I'm James Hague, a recovering programmer who has been designing video games since the 1980s. This is Why You Spent All that Time Learning to Program and Organizational Skills Beat Algorithmic Wizardry are good places to start.
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Flickr's Redesign is a Series of Evolutionary Changes
After years of teetering on the brink of relevance, Flickr is back in the limelight thanks in part to a more modern appearance. But here's something that may not be so obvious: it wasn't a sudden reworking of Flickr. It's been evolving through a series of smaller improvements over the course of fifteen months.
In February 2012, photo thumbnails presented as grid of small squares floating in a sea of whitespace were replaced with the justified view: images cropped to varying widths and packed into aesthetically pleasing rows in the browser window. Initially this was only for the favorites page, but a few months later it was applied to the amalgamation of recent photos from your contacts, then to the photos in topic-oriented groups.
In December 2012, the iOS Flickr app was replaced with a completely rewritten, better designed version. It sounds drastic, rewriting an app, but it's only a client for interacting with the Flickr database. The core of Flickr remained the same.
Around the same time, the justified view spread to the Explore (top recent photos) page.
When the May 2013 redesign hit, most of the pieces were already in place. Sure, there was some visual design work involved, but if you look closely one of the most striking changes is that the justified view is now used for individual photostreams.
I love stories like this, because it's my favorite way to develop: given an existing, working application, pick one thing to improve. Not a full rewrite. Not a Perl 6 level of manic redesign. Not a laundry list of changes. One thing. The lessons learned from that one improvement may lead to further ideas to try which will lead to still further ideas. Meanwhile you're dealing with an exponentially simpler problem than architecting an entire lineage of such theoretical improvements all at once.
(If you liked this, you might enjoy What Do People Like?)