Why do we keep waiting?

I don't know, but I think we should stop

The honest answer is that it's rarely about incompetence. It's almost always one of three things:

1. Political shielding — someone has to be accountable, and the person who says "this is a disaster" becomes the owner. Most organizations would rather fail slowly than loudly.
2. The cost of being wrong publicly exceeds the benefit of being right privately. That incentive structure produces every delay you can name.
3. Real dependencies that aren't visible in the thread — data quality, legal clearance, downstream contract rework, budget cycles.

We keep waiting because we've been rewarded for it in the past (projects were delivered "on time" by pushing deadlines), which created a culture where shipping late is acceptable and shipping early is penalized if anything goes wrong.

Waiting is not the problem. The framing of this entire question presupposes that there's a causal link between inaction and failure, which I find deeply teleological. What you call "waiting" might just as well be called "contextualizing," or "observing system boundaries before committing resources." Both interpretations are valid; one is frantic, the other is methodical. The user who waits for 40 years to start a business isn't necessarily failing at something — they may have been developing an internal infrastructure that makes the eventual execution more likely to succeed than a hasty attempt would have. We've pathologized deliberation as though it were always synonymous with procrastination, but deliberate inaction is also a form of action, just one whose output is not immediately visible and therefore doesn't fit our bias toward rapid feedback loops. I think we should stop pretending there's an objective "right time" to start things; the question isn't why people wait, it's what definition of waiting are you operating under, because if your definition conflates every non-immediate action with failure then your definitions are doing more work than your analysis is.

Analysis paralysis is real, but it's usually a proxy for something else: fear of making the wrong decision or loss aversion framing everything as high-stakes when most moves are reversible. The framework that helps is "one-way vs. two-way doors." Type 1 decisions (irreversible) should be made slowly with lots of data. Type 2 decisions (reversible) should be made quickly because you can course-correct later if it's wrong. Most decisions in daily work are Type 2 — we treat them like Type 1 and get stuck.