Over the last couple years I’ve had to learn sales and understand the thought process behind this better, and I think I’m beginning to understand it

The psychology is that most people aren’t really trying to optimize for productivity (even most people who think they are) on an ROI basis, because their compensation is too decoupled from their actual raw output, and more closely coupled to how differentiated their marginal contribution is to peers. They’re much more incentivized to spend their personal/work time optimizing for being more skilled or acquiring some kind of competitive advantage relative to baseline.

Most people don’t consciously run the numbers of “I get paid $X/hr to add $Y of value” or model pay at work as something with variable inputs (eg something that can be increased with high performance), so it makes sense to them to spend 20 hours of time to save $100 or to make themselves 5% less efficient to take home 0.5% more or avoid doing something they don’t want to start doing.

NOT saying this always happens or that they’re stupid for doing so. I didn’t even realize how much I had been doing it myself until I started recognizing it, and shifted to having my own comp/performance fully aligned with the company’s P/L.

It actually makes a lot of sense IF you can accurately estimate incremental upside (which is much harder and more diffuse than modeling downside if you’re salaried a employee) or if the upfront skill/knowledge investment that looks like bikeshedding pays off in the long run.