An iPad and a Pencil

In 2018, I switched to using an iPad Pro and Apple Pencil when not using my computer, replacing notebooks, scraps of paper, Post-It notes, and ink-leaking pens. After a year of being digital, here are some of the processes and habits I have picked up.

The Setup

I have a late 2017 iPad Pro 10.5" 256GB Cellular model, with an Apple Smart Keyboard and the original Apple Pencil. It’s running the latest iOS 12.1.4 with no problems at all. Both the main unit and the keyboard have been through one repair.

I generally leave it charging at night, then drop it in my backpack for the walk to work where remains in my presence at all times. The MacBook Pro remains docked in clamshell mode all day at my desk, while the iPad and Pencil are dragged into meetings and around the office.

Since most of my day is spent programming, the MacBook Pro gets a proper work-out. But as soon as I leave my desk, I grab the iPad and Pencil.

Note Taking

I’m generally perceived as old, so handwriting notes is what I grew up with. I wanted to reproduce that experience on the iPad. It took me a short while to get a handle on it though. First I had to get comfortable writing on glass with the pencil, then I had to get used to trusting the palm detection so I could write comfortably. After a year of doing this, it kind of feels unnatural to me to write on paper with a real pencil.

I tried several exceptional note taking applications, but settled pretty quickly on Apple Notes. The convenience of a double-tap to start taking notes, combined with iCloud replication (so I could see my scribbles later on the Mac) are just perfect.

Of course, my handwriting is still human and therefore mostly unintelligible to the recognition software, so all my handwritten notes gain very, er, interesting titles.

But the benefits of quick access to jot down a note and the ability to find my notes anywhere, anytime are priceless.


As I am a visual thinker, I often start thoughts and projects by drawing flowcharts, architecture diagrams, concepts and other doodles on paper. Once the sketching is over, I generally redraw the final versions in OmniGraffle.

Apple Notes is fine for this, but the release of Linea Sketch changed everything. Now, all my thinking sketches are done there. The ease of changing colors, locking layers and showing and editing scribbles live in conversions when shared via Airplay to a central TV make it the perfect thinking and discussion canvas for me.

And when the sketching is done, I use Linea Link to copy the result sketches to the Mac for reference, backup and review.


I really thought I would do more writing on the iPad. In 2018, I tested out a Ulysses subscription, using it on the iPad and Mac to handle my short form writing duties. But their Markdown, code handling and UI did not suit my needs. I’m now all in on iA Writer across all platforms and that has worked exceptionally well for me.

The Smart Keyboard is OK for writing. If I need to spend time, I generally go back to the Mac, but for drafts, edits, day-later reviews, I almost always do it on the iPad.

As yet, though, I have yet to actively switch to full time writing the iPad. As much as its convenient, I still type best on the my WASD 87-key keyboard, great on the MacBook Pro keyboard and worst on the Smart Keyboard. More time is needed here.

File Access

I made the decision to move my Desktop and Documents folders to iCloud Drive as a test to see if it worked. Mostly to see if I could use it as a backup in case the MacBook Pro died. It took me a while to realize that the Files app on iPad would allow me to access all my files seamlessly.

When slow me finally figured that out, I realized that I had access to all my files anywhere any time. Which meant that I often use the Files app to browse my document tree to find files whenever needed in meetings or discussions.

I am also starting to use the Files app to launch editors to change documents on the fly when away from my computer, and, so far, iCloud Sync has performed flawlessly. I did need to upgrade my iCloud Drive storage to a paid plan, but for a few bucks a month, the access is invaluable.

Document Review

One big change of going all digital on the iPad is document review. I get a lot of Statements of Work, White Papers and other such documents to review, comment on and correct. Before the iPad, I used to print and scribble on the printouts using a pen, then hand them back and forget what my changes were while losing access to the marked-up copy.

With the iPad and Pencil, I do the same digitally, using the Pencil and Preview tools to review and comment. I then email or otherwise share the document back. The difference is that I now have a safe and accessible copy of the original, my marked up version and the next edition to work with, meaning that changes, ideas and notes never get lost. More often than not, this has ensured that notes and ideas that would have fallen though the cracks get acted on.

Emergency Tech Support

Since I have my iPad with me when away from my desk, I added a bunch of tools to enable me to provide emergency technical support. I use Panic’s amazing Prompt to provide quick and secure terminal access to my servers to restart processes, Transmit to get to our FTP servers, Navicat to access and maintain our databases, and Working Copy to check out, review and occasionally patch code.

I’m still trying out a bunch of programmer’s editors to see which is best, but none seem to stand out. If you have a recommendation, send me a tweet.

Regular Work

Of course, all my usual work tool as are also available on the iPad and I often open them to review or edit information, including:


When not working, the iPad also serves as:

  • My primary book reading device, via iBooks,
  • My primary news reading device, via Apple News, Reeder, subscribed newspaper apps and sports news apps,
  • My primary recipe device when cooking, Paprika of course,
  • My primary tool for social media, mostly Facebook for family and Twitter,
  • And TV, using Netflix or Prime Video.

The Big Picture

By moving mostly-in on digital on the iPad, I find I am able to capture and find notes far more quickly, am able to think and sketch personally and in a shared environment, write and edit when I can, am able to access any file any time, keep track of my reviews, jump in on technical support when needed, and do a lot of my regular non-programming work. And chill.

An iPad and a Pencil is often all I really need.

Follow the author as @hiltmon on Twitter.

Posted By Hilton Lipschitz · Feb 16, 2019 11:36 AM