If you’re over 50 years old, your career started before email was the dominant work communication tool. Once email became the dominant communication tool, most of us spent decades working with Microsoft Outlook as our primary desktop email application. Remember the days when you couldn’t attach large files (and the definition of a large file was 1MB) or you had to get your IT department to clear off room on the Microsoft Exchange server from time to time (usually after it crashed)? 

Microsoft Outlook is a software program that solves the challenges of managing email in a particular way. Gmail is a software program that solves the challenges of managing email in a very different way.

I felt confident with Outlook. It was comfortable for me. I knew all the keyboard shortcuts and I had very complex rules set up for all my emails. Email is mission-critical; I have resisted changing for a long time. So I developed a lot of complexity in my work life so that I could hold onto this tool. I have only Apple hardware so I loaded a Windows virtual machine onto all my Apple computers so I could run Microsoft Outlook for Windows. I use Google as my email provider, so I had to install and configure the Gmail–Outlook sync (which is junk, by the way). Why am I telling you all this? Who cares? Good question.