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Hi Steve. I handle this by having a context specifically for people I work with on a regular basis. I keep them under a parent context called People (so the list can be collapsed), with about a dozen named individual contexts inside (like John, Jenny, Mike, etc.). For other, less frequent and less important contacts, I fall back on my more generic "Email", "Phone", "Mail" contexts.

Now, you might argue that by assigning a specific context of "John" to an action, the action loses its original, more generic context of "Email" or "Phone".

That's true, but context is all about choosing the single-most-important person/place/thing/mode/circumstance required to handle an action. In cases where I'm working with one of my key contacts, the most important thing is that I be in touch with that specific person, not the medium over which the conversation is taking place. In other words, I need to discuss something with John and it doesn't matter if it's by phone, email, or face-to-face over lunch. So for that action, the "John" context trumps all other contexts ("Phone", "Email", etc.).