iPad Pro Work: Setup


I’ve wrestled with this before, to use an iPad or to not use an iPad as a primary productivity machine. I work in financial services, specifically as an investment advisor. I don’t run any heavy-duty programs, I use Microsft’s office suite, a few communication apps, and a lot of web-based programs, so it’s not untenable. But in previous years the compromise has proved too great and my MacBook Pro too trusty.

iPadOS seems to have solved most of the most egregious of those compromises. The addition of the desktop-class browser (almost, Safari extensions are not yet available, but websites do render as desktop sites) is specifically a game-changer for my work. The improved multi-tasking abilities help too, and mouse support opens up a whole new world of possibilities (think, I could connect the iPad to the conference room display for a client meeting and run it from a Bluetooth keyboard and mouse on the table).
So I’m back, I’m giving it another honest try.

Here’s the setup:

• I bought the 12.9 inch variant over the 11 inch. The larger screen offers so much more utility. On top of simply having way more space to work with, it will also give two full-sized apps when running them in split-view instead of the phone versions of those apps. Subjectively, it’s the difference between working on a computer and an oversized phone.

• I chose silver over space gray. Space gray looks awesome, but as soon as it suffers one little nick or dent you see silver underneath. I’d rather the whole device stay one color. Also, silver looks awesome too.

• I chose the WiFi-only model over the addition of cellular. One great benefit of iPads over MacBooks is their ability to connect to cellular data and be always on and always connected. The thing is, I don’t want to be always on and always connected. I like to close my work machine and stop thinking about it for a while. Plus, I still have an iPhone, so on the rare occasion that I’m working and out of range from WiFi, hotspot is still available. The WiFi-only model is also a way to save some money, the iPad itself is cheaper and it won’t incur the extra monthly data cost. This is the one decision I can see myself waffling on in the future, but for now, I’m content.

• I went with 256gb of storage. For people who do a lot with photos and video, the higher storage tiers make sense. For me, 256gb is probably overkill. The only thing that will take up any noticeable amount of space for me is the occasional Netflix or Amazon Prime movie download for watching on the plane.

• Along with the iPad Pro, I purchased an Apple Smart Keyboard, 2nd Generation Apple Pencil, and an Apple Magic Mouse 2. I’ll comment on each of these accessories in the future.

Here goes!

Consumer vs Creator

On its surface, distinguishing between consumer and creator might seem to imply that you should stop watching Netflix and start writing a blog, at least that’s what comes to my mind. That’s an incomplete picture, but I do want to think about the difference between consuming and creating, and how we can be better creators.
A consumer is someone who maximizes intakes. Watching too much TV, eating too much food, or buying too many unnecessary things could all be symptoms. At its base, it is excessive, wasteful, and unfulfilling. That’s not to say consuming is all bad. If you don’t consume food you’ll die, we’re made to consume things. But the definition of a consumer here is someone who is addicted to over-consuming, who lives to consume, and that’s generally bad. You could say the point of consuming is to take.
A creator is someone who focuses on outputs. Creating doesn’t necessarily mean writing or drawing or filming, it can be almost anything that’s contributory. When you engineer additional efficiency into a process at work, or cook a meal from a new recipe, or finish your latest house project, that’s also creating. You could say the point of creating is to give.
None of us are only a creator or only a consumer, but people do seem to shade one towards or away from the two. If you find yourself too far over to the consumer side, which is where we tend to fall by default, it can be tough to dig yourself out and start creating. But here are a couple tips to get started:

  1. Think about your purpose. What are you here for? Who do you want to be? What do you want to accomplish? When you give those questions a good mulling over you’ll probably come up with answers that include creating. Write your answers down, set goals around them, keep reviewing them. A connection between purpose and goals, even between purpose and specific activities, is your guide. If a goal or activity doesn’t match up with your over-arching purpose you can cut it out, if it does match up, go after it. Without the clarity purpose brings, you’ll be tossed around and most likely end up settling back into comfortable consuming. The best way to start moving from consuming to creating is to know why you’re doing it.
  2. Read good books. This could technically be considered consuming, but it’s the best type of consuming, even a necessary type of consuming, in order to be able to create. If you’re not learning and growing it’s tough to have anything to share. Think about a preacher, they do lots of creating, to the tune of a 10+ page document (or two) per week. How can they possibly produce that kind of output? They read, a lot. They fill themselves up with ideas and information which they bring back to their congregations. The same is true for this blog, I wouldn’t have anything to write if I wasn’t reading. Reading should include articles and blog posts, but I specifically mention books because they’re the best way to interact with whole ideas and complete thoughts. Instead of only picking up bits and pieces of information, a book can change the way you think.
  3. Separate your consuming and creating tools. I’ve made multiple attempts to switch to an iPad only workflow in the last few years. One of the main problems I’ve run into is a confusion of purpose. My goal was to use the iPad for both creation and consumption, thereby reducing my technology loadout. It was a noble goal, but one which resulted in a lot of consuming and not much creating. For whatever reason, my mind has a hard time creating on a device that I also use for consuming, regardless of its capability or functionality (which is a whole other issue). Instead, when I use my MacBook mainly for creation (work, writing, projects, etc.), and my iPhone mainly for consumption (news, information, games, etc.), I’m much more productive.
  4. Carve out the time. This is where we often get stuck, who has the time to create things? You might have to get creative before you can create. The most important thing you can do here is to block out a chunk of time on your calendar. This time is sacred. During the block, turn off as many notifications as you can. Choose a place that will minimize distractions. I like to be somewhere other than my desk where normal working habits kick in. A coffee shop could be a nice change of pace, plus it provides a little extra motivation to commit to the time block. The point is to decide on a time and a place where you can focus. It takes some work to create a successful time-block, but it’s surprisingly enjoyable and energizing when you do it.
  5. Start small, continue daily. You don’t have to change your life to create something. Just pick one small thing and do it, today. Then do another small thing tomorrow, and then the next day. Your first time block could be 10 minutes deciding what or how you want to create. It can be directly related to your work or it could be the start of a new side hustle, as long as it involves creating. One thing I’ve committed to is writing 250 words per day. Before I set this goal for myself I had already been writing, but mostly in fits and starts, nothing consistent enough to build upon. That one small daily goal has been critical for me to remain consistent. It’s a lot easier to write 250 words per day than to write one blog post per week. Many small achievements performed consistently over time, one day at a time, will beat a big breakout effort one hundred times out of one hundred.

I will be the first to admit that I don’t have this all figured out, I still spend too much time consuming, but these are a few things that I’ve learned and found helpful. Consuming is easy, let’s do something hard.

Why I switched back to physical books

For the last three years or so I have been ravenously building and reading my Kindle library. I love reading and I love iPads, and I really loved putting the two together. But, the title gives it away, I’m switching back to normal physical books. Here are some quick pros and cons to Kindle books, and why I decided to go back.



  • Convenience. The fact that one portable device can store thousands of books, literally an entire library, is compelling, and super convenient. My iPad, or at least my iPhone, is always with me so the books are always available. No packing, remembering, planning, nothing. They’re all always with me.
  • Not physical. The books are electronic, which means no maintenance. I never worry about spilling coffee on a book (although that might have been worse on an iPad), ripping a page, drool from my children, or any other thing that would ruin a book. Their general well-being is never a concern, they’re always in mint condition. An iPad can obviously sustain some serious damage too, but even if my iPad was destroyed or lost, the books would still be there to download on the next device.
  • Easy to organize. The direct sync between Kindle and Goodreads is a helpful feature. My Goodreads profile and book tracking is always up to date without ever logging in to Goodreads. Kindle also uses Collections, which basically function like tags, and I love tags.



  • Progress as a percentage. I found myself constantly tracking that stupid number. I’ll admit, it could be a personal problem, maybe you can ignore the numbers, but they’re pasted right on the cover of each book. I can’t stop paying attention to them. I get immersed so much more easily in a physical book.
  • It’s distracting to read on a device. The percentages are distracting, but that’s only where the distractions begin. If you’re reading on any type of tablet or phone there’s a pull to check email, look something up online, or get a quick game in. I would suddenly remember something in the middle of reading and, since a little computer was in my hands, I would just switch over to quickly take care of the thing I forgot. Even if every notification and connection setting is turned off, you still can’t turn off the capability. The counter-point to this is to use an e-reader of some sort because they don’t have all that capability. While they seem to be a great solution for many people, I have found them lacking for a few reasons. 1) They have small screens, six inches is too small. 2) The e-ink flashes every time a page turns, talk about distracting. 3) Books lose any distinguishing characteristics, even more so than in the Kindle app. 4) They’re made of plastic. 5) They’re boring! If I’m going to read books on a device, give me an iPad with all the capability it comes with, distracting as it may be.
  • What happens if Amazon goes out of business? This could be stupid, but I get a little nervous that someday my library won’t be accessible. Companies go out of business all the time. There would probably still be some way for people to keep their electronic copies, but I, for one, am not interested in watching it play out.
  • I missed seeing my whole library. It’s exciting to scan an entire shelf of books and pick one out. When a Kindle library grows the only option to find books is to type titles in the search bar or get scrolling. The library feels hidden.
  • The human element. I’m human, I like to touch and feel and see and smell things. iPads and e-readers are great, but they make every book feel and look and read the same. Books lose some of their personality that way. You can develop a sort of connection with a physical book that isn’t possible when you read it on a device. I guess my point is that books are personal, and that’s important.
  • I have young kids. Studies have shown that households with books raise more literate and successful children. Interestingly, this specific study found that 350 books in a household is a kind of threshold. The benefit for children rose with the number of books in their house until they hit 350, then the benefit leveled off. 350 books appears to be enough to saturate the home, there will be books lying around on end tables and shelves, they’ll be in each person’s room, they’ll be visible all over. I started reading normal books again before coming across this article, but you can bet I counted right away to ensure we had over 350. Besides the study, I’ve noticed an interesting change in my own house since I recommitted to physical books about three months ago. The kids have begun to read more. When they saw me on an iPad they had no idea if I was reading a book or playing a game or whatever, they just wanted to play on an iPad too. There’s something about a Dad’s example that seems to inspire kids, they watch and copy. It’s not like rules changed three months ago, but the example changed, and it has made a noticeable difference.

All told I have no regrets returning to a library of physical books. What I miss most about using a Kindle library is the convenience, it’s a bit of an adjustment carrying books around again, but the advantages have far outweighed the extra weight in my bag.

iPad Pro Trial 2018

I really wasn’t going to buy an iPad Pro this year, I was pretty serious about that decision. But then I popped by the Apple Store, just to see what the new 2018 models look like, just to stay in the loop. I was immediately enamored. In the twenty or so minutes I spent with the new iPad Pro I wasn’t sure it would be enough to replace my MacBook Pro, but I was sure that I had to give it another shot.

I do this every year. I’ve owned every iteration of the iPad Pro since it’s inception (some not longer than the return period). I’ve tried very hard to make the switch, give up the MacBook Pro, go all in with the iPad. So far it hasn’t caught, but that’s not to say my desire has been quenched. Here are my quick thoughts from two weeks with the 2018 iPad Pro 12.9.


  • New keyboard case. It’s way more sturdy. You can pick up the iPad, keyboard deployed, without it flying off (that happened on the regular with the old design). It also is a lot easier to use on my lap, or anywhere besides a desk. I appreciate the full-ish protection it offers without having to buy another back case. The keyboard itself is the same, which I like, but the overall case is improved.
  • iOS seems to be slowly making progress. This feature was probably available before but I didn’t know about it: you can turn off the bottom auto-correcting/suggestion/copy-paste bar when typing, a huge plus. Dashlane (my password manager of choice) now sort of integrates with Safari which, though not as comprehensive a solution as in Mac OS, has been super helpful. There are also more people using iPads regularly and posting helpful tips. I wouldn’t say iOS for iPad has arrived or is even close to arriving, but it’s a little better than last year, which was better than the year before. Based on internet rumors, iOS 13 should bring more significant updates next year.
  • It runs fan-less. This is one of the first things I noticed with the iPad Pro, it’s so quiet and cool. Nothing ever whirls or heats up. The keyboard never makes my hands sweaty. It just cruises along, no hiccups, no freezes, no spinning wheels, no heat, nothing. Really impressive performance for a fan-less device.
  • Battery life and connectivity. Those two things really appeal to me, they’re two of the main reasons I keep coming back to the iPad Pro. It’s the ability to literally work anywhere, to be free from the need for an outlet or a wifi router.


  • Browser. It’s still mobile, which usually works but is infuriating when it doesn’t. One of the key components of my work is writing and editing a blog. WordPress on mobile Safari is far from ideal. Another specifically painful example: I simply can’t add a contact in Pipedrive (my CRM of choice), the ‘save’ button is located beneath the bottom of the screen and Safari won’t allow me to scroll to it while the ‘add contact’ window is open. This is close to a deal killer by itself. Sure, there’s a Pipedrive app, but it’s got about 20% of the functionality.
  • I get kind of dizzy leaning over the iPad Pro for long periods of time. I can’t lean back and look at my big external monitor like with the MacBook Pro.
  • OmniFocus, professional apps in general. I rely heavily on Omnifocus to keep my life and work organized. The iOS app is so much tougher to use than the desktop version. I’m sure it’s partly because I’m used to the desktop version, but the app is also simply less capable. The same is true for the majority of productivity tools in iOS, they lack features included in their desktop or web-based counterparts. A few that I use daily, Microsoft Office, Zoom, Files, Mail, Notes, are all missing basic features included with their Mac OS counterparts.


  • I feel uneasy using the iPad Pro for work. Do I not like it because it forces me to zoom in on things? It is definitely harder to bounce around and/or have multiple things going on, it takes more effort to be distracted which can be a good thing. But maybe iOS is just too restrictive. It almost always takes extra effort to do things that are easy in Mac OS.
  • It feels daunting to think about something like recording and uploading a video to my blog. I’m sure it’s doable, but I’m also sure it’s going to take extra work to figure it out and I’m already tired just thinking about it. Maybe that’s a personal problem, but hey, still a problem.


  • I love the form factor, the power, the lack of a fan, the battery life, the simplicity, the ease of use, the lack of loading time. There are real pros to this machine, especially on the hardware side.
  • iOS, for all that it does well, presents obstacles for my normal workflow. It’s surprisingly capable and surprisingly frustrating at the same time. I can’t save additional signatures in Mail, it takes twice as long to add and organize tasks in OmniFocus, I run into frequent website limitations with mobile Safari, the list goes on. Almost all of my issues can be ‘worked around’ in one way or another, but I find myself spending a lot of time on workarounds instead of actually working.
  • While the fact that the iPad Pro is always on and always connected is certainly a benefit, I don’t think it’s worth the trade-off for the sacrifices in the OS. In fact, because it’s so easy and fun to use, and it’s always on and always connected, I end up turning it on just to waste time. It’s fun to use but it’s hard to use for work, those two don’t make a great combination.
  • Mac OS is already great for working. All my workflows are there. It seems that the key for the iPad Pro is to recreate workflows, kind of like starting over. There could be value in that purely as an exercise, but I can recreate my workflows on my MacBook Pro too, and I’m not ready to put in all that work for the iPad Pro. Going back to my CRM: I just set my company up to use Pipedrive, and Pipedrive suffers on the iPad Pro because there’s no desktop browser. I can’t just switch the company over to something different to facilitate my desire to use an iPad as my primary work machine. I need the iPad Pro to mirror the functionality of my MacBook Pro at least a little more closely to realistically make the jump. Give me a desktop browser and windowed apps, give the developers more time and encouragement to add all the features to their iPad apps, then maybe it’s not such a compromise. For now, my MacBook Pro offers fewer compromises at a comparable price. Here’s to next year.