I’m not big on New Year’s resolutions–if you want to do something, just do it, why wait for that magic date–but here timing played a role…
My resolution is to use email better, both in terms of how I write/send emails and in terms of how I use my email system, which is Microsoft Outlook/Exchange.
It all started with me having to do a complete rebuild of my machine in late summer due to bit rot. That’s when I switched to Kaspersky anti-virus for better performance. Little did I know that Kaspersky had a bug (which I unluckily discovered) where some Outlook messages moved between folders have their received date changed to the current time. Many messages over a period of several months had their received dates quietly changed. I finally found out what was happening during a routine batch macro job which changed many thousands of messages this way, making the task of locating an email from that period almost impossible.
Let me back up. I spend much of my time in Outlook managing many separate threads of conversation that cut across multiple portfolio companies as well as many startups I’m engaged with. Folders simply don’t work (for me) for M-to-N relationships so I use categories (what Gmail calls labels) combined with search. I’ve extended Outlook with custom code to provide behavior similar to some of what Gmail can do with labels, except that Outlook isn’t designed for this and so there is the need to work around limitations in mailbox size as well as how many items can be in a folder, etc.
I spent many hours on the phone with Microsoft tech support right before Christmas to track down the root cause of my problem to Kaspersky and then use utilities custom-built by the MS support team (a very helpful bunch of guys) to get me back on track (we batch set the received time to the sent time as a close-enough approximation).
The entire ordeal has prompted me to rethink how I work with email. If you have efficient systems for handling lots and lots of email where messages belong to one or more logical groups, let me know.
Update: there are some good pointers in the comments worth reading.