My 2 months switching from Mac to Windows

From one ecosystem to another…

From the beginning, I decided to resist the urge to do all the normal "IT admin" things that I would've done in the past. I left the preinstalled software on. I attempted to use the Windows Store to get apps. My goal was to never touch the registry, let alone open PowerShell. I wanted the power user experience, not the admin one.

At first, things went well. The out-of-box (OOBE) experience was great. I installed my password manager, Evernote and even iCloud because I still had photos, music and other files that I need access to. Keyboard shortcuts are quite different, but not too bad. However, I quickly realized that I needed to swap the direction that my external mouse wheel scrolled.

I know how to do that in Windows Registry Editor (regedit), but since I was trying to avoid that, I thought I'd turn to Copilot. I pushed the new Copilot key and asked, "How can I change the mouse scroll direction?"

I might have well asked "What's the price of tea in China?" because the answer was worthless. It told me the process for Windows, which was wrong, and told me to toggle the "Scroll inactive windows when I hover over them" option.

My reply, "I'm not sure that's what that setting does," was met with, "You're right, I apologize for the confusion," which was then followed by a seven step process that coached me through opening Device Manager, finding my mouse, getting the Device Instance Path, finding that path in regedit, and editing the FlipFlopWheel registry key, followed by a reboot for each mouse.

Anyone who has done this knows my frustration at this point, especially because my goal to not use regedit was already abandoned. I replied to Copilot, saying "That's not a GUI setting yet? I still have to drop into regedit? It's 2024!" Its response was priceless:

"I know, it seems like such a basic feature that should be easier to change by now!"

That's no hallucination. It is ridiculous that Microsoft hasn't made this easier. It should be a checkbox and not require editing the registry or adding third-party tools. Even more frustrating is that this setting exists, but only for the touchpad.

I'll spare you the details of all the other little things that bothered me, but I wanted to share that story because it shows the level of commitment I had to this process, and it is a pretty representative example of the many other challenges I had.

There are, however, a few things that I want to point out that will be a huge deal to Mac users: integration with other devices, along with shortcuts and workflows.

Integration with other devices

I've freely admitted that one of the key reasons I remained a Mac user for all these years is the seamless integration between iMessage across all my devices. This, coupled with effortless integration of devices and settings such as headphones and Wi-Fi settings between devices has spoiled me. I tried as hard as I could to set that aside for this knowing full-well that I was breaking that integration.

Still, Windows has Phone Link. How bad could that be?

Pretty bad, it turns out. While text messages mostly work, sending or receiving images doesn't, leaving me with a half-baked experience. Surely Apple has played a role in making this more difficult than it needs to be, but the fact remains that Phone Link looks and works like an unmaintained afterthought of a feature.

I realize that Microsoft and others might overlook this and think it's not that big of a deal, but it is.

I should also add that hardware vendors such as Dell and HP also are building their own peripherals that integrate with each other seamlessly. Lenovo even has an Android phone that they've integrated with their laptops. Of course, you have to buy into their ecosystem. That involves more switching, and like it or not, frustration as you make the change. It's not effortless.

Shortcuts and workflows

The hardest transition of all was adjusting to the little things, starting with Ctrl-C and Ctrl-V instead of Command-C and Command-V. 16 years of muscle memory does not go away easily. It's not a major problem, but it is friction. After a while, it feels like death by a thousand cuts, and that powered off Mac in the corner starts looking mighty lonely.

There are other examples of things that I took for granted that have led to frustration during the switch.

• On Windows, you can't change desktop icon font size without changing the entire zoom level for the display.
• Screenshots are more cumbersome. There are tools, and Alt-PrntScrn still exists to take a screenshot of the active window, but even after two months the Mac feels more intuitive.
• Alternate characters such as the pound or cents currency symbols on the Mac are as easy as Option+3 for £ or Option+4 for ¢. On Windows, you still have to know the American Standard Code for Information Interchange or have a separate font and symbol library to insert from.
• Accessibility features such as CTRL-Scroll to zoom are extremely useful. While Windows has the magnifier, it too hasn't been updated in ages. Its clunky interface and chunky scrolling leave a lot of room for improvement.

My biggest challenge, though, and one that dramatically affected my productivity, was Alfred.

Moving from Alfred to Jeeves

Alfred is a Mac app that's most closely related to PowerToys for Windows, though their implementation and usage are quite different. My use for Alfred is simple but essential: I type Ctrl-S anytime to bring up a search window, type in a term, and press Enter to search with my default browser. I can even add keywords for specific sites -- for example, "yt pinball machines" searches YouTube directly. It's fast, intuitive and a fundamental part of my day-to-day workflow.

Finding an equivalent for Windows was extremely important but proved impossible. Despite trying PowerToys, Wox, Listary, Keypirinha and others, nothing came close to the simplicity of Alfred. My solution was to build my own tool -- Jeeves. Jeeves is an AutoHotkey script that replicates the exact functionality I needed to get back to being productive.

I don't say this to promote my "software" -- ChatGPT wrote it and it's free on GitHub under an MIT license. Rather, I wanted to point out how hard it is to swap OSes. It's not enough to just take care of all the macro stuff like apps, browsers, desktop backgrounds and peripherals. There are thousands of other microscopic things that have a legitimate effect on the day to day, hour to hour and minute to minute user experience.

My takeaways after transitioning from a Mac to Windows

I realize some of this might seem like a cranky person complaining about every little thing that's different. It's not meant to be that. I assure you, I left a lot out. But this is why I gave it two months instead of a few days. There are a ton of positives to take away from this, such as:

• Windows has evolved, and there are many features that I liked. The last time I had Windows as my day-to-day OS, it was Windows 7. This is an improvement from a user perspective, for sure.
• Office is flat out better, and all the current features that Microsoft is working on, such as Copilot, are included. There are some frustrating differences, but there's no doubt that Office on Windows is the more capable platform.
• OneDrive integration just works.
• The OOBE was fantastic. I connected to work right away and was provisioned everything I needed.

If I was a Windows user progressing through the OS versions over the years, I'd be happy. But the reality is that switching shines a light on everything, and even the little things tend to add up. While you're mentally trying to overcome those, you're also swept up by more icons, more words, more steps, more everything.

I want to be very clear -- the device I'm using is not the cause of these issues. The onus belongs almost entirely on Microsoft, and there are key things that they need to do if they want to help their hardware partners attract Mac users:

• Make a specific transition helper for Mac users. This could be as simple as a software overlay for the keyboard that helps remind people to press Ctrl-C instead of Alt-C, where their finger will probably go when trying to hit Command. It could also help create keyboard shortcuts that replicate those on the Mac for taking screenshots or magnifying.
• Make Copilot useful. Where Copilot could've been a game changer in terms of getting adapted, its current form left me high and dry too many times for me to be enthusiastic about it as a tool that can ease the transition between Mac and Windows.
• Fix Phone Link. Put some resources into making it as full featured as possible. If Apple is a roadblock, put some pressure on them publicly like the Android community did to get them to finally enable RCS instead of SMS.
• Pay attention to the little things, including typing symbols or changing the desktop icon text size.
• Make it easy to change the mouse scroll direction. Even Copilot agrees with me on this one.

The point is, switching is not trivial, and everyone needs to be mindful of that. And to be clear, this goes both ways. Mac users switching to Windows and Windows users switching to Mac face similar challenges, just with different specifics. The ecosystem lock-in and muscle memory issues are universal.

Mac users switching to Windows and Windows users switching to Mac face similar challenges, just with different specifics. The ecosystem lock-in and muscle memory issues are universal.

Organizations that want to standardize on Windows need to know that there will be friction when transitioning Mac users. They need to dedicate resources to support and training if they go down that path. PC vendors need to understand that it's not enough to have a great device. There might be ways they can help bridge the gap, but then they have to determine if it's their role as a third party to build and support programs and tools to help ease that transition.

Considering all the investment that it would take to address each of these things and the lost productivity along the way, it might or might not be worth it.

As for my experience, I'm probably going back to the Mac full-time, though I switch back and forth right now just to see if it's possible to be in both worlds. While I don't love the idea of being stuck in one ecosystem, it's an easier overall existence. I spend less time fussing with certain features or stumbling over keystrokes and more time being productive. In the end, that's what makes the decision for me.

Gabe Knuth is the senior end-user computing analyst for Informa TechTarget's Enterprise Strategy Group.

Enterprise Strategy Group is a division of Informa TechTarget. Its analysts have business relationships with technology vendors.