Most of these are either management issues or written as if the person is acting in bad faith. But there are plenty of engineers who are 1) smart 2) driven, and

Most of these are either management issues or written as if the person is acting in bad faith. But there are plenty of engineers who are 1) smart 2) driven, and 3) well-meaning that still find themselves in this position One time I found myself in this position was overseeing an infrastructure migration for scaling reasons. The goal was to have it done before we hit scaling limits, and we had a team of 2 people and a fairly complex architecture. From the start, I suspected it might be difficult to do with the current staffing, even after extensive planning, but I underestimated what the costs would be to not completing the project on time. I was told by my manager that completing the project before hitting scaling limits was life or death for the company (it wasn’t, I know this because the sales team didn’t hit their targets and we survived). I now realize this was my manager attempting to motivate me to take on a tough project, rather than real truth. Had I pushed back harder, inquired about company financials, this would have been exposed as not true. While we eventually ended up completing the project, we completed our largest phase of hiring while in limbo between 2 architectures. The company became disorganized, accepting large amounts of tech debt as it was tough for new hires to understand what the “correct” thing to do was, and many people ended up adding to the legacy architecture in cases where they didn’t need to. It was a mistake that likely cost millions, even tens of millions in my eyes. The correct thing to do, of course, was just to insist that we couldn’t scale until we trained or hired more people to help. Limiting growth is often seen as unacceptable in startup culture, but IMO should be considered more often.