#davagoeswindows was a social experiment inspired by my podcast Shop Talk Show. Every so often we’d get a question like “How do you I do [Sass] on Windows?” and our answer ended up being “Buy a Mac.” This was not a great answer to me because most of the world uses Windows and Macs can be prohibitively expensive in countries like India, Kenya, or Indonesia.
I hatched a plan with Rey Bango at Microsoft to switch to Windows and see what that experience was like. The dare was that I provided a Surface Pro hardware and I used Windows and non-Chrome Edge as my daily driver for a year. Throughout the process I blogged my experience and they upstreamed feedback to higher ups inside Microsoft. I had calls with Scott Hanselman to debug Ruby issues, I flew to San Francisco to attend their annual Build conference as a VIP, I flew to Seattle to meet with the Microsoft Edge team.
During that time Microsoft was highly receptive to feedback. Not the impersonal giant that most developers are familiar with. I sat at roundtables, hopped on calls, and felt like my experiences and made a dent the roadmap whether I was sharing about Edge of the Windows Subsystem for Linux (WSL). How’d the experiment turn out? Well, I ended up using Windows for five years, so pretty good actually.