Maybe we all live in the email anti-Lake Wobegon, where we're all "worse than average" at email, in our own minds. One problem with email is the giant guilt pile it creates -- the psychological consisting of the number of emails you know are in there that you have forgotten about, ignored, or missed. My guess is that there's actually a disconnect with the *actual* problem in your inbox and the size of the guilt pile, as much of what's in there is probably out of date or irrelevant anyway. But nevertheless the guilt pile persists, and only grows. I do my best to tackle this. I try and respond to short emails in-the-moment as much as possible, and I star things that require a more thoughtful response, and work through my starred box regularly. Recently, I started using Zirtual, and my new virtual assistant Michelle is handling all of my scheduling emails -- that helps a LOT. But still, the guilt. And, on the flip side: it sucks when people don't respond to your emails. Especially when it's someone or something you care about, and that message can leave you wondering: "did they miss this or am I a loser?" So, here's one idea for a solution, inspired by Joel's text-me footer: an auto-apology email bot that periodically scans through my inbox and sends an apology to everyone who has a lingering message with me. The apology would say something like:

"hey -- I'm really sorry but it looks like I've gone and ignored/missed/forgotten your email. I suck at email and it kills me. Here are the messages in my inbox that I haven't responded to in the last [7|14|30] days: {list of email subjects} If anything in there is really important, please respond here and I promise I'll get back to you."

Perhaps this is impersonal and robotic, and it's clearly not as good as me actually responding to your email the first time around, but wouldn't it be an improvement?

Maybe we all live in the email anti-Lake Wobegon, where we're all "worse than average" at email, in our own minds. One problem with email is the giant guilt pile it creates -- the psychological consisting of the number of emails you know are in there that you have forgotten about, ignored, or missed. My guess is that there's actually a disconnect with the *actual* problem in your inbox and the size of the guilt pile, as much of what's in there is probably out of date or irrelevant anyway. But nevertheless the guilt pile persists, and only grows. I do my best to tackle this. I try and respond to short emails in-the-moment as much as possible, and I star things that require a more thoughtful response, and work through my starred box regularly. Recently, I started using Zirtual, and my new virtual assistant Michelle is handling all of my scheduling emails -- that helps a LOT. But still, the guilt. And, on the flip side: it sucks when people don't respond to your emails. Especially when it's someone or something you care about, and that message can leave you wondering: "did they miss this or am I a loser?" So, here's one idea for a solution, inspired by Joel's text-me footer: an auto-apology email bot that periodically scans through my inbox and sends an apology to everyone who has a lingering message with me. The apology would say something like:

"hey -- I'm really sorry but it looks like I've gone and ignored/missed/forgotten your email. I suck at email and it kills me. Here are the messages in my inbox that I haven't responded to in the last [7|14|30] days: {list of email subjects} If anything in there is really important, please respond here and I promise I'll get back to you."

Perhaps this is impersonal and robotic, and it's clearly not as good as me actually responding to your email the first time around, but wouldn't it be an improvement?