New Year’s Resolution

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.

About Simeon Simeonov

I'm an entrepreneur, hacker, angel investor and reformed VC. I am currently Founder & CTO of Swoop, a search advertising platform. Through FastIgnite I invest in and work with a few great startups to get more done with less. Learn more, follow @simeons on Twitter and connect with me on LinkedIn.
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17 Responses to New Year’s Resolution

  1. Hey Sim, you should look into “Inbox Zero”. It’s not a technology, but a methodology to handle with email. I adopted it about 2 months ago and I’m loving it. I have no pending emails and I’m faster and more effective at handling all my messages.

    There is a great video on Google Video of a presentation given at Google about it. Very good.

  2. Vladimir DImitroff says:

    After living a decade or so with Outlook (and its predecessor/s) as inevitable evil, I was just gathering resolve to switch to something open source that has all the functionality minus the limitations and bugs. Are you now telling me it doesn’t exist and I have to write my own? 🙂

    Mammoth task for ’08, given my rusty skills and time I can spare 😦

    How about off-th-shelf stuff like Thunderbird or the ‘new’ Eudora? What do yo know of their threading abilities, spam handling and multi-server behaviour?

  3. Marcelo, thanks for pointing me to Merlin Mann’s talk (YouTube link. More on the subject here.

  4. Vlad, we are an Office shop so Outlook really is the way to go for me. I haven’t heard great things about any other client. And, for the record, while I love some things about Gmail, I simply hate some of its behaviors and user interface.

  5. Ha, easy for you to say, Bob. 😉 If you recall, when I was starting at Polaris in 2002 you and I talked about Notes/Exchange integration and it wasn’t a pretty story back then. It was R6, if I recall correctly.

  6. Vladimir Dimitroff says:

    So – better the evil we know, then 🙂

  7. Brad Terrell says:

    I started using the approach advocated in the following book this year and have been pleased with the results (this approach is customized for Outlook):

    http://www.workdaycontrol.com/thebook.html

    I’ve also heard good things about this (also Outlook-specific):

    http://clearcontext.com/

  8. Thanks, Brad. I’ll check them out.

  9. John Troyer says:

    Nelson Email Organizer — every email automatically lives in multiple places — automatic virtual folders for people, dates, categories, flags, Outlook folders, newly-arrived mail, attachment type, etc. People folders include sent and received mail. Full text index.

    It’s my one cold-dead-hands app, and they aren’t updating it anymore. I haven’t seen anything else like it, which is a shame.

    http://www.caelo.com/

  10. John, I tried Nelson a while back. Slowed down Outlook noticeably so it wasn’t for me. I’m a performance nut. I hate waiting for SW.

  11. Pingback: Implementing Inbox Zero « HighContrast

  12. Pingback: Mini-App Software Quality « HighContrast

  13. Tim says:

    Hi Simeon
    I’ve had hundreds, if not thousands of emails set with the wrong receive date, due to previous migrations from outlook express. It wouldn’t matter if I had sent and received emails in separate folders because I could just view the sent date field for the send folder and the received date for everything else. However, I’ve previously relied on the fact the the received date was set to the same as the sent date so for archiving, I mixed my send and receive folders together into one archive folder per year. Sorting by received date put everything into order. Now, after the import from outlook express to Outlook PST files, the received dates were all set to the date of that import – so my archive folder can no longer be sensibly sorted.
    I’ve been searching for a long time for a utility (none of the fix pst files seem to have this feature) that could set the received date on selected emails back to the same as the sent date. I’ve just read your article where you mentioned that you managed to get such a utility from MS. I’ve love to get a copy! Could you please let me know the name of that util and if possible send a copy if the license permits ?
    Many thanks
    Tim

  14. Tim, I’ll check with MS.

  15. Tim, heard back from MS. The utility was custom-built for my system. It has various hard-coded assumptions in it that may not work for others. It doesn’t make sense for me to share it. How about trying rentacoder.com or elance? It should be a short piece of MAPI work.

  16. airspeed says:

    Hey everyone, I found the solution, I think!!
    Instead of allowing outlook to import email, export the email from outlook express.

    I am going home right now to try it. I have read it on several posts now, so this should work

    airspeed

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