Organizing Sent Email

I’m having a really tough time finding a useful tool or system to easily organize sent email. Every “organizing your email” tutorial out there seems to focus on the deluge of inbound email and how to handle, process, and organize it.

An overlooked problem, it seems, is organizing your sent email. Typically, most of us, when we need to find an email we sent previously, just search through our email Sent folder. Thunderbird and Outlook are more than capable of doing this.

What if I just want to easily browse through the last 20 emails I sent someone?

What if I just want to find the very first email I sent someone?