@rrhoover I wanted a tool I could use anywhere — on the train, in the break room, etc. — for quick sessions of free-writing. However, I've built a bookmarklet that I'm considering releasing, an extension or OS X version of the app has been planned as well. Are there any specific points you'd ideally like in a desktop version (whether it's an extension or native app)?

@tannerc a chrome extension or native Mac app would be equally desired, I think. I'd like something that can help me write better (perhaps something like Hemingway) and inspire thought. Here's a thought: can you use public (e.g. Twitter, FB, Instagram, news) and private (e.g. emails, location history) to kickstart ideas for writers? For example, if you know I'm tweeting about Snapchat's new geostickers, Prompts might ask questions about them and provide supplementary articles, images, and other content to include in my essay. For more casual writers (maybe they write a private diary), you could prompt them to share their experience at Coachella, surfacing Instagram photos from the event.

@rrhoover Interesting. I've started experimenting with what I call "intelligent" prompts that look at the last paragraphs of writing to offer smarter prompts, but nothing in context like you've mentioned here. Your comments have given me enough of a push to get back on developing a native app. Thanks Ryan!

@tannerc nice! :) cc'ing Medium's @evansolomon and @dustin in case they have any thoughts on this. I'm curious how they're thinking about this topic.

@rrhoover I don't personally believe that semi-random prompts will get people to write more or better. Based on a bunch of qualitative data from working on WordPress.com and Medium, I'm skeptical that "I want to write but don't know what to write about" is a real customer use case. I have occasionally heard that, but when pushed further people usually evolve their reasoning into "I want to write but writing is really hard." If you believe that's the underlying problem to solve, I think there are two obvious ways to approach it... 1) Make writing easier. This one is super straightforward, but I think it's really, really hard. In some ways you could say something like a prompt does it, but I think an important part here is that you have to actually want to write the thing and in general I assume people aren't going to be that excited about some random topic that is potentially being shown to a lot of other people, too. 2) Make writing more fun. Lots of things are hard, but we still do them because the reward is greater than the cost. Personally this is approach that I believe has the most potential. The web has done a tremendous amount to make writing easier, but only a tiny amount (imo) to make it more rewarding. We just had a hack week at Medium and there were multiple teams working on both of these approaches (along with other projects that were not directly about writing). My team worked on a project that went the #2 route and I'm super excited about it.