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Stranger in a strange land: a long-time Windows power user switches to the Mac



I spent decades using Windows as my primary computing platform. I may not love Microsoft’s OS, but I had learned to live with it, tolerating its quirks and forgiving its faults. By the time I had turned thirty, I was comfortable (if not quite content) in the Windows world.

More recently, though, Apple has managed to win me over. Since picking up an iPod Touch back in 2009, I’ve bought nearly a dozen different iOS devices. Then, I installed OS X in a VM, just so that I could run Omnifocus. And finally, this past July, I switched to an actual Mac as my full-time machine.

Adopting macOS wasn’t quite what I expected—hardly the aesthetic epiphany promised in those old John Hodgman ads. Here are some thoughts on switching to the Mac as a long-time Windows user:

The good!

  • After years spent Alt-Tabbing back and forth from a VM, I’m glad to have all my favorite software integrated into a single platform. There’s only one machine to shut down at day’s end, and I can freely shuffle data between apps. For example, I can now use AppleScript to push work emails to Omnifocus in just a few keystrokes.
  • I love that the Mac gets so much attention from design-minded software developers. Drafts, Fantastical, and Tweetbot are now indispensable parts of my daily workflow; none of these apps have true equivalents in the Windows world.

The bad.

  • Windows may lack polished indie apps, but there’s an equivalent problem on the Mac: underbaked enterprise-grade software. Microsoft Office is far superior on Windows: faster, more reliable, and more feature-rich. In fact, I’m forced to keep a PC close at hand, just so that I can occasionally boot into Windows to fix the formatting of an email or a PowerPoint deck.
  • It’s not just Microsoft’s apps, either. Cisco’s Webex is terrible on all platforms, but it’s far worse on the Mac. It takes me twice as long to join meetings as my Windows-running colleagues, and entire features are absent in the Mac app. For example, I can’t choose which display to share when I’m on a conference call.
  • macOS’s native PDF export options are surprisingly sub-par. Back on Windows, the PDF print dialog offers a rich suite of formatting options. But on the Mac, exporting a PDF feels like a guessing game, with no rich preview and a paltry set of levers to try.
  • I miss the ability to pin documents to apps in the taskbar (or the Dock, in macOS parlance). The built-in “Open Recent” command doesn’t cut it—and it’s only available when the app itself is open!
  • Windows is far better than the Mac when it comes to onscreen app arrangement. “Snapping” windows works so well that the Mac’s “Split View” feels like an afterthought. Yes, you can install third-party Mac utilities that imitate Window’s native behavior (I’m partial to Magnet), but that functionality should come baked in, for free.
  • Finally, this isn’t a software issue, but I don’t understand the MacBook’s charging brick. On the one hand, I like being able to disconnect the USB-C cable and wrap it up separately. On the other hand, the pluggable brick can easily fall out of some outlets, depending on the angle and slot design. That never happened with the PC power cords I’m used to.

The ugly.

  • macOS feels slow. Honestly, Windows feels downright snappy. On the Mac, it takes longer to launch programs, switch between them, and close them at day’s end. And macOS’s penchant for animating everything often gets in my way. Windows somehow felt “closer to the metal” (even if that’s not technically true).1
  • The Mac’s window model drives me crazy. For some reason, closing an app’s window doesn’t close the app. Instead, the program hangs around, burning resources in the background. And because there’s no easy way to close apps with the mouse, I often end up with far more apps open than I need.
  • There’s something wonky about macOS’s Bluetooth stack. I can’t use more than one Bluetooth device at a time. When I connect both my Logitech mouse and my Plantronics headset, audio playback stutters and skips. This is apparently a known issue, and there are a variety of proposed workarounds, but this never happened on my PC.

Wrap-up

To be fair, most of my complaints boil down to unfamiliarity. A life-long Mac user would probably have the reverse experience switching to Windows. For me, though, macOS feels like foreign territory; I don’t know the terminology and I sometimes struggle to find my way around. ■


  1. FWIW, my most recent Windows machine and this 2017 MacBook Pro are roughly equal, spec-wise. ↩︎
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technology Uncategorized

“Morning pages” login idea

One of my New Year’s resolutions this year was to write “morning pages.” I wanted to write 750 words every morning before work. When I’ve stuck with it, this practice has proved fruitful, yielding blog post ideas and helping me journal daily.

But actually establishing that habit is difficult. How do you learn to write every day? How do you overcome the intimidating specter of the blank page? How do you work around your self-critical hang-ups—those gnawing fears that encourage procrastination and discourage creativity?

In short, you force yourself. You gag down the part of you that protests new habits and just choke down your medicine for a few weeks. You grit your jaw, you glue your ass to the chair, you are ruthless with yourself. You git ’er done. Before long, you’ve made it an automatic, daily rhythm.

Being mean to yourself isn’t much fun. What if you could outsource it? What if someone—or something—else cracked the whip?

More concretely: what if your PC wouldn’t unlock in the morning until you generated 1000 words? Boot up the machine, and—instead of a password prompt—a blank canvas pops up. Your laptop refuses to do anything until you’ve made the clackity-clacky noise. No “I’ll just check Twitter real quick before I write” or “I can’t think of anything; maybe Reddit will generate some ideas.” And definitely no “I’m not feeling up to it today; I’ll start fresh tomorrow.”

Just a big, blank text box. Nothing else ’til you make the words. Start typing, or forget doing anything else that day.[1]


  1. Of course, you could cheat. Just bang the keys until you reach the minimum word count. But at least then you’re consciously sabotaging yourself. The point isn’t to create a fool-proof mechanism for self-improvement. The point is just throw a few low roadblocks on the path to passivity and malaise.  ↩