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Sunday.
There are people out there whose mood and spirit seem immune from weather and I’m not one of them. I don’t have the grayness antibodies. This morning I felt as dull and sleet-slapped as the scene outside the window. I took two naps today.

I was walking my bike back to my apartment yesterday in lesser frost but equal cold, talking to A. on the phone and wondering what out loud what distinguished the really good days – or even the slightly-better-than-normal days – from the crummy ones. Weather for sure, but that’s not always under my control. Good days tend to be productive, I know that, but how do I measure productivity? Page count? Time spent writing? Whether or not I exceed my own expectations? And what distinguishes two-pages-and-I-feel-invincible from ten-pages-but-I-feel-like-crap? How do I salvage days of the latter kind, transform that energy into good-day energy?

I’ve been thinking a lot about Questions in this week of unmotivating cold. I started using an app called Reporter, which pings me randomly throughout the day with questions I tell it to ask me. I’m three days in and still very much learning how to use it, uncovering what’s appropriate to ask. I realized, for instance, that I don’t really want a robot asking me, six times a day, Do you feel excited about the future right now?

Buster Benson has a great Reporter question: Is this quality time?

But that same combination of words carries a slightly different meaning for him than it does for me or you. And one thing I still remember from the lone statistics class I took in college is that way you frame a survey question can produce wildly different responses. It can effect its own mindset. Trying to determine what I want Reporter to ask me is the same as trying to determine, essentially, the ways in which I want to condition myself to think about my world.

David Whyte says, “The ability to ask beautiful questions, often in very unbeautiful moments, is one of the great disciplines of a human life.”

He continues, “A beautiful question starts to shape your identity as much by asking it as it does by having it answered. And you don’t have to do anything about it, you just have to keep asking, and before you know it, you will find yourself actually shaping a different life, meeting different people, finding conversations that are leading you in those directions that you wouldn’t even have seen before.”

It wasn’t until I re-listened to Whyte’s words just now that I realized what sets Reporter apart from other apps of its kind. Reporter isn’t just a life-tracking app; it’s also a life-sculpting app. The app itself poses, implicitly, the question, What do I want I ask myself each day?

For me, that's a beautiful question, in a very unbeautiful week.
—Jack
Written from Detroit, Michigan. Questions, comments, hellos—all welcome. Just hit reply.

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