Dustin comments on Anti-akrasia remote monitoring experiment - Less Wrong
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Enhancement suggestion: time-shifting. Make periodic screenshots and deposit them on the server. Of course this will not work with IM, but the shame factor might just be enough. Plus you can occasionally use "privacy privileges" and delete x% of the screenshots, in case of the obvious.
I could actually see this as a product.
This would be fairly trivial to implement in many different programming languages.
In fact, to lessen bandwidth requirements, you could expand this idea.
Set up your software to take the screenshot and automatically upload it somewhere and share the link via instant message with your watching buddy every X minutes.
I'd vary the amount of time some random amount so that you didn't start gaming your own system.