Late Night Emails

I have a bit of a habit – I send all my thoughtful (well, relatively thoughtful emails) late at night. One of my staff members commented during a 1-1 session that he’s torn – he generally does want to respond/converse when I comment on process, philosophy, and the like (+1) but… it’s like 8,9,10PM and he doesn’t really want to think about it right at that time (-1). Also,  I don’t actually expect people to be online and checking their email after hours, and don’t want to inadvertently set that expectation or build that kind of culture.

In reality – the plague of email philosophy is largely a byproduct of NJTransit – for some reason (possibly the tunnels which stop internet access) I find myself as part of settling down from the day, often jotting down thoughts on processes, observations, or – dangerously close to philosophy. At least some of these ideas are even good (better than par).

So… the solution clearly is to defer broadcasting my thoughts. Admittedly in some cases I do end up doing that, using a text editor while roughing out thoughts (currently looking for a good Windows one – playing w/PsPad – would like something open-source ideally) though that’s not really a great workflow.

Something along the lines of the ability to “SendLater” – for me to write as the thoughts are flowing, but send when recipients are likely to be reading – as opposed to spamming their blackberry would be ideal. Since we’re on Exchange, which means Outlook is pretty much the only sane way to interface with my email (I run Linux on my desktop, but Evolution seems very broken against Exchange 2003). Doing some quick Googling, there appear to be something like 3 solutions.

  1. Outlook, in “options” does have buried a “don’t deliver before XXX” setting
  2. SendLater – an add-on (~$25)
  3. EmailScheduler – another add-on, part of a bigger suite (~$25 for the suite)

For the time being I’m going to go w/#1 and some good old mental discipline – from a usage perspective I’d love to have a couple of different options, perhaps off a dropdown that late me define something like “xxx day @ yyy time” and have a couple easy options – I’m dreaming of something like:

[Send Later | v]

— Today @ 5PM
— Tomorrow @ 9AM

I’ve been meaning to do something in .Net – this may be what tips me over the edge, given how much time I spend inside outlook these days – don’t want to lose all my street cred.