it could be different for them - I’ve had friends make shocking statements like “as long as it is free from a conference and holds my laptop, who cares?” and “I want something big and bright so it really stands out!” Others had seemingly sane comments about security features and the ability to hold up to a lot of use and abuse. Both Tom Bihn and NutSac ended up on my radar as companies that sell decent products because of recommendations by friends.

Online Woes

Buying a bag you can place your hands on is great, since you can see the materials, note the space inside, and in general check off a lot on the checklist. It is still possible that you might find the exact bag that checks all the items on the list. But often you have to resort to buying online, relying on reviews, vendor pictures, and a bit of luck. However it isn’t impossible.

There is a minor disconnect you will have to deal with if you are buying a laptop bag online - many laptop bags will not state what size of laptop they will hold. They will often say things like "any laptop with a 13 inch screen" which refers to the diagonal measurement of said screen - without taking into account the bevel around the screen and certainly doesn't cover thickness. I mentioned above my Galago Pro is the same size as a 13” MacBook Pro, so I simply noted if a bag I was interested in specifically said in its description that it could hold a MacBook Pro.

Reviews of bags are hit and miss. A video review is preferred as you can often see the bag in use - although you cannot rely on the manufacturer to provide a decent video as every camera angle is set up so everything slides in and out of the bag without effort. You know, not real life, but staged. The best reviews of the bag you are looking at are ones of it in use by someone who has purchased the bag - particularly if they are packing it full of gear on camera. A lot of travel-related vlogs will cover this, but unfortunately you may have to sit through a lot of terrible videos where someone rambles on for 15 minutes about who the hell knows what until they finally start showing the actual packing. I have seen videos where it was the only way to determine what sized laptop would fit, or things like a pouch inside that looked roomy on the vendor website suddenly appear nearly non-functional when a real person tries to pack something in it, so horrid bag reviews do have the occasional benefit.

Sometimes the vendor themselves will have “customer forums” where you can look at a bit more honest reviews, and sometimes just travel sites in general will feature a bag you are interested in. For example I find Pack Hacker to be a great resource, as they specialize in travel-related tips including in-depth reviews.

Take Your Time

Once I had my list of criteria I was able to narrow things down to five different bags, and the online reviews let me narrow it down to two - a NutSac Satchel Pro and a Tom Bihn Pilot. I ended up with the latter. I already had purchased a Tom Bihn Brain Bag backpack and had a bunch of their packing cubes, so I knew how good the quality was. What really decided was the fact that the Pilot had all of the nice-to-have features - the YKK zippers lined up enough to run a lock through them as the security element - and there was an integrated spot for a water bottle (with a drain hole). So this ended up being the best choice, at least for me.

This entire process for me took about two years - in part because I had a fairly decent backpack that met my needs, with its main failing that it just wasn’t a messenger bag. Also, I would look into researching a new bag maybe once every 2-3 months as it was kind of a lower priority.

Follow-up

I’ve had the bag nearly two years now, and it is both a great day bag when traveling, a great EDC-type laptop bag when I’m out and about during the day while at home. There is the added bonus that it will in fact (barely) hold a MacBook Pro with a 15” screen; it’s tight but it will fit, and there’s still enough room for my iPad with keyboard case. The bag itself still looks brand new.

The only thing I can take issue with as a fault is the integrated water bottle holder. Make sure you only put in a water bottle in it that you know is properly sealed. I recently tried out a mug with a lid that apparently did not seal completely, and it sat over the drain hole preventing much of the leak from draining out. Instead the water-resistant outside of the bag helped seal most of the liquid in, and it leaked from the water bottle compartment across the entire bottom of the bag. Fortunately the laptops survived, but a $900 camera did not.

Other that one issue, I have no problem with the bag and highly recommend it. How’s your bag? Are there other steps you do that I don’t? Let me know in the comments.

It's Our Fault

It's Our Fault

ShmooCon 2020

ShmooCon 2020