If the problem is hard, you have to start thinking about it early. But every day you've thought about it a little without committing, you have a little more information about how it'll feel to take each path, and how it's likely to affect your operations people and customers.
Also Observation Bias may cause you to read that one article that explains why one of the choices seems like a good idea but is a trap. Or why you definitely should or should not use the latest major version, because of some change for the better or worse.
Frustratingly, some people see any discussions about such things as non sequiturs, distracting them from today's problems.
Worth noting:
Most decisions are 2-way doors. Very few decisions are 1-way doors. It takes experienced folks to identify true 1-way doors and apply the brakes. Having a culture of thoughtful document reviews, for example, gives space for people to identify 1-way / 2-way doors and push back. Having institutionalized knowledge gained from 20 years of running the largest public cloud provider helps in identifying 1-way doors in software development too.
All of that is to caution... yes, Bezos says useful things, can you take it and apply it to your company? Maybe. Do you implement / have the rest of what made it work well for Amazon too?
So he basically says "It will either rain, or it will not rain".
That some decisions are more important to get right than others (that "the dichotomy exists"), is just a trivial observation, the kind that people like Bezos make to appear insightful "technical leaders", but which are ultimately empty, amounting to "some decisions are important, others are not". Gee, thanks, Jeff!
The interesting part is knowing which case is which, or advice for that - which the above leaves out.