iPad Life: Update to Playing D&D on the iPad

For reasons I can’t even begin to understand, an almost two-year-old post about how I play Pen and Paper Dungeons and Dragons on my iPad is the top hit page on this site. A lot has changed in my workflow, so I am providing an updated post.


With the release of D&DBeyond, Wizard’s online compendium, they also issued Cease and Desist orders to a lot of the sites that provided character builder services. While it was possible to upload configuration files that had D&D source material, it became too much of a pain in the ass for me to manage. Instead, I figured for short money I could buy direct from Wizard the material I needed and just manage my characters on their web page.

I have been very impressed with the online portal. It’s damn easy to quickly create and update a character. A few times I have been at a con and suddenly needed a level one character in about 5-10 minutes had a workable character for the play session. Updating them when I get new gear or a new level is also very easy.


Gone, obviously, is the Numbers sheet I was using as a hacked-together character sheet. Also the 3rd-party PDFs are gone. I instead use the portal manage my character.

Luckily, the places I play D&D have decent WiFi. With the 12.9” iPad I can view the entire web page for the character manager. From there I can adjust hit points and check off used abilities. It’s also easy to invoke mechanisms like short and long rests and the web page will automatically reset used abilities. There is also an added bonus that having the iPad laying flat on the table lets other players see I am actually using it to play the game, and not Minecraft. I also makes seeing dice rolls easy without a laptop screen in front of me.

The one area I am not thrilled with is the PDF export. For non-spell casting characters it’s fine. However, the amount of information it exports about spells is lacking. It doesn’t tell me that effects, damage, and other crucial information. This isn’t the end of the world since I just keep that PDFs in case the WiFi is crappy. There is a companion app that I can use to look up information. Unfortunately it doesn’t handle characters yet. The PDF is just a backup in case the WiFi craps out. I sync them to my iPad but I have’t needed to use them in a session yet.

I have used this system in roughly 6 games, mostly at conventions. It is working well and for about $30 I solved a lot of character management problems. Hopefully they will implement a character manager to the iPad app. The only issue I have is battery life since I am hammering the WiFi connection. I do keep a small battery charger in my bag, though.


On Apple’s Earning Adjustment and Upgrade Cycles

Apple today announced expected revenue for the holiday quarter would fall short of expectations. They didn’t miss by much, only by about $5-7 billion1. Tim Cook blamed a lot of things: China’s slow growth, longer upgrade cycles due to the elimination of cellular subsidies, and that people paying $29 to replace old batteries allowed them to keep their iPhones longer2.

What he didn’t mention was Apple raised the prices on everything over the last few years.

Now, some of the complaining about prices wasn’t justified. The new MacBook Air starts at $1,199, up $200 from the old-model’s $999 price tag. That old Air, however, was outdated. No Retina screen. Old internals. It did have MagSafe and USB-A ports, so for a lot of people it was still worth it.

The price increase on a lot of other items, yeah. I bought my 2016 15” MacBook Pro in March 2017. It replaced as my main Mac a 2011 15” MacBook Pro, and an 11” MacBook Air I bought in early 2015 right before Apple released new upgrades. The 2011 I farmed off to a co-worker; the 11” I still have3. While performance was a driver for the upgrade, a large part of it was getting a Retina screen. The 12.9” iPad Pro really made the older screens hard for me to use. I sometimes wonder if I got a 2014 13” Pro instead if it would still be my main Mac. The dual core processor would likely show its age by now. I still use the Air though, when I need MacOS and an ultra-portable computer.

My theme for 2019 Evaluation. For the record, I’m not looking at making major life changes. I am, however, evaluating the devices, apps, and services I use. For now, it’s a lot of data collection. What do I use my Mac and iPad for? I say I want to use x app more, but over the year I use y app instead. I promised myself it was unlikely I was going to upgrade any of my devices. Some of this is price. The increased price of the new iPad Pro may not have completely turned me away, but also needing to buy a new Smart Keyboard and Pencil (also at a roughly 20% price premium) surely did. The same with my iPhone. I used my 6 for three years, and I expect to get 4-5 out of my 8 Plus. New iPhones are more expensive and my existing one works just fine. For me to upgrade I need to see real-world improvement; not just benchmarked improvement.

As Patrick Rhone would say, a lot of people are finding out their current phones and devices are enough.

  1. Since this is the internet, I feel I need to mention I am being sarcastic.
  2. I am not making that one up.
  3. It’s on my desk next to me, actually.

iPad Life: Moving the Goalposts

Any discussion of using the iPad as productivity tool — be it a primary or secondary device ends up with: “Until x application is on the iPad, it can’t be a ‘real device.’” Said application is usually Photoshop. Adobe recently announced plans to bring Photoshop to the iPad. Naturally, the anti-iPad crowd folded their tents, admitted you can now do “real work” on an iPad and the argument ended.

I will give you a few moments to catch your breath from laughing so hard. The MacRumors forums — where most of the arguments I see take place — the big discussion point is that clearly it’s not the real full version of Photoshop, and here are all the reasons it will fail without even looking at the app.

This is the problem I have with people saying you can’t do “real work” on an iPad. Most of the arguments are from people who have never used the iPad for such tasks. They immediately dismiss the idea, and insist until the iPad is exactly like a Mac, it is but a child’s toy. Maybe they feel threatened that Apple will one day stop making the Mac. Maybe their fears will come true. My own issues going to an iPad-only life are well-documented. Which is why the only opinions in these arguments that matter to me are the people who have attempted to use the iPad for more than surfing the web.

Photoshop coming to the iPad is a big deal. While apps like Affinity Photo & Designer, Procreate, and Pixelmator are quality apps, Photoshop is the standard for any photo editing. It’s great to see Adobe finally realize they need to bring their apps to the iPad.

.plan Files and Tracking & Thinking About Personal Goals

For working on some of my personal projects that have longer timelines than “install this tool on my Mac”, I’ve been struggling with how to track and report on progress. Things, which I love, isn’t good for these. These efforts aren’t really something that can be broken down to task levels. A good example is learning about security tools. I have a task in Things to remind me to install a tool on my Air. But tracking progress, notes, and high-level tasks I need something else. The same for working on coming up with a side-hustle and secondary revenue streams.

I was thinking of how John Carmack of id software used to maintain .plan files. It used the finger protocol as a type of blogging engine, but I liked the simple, text-based structure. As I was thinking about tracking some of my personal stuff, I debated between a separate Ulysses sheet, or using Apple Notes, or just Day One Journaling. I ruled against these because I don’t want it to be in my face. I didn’t want a constant reminder that I hadn’t gotten to those projects because work, school, and life got in the way. I also want to keep it private. I did want the ability to edit the file on Mac or iOS, so that sort of limited the app I would use.

So, I decided on keeping a sort of .plan file in Byword. It’s a simple text file. It’s out of the way since it’s not an app I use a lot. It’s just one file now named “plan” and I will be keeping some notes and goals over time there. Maybe it’s close to bullet journal, but I just wanted a separate way to track a lot of this.

iPad Life: A Post-iPad-Only Life and Rendering Unto Caesar

I have largely abandoned the idea that I can go iPad-only. While I never actually thought it would work for me, and admire people like Matt Gemmell who can, I have come to the grudging realization I cannot join their ranks.

In the parlance of many failed relationships, it’s not the iPad; it is me.

When the focus of my non-day job stuff was writing and drawing, the iPad was perfect for that. Even architectural drawings, while I can’t do full AutoCAD on the iPad, I could still draw buildings and have some fun with that. Schoolwork was a little more challenging where I’d run into some limitations with Word, I could still get around them on the iPad. It was when my career path diverted into information security the wheels fell off the iPad bus. There are some discovery and recon tasks I can do on the iPad, but the tools I use require access to the Unix parts of macOS I don’t ever expect iOS to allow.

I wrote earlier about how I carry too much crap with me and did some data analysis on how I use my mobile devices. While the numbers clearly point towards the iPad as my primary mobile device, they don’t tell all the story. There is a line from the Bible I like which is Render to Caesar the things that are Caesar’s… and a variation of this applies here. While I cannot go iPad-only, the iPad is still pretty much my primary mobile device. Unless I really need a program only available on the Mac, I only bring my iPad with me. I’m writing this post now at lunch at work on my iPad. I bring the iPad to to take notes, read materials, write, and draw. The reasons I outlined in A Year of Using the iPad as a Laptop Replacement for using the iPad as my primary mobile device still apply. But, I felt like my quest to either go Mac-only or iPad-only were causing me to focus on the negatives of each system, rather than the positives. By accepting I need each device in my life freed up a lot of mental energy. I love writing and drawing on my iPad. I love using Unix tools on my MacBook Pro. If that means I leave the house with both of them in my bag some days, well, so be it.

Addendum to the “I Carry Too Much Crap” post: The Rest Of The Stuff

Since the focus on the last article was just the iPad and MacBook Pro conundrum, I thought I’d also summarize the rest of my daily carry. This is mostly what I leave the house with for work. Items with (in a small bag) are in a bag I can throw into whatever larger bag I am bringing if I need them. Here goes:

The Main Load-out:

  1. My main bag is an Ogio Tribune.At some point, I want to get a Goruck, but this fits my needs. I wanted something I could store a few things, like my access badge for work, in a secure, yet easy to get to spot. I also wanted drink holders for my coffee thermos.
  2. My work access badge
  3. A microfibre cloth (in a small bag)
  4. A USB A-USB-C adapter (in a small bag)1
  5. A lightning to audio adapter (in a small bag)
  6. A set of lightning EarPods (in a small bag)
  7. A few lens cleaning packets for cleaning glasses and screens (in a small bag)
  8. USB-C to HDMI adapter (in a small bag)
  9. A Belkin Rockstar with two Lightning Ports (in a small bag)
  10. Advil
  11. Deodorant
  12. A small notebook
  13. Two pens
  14. Hand Sanitizer
  15. Altoids
  16. An Apple extension cable for charging

The Minimal Load-out:

My secondary bag is a Tom Bihn Ristretto. I will use it for when I am not going to work, but need to bring either the MacBook or iPad with me, but not both. The MacBook and iPad are each in their sleeves. The sleeves have the charging brick and cables. If I am just running out to the coffee shop, or something non-work related, I just grab the sleeve and a smaller bag. The Tom Bihn also has a tin of breath mints and hand sanitizer in it.

  1. This only gets used at work, so I might just keep it there.

The “I Carry Too Much Crap” Edition

From Ben Brooks:

My rule here is very simple: take a phone and one other device. Unless you have a major reason why you need three devices, take only two. For me the second device is my iPad Pro, and before that it was my MacBook. If you need a Mac, take a Mac and use your phone for anything else. But decide if you even need that second device — I take mine strictly because if I can squeeze in writing time, it is worth having the iPad Pro. But I could do it all with my iPhone if I wanted

I’ve been in a weird state where I’m straddling a few tech lines and as a result I’m leaving the house frequently with both my iPad Pro and my MacBook Pro. The short version of a long story is I can’t really go iPad-only, but, I also can’t really go MacBook-only at the same time. My primary, non-day job, yet productive, tasks are: writing, drawing, photo editing, and security analysis. I’m oversimplifying here, but the iPad is best at drawing and the MacBook is the only platform I can do security analysis with. The other tasks I can do close to equally as well on either platform.

Ben’s post helped illustrate a growing frustration I have with my daily load-out: I routinely leave the house with my iPhone, MacBook Pro, and iPad Pro. That is one device too many. I’ve made my peace with the fact that I need a powerful Mac, an iPad Pro, and an iPhone as part of my technological setup. What I struggle with is why I feel I need to bring both the iPad and MacBook Pro with me. Core apps I use (Ulysses, OmniGraffle, Affinity Photo) are reasonably feature complete between iOS and macOS1. The iPad-only apps are Procreate for drawing, and the macOS-only apps are my security toolsets.

The practical answer is to just go back to a MacBook Pro. It’s a more flexible platform and the walls I hit are fewer than on iOS. Drawing is the least-performed of my activities. Even today I ran into a weird iOS limitation. I needed to export a multiple-canvas Omnigraffle document to png files. On the Mac, there is a checkbox to export the entire document. On the iPad, no such checkbox exists. [UPDATE: I have since learned there is a workaround] Practicality is not the only driver, though. I really like using the iPad Pro. Typing on the Smart Keyboard is a dream and I love the portability of the device. As with creative work, security work when away from my home is also a rarity.

Since I can’t decide, and impulse and emotions aren’t good points to base decisions on, I’m falling back on my analyst mindset. I created a spreadsheet where I will record on a high-level my device usage. Three columns: Date, iPad, MacBook. The value will be Date (obviously) and for each device row I am using a 4-point grade: 0, did not use the device; 1, used the device lightly; 2, used the device heavily; 3, did something I can only perform on that device. As an aside, this is only for when I leave the house. I don’t care too much right now about my day-to-day usage at home. I will also take care and not cheat the data. If I brought my MacBook, have it on the desk, and the thing I want to do can be done on either the Mac or iPad, unless necessary I won’t drag out the iPad just to give it a checkbox for the day.

  1. There are edge cases on things like some filters for Affinity Photo, but for the purpose of this article we can call them feature-compatible and not get too far down in the weeds.