.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.

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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.

TotalCon 2018 Thoughts, and a Love Letter to Future Me

As always, TotalCon was a blast. My games ran great, the people I met were awesome and every table I was at yielded a memorable story. As a note point for this post, I am an analyst and work in process improvement. So, I will be talking a lot about things I want to different. These observations don’t have anything to do with the Con itself; they are just personal point for me. The Con staff, and the hotel were amazing. No complaints there.

A HISTORY OF ME AND THE CON

Before I get into what I want to do differently next year, let’s talk about how I got here. This is the 5th year in a row I’ve gone to the Con. The first year, I played exclusively Dungeons and Dragons 4E, with maybe a few Deadlands games mixed in. That year, I also signed up to play Arkham Horror, but the GM was a no-show. Fortunately, I brought my copy with me and we were able to play. This also showed me that you don’t need any special skills to run games at the con, other than an aptitude for teaching it, and helped shape what I did next year.

I’m fuzzy on the next year, but I started running some board games and playing some D&D. Wizards was getting ready to release 5E so the usual organized play was coming to an end. In 2014, I am pretty sure I signed up to run a ton of board games that year. It was fortuitous that I did, because there weren’t a lot of games offered I was interested in and might have skipped the Con entirely. The next year, I did the same thing: ran about 8 sessions of four-hour games. But, I knew I’d be playing games I liked. I was in control of my own destiny. It worked out well.

In 2017, organized D&D came back very strong. I forget if there were Adventure’s League games offered in 2016, but last year they had the big multi-table Interactive I’ve always enjoyed playing. But, alas, I had signed up to run games and couldn’t make it.

This year, when I signed up to run games, I was hesitant and waited until almost the last minute. For the most part, my rule of thumb is if a game I really enjoy is also one my regular gaming group hates, I will run it at the Con. There are a few games like Blood Rage that are quick games where the more players the better that I might run, but more on that later. I almost kept my Saturday open to play the Interactive, but wanted to see how two years in the new hotel went. Naturally, they did run it.

For a variety of reasons, I wasn’t as mentally prepared for the Con leading up to it and realized that Ambitious Me wrote checks that Present Me would have trouble cashing. Each year, I forget that running 32 hours of games in 2.5 days1 is tiring. This year I had the added challenge of a crazy work schedule the weeks before and grad school kicking my ass. When I got there, I realized the corner I had painted myself into and I had no free time to grab a pick up game or get into a different game. That said, all the games went well. It turned out my Saturday night Arkham Horror game was comprised of people who all knew how to play the game and I was able to sit back, play the game, and enjoy it. It was a good ending to the Con.

WHAT I WANT TO DO DIFFERENT NEXT YEAR, GAMES EDITION

This year throughout the Con I kept a running note in Notes2 on my iPhone for things to do different and I hope to hell I refer to it when I go to submit games at the end of the year. The immediate one is to run less games3. I need more flexibility when it comes to my schedule and not to get worn out. By Friday I was getting tired. I ran the same game twice a lot. Next year, the two big games that fall into the camp of “regular group hates it” are Fury of Dracula and Arkham Horror. Both games I can get onto the table fast. Fury of Dracula I will likely run twice, but definitely the 8am Saturday slot. That one had a few repeat customers from previous years. It is also the game the regular gaming group really hates so the only time I get to play it as the Con. I am also adding another qualifier of can I get the game, with no outside the con prep time, on the table in 15 minutes or less. Arkham Horror, believe it or not, with the inserts and organizers I have, I can get on the table in around 15 minutes.

Firefly, a game I truly enjoy, does not meet that criteria. It has a lot of components and takes up too much space on the round tables. I have the Meeple Realty insert which helps with setup and running the game, but it just isn’t working as a formal game at the Con. If it is all experienced players, I can kinda get the game on the board in roughly 15 min. I think if I could use one of the big tables the miniatures people use I could pull it off. This year, I did a little more prep time and prebuilt crew packets that had all the items players need. Next year I am not running Firefly as a scheduled game.

Arkham Horror I usually get a few people who know how to play it. Next year, I am not running it as a teaching game. I will run it for experienced players only. That should help with teaching exhaustion.Blood Rage, maybe. I might do an experienced players only with the Gods expansion.

So, instead of running 8 games officially, I will probably drop that number to 3-4: Fury of Dracula twice, Arkham once, and maybe a Blood Rage. No matter what I do, though, I will stop running games at noon Saturday. The 8am Saturday Fury is a good slot. I will still bring games I like, like Firefly and Star Wars Rebellion.

As you can tell, the theme for next year is flexibility. Someone wanted to get a pick up game going of a game I love, and I just couldn’t get schedules to line up.

WHAT I WANT TO DO DIFFERENT NEXT YEAR, NON-GAMES EDITION

There are a few minor non-game related things I want to play attention to next year. The first is bag choice. I usually bring my Tom Bihn Ristretto. It’s a great bag, but it’s only good for when I go to the coffee shop or into Boston for the day. I ran out of room fast and didn’t have room for my drinks, protein bars, and dice thing. I have a larger L.L. Bean messenger bag I will bring next year.

Food is another one. I want to stop at the super market and grab some deli meat and use the fridge in the room and be able to make fresh sandwiches. The grab and go at the hotel isn’t bad, but it’s not great. The one deficit — other than sleep — was getting decent food into me. I brought a large bottle of my favorite juice, but next year I will just bring some smaller bottles. Eating at the con is a tough one. Even the regular food options at the restaurant are pub food.

I averaged about 4 hours of sleep at the con. I want to try and get more, but it’s hard to get a lot. I’m usually a little ramped up so it’s hard to get back to sleep. That is why my 8am game (if I’m running it) is Fury of Dracula, a game that is super-stupid easy to set up. This was good because Friday I woke up at 7:56 for the game. I don’t want to take a sleep aid because I’m afraid of oversleeping.

Usually, I take a half day the Wednesday before the Con and am off through the following Monday. Because it is after President’s Day every year, I’m seriously considering taking the whole week off next year. It will help a little more with prep and getting mentally ready. I’ll just head up to the hotel around 1-2, check in, and get settled in.

That leads to the last point, which is my laptop. For two years in a row, I’ve brought my MacBook with me and barely used it. Unless there is a clear need for it, it can stay home. My 12” iPad Pro at this point does everything I need.

  1. I run games from 1pm Thursday to 11pm Saturday. I keep Sunday open.
  2. The note is pinned, to make sure I don’t forget.
  3. Spartacus at this point has become a private game. It’s a full table of friends and will not be run as an official game next year. It will instead be a pick-up game.

On Writing for Exposure

Traditional writing advice is to not write for free, or for “exposure.” The idea is writing for free for another outfit cheapens your work, and lets someone make money off your work with nothing tricking back down.

From 2003-2006 I wrote for free, and for exposure. The freelance success I had after that made it all worthwhile. I am the exception to that rule.

In 2003, the web and blogs weren’t what it is now. WordPress was just coming out. Free or low cost web hosting wasn’t as ubiquitous as it is now. A lot of blogging type sites required custom CMS platforms. Also, in 2003 I was rapidly approaching my 40th birthday. I didn’t want to be that guy bemoaning I didn’t give writing a chance.

At the time, I was pretty passionate about video games1. Worthplaying was looking for writers and were very clear the gig wasn’t a paying gig. I contacted them because I figured getting my writing out there in a public fashion would help my writing. I’d get used to working with editors, the inevitable commentary from internet readers , and writing on a deadline. It worked. I wrote a ton of stuff for them over those three years.

Massively Multiplayer Online Games (MMOs) were just starting to become the rage then. EverQuest was a few years old. World of Warcraft was close to coming out. Not many writers wanted to invest the time it took to review and understand these games. A traditional game might take 20 hours to form an opinion on, but an MMO was at least 50 hours of base work. I liked these types of games quite a bit and started to become known as “that MMO guy” in a period there weren’t many of us. I was also able to start building up my contacts with developers and PR people.

In 2006, I decided to take the next step: to see if I cold get paid. I sent clips packets off to the three major game magazines: PC Gamer, Computer Gaming World, and Computer Games Magazine. I remember standing in line at the Boston Post Office with my manilla envelopes of printed out samples with a cover letter offering my services. I had the weird idea that printing them out on glossy paper would make them look more like they were printed in magazines. These were also magnum opuses of reviews. My EverQuest 2 review was about 8-10 printed pages.

I was almost immediately contacted by the EIC of PC Gamer magazine. He knew of me from Worthplaying and needed someone to write a review of an EverQuest expansion. There was just one small wrinkle: famed Red Sox pitcher Curt Schilling usually wrote the EverQuest reviews for PC Gamer. This was good for PC Gamer since they could put “Curt Schilling reviews EverQuest” on the cover. The EIC was torn at the time since Curt hadn’t said yes or no. I called him back a few days later and said something along the lines of: “Hey, if you want me to review this let me know. If not. I’ve got another place wanting me review it and I can just go with them. We can do the next review together.”

He gave me the gig.

This was an immediate eye-opening experience. The reviews editor emailed me and said, “Yep. We want you do the review. Give me 150 words in two weeks.” One hundred and fifty fucking words. My opening paragraphs for a review were 150 words. How the hell was I going to write an entire review in 150 words. I did it, though. A few minor revisions later, a few months later my review hit the newsstands. I wrote for PC Gamer until 2008 or so. I then wrote for WoW Insider for a year, then Gigaom for another five years. I haven’t had a paid writing gig since 2015.

The line for me is clear: writing for free for Worthplaying lead to paid writing gigs. It gave me the experience I needed to go pitch to editors with a body of work from a reputable source. I also got a lot of free games out of the deal. Where the exposure gigs falls flat for some people is no one approached me wanting to pay me to write. I had to go out there, pitch the work and do the legwork to make those contacts. I also established myself as an authority on a niche market that was going through a growth spurt. Even now, spending three years trying to cram massive reviews into 300 words or less has help make me an economical writer at work.

I don’t know if this path would work today. Back in the 2000s, there was a viable print market and publishers would pay for writers. For gaming PC Gamer is the only real gaming magazine these days. CGW and Computer Games Magazine are gone. A lot of the big gaming sites are now consolidated into IGN and Gamespot. The market has consolidated. As I said in my piece about writing, making money creating content these days is hard.

As much as people bemoan the idea of writing for free, I feel you gain some valuable experience. Even if you start your own blog and pump out content, paid writing typically requires collaborating with someone. Be it an editor, or the artist for something you are working on. The ability to create content on someone else’s schedule is invaluable for creators. Obviously you have to weigh the pros and cons. With Worthplaying, it was obvious the site was such a labor of love for Rainier and Judy I didn’t mind helping out. I’d write for them again, even for free.

  1. Still am, to be honest

iPad Life: My iPad Pro Usage post-MacBook Pro Purchase

Fraser Speirs — a long-time iPad-only advocate — is leaning towards getting another MacBook Pro. Fraser is famous for a piece he wrote about going iPad-only entitled: Can the MacBook Pro Replace Your iPad? It was an interesting reverse take on the whole “Can your iPad replace your laptop” argument that is bandied about.

I am both glad and disheartened to hear this. I was glad because it’s easy to get into a situation where taking a stance on something like going iPad-only is tough to back off from. Your identity can be wrapped up in “that guy who went iPad-only”. Inevitably, you hear from all the people who gave you grief about it two years ago with an extra helping of “told you so.” So, being able to publicly and critically assess whether a tool works for you, and change course if it isn’t, is a good trait. It’s disheartening that Fraser feels that iOS 11 doesn’t meet his needs anymore and he needs to use a Mac again.

There are four people I follow on Twitter that are iPad-only folks. Not sorta-iPad only, but full-time, only use an iPad people: Matt Gemmell; Ben Brooks; Fraser Speirs; and Federico Vitcci1. CGP Grey is also a heavy iPad user so he deserves honorable mention here. Of these five, two of them are either using the iPad less after iOS 11 or are thinking of moving back to a Mac. CGP Grey needs a Mac to create his YouTube videos, so he’s always straddled that line. iOS 11 was supposed to be the big start of iPad productivity, but instead people I follow who use the iPad heavily are leaning towards walking away from it.

I am happier with iOS 11 than I was with iOS 10, but not drastically. I think the new Files app is a great step forward. Drag and drop is pretty useful. iOS 11 has helped me not use Workflow app as much as I used to. However, iOS 11 has some weird bugs that are driving me nuts. I’ve been having a lot of rotation issues where I unlock my iPad and the rotation is stuck until I engage the gyroscope again. The Apple Smart Keyboard has been flakey and I need to snap it on and off again to get it work. That said, I think the drag and drop, the Dock, and the new Files app are a net win. I wouldn’t go back to iOS 10. I don’t think I can do tasks I couldn’t do on an iPad before iOS 11, but some of the suffering around those tasks has declined.

Fraser’s comments made me think a little more about my iPad usage after I got the MacBook Pro in March. Has my iPad usage increased or decreased? Unfortunately, I don’t have any data to back up my theories. The best example is my iPad usage last night when I was working on my schoolwork for the week. I’d been taking part in an informal case study on a MacRumors post regarding using iPad Pros for school. Like any thread about iPad productivity it devolved into a thread of half-truths, assumptions, lies, and bold statements of what you can and could not do on iPad. So, when this semester hit the midpoint I posted my findings about 5 weeks with the iPad. I considered the experiment closed at that point. I haven’t gotten any responses to that thread in a few days, so I guess a lot of people consider the experiment closed as well. I could go back to using my MacBook Pro for school and not think twice, or feel I had sold out the cause. Instead, when I got down to the business of doing this week’s assignments I just picked up my iPad fired up PowerPoint and worked on the assignment. When I was done, I uploaded it to the shared Google Drive folder and emailed my classmates.

Was this inertia from having a rhythm of working on school work this way for the last 5 weeks? I don’t think so. When I was doing some writing this weekend I found myself always reaching for the iPad first. For a lot of creative work like drawing and writing, the iPad is such a natural fit now for how I do that work. That’s not to say the MacBook Pro will sit unused. My beloved Topaz filters only work on my Mac. I use Tableau a lot and there is no iPad version. Sometimes I need the might and power of the full Office suite. Today I am working remote and need to connect to our virtual desktop system to do work. That type of work is still best done with a pointing device you can right-click on easily.

So, in conclusion my iPad use hasn’t really changed for the core work.

  1. Federico uses a Mac to record his podcasts, but that is it.