When I was in my 20s I had a steel-trap memory, but that started to change in my 30s. As my memory became less reliable I felt increasingly at risk of embarrassing myself by forgetting to do something I had promised to do. That made me intensely interested in learning how to keep track of everything I was responsible for without relying so much on my memory. I must have spent hundreds of dollars over the years on day-planners with their specialized pages for managing a calendar and a to-do list, and tracking projects and goals. I was always up for reading an article or attending a seminar that offered to teach me more efficient ways of keeping track of everything.
To some extent this was all in the service of being reliable and effective, but more than that it was because I wanted the peace-of-mind that came with knowing that nothing was going to blow up in my face because I’d forgotten to deal with it.
As personal computing became pervasive, I started looking for software equivalents of my paper-based system. Of course, the most significant change that accompanied the PC era was the prevalence of email. Today email can seem like a curse, but back in the ’90s I loved it. There was always something new in my inbox, and I never knew when it might be interesting or important. Many of the assignments I got from my manager and the requests and questions I received from co-workers came to me via email, so before long I was in and out of my email inbox all day long.
At some point, though, I realized that all that time spent dealing with email was making me more reactive. The things other people wanted me to do were right there in front of me, in my email inbox, while my own to-do list was . . . somewhere else. Other people’s priorities tended to get more of my attention than the things I might have decided were important, if only I’d stopped replying and responding long enough to consider what those things might be.
Eventually I realized that if there was something I wanted to make sure I got done, I had to send myself an email. That was the only way I could be sure it got as much of my attention as the things other people were asking me to do. Once I got into the habit of doing that, I could rest assured that everything I needed to do was accounted for in my email inbox, not just the stuff other people had asked of me. My email inbox, in other words, became my de facto to-do list program.
Unfortunately, an email inbox makes for a really poor to-do list manager. In fact, if the devil’s own software designer sat down to write the most diabolically dysfunctional to-do list program imaginable, they might very well come up with something like the email inbox. First, the subject lines of all those actionable emails rarely described exactly what I needed to do, so I found myself repeatedly re-opening and closing the same emails to remind myself of why it was there and what I needed to do about it. What’s more, the emails in my inbox weren’t sorted in priority order — the least important thing might be at the top of the list while the most important could be below the bottom of the screen. There were also no visual cues as to when anything was due — an email that didn’t need to be dealt with for another three months might be right next to one that needed to be handled that afternoon.
So I started inventing ways to overcome those limitations. Two key things needed to change: I needed to revise the subject lines so that each one described what I actually needed to do about the underlying email. That way I could scan my list and see what I needed to do without reopening any of the emails. And I needed to be able to arrange the emails in some kind of priority order.
The solution was to forward each actionable email to myself, revising the subject line prior to sending. I would start the subject of each forwarded email with a pound sign (#) followed by a number to signify its importance. #1 meant ‘Do It ASAP,’ #2 was the next most important, and so on. The rest of the subject line was an explicit description of what I needed to do about that email. Of course, in addition to forwarding emails from others, I continued to send myself new emails whenever I wanted to add something of my own to the list, using the same kind pound-sign/number prefix.
Now my email inbox did double-duty. When I wanted to read new mail I would sort it as I always had — with unread emails at the top in reverse chronological order. But when I was finished processing my email and wanted to start working from my to-do list, I would sort my inbox in alphabetical order by subject. Because the pound sign sorts ahead of any alphanumeric character, all the emails I’d sent or forwarded to myself popped to the top. And they were arranged in priority order according to what whatever number followed the pound sign. I could simply work my way down the emails from top to bottom knowing that I was handling everything in order of importance.
A few years later my company migrated from its old mail system to Microsoft Outlook, at which point I discovered that Outlook had built-in features that allowed me to do the whole integrated email/to-list thing without resorting to any kludgy workarounds. But those features weren’t obvious or widely known and I was one of the few people to use them. Eventually my boss came into my office, said I was the “most personally effective” person he knew, and asked me what my system was for keeping track of everything. More on that tomorrow.