Gustave Doré

Paradise Lost: My Mac2Win journey

Scott Jenson
8 min readDec 3, 2016

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Yes, I’m ‘doing it’. I’m putting my money where my mouth is. If I’m going to rant on twitter about the inadequacies of the new MacBook Pro, I should back it up with action. After 30 years(😱) of using Macs (and even working for Apple for 8 years) I’m moving to Windows. My colleagues consider me a masochist, politely implying I’m overreacting.

Honestly, I don’t see how I can lose. This is a glorious chance to explore, learn, and appreciate how things work, seeing my technology world through new eyes. Either it works, and I’ve got a whole new world to explore, or I return home, tail between legs, having learned what makes these two platforms so different.

Dear Internet
For those Apple Fanbois that will want to defend Apple’s new hardware, save your breath. I’m not saying Apple is doomed in any way. I’m not even saying the MacBook Pro is a bad computer, so put down your knives. I’m just saying that it’s a bad computer for me. If you think it’s great, God’s speed.

I’m trying this experiment with two different Windows laptops: a SurfaceBook (evaluation unit) and a Lenovo Yoga (corporate issue). Both are “Ultrabook class” laptops running Windows 10 with touch screens. This isn’t meant to be an in depth Ars Technica style review. This is my personal journey of what’s important to me, an unrepentant UX geek.

I received the SurfaceBook first so will focus on that for this post...

The Surface Book is a joy
The hardware is a complete joy. I love this machine. The screen and the keyboard (even the pen!) are first class. I was surprised how quickly I was up and running. During Thanksgiving, my niece commented on a video I was watching so I hit the “undock” button. The screen made a satisfying “click”, and I just handed her the keyboard-less screen. She ran off and started tapping away, impressed.

The only issue that initially struck me was how clicking on the touchpad sometimes didn’t work. I was very confused until I realized the lower right corner of the touchpad is for right-clicks. As there are no physical affordances to delineate this area, it’s extremely easy to think you’re clicking normally but drift over to right-click-land. As a Mac refugee, I found this surprising and frustrating. I dug around, found the setting, and turned it off. It turns out that ‘turning off strange Windows behaviors’ is something you often have to do (more on that when I review the Lenovo).

Touchscreen, where have you been all my life?
Using a touch screen is a work in progress. But when it shines it really shines.

  • Every time I log into the machine I do a very satisfying flick upwards to display the login prompt. Emojis are quick and easy from the onscreen keyboard. Yes, these are both frivolous examples, but who would have suspected Windows could ever be fun?
  • I can drag a window to the right edge where it snaps to half screen, offering up miniatures of my other windows. Selecting one of those then snaps it into place: two side by side windows full screen. I can’t imagine doing that with stock Mac OS.
  • The two finger left-to-right swipe for “Back” in the browser is strangely satisfying in a way I can’t really justify.
  • When my wife and I reviewed Google Photos together we could both “drive” the screen. I can not stress this enough. A touchscreen let us collaborate simultaneously. I could select a photo, she could scroll. This completely changed how I perceived the touchscreen.

The screamingly obvious point here is that we’ve been using (and loving) tablets for years now. Apple invented this category for God’s sake. Why on earth would you settle for a Touch Bar™ when you can have the entire screen?

Actually, I have a theory. There is a clash between the cursor world of the mouse and the gesture world of tablets. Dragging a finger on the touchpad moves the cursor. On touchscreen, it scrolls. Smashing these two worlds together is messy. It’s hard for me to imagine Apple hasn’t considered this. It wouldn’t surprise me that Apple’s perfectionist tendencies are holding them back. They can’t make it perfect so they aren’t doing it at all. Windows is clearly rebuilding the airplane while in flight. It’s a bit of a hot mess. But it’s exciting and I want to be a part of it.

I want to be clear that touch on a laptop still has a long way to go. It is an uneven experience as too many targets are too small to hit easily. But even in this first week, I’m thinking ‘deep thoughts’ about the shared roles of keyboard, touchpad and touchscreen. We’ve internalized what it means to be a tablet but not the combination. I have no illusions that touchscreen laptops will ever replace phones, that boat has sailed. However, I’m excited about the combination for high-end creative work. There is some clear potential here I’d like to explore.

But it’s not all roses
The SurfaceBook Pro shines most when you stay within the carefully crafted world of Windows 10. This is a place of beautiful fonts, intelligent white-space and large, touch friendly targets. Then I thought it would be a good idea to open File Explorer…

<record scratching sound>

The Achilles heel of Windows 10 are the parts of Windows 7 that still remain. These ancient views rise up like troglodytes, misshapen and unwanted. It’s astounding to me that File Explorer, a core aspect of Windows, doesn’t have a Windows 10 update. I don’t need much, just a nice list view that works with reasonable fonts and larger icons.

This is where a Mac refugee can get lost. I kept saying “There must be a way to increase the font…” and searched the web over and over. But no, you just can’t, there is just one system font setting. Given that Windows 10 uses one font size and File Explorer another, it makes no sense to change. If I make Explorer big enough, Windows 10 would be huge.

I can only hope that as Windows 10 matures, a better File Explorer is close behind.

Let’s talk about that Windows App ecosystem
For the most part, I was able to get Windows equivalents of everything I most use on the Mac: Atom, CyberDuck, Twitter, Chrome, VLC, Handbrake, Google Drive, and Dropbox were all there. My note taker of choice, DynaList is a web app but they have an experimental Windows only standalone app. My first only-on-Windows-not-on-Mac moment!

But trying to find a File Explorer alternative, hooo boy… That was a mess. For the first time, I waded into the Windows app world of complex geeky apps that didn’t work well, looked horrible, and couldn’t even get working after some reasonable effort. It certainly feels like clean design and simple out-of-the-box functionality isn’t valued in most Windows apps. If anyone has a good suggestion for a Finder-like File Explorer equivalent, do let me know.

What I haven’t found yet is an equivalent of Mac’s Preview. This is an under appreciated gem on the Mac. A Swiss army knife for images that lets me resize, crop, and add transparency easily. I’ve tried a few on Windows but I’m just reliving my File Explorer experience. Suggestions most welcome.

Keyboard surgery
My last comment is a geeky one and likely quite personal. It’s about getting the keyboard to work for mere mortals. I was initially astounded by the sea of keyboard modifiers (Alt, Windows, Control, Function, and yes even CAPS if you want to use the text to speech engine) For the first 3 days every-single-command was preceded with ‘which modifier do I use?’ moment of panic. It’s calmed down of course, it was just the initial culture shock but let me list what I’ve done if you’re considering the same thing:

  • The main app commands are through the Control Key: cut, copy, paste, close window, new browser tab, open file.
  • The main windows commands are through the Windows key. Magnifier is Windows-+ (I’m a designer…), File Explorer is Windows-E, Desktop is Windows-D, Lock screen is Windows-L.
  • Get the app SharpKeys. It’s a bit geeky but use it to remap the Caps-lock key to Control. Yes, this is non-standard but it’s SOOOO much easier to reach. Commands like Control-T are actually possible now.
  • Get AutoHotKey and remap Control-Q to Alt-F4 (quit app) Also geeky to use but If you’re a die hard Mac user, this is so much better than Alt-F4, which is an ergonomic disaster, especially on laptops:

If I can be so bold
It’s clear to me that Windows 10 is a work in progress. If I were Microsoft, I would be making the following things top priority:

  1. Get a Windows 10 friendly File explorer. Now. It doesn’t even need to functionally complete, just get something simple up and running and improve it over time.
  2. The same for a Preview like image editor app. You want to appeal to creatives? Get one of these pronto.
  3. Somehow get me an option for bigger windows so I can drag them easier. Either that or have a gesture for it.
  4. Unify the touchpad and touchscreen gestures. 1 and 2 finger gesture unification is tricky, I get that, but why not 3 or even 4 finger gestures? Three finger swipe on touchpad is very useful. Why doesn’t that work on the screen?
  5. Create a design language like Google’s Material Design, with assets and style guides to encourage this new model (This could exist of course, please link in comments if I’ve missed it) Evangelize this, get more apps coming!
  6. Create a category in the Windows Store that collects Windows 10 friendly apps so I have a safe and easy place to find apps that actually work with your OS nicely. This would greatly motivate developers. Don’t force me to scour that apocalyptic landscape of Windows apps.

To be honest, the jury is still out for me. Yes, I’m rather positive now but I’m also realistic. I haven’t documented some of my more tedious setup issues. That’s coming next post. What I can say is that I’m still here and I’m looking forward to staying a bit longer. The majority of my work life is spent in the browser so I haven’t really stressed things too much. My next steps are to move over to the web based Figma for my graphics work and Powerpoint for my slides. That will take a bit more time…

If any of you have switched over, please let me know! I’d like to share tips and tricks. I’ve started a subreddit Mac2Win which, to be honest, hasn’t got much traction but it is an attempt to find place to capture helpful resources for those of us trying to make this switch.

This post is from my blog Beyond Mobile, special thanks to @AaronGustafson for the loaner SurfaceBook Pro. Did you like this post? Then click the green heart icon. It doesn’t really matter but I get an awesome email every time it happens.

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