In my reasonably recent past, I had a job I hated. I was far from the only person who hated this job – pretty much every coworker did too. One of those people asked me today, “are we the watercooler gang?” Sadly, I think we were.
We spent a lot of time complaining about how bad things were, but we did better than that. We spent a fair amount of time – sometimes disobeying direct orders not to – building tools and infrastructure to not just stomp the fire but effect a lasting change that would solve this problem not once, but always forevermore. We create build automation when the situation presented to us was “If you want your stuff to go into this version of the product, move your compiled binaries to this folder.” We found we couldn’t live like that, and we pitched fits but more than that we built real solutions to those problems. Slowly, they moved the company from a garage operation to an actual business that could do things like match versions of the released product to the source that built it, standard everyday stuff that should be there in a grown up operation but wasn’t.
If I had it to do all over again, I’m not sure I would. We did an awful lot of complaining, spent a lot of time and energy and emotion raging against the machine. Demonstrably, the company was better off for us having done it but were we? I don’t know. Neither I nor any of my coworkers feel like we ever were or ever will be paid back for the pieces of ourselves that we put into that place. I think my heuristic moving forward is that when presented with thse sorts of problems and after proposing solutions, does the management and structure of the company fight the solution? If so, maybe you shouldn’t put a lot of yourself into this fight. The failure of the joint is a done deal, and you are merely prolonging the inevitable by helping them limp along better. Perhaps it is better to let the situation get worse, such that either they don’t fight your solution or the people fighting it get fired (as did happen at this company eventually.) It is hard, though, for motivated people who want to make things better to sit by and allow them to fester. I do know that the complaining didn’t really help, even though it seemed like a necessary thing to do or else suffering an embolism every day. I wish I had taken all that fire and energy and turned it into something that mattered, though.
We still talk about writing a business book based on the amazing example in how to do nearly everything wrong in an organization. It really was quite amazing. When the VCs gave the company money, I was surprised and frankly disappointed in their shoddy due diligence. My recommendation would have been to keep their cash in their pockets, because this bet ain’t ever paying off. Said book would be a case study for how to take a good idea in a business space with a booming market and a group of smart, motivated developers and parlay that into nothing. My proposed title: “How to Fuck Up a Wet Dream Without Hardly Trying: Case Studies in Destroying Start Ups ”