Hipchat:
1) Paste image
Imgur + IRC:
1) New browser tab/window
2) Paste image
3) Click "Start Upload" button
4) Wait for upload + redirect to new page
5) Right click, copy image location
6) Switch back to IRC
7) Paste URL
I use this somewhere from 10-100 times a day, so it adds up. And it doesn't interrupt the flow of whatever I'm working on, just a single action that doesn't require any thought or aiming my cursor to click on things.
Could I write an automated tool that takes my clipboard, uploads it somewhere, and replaces the clipboard with an image URL? Probably. Or I could use a chat platform that supports images.
Edit: Trimmed one step with copy image location instead of actually navigating to the image