The fundamental goal I have for a wallet via its design is that it prevents me from randomly collecting crap.

Years of folding leather wallets with myriad pockets and flaps all yielded precisely the same result: a Costanza-sized monstrosity that contained random crap that at one time I thought I needed, but eventually became useless clutter. This collection sat in my back pocket as a constant reminder of a tidying task I never did. Meanwhile, the massive collection of clutter ultimately destroys the wallet because no wallet is designed to perpetually hold everything.

The current wallet is perfect.

It’s perfect because:

1. There are zero moving parts. Whether it’s a flap or a mechanical money clip, moving parts fail.
2. There is limited capacity. The card sleeve barely allows me to hold eight card-shaped objects. Eight. This means that each time I attempt to keep a receipt I think I’ll need I have to fold it and slide it into the money clip. This means each time I handle my cash, I have to make a critical decision about the receipt — do I still need it? You’d be surprised by the half-life of items in your back pocket that you recently thought were important when you’re forced to look at them an hour later.
3. I’m not constantly stressing the architecture of the wallet attempting to contain everything. The current wallet has already lasted 4x as long as its predecessor.

It’s with this wallet design win that I embarked on a quest for comparable bag.

The Bag Requirements

My requirements for a bag start with those of the wallet, but with an important essential addition: my bag has multiple use cases. My bag needs to adapt to whatever journey I’m currently on, whether it’s a trip to work; a trip far, far away; or a trip where I’m sleeping in the dirt under the stars. A trip is either work or play, and since I work a lot more than I play, I chose to focus on work scenarios for my bag research.

I’ve heavily used two different types of bags over the past five years, and each has some win. To understand my initial requirements for a good bag, let’s quickly look at each.

A Christmas present, this Johnson & Murphy messenger bag was the first work bag I loved. I find it gorgeous. A large, comfortable shoulder strap and decent space made this my go-to bag for years. All that was missing was the addition of a Incase sleeve to give my MacBook a little cushioning and I was set.

In the past few years I began to travel more, and the travel exposed a core weakness: the bag doesn’t scale to far, far away. I found myself stuffing, shoving, and reorganizing headphones and power supplies in the bag, and while the magnet clasp works fine for a trip to work, when the bag is at capacity, it feels like it might pop open at any moment. I had a similar over the shoulder Tumi bag that was my workhorse for far, far away, but after sitting in a lot of airports, I’d seen a new development. Folks were wearing backpacks again.

I’m scarred by backpacks. My memory of backpacks was of these massive canvas-like bags full of immense and dense text books, crumbled paper, and a distinct smell of partially rotten peanut butter and jelly sandwiches. I remember constantly losing important papers in what was the seemingly infinite space contained within my bag, and I wasn’t interested in returning to that frustration.

However, after countless hours watching travelers sport backpacks, it was time to get past my scarring and give backpacks another try. Tom Bihn’s Smart Alec backpack was a chance to test this development.

After six months of steady use of my Bihn backpack, not only do I understand why people love them, I also better understand the complete set of questions and requirements I have for a good bag.

Does this bag make me look like a nerd? (Because I am.)

Bag religion is rampant. The only thing I’m looking forward to more than finishing this article is the crazy, foaming at the mouth bag nuts that are going to comment on this piece. My research is far less complete than in prior obsessive excursions, so bring it. I want to hear it. I’ve seen a lot of different bags, and my first requirement is that while I need my bag to be nerd-compliant, I don’t want it to scream “nerd”. This was part of my love affair with my messenger bag. It looked like I was part of the Pony Express when I was actually just a nerd hoofing my nerd crap hither and yon.

My bag needs to walk a delicate line between form and function. I need it to elegantly contain my various nerd crap, but I don’t need to broadcast to the world that, yes, not only am I sporting my nerd gear, I also have a back-up of the aforementioned gear because I’ve built in redundancy. That’s how I roll. I’m a nerd.

The messenger bag is a slight winner in this very subjective category. While the Smart Alec avoids most design disasters that remind me of JanSport-esque high school backpack monstrosities (straps, zippers, every kind of fabric everywhere, minimal pockets, and the color taupe), it makes less of a statement. It’s slightly more function than form. However, it is a better answer to the question…

Am I going to beat you through the security line?

The hands down collective best measure for any bag is its relationship to your situation in the security line at the airport. Let’s start with my mindset when I’m standing in line at security. I’m furious. Everyone’s furious. While we suspect the security line is essential, as we stand in that endless line, we know — we’re absolutely sure — there is a better way.

I’m fuming with this frustration when I finally get to the front of the line, but more importantly, I want to prove a point: I will now demonstrate to everyone the value of efficiency. Grab two trays, slip shoes off and put them in tray #1. Stuff wallet, iPhone, and boarding pass in shoes, belt off — NEXT TRAY — MacBook Air in second tray. Bag behind second tray, luggage behind that. And done. Why yes, I can do this and move the trays at the same time — WHY CAN’T YOU?

No where in the above process did you see “futzing with my bag and looking for shit”. In times of stress, a good bag demonstrates a couple of essential design points:

• Easy access to the items I commonly need. This means my computer is a single zipper away, but this ease of access does not mean the safety of these essentials is compromised. The Smart Alec is a clear winner here. In addition to the main compartment, there are two external side pockets that are large enough to hold the answers to most travel questions.
• Simply amazing zippers. My messenger bag has a magnet clasp and that works, but when I’m moving quickly, I’m wondering when this bag held together with a magnet is going to explode. When I close any pocket on my bag, I want to be left with the clear impression that the pocket is seriously closed.
• A minimum of crap hanging from the bag. Each strap is an opportunity to snag myself on a random piece of crap that I didn’t happen to see at the least opportune time. Traditional backpacks are the worst offenders when it comes to these straps. The designers seem to think I’m always mere seconds away from base jumping off a bridge where I need my backpack affixed to me in seven different ways. I don’t. I need two straps. That’s it.

However, I do want to know…

Can I go ninja?

The rule is: the further you are from your cave, there’s the exponential increase in the chance something will go wrong at the least opportune time. The best example of this is standing in front of 1,000 people who are expecting you to smoothly and expertly talk for the next hour and you’ve just discovered your MacBook doesn’t connect to the venue’s projector.

In my bag, I’m certain I have video connectors for most projectors on the planet. Furthermore, I have a universal power converter, a power supply, two presentation remotes, and sundry other essential white cables. All of these items are expertly collected in what Tom Bihn calls a Snake Charmer bag. This mesh bag is not only of a size that it can handle all of these items, it takes oddly shaped items such as power supplies and Jamboxes and molds them into an easily transportable rectangle that fits inside of my bag.

To allow for ninja-like moves, a good bag is designed to maintain state, which means:

1. There is a knowable set of intelligently aligned pockets of a size and shape that make sense. This is where my messenger bag fails. In order to maintain that Pony Express feel, the messenger bag design assumes that everything I’m going to lug about is roughly shaped like a stack of 8.5×11 paper. While the MacBook and the iPad are paper-shaped, I have essential items that aren’t square: delicate sunglasses, clumps of pens, and bizarrely shaped collapsible headphones. When I attempt to gear up for the long trip, it’s clear from the resulting lumpiness that the messenger bag was designed for a pleasing form and not useful function.

   The Smart Alec backpack not only has a sensible number of pockets, they are of a size that accounts for the fact that oddly shaped items follow me on my travels. More importantly…

2. In time of stress, the items are readily accessible, remain safe, and don’t shift around. I can’t predict when I need to go ninja. I don’t know when it’s absolutely essential that I have a pen ready to go in five seconds. When this moment does arrive, I don’t want to be digging feverishly around my bag, placing various items on the floor as I search the bottom of the bag where the small stuff has fallen. The Smart Alec backpack not only has a sensible number of pockets, they are readily accessible and not cavernous. At this moment I can tell you: right side external pocket is notebooks and the essential small crap bag (which I’ll explain in a moment), left external pocket is pens, mints, and playing cards, and the internal top pocket is safe and easily accessible for sunglasses, random small pieces of paper, a passport, and the occasional stash of hard candy.

All my stuff, readily accessibly at a moment’s notice — that’s pretty ninja. Still…

Is my bag smarter than I am?

Everything is exponentially and unnecessarily harder when you’re stressed, and it’s in these moments that you appreciate the design of a good bag. A well-maintained state allows me to go ninja, but knowing precisely where my stuff is safely located is just the first step. A well-designed bag is thinking for you when the last thing you’re doing is thinking. Some examples:

• Sub-bags. In addition to intelligent pocket size and positioning, Bihn pushes an idea to help me maintain state: sub-bags. For everyday trips, I have a single sub-bag that I’ll call “essential small crap”. Everything I’d normally lose or constantly be untangling is in a small bag that is transparent on one side, and which sits well contained precisely in the same pocket.
• An unexpected sense of space. This is a direct contradiction to my requirement that my bag prevents me from randomly collecting crap, but part of being ninja is the need to scale. I will randomly need to lug around a randomly shaped something from here to there and my preference is that my bag does this without fuss. The messenger bag fails here, especially on longer trips. I’m at max capacity on a long trip, which means I’m shoving newly acquired items in coat pockets or onto fellow travelers. As for the Smart Alec bag, I never felt I’ve filled it. Sure, I can lug your randomly shaped something… anywhere.
• Agility. My agility test is relatively simple: how many people are impacted/aware when I attempt to retrieve my MacBook while sitting in the middle seat? Any answer higher than one is too many. For the messenger bag, I first need to find the handle, which, given how it was shoved under the seat in front of me, is trickier than it needs to be. Then, I slide the bag out, lift the flap, unzip the Incase, and slide out the hardware. If you’re sitting on either side of me, you’re going to be well aware of this process because of my odd elbow gyrations.

  The backpack is shaped like a bullet. You slide the base easily under the seat in front of you, leaving the tip pointed directly at your feet. When I need something, the handle is at the tip of my toes, the zipper is easy to grab and works every time, and the Brain Cell holding the MacBook is right there. If you’re sitting next to me you’ll end up wondering, “When did he pull his computer out?” Whether it’s shoved into an overhead compartment, slid under a seat, or thrown in the back of a taxi, my bag needs to remain accessible and useful. This means I can get to it, and once I get to it, I can perform whatever action I intend without annoying every single person around me.

• Full range of motion. The defining aspects of a backpack are its most obvious — it’s on your back. After many years of single-strap messenger bags, I was shocked when I moved to the backpack and suddenly had two hands. A messenger bag does not full occupy one of your arms, but your shoulder is in a constant balancing dance with the bag to make sure it’s in the right place. With a backpack, this is a non-issue. When it’s on your back it’s gone and you’ve got a full range of two-handed ninja motion.

Through its design, a good bag makes me look smarter by giving me deft answers to most travel disasters, but I have one more request.

Can I take a bullet? Do I look good after I’ve taken a bullet?

As my bag accompanies me everywhere on the Planet Earth, it’s apt to encounter small random disasters. Briefly dragged on the asphalt, being drenched by half a cup of airplane coffee, or being unceremoniously thrown in the back of a cab. When these micro-disasters are going down, I need two things of my bag:

1. Everything in it needs to admirably survive and generally remain in the same location, and,
2. The disaster results in the bag acquiring additional character.

Sturdy is the word you’re thinking. Good solid craftsmanship. Yes, this is all true, but the art lies in building a bag that doesn’t look tired after the unexpected has occurred — the bag needs to look like it’s lived.

The messenger bag is a solid winner here. The bag has had the shit kicked out it, but it doesn’t look like it’s beaten, it looks worldly. The Bihn bag is well constructed out of impressive sounding materials such as ballistic nylon. It looks sturdy, it looks like it can take a bullet, but once the damage is done, I don’t know what story the damage will tell.

Efficient Disaster Management

When I stand up to go somewhere, the routine is precise. Right pocket, wallet. Left pocket, iPhone. Keys in hand, grab my bag and go. It’s this sort of workflow precision that allows me to stay cool when the unexpected occurs. My inner dialog during the situation is, Well, see, I’ve got my shit together, so even though this unpredictable thing is going down, I’m doing my part to support predictability.

Whether it’s a wallet or a bag, its design needs to encourage and support my irrational worldview that with the proper level of organization those disasters, large and small, are all manageable.