Use self-BCC to tame your sent folder

Over on Simplifying Complexity, I recently doubled one of our software bounties from $250 to $500.

Here’s a deeper background on the topic:

Unlike people who use their sent items folder as a giant bucket to keep track of things they sent to people, I prefer to BCC myself and then file the actual email I sent in the proper folder. Using  the sent folder in this way and then also separate folders (however many) confuses me in part because I’m a folder guy, not a pile guy when it comes to saving emails. As for the actual sent folder, I just delete everything in it.
Another advantage of the BCC vs. just checking the sent folder is a clearer signal, easier to track in my workflow, that an email actually went out than switching back to the sent folder to check. If I bcc myself on something that I actually don’t need to keep, I just delete it. Deleting emails is part of my normal workflow in the inbox; if that email were part of sent mail, it would just be extra garbage in the pile.
My sense is that my preference for folders is a probable  aftereffect of keeping legal client emails separated as much as possible to avoid inadvertent disclosures.
Certainly, better search tools, whether from gmail, Outlook, or Xobni, have improved the viability of the pile/bucket method. Fewer places to file things makes it faster to handle email, and better search reduces the need to separate things so much upfront. I’m slowly moving toward fewer buckets, and there are still some things that will have to be segregated. For example, I expect to slowly transition to this general framework:
  • Marketing/networking (all “keeping in touch” that doesn’t get put into folders for Pam, the boys, and my brother/sister-in-law/twin nieces).
  • ASD will be a new folder to collect autism-related items, separated into REED, Dylan, 30seats, and client-specific folders (same rationale as above).
  • Under a “Business” folder, I’ll track these:
  1. Client/project-specific folders
  2. Admin for everything that is business admin-related and doesn’t go elsewhere.
  • Nonprofit for my work on various charitable efforts (including Allegheny and other autism efforts)
  • Usernames to keep password emails all in one place. (Still seems easier to find that FedEx username without having to look through tracking notices.)
  • Z-Quicken for everything that’s an e-receipt, order confirmation, or payment (I use the “Z-” prefix to keep it at the bottom of the list).

Putting the list down on paper does make me feel happy about the impending reorganization. As for waiting-fors, actions, etc., we use the NetCentrics GTD plug-in for Outlook, so it creates a few extra folders. My biggest reason for not putting stuff in an “action” folder for emails that have to be checked is the sense, proven by my experience, that I will ignore that bucket and it just becomes another black hole. Things need to be handled, and my goal is to use the plugin to take emails with embedded tasks and turn them into actual tasks rather than move them to a different pile.

As I scan the inbox now, there are 187 messages, 2 unread. 1 is a furniture ad I’ll delete shortly and one is a BCC from me. There are probably 30 messages related to a blast I sent out yesterday related to Dylan’s CBS appearance. I’ll get caught up on those today and get back down to 100 by COB today. The rest that require more work: I recognize that I need to frame them into tasks, and I want that burden right in front of me, whether it’s things to read, track, or respond to. In many cases, for those items where I’m writing things such as this post, I prefer to just handle them by writing the post (or at least starting it and adding a link) rather than going through an intermediate step of creating a “BLOG xyz” task in Outlook. (I promise I’ll break that habit soon!)

In any event, I thought that this brief explanation will be helpful to some of you. My recommendation is that you consider attending one of People-OnTheGo’s “Total Organization” workshops by my colleague Pierre. The ToolsMap (™) is absolutely amazing, and even now, years later, I think it’s terrain completely untouched by anyone else in the productivity field.