The first computer I had in my house growing up was an IBM 386 something-or-other. I think it was an old one my dad’s job had that he picked up when they upgraded. It had WordPerfect 3.1 on it, and I became a whiz at all the things you could do at an MS-DOS prompt.

Unlike many designers, I didn’t grow up with a Mac. One of my cousins had a Mac, which I thought was weird and inferior to my PC. The first time I really used a Mac was when I went to design school for college. I had my personal PC in my dorm room and the computers in the labs were all PCs because we were all doing 3D modeling and animation work, but the handful of computers in the photo lab were Macs.

My work computer at my first job where I was a design intern was a PC, but for every other job I’ve had, a Mac was always sitting on my desk for my first day. I’m now pretty entrenched in using Apple products to do my work, but in my history of using computers, Mac usage is actually in the minority.

A little while ago, my friend Aaron Gustafson asked me if, like my very brief foray with an Android phone, I’d be interested and willing to switch to Windows for a while, specifically the new Surface Book. I was hesitant at first, mostly because I didn’t want to take on anything that would negatively impact my client work, but I’m pretty open about trying new hardware and software as I’m not terribly tied to tools in particular. I was also closely following and intrigued by Dave Rupert’s #davegoeswindows adventures, so I decided I’d give it a shot myself.

I originally asked Aaron and team to replicate my current setup so that I’d have the least painful time switching over. My main work machine is a pretty beefed-up iMac with an older external 23″ Dell monitor, Wacom tablet for the right hand, and Apple Magic Trackpad for the left. Along with the Surface Book, Microsoft sent me an external monitor, a mouse, and a keyboard, but asked that I forego the Wacom tablet to give the Surface Book Pen and clipboard/draw modes a run for their money. Fair enough.

As of this moment, everything is still in the box, but publishing this post is probably one of the last things I’ll do on my Mac for a while, if all goes well. I’ll be writing about the good, bad, and the ugly of this switch as often as I can. Initially, there are a few things I’m pretty excited about:

• I’ve had the primary desktop machine + laptop as travel machine combo for a while, but I’m excited for the excuse to go to one portable laptop that docks as the primary machine. Hoping that’ll save me some headaches in the “whoops, I forgot to sync that file to Dropbox” department.
• Because of that change, I’m also making a few more changes to my workstation, like switching to an adjustable standing desk.
• Switching to a completely different OS makes me realize how tied I probably am to OS-specific software, so I’m interested in finding and using more OS-agnostic software, namely web-based things. I’ve been idly sitting on my Figma login forever, so this seems like a good time to give it a whirl as it may help to make this transition more painless.
• It’s been a few years since I’ve compared, but I seem to recall Adobe products that I use often (Photoshop, Illustrator, etc) running better on a PC than they do a Mac.
• I have a few corporate clients that who all use PCs internally, so being on a similar environment as them will give me a bit more empathy and also generally help out on testing.
• A lot of the new Windows 10 features look great. I’m particularly looking forward to seeing how the full pen support can help my design process.

Of course, there are also a few things that I’m pretty hesitant about:

• Apple products are easy to use. From what I remember of Windows products and the little browser testing I do in firing up my cheap HP testing machine, it’s less easy.
• I’m wondering if there are things I take for granted in the iPhone/iPad/MacBook/iMac combo that will suddenly break now that I’m on a Windows machine.
• Most of my worries are software-centric. There are a bunch of Mac-specific apps for which I don’t know if there’s a PC equivalent. What do I do with my Sketch files? Shush is probably my most-used Mac app; is there something similar for Windows?

We’ll see how it all goes. If I can get through a few months on a Windows laptop, I think my ideal scenario would be to have an iMac and a Surface Book as my two primary machines. I quite like the idea of having a seamless enough setup that can allow me to bounce back and forth across different operating systems with minimal fuss. But, at this point, I have no idea how realistic that is.

If you’re curious about how this is going, tweet at me, and I’ll also try to post as many updates as I can here. Expect me to be randomly tweeting Windows questions every so often. I’ll probably use a hashtag to collect all of this, but I can’t come up with a clever one right now; suggestions are welcome.

Time for the unboxing.