Look for the duct tape
I've been having some wonderful conversations in the real world since resigning and jumping off the merry-go-round. Besides just talking about what happened, why I left, and how to succeed in the "2018 version" of the culture which now exists, I'm also still doing the same mentoring stuff I always did.
Many of these conversations have yielded some real gems, and one I had not long ago is no exception. I didn't realize it at first, but it was actually a conversation about how to find interesting things to work on. It started as a simple question: what bugged me about the (X) environment when I was there? What would I change?
Normally when something bugs me and has outstanding issues, there's this mental laundry list in my head and I can rattle off a few things. But for this, I didn't have anything. I wasn't sure if it was because I've been free for about a month now, but the answers just weren't forthcoming. Still, I tried to give some kind of answer because this person needed direction. If I said "it's all good", that wouldn't help them at all.
After a bit of pondering and feeling really bad about not having anything to say, it hit me. I had rigged up a bunch of local tools in my own "bin" directory to do things that the "X" environment did not handle. Those had been issues for me, but were no longer, because I had covered the rough edges with my own workarounds. The system now worked in a way that didn't annoy me too much.
With that in mind, I was able to rattle off a whole bunch of dumb little shell scripts and other tools that I had written over the past 4.5 years to make my life better when operating in that space. This turned out to be a treasure trove of things worth digging into. To think that I almost said that everything was fine and nothing was wrong!
Next I tried to pop up a level to give a general tenet instead of just a laundry list of dumb things I had worked around, and looking around at the public furniture in the town square, it came to me: look for the duct tape. Look for the patches to the original system which were done by people who actually work in a given space. Track down the sharp edges which have been systematically covered up by users who were more interested in being productive and weren't willing to fight with the owners of the system to get things changed upstream.
In concrete terms, go around and find out what kind of little one-off tools people have designed. Talk to them and hear their stories. Look in their personal bin directories. Take notes and look for patterns. See if anything stands out, or if anything particularly compelling grabs you during the interviews.
Then, if you go off and build something new to soften a rough edge, not only do they get to remove the duct tape, but you have a bunch of interested users from day one. Also, just think of the goodwill that is bound to follow when they realize that finally, someone cares about the end-user experience, and is willing to adapt upstream to make their lives better.
Look for the duct tape.