You are lucky if deadlines with actual penalties have been a "tiny minority" of your experiences. The problem I experienced too much at some companies is "management" making artificial deadlines become real deadlines. VP of X sees feature set for delivery on Friday, sets up demo for potential client on Friday. Now everyone is in crunch mode or the company suffers when client can't see the feature. Or CxO drops in and says "I got invited to Conf Z in two weeks, I told them I'm going to demo Feature C and they just tweeted it, that's still on track, right?" Now, those were not the best managed companies, but I'd imagine there's a lot of people who end up in similar situations. As well, the author works at a consulting company, where I imagine many of the deadlines are baked into the contracts as deliverables with financial penalties for not meeting them. Consulting is a different world than a startup where you get to build something you hope to personally use for years.