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Quote: In my view, entrepreneurial judgment is the ability to tell the difference between a situation that's not working but persistence and iteration will ultimately prove it out, versus a situation that's not working and additional effort is a destructive waste of time and radical change is necessary.

I don't believe there are any good rules for being able to tell the difference between the two. Which is one of the main reasons starting a company is so hard.

I asked almost exactly this question here on news.yc. PG was kind enough to post some advice that I've taken to heart: Your existing users are the place to start. There must be something they like about whatever you have, or you wouldn't be there. So you just have to learn to understand them well enough to turn that like into love. In the process you may appeal to a broader set of users, and as you iterate the "typical" user you focus on can move.

http://news.ycombinator.com/item?id=116383




I think this insight applies to many life challenges, not just starting companies. Some that come to mind:

* Courting, relationships

* Building a career within an organization

* Some unproven solution to a technical problem

* Building a blog readership

etc.




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