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Several people have been asking me if I'm serious about the $100! Wasn't expecting this to catch on, but here's what I'm going to do- I'm going to try out every solution that people send or suggest, and I'll document it in my blog, and I'll paypal the $100 to whomever's solution works best for me. :-)

I see someone suggested Beeminder in the comments of your post (thank you, whoever that was!). Also by the creators of Beeminder (me and Bethany Soule) is TagTime, which is related to your idea of periodic prompts. We call TagTime "stochastic self-sampling" or "time-tracking for space cadets". It's not super friendly (a huge pain to get working on Windows, for example) but it's on github here: http://tagti.me

If you don't want to deal with TagTime (and I don't blame you) then just hooking up RescueTime to Beeminder is a great way to go. Here's what RescueTime says about Beeminder:


I'll take your challenge. Does a Chrome extension work for you?

I am going to add this feature to a new version of my Productivity Owl: https://chrome.google.com/webstore/detail/productivity-owl/e...

Even if a Chrome Extension isn't what you're looking for - thanks for this idea. The way my owl works is that you schedule freetime, and during non-freetime all pages have a timer, and when the timer reaches 0, the owl closes your tab. It also has a block list for time-wasting pages like reddit or HN.

Lately my problem is that I delete the owl's timer, or schedule freetime when I shouldn't to avoid doing work. I was going to implement a "Respect Score" which I'm still planning on doing - but I really like the idea of the owl recognizing my 'workarounds', and prompting me with questions about my goals, instead of just berating me. Maybe I'll let users add their own prompts.

So I think your idea is a perfect addition to my current system. I plan to have a new version in 2-3 weeks.

I have the same experience as you and the author. Chrome extensions with timers such as StayFocusd have not worked for me. I just disable it or use firefox or something.

What if the user had to enter a predetermined answer to the question prompt in order to continue? By making the user actually type something that they themselves chose the prompt becomes more powerful.

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