These are my thoughts on product, tech and design.

For a few years now, I've been chipping away at a historical research project about Will Rogers, the early 20th century humorist and one of the most widely read newspaper columnists in America. I find his story and his role in American cultural history fascinating, and as a fellow Oklahoman I feel somewhat obliged to help tell it. He died 91 years ago in 1935, so the vast majority of his life's work has already rolled into the public domain, and the rest will soon. My project's bottleneck has never been a lack of material, but getting access to it in the digital vaults where it is imprisoned. There are many paid-only, private databases that hold incredible, sprawling troves of public domain content but are barely indexed and have interfaces that seem almost designed to punish efficiency. Using them feels like the company is daring you to reverse engineer a better option.

I used to judge people for their overflowing inboxes. You know those screenshots where someone's mail app shows a gargantuan unread count? I'd cringe wondering why they wouldn't just deal with it. How hard is it to stay on top of your email?

Turns out: very hard.

I'm in year two of working for a startup, which has meant a lot of late nights and weekends with less time for small but important tasks like working out, laundry, and deleting D2C email pollution. In less than a year I went from inbox zero to inbox disaster. I'd try to clean up here and there, but the Gmail app on my phone is barely equipped for it, and even the desktop web made deep cleaning surprisingly painful. The power was there, it just took six or seven clicks and queries to reach it. It was so much harder than I expected that I built my own app to help (more on that another time). I've finally got it down from 14,500+ emails to 14 and I can breathe again, but I have a lot of thoughts about how I got here in the first place.

I often need sane estimates I can say out loud without cringing later. To solve this, I've made the Point-O-Matic to "price" project friction.