Returning to macOS After 20+ Years on Windows

2002 was the last time my home computer was a Macintosh … until I bought a MacBook Pro last November.

“Migrating” over two decades of computing habits from Windows to macOS was a daunting task. I’ve chronicled the journey in a blog post I published this morning.

I’m sharing the link for anyone interested in reading about my experience (including my somewhat “unorthodox” early history using Classic Mac OS).

There and Back Again: Returning to Mac After Over 20 Years On Windows

Looking forward to your questions and comments.

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Your post reminded me of a couple of breaks in Mac history and yielded a surprise tip for me. As a data point, I’ve dabbled in Windows very lightly when one of my work sites was heavily invested in it. Otherwise, I’ve maintained an all-Apple environment since 1988, when I had typed my last grad school paper on a C-64 using Quick Brown Fox (on a ROM cartridge!) and purchased a MacSE with my about-to-expire student discount.

One break was the jump from Classic Macintosh (or as we called it then, “Macintosh”) to OS X. I’ve had 24 years to get used to the feel of the OS X interface, which for the most part still adheres to Apple HIGs but is extended in so many directions. You had a long hiatus from it (except for dabbling on your son’s MBAir). The post reminds me of my first days working on a system that felt familiar but lacked all the supports I had added over the years.

The second break was the iOS eco-verse. My first iPad did not remind me at all of the Mac experience. The home screens were rigid—I recall it was easier to edit and organize them through iTunes than on the iPhone itself. But by the time you jumped back over the experience had gradually evolved enough that it’s pretty much as you say.

And the surprise: I had overlooked that BusyCal alarms could come through the BusyCal alarm window rather than Notification Center, where they get lost and dismissed without my ever seeing them. I’m glad you found this app. I also came from NUD and Now Contacts, and BusyCal in particular still expresses the DNA from those earlier applications. I wish that Busy Contacts did, though it’s finally received some welcome steps in that direction after years of languishing.

Thanks for the post!

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Thanks for the comments. I’m glad my post informed you of the BusyCal Alarm Window. They mention the feature on their marketing page, but maybe they need to improve the SEO to make it more discoverable. It’s a unique selling point, or at least hard to find in other calendars.

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Will likely have a number of replies as things occur to me. I also used Evernote fairly heavily for well over a decade, but once they sold it and started raising the price and adding features that weren’t useful to me, I searched for an alternative. I ended up with DEVONthink3. I’d flirted with it since 2009 when I went back to finish my degrees, but the cost was always a challenge. Evernote’s price hikes eliminated that curb, and I like that DT3 isn’t a subscription. It offers a choice of sync services (I’m using CloudKit and my iCloud storage), and I don’t have a running cost. My primary use case is semi-archival storage - I scan papers and print to PDF (one of my favorite things about the Mac has ALWAYS been the ability to click the arrow next to PDF in the print dialog and choose to save a PDF to my note-taking service). Searching is important to me, and it was able to do a reasonably good job of importing my Evernote data (there are some hoops, but it worked OK for me). There are very deep features if I get to the point where I need to use them, and their support community using discourse has been top-notch.
If you decide to pursue that, they offer a 15% discount to TidBITS members (both new purchases -and- upgrades apparently, although I bought my license before I joined TidBITS).

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My “revelation” is documented here

and here

https://www.vdrsyd.com/aoaug/ms_dig.html

:grinning:

I’ve been running an old Windows-only app for years on my Macs using wine. No need for a Windows license or emulation. Works on both Apple Silicon (via Rosetta 2) and Intel. I find the simplest way to get it installed is using Homebrew.

My hope was to avoid Wine and similar solutions by finding macOS equivalents for all my software. Didn’t want to drag around Windows corpse behind me. :wink:

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Good article!

Thanks also for reminding me about Now Up-to-Date and Now Contact. I loved using them all those years ago. I think the years I used them, along with Claris Emailer and contemporaneous versions of major apps, were the most satisfied and productive I’ve been with daily computer use.

Obviously, today’s systems and software have more capabilities and are far more stable, but I think they lack a certain coherency that was present during the peak of the Classic Mac era. I have a fantasy of resurrecting my old SE/30 as an experiment and using it for daily work for a week or so. It would be all but useless for anything Internet-based, but my intuition is that it would hold up very well and possibly even prove to be an improvement for many purposes, especially writing.

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Those Now apps were great! It was surprising that other apps went on for so many years without coming close to their ease of use and feature sets.

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I started with Now Up to Date and Now Contact when they were new (20 years ago?) and continued on when it became BusyCal, which I couldn’t live without. I was already committed to BusyCal, but separating tasks/reminders from the calendar app like Apple did never made any sense to me.

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