I’ve worked at a few places where we pushed an agenda of always getting better at our jobs, so that doing things like we’ve done before gets cheaper, and things we couldn’t do before become feasible.

It’s great for some things, but it also gives the devs more time (and moral authority) to think about the flaws in other parts of the organization. It seemed like there was just as much complaining and stressing about things, it was just different things.

I suspect this is why the “good enough” culture of thick-skinned, slightly masochistic people who put up with the same busy work is the de facto standard.

Part of what drew me to software was that you “figure out” how something works, you write a bit of software to manage that task, and move on to the next problem. I amazes me how many people who are capable of automating simple tasks are content to simply repeat them instead.

Its very, very, VERY hard to keep such a company culture when you grow company big time.

You would effectively have to have people dedicated simply to this task, with massive managerial powers checking all management decisions and keep reminding all folks to stick to them (I can't imagine any other way). Its not only about things on paper like benefits and working hours, but overall company culture, agility to change and corner cases. If you manage that, kudos to you, but you are rather an exception.

I've seen it first hand - an amazing, startup-like company, growing super fast, and culture suffered.

Sure, if you have plenty of money flowing in (whether it’s VC funds or paying customers) it’s relatively easy to provide good working conditions and benefits. Is it sustainable though? Investors will push for an exit, and once you get bought it’s out of your control. If the buyer is a publicly traded company, its shareholders will mostly care about short-term profits rather than the conditions you provide for your workers.

The shenanigans and culture drift happen once you need a layer of “middle management”. Their goals are often focused on their own careers rather than the success of the company as a whole.

I agree, but I would expect to that growing fast usually means bringing in lots of people over a short amount of time. I’ve never done something like that, but I imagine keeping the culture of the company might be challenging.