What's in your bag? More report on the iPad journey

As we wait again for more report from WT on exactly what (if anything) is going on, I’ll throw in my own report on my journey toward using the iPad as my end-all, be-all system for work, play and everything in between.

It’s now been over a month since I’ve been toting around my iPad Pro to work, leaving behind my laptop and most (but not all) the accessories that come with it. I guess I should mention that I’m a longtime sysadmin for a company HQ’ed in Silicon Valley with satellites in both the Bay Area and the Southland, As most of you may know, sysadmins must wear several hats, and in my case I hang mine at around six places in California. A good part of my work require that I float between all the places, requiring me to set up shop when needed, especially when doo doo hits the proverbial fan. I must also be ready to do the same at a nearby Starbucks (or Peets which I prefer) while in transit, because I always seem to get stuck in a place where LTE coverage sucks.

Though I don’t “float” every day, I must be ready to do so every day. In my early days I was also tasked with security and being younger, I thought I’d require some heavy iron, with a bag to match. I’d carry a large messenger bag filled with a 10lb laptop and all kinds of weird accessories, including a CD case and even manuals. When my wife said I look like a hobo, I downsized to a simpler laptop bag with just a Macbook Pro 15", then a 13", then an Air.

After last year when I was able to revive a network and servers with just a jailbroken iPad that was fortunately loaded with enough GNU utilities and some custom security software I wrote, I realized I was still overdressed for my job. It seems all I really need is a decent Unix base and a shell to work from. Since corporate policy frowns upon a jailbroken devices, I began carrying around a Raspberry Pi with a bastardized version of Kali Linux and began dabbling with the idea of losing all my gear in favor of just an iPad. And this prompted me to purchase the 9.7" Pro.

One thing that this experiment made me appreciate (that I didn’t before) was the bag, which if you think about it is the unsung hero of this whole exercise. While my Timbuk2 messenger bag served me well when carrying loads of iron, and would fit right in in a safari trip, because my particular model has room for three laptops, water bottle, USB charger bank, on top of tablets, smartphone, and perhaps all my clothes. Sure, there are smaller versions, but none of them are for aspiring minimalists.

On the other hand, most simple laptop/tablet sleeves I found are too bare, providing no room for anything but the tablet. No pockets for even a charger or cables. When someone on the forum suggested a Waterfield bag from sfbags.com, I immediately went to the site and ordered the Travel Express bag, and for the past few weeks I’ve run it through the ringer. Let me tell you, it’s a keeper as it’s been perfect for my iPad experiment. It’s almost thin as a sleeve, but it’s able to accommodate everything I need. It’s also tough (perhaps tougher than the Timbuk2) for all the things I need to protect, but soft enough in my hands (I got the waxed canvas one which supposedly ages well). I’ve dropped it a few times and even stepped on it while making my travel rounds with nary a mark.

It’s a smart looking bag with a touch of class. I can carry it around with just one hand, tuck it under my arms, or even use a hand strap or shoulder strap if necessary, I guess.

With all the necessities packed inside, it’s about the size and weight of my MBP 13". A tad thicker due to the wireless keyboard. With a Textblade instead, it would be about as thin. There’s actually room for two tablets, which may be important when I’m issued a Surface Pro 4 later this year. As WT likes to tout, the insides are well crafted as well, with two nylon pockets for hard items, and two soft felt pockets for fragile stuff:

What can it fit, and how much? Well, let me show you:

  • iPad Pro 9.7 with Moko smart cover
  • Apple Pencil + three pens
  • Apple Wireless Keyboard
  • iPhone 6
  • Lightning cable + charger
  • Apple earbuds + Jaybird Bluebud X inside the black felt bag
  • Two flash drives
  • Raspberry Pi in a clear case (not pictured)

And everything all fits in nicely. And believe it or not, this is what I’ve been using every day for the last month or so for work (sysadmin’ing, programming, as well as regular Internet stuff like email, browsing, skype/facetime, writing documents, marking up PDFs, making diagrams for personal and presentation purposes, even to make this post). I’ve not touched my laptop or desktop, neither at work or at home. After hours, the wife and I cozy up and watch Korean/Japanese dramas together or airplay it onto our TV. Or we take turns with it. I dabble in novel writing while she dabbles with first person shooters (don’t really understand her fascination with that).

And that’s about it as far as hardware’s concerned, and it’s exactly what I plan on taking with me in an island hopping trip I plan on taking later this summer (and quite possibly the only thing). If the textblade can arrive by then, it would reduce my load significantly as the most cumbersome part of all this is the keyboard. I should also mention that the beauty of this bag and setup is that I can simply toss it into my messenger bag or something even bigger depending on the trip. But lacking that, as it is, it’s been my daily carry-on for the last month. And it’s worked out great.

Software, of course is another story. Maybe I’ll post another if anyone’s interested.



Great story. Thank you. I have been trying to reduce what I carry as well, but I have not been as brave as you.

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I have been trying out a similar combination of an iPad Pro 12.7", Pi Zero (in PiBow case to make it sturdy) and TextBlade. Just a few cables on top of that for charging and connecting items to the Pi Zero. Probably the bulkiest thing is the iPad Charger (which I also use as the Pi power supply).

Are you using thevipad as the screen for the pi? If so, what program are you using?

If I want the Pi command line then I use ServerAuditor. If I want the GUI I use Microsoft Remote Desktop. I also have a VNC client I can use for the GUI.

Thank you. I installed Microsoft Remote Desktop on my Phone and am now able to access my Windows laptop. Could come in handy when out of the house and need to get to something on the laptop. I’m not sure I would want to go on a trip and leave it behind, though. I would be afraid that something would happen where I would not be able to access it and not be able to do any work. I guess baby steps for me.

Are you using XRDP on the Pi for remote desktop access or have you found something better?

I am using xrdp. I also have xvnc installed but prefer xrdp as it gives better performance.

Very nice write up, thank you. Please do let us know your software set up as well.

Thanks, I have an extra Raspberry here and I think I will set it up for travel use with my iPad Pro.

I still have an original waterfield cargo bag back when they used the airline buckles. The thing is built like a rock and I’ve abused that thing to no end and its still going strong.

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@sosurim thanks for this awesome post. I’ve been intending to head the minimilist route, with the TextBlade as the catalyst for me to do it. Needless to say I’m 18 months behind my original plan, but on the bright side now the iPad Pro human sized edition exists which seems like a nice choice (since I can’t yet imagine existing on a mini).

One question. It seems one of your bulkiest items is that charger on top of the iPhone. Is it just a USB charger? Why not switch to the smaller cube ones, or maybe find something third party that would be slim? Just seems to take up about 2-3x as much volume as it needs to.

The charger is the standard one that comes with the iPad. I also use it to quickly charge up my iPhone. I guess it could be the bulkiest thing, were it not for the wireless keyboard, namely its battery compartment, which is far bulkier from my experience. But it’s the only BT keyboard I have until the TB arrives.

Is there another charger that will work with iPads that is of smaller, less bulkier form factor? I wasn’t aware.


I prefer to do everything via command line. I’ve also used ServerAuditor, but find myself using Prompt more and more. I like the ability to group sets of servers, having multiple sets of oft-used keys available, and the finger print security.

While I try to avoid doing remote GUI, we have several AD servers that seem to go awry on a regular basis (almost like clockwork). And for those I prefer RDP. Never been a big fan of VNC due to poor performance. For personal use though, when I need remote GUI in a pinch, I’ve used Chrome Remote Desktop and it’s worked well for me.

The fastest remote GUI I’ve ever tried has got to be the NX server, which I’ve used long ago. But that’s only good for X (no Windows). I don’t know what the status of it is nowadays. Designed for low bandwidth environments, if you want the best performance, this is it. On a LAN, it felt like you’re on the console itself.


I was thinking of the iPhone charging cube. It would charge your iPad at half the speed, but also take up much less space so that is the tradeoff.

As I said there might be third party chargers with better tradeoffs (for instance I bet you would value thin over total size). Or even a thin USB battery (10,000 or 20,000 mAH) that you would charge overnight with a charger from home or packed in travel bag when away? Just my thoughts so far.

While I have you I noticed your discussion elsewhere about not being happy with a high end stand. You might consider this tiny cheap one that takes no space and works even for my iPad (barely).

For my travel purposes, considering I usually don’t travel alone, I picked up an Anker 60w six port sub charger. It has variable output to connected devices, up to ~2A each. So I ha e a power cable to one block and it can charge both our iPads and phones and two additional devices. Since most other devices don’t need charged every day, it works great. I also plan to get their 26800mah battery.

Guests at my house love that I keep an Anker 60w 6 port in the spare bedroom. I always carry one when I travel overnight.

I tried Microsoft Remote Desktop on my iPad to use as a client for xrdp on my Raspberry Pi and was unable to get the keyboard to work correctly. I added x11vnc to the Raspberry Pi and now am using my normal iOS VNC client (Screens) and all is well. An added bonus is that the TextBlade and iOS Screens play real nice together. So far my travel setup looks to be an iPad Pro, a Raspberry Pi, iOS Screens and iOS Prompt and Air Video HD for entertainment. I also have a VPN running on my home server so I think I am set for my next trip.

I need to figure out something for when I am out of the house as Microsoft Remote Desktop is only working on my local network. I need to setup remote access through my router.m (Airport Extreme).

I guess they’ve been around for a long time. I really like the bag, and their customer support is one of the best I’ve seen, answering few of my questions quickly and courteously. A colleague of mine spilled some water on it and nothing was damaged inside. I doubt it’ll survive being drowned, but now I’m sure it’ll be okay to take on my trip which will consist of multiple boat rides.

I’ve since made do with the makeshift stand feature of my Moko smart cover where the cover folds into a triangle to form a stand. It acts as stand in two positions, and only in horizontal mode but it works well enough.

Regarding the Plinth, I think I just got a dud. But I didn’t really care for the email I received from the owner who kept insisting I was using it all wrong. So I returned it, and it’s worked out for the better. Just less gear I need to carry.