What's the best way to kit out your Pilot bag, you ask?  Well, it depends...

You might not need much, if any, additional organization at all!  For many folks, nothing more than the included Key Strap (or perhaps one or two extras) is needed to keep oneself organized with the Pilot.  After all, it has five separate sections, with additional pockets and slots built into three of them.  Plenty of places to put that ever smaller version of your stuff.

For those who'd like to keep things well sequestered, though, the answer will still depend - how will you be using your Pilot?  As a briefcase for work?  A daily carry cross-body?  Diaper bag?  The possibilities are endless!

I'll go over a general list of what-fits-where, and then zero in on a couple specific use cases, and how to get the most from your Pilot in those situations.  Let's go by pocket:  

First up is the main compartment that takes up the rear half of the bag.  This is where you'll put your laptop, any large books, papers or folders, and other large things.

• The Cache - Our padded laptop sleeve.  It comes in many sizes, and the 13A is the largest that comfortably fits here (technically the 15D can fit, but it's pretty tight, and isn't as smooth to remove and replace.  If you think you're just going to keep the Cache in the bag and only remove the laptop, you might use it for a slightly bigger device).  The Cache can connect to the Pilot using its rail system.
• Packing Cube Shoulder Bag - Great for an extra set of clothes or to contain a light jacket/rain shell.
• 3D Clear Organizer Cubes - Inside the main compartment are two sizable pockets on the dividing wall between this pocket and the front pockets.  The 3DOC fits perfectly in these (almost like we did it on purpose...), so while they'll fit great in the front pockets, too (we'll get to that, hold yer horses) keeping one or two back here can help you keep certain things you might need handy, but free up the front pockets for stuff you'll reach for more often.
• The Snake Charmers - Either size fits great back here, and will give you two further pockets to organize your cables and chargers.
• Travel Stuff Sacks - The smaller ones fit nicely in the front three pockets, and the bigger ones can live in the back.  Great for collections of small, random items, or more storage for light, stuffable jackets and rain slickers.
• A5 Ghost Whales and Medium size Clear Organizer Pouches - The largest of the organizer pouches can go in the rear compartment, holding larger flat items you'd like to keep separate from everything else.
• Handy Little Thing Size 2 - The HLT has small pockets and loops inside to store and organize cables, tools, or whatever.  The larger size 2 is great in the back, and the size 1 works in a front pocket (or vice versa, it's up to you!)

Next are the two side pockets on the front of the Pilot.  They have the same volume, but have different internal pockets (an open pocket in one, and four pen/tool slots in the other).  Some accessories that work well in them are:

• Vertical Packing Cubelets - Similar to our 3D Organizer Cubes below, these guys are turned 90­° so the zipper is around one of the short ends.  Makes it more accessible without having to remove it from the bag!
• 3D Clear Organizer Cubes - Mentioned above, these fit great in the side pockets, and are easily accessible.
• 3D All-Fabric Organizer Cubes - Same as above, just with full-fabric sides instead of clear urethane sides.
• Small Snake Charmers - The Larges are too big up front, but the Smalls are just right.  Keep the big guy in the back.
• Travel Stuff Sacks - Size 1 or 2 work great in here.
• Ghost Whales and Clear Organizer Pouches - Small size pouches (or anything smaller) fit excellently, and are great candidates for attachment to Key Straps and then to the built-in O-rings in the bag.
• Handy Little Thing Size 1 - Or Size 2!  Either one fits (these are chonky pockets)
• Cubelet - Little brother to the 3D Org. Cube, Cubelets are squarish, fabric-sided minicubes perfect for small chargers, a single nice cable you want to keep from getting tangled, or an array of ethically sourced, organic lip balms.
• Everyday Cubelet - A nice little side-bag that fits perfectly in one of these pockets.  The Everyday Cubelet is a great place to store your most important items when using the Pilot as a briefcase, diaper bag, or other specific use; it allows you to carry these securely, and easily keep them with you if you need to leave the Pilot behind.
• Nik's Minimalist Wallet #4 - All the styles are great to toss in any of the pockets, but the #4 has a loop that allows you to connect it to the bag via the included Key Strap, and keep it secure.  Or move the Key Strap to any of the other interior pockets and keep your wallet there, it's up to you - you are after all the Walter Payton of your wallet location.

The center-front pocket is the water bottle pocket, but it can hold other things as well, like a small collapsible umbrella or a few small accessories:

• Size 1 Travel Stuff Sack - The smallest size fits great in here!
• Clear Organizer Pouch, Pen/Pencil size & Ghost Whale Organizer Pouch, size Small - The Mini size of both pouches (and Super-Mini Ghost Whale) will also fit in here, but the long skinny pocket fits the long skinny pouches linked above perfectly!

Lastly, the open-topped pocket on the back of the bag will likely stay accessory-free for most folks, since there's no way to close the pocket, or attach things to the bag back there.  It's a great place for an easily accessible book, magazine, file folder, or newspaper (a news-what?).

So there are our pieces to work with; now let's build a loadout for a few specific uses.

First up is as a daily carry work bag: 

• We'll grab a Cache for our laptop or tablet in the main pocket and a 3D Clear Cube or Cubelet to pop back there in one of the small inner pockets to hold whatever cables we need for it (or a Snake Charmer or HLT if we have a bunch)
• Next we'll add a Mini Ghost Whale Pouch on the included 8" Key Strap on the left side for our wireless headphones (podcasts and audiobooks make the bus/train a lot more fun).  We can pop our phone in the large inner pocket here, too, if we don't want to carry it in our pocket
• On the right, we'll add a Cubelet on a Key Strap for small incidentals, and stick some good, non-leaky pens in the slots, along with a good multi-tool for emergencies
• The water bottle pocket is left free for our favorite bottle/coffee tumbler
• The back pocket is open like our minds, ready to be filled with whatever the day brings

Next, what if we've got a miniature human in our care?  Babies, and even older kids, require a lot a specialist equipment, which can fit neatly in the Pilot's (relatively) cavernous holds while the fam is out for the day.  For a quick day trip, it beats a huge diaper-duffel!

• First off, if your tiny tot is still unclear on the whole "porcelain throne" thing, either due to tender age or a perfectly understandable wariness, you'll be bringing plenty of diapers - either side compartment should be able to hold enough to get you though whatever errand you find yourself on (disposables fit best in here; if you use cloth nappies, they'll fit better in the main compartment)
• The other side compartment might hold a pack of wipes, snacks, baby food/formula, a 3D Org. Cube with baby cream and sunscreen for older babies/toddlers (to prevent messy spills), or small toys/rattles/teethers
• The water bottle pocket is a perfect home for baby bottles (one large or two smalls stacked up)
• The main compartment will hold the bulk of the gear, from extra clothes and burp cloths (in a Packing Cube Shoulder Bag), to a light blanket and a sun/winter hat for the wee one; Travel Stuff Sacks or a Travel Laundry Stuff Sack (for keeping dirty stuff away from the clean stuff) can help keep different categories of things organized and ready-to-hand
• The open-topped pocket on the back is a great place for your foldable changing pad (and anything else you need to stick back there while you chase your spawn around the restaurant)

 And finally, what if you just need a bag?  Just a bag to keep your stuff in while you explore this weird and/or wonderful world?  Here's an example loadout that covers most daily adventures:

• Cache in the main compartment for your device of choice, along with a Small Snake Charmer for cables/chargers, and a small pouch/cube for basic first aid items
• An organizer pouch (Clear or Ghost Whale) in each side pocket for little stuff, and a #4 Minimalist Wallet on a Key Strap in one for wallety things you want on hand, but not in your in-pocket wallet
• Water bottle pocket and outside pocket empty and ready to accept whatever makes sense that day; coffee tumbler and magazine?  Water bottle and paperback?  Tiny umbrella and scientific journals?

The Pilot is one of the most versatile bags we make, and these ideas are only the tip of the nylon-enrobed iceberg.  There are many other ways to pack it and load it up - we'd love to hear how you use yours!  Let us know in the comments if you have any alternative packing strategies, or ideas on how you'll pack it out when you get one!