Keep your ideas in a list. For each idea, keep a collection of reasons for and against each one. Categorize each reason as strong or moderate -- don't bother to keep track of weak reasons, whether for or against.
As you run across new information or think of new considerations, add them to the list (which is really a tree) and re-rank your ideas. The ranking of your ideas will be very dynamic -- they will go up and down. And hopefully, the ideas themselves will evolve. Workflowy could be a viable UI: It provides the ability to re-order, restructure, and collapse/expand bullet points.
Ultimately, go with your gut. But the gut feeling you should go with is the gut feeling you get when this list is fairly well-developed and the entirety of it is loaded into your working memory.
Work at a company in the space you wish to get into and identify what the technical bottlenecks are for achieving a 10x better experience. Enter a research program at a university with favorable policies around intellectual property, build the tech, and start your company.
If you're not scratching your own itch, try to get into it. Perhaps you'll "get it," become a "superuser" of the product, and feel the pain points (or limiting factors) yourself.
Keep your ideas in a list. For each idea, keep a collection of reasons for and against each one. Categorize each reason as strong or moderate -- don't bother to keep track of weak reasons, whether for or against.
As you run across new information or think of new considerations, add them to the list (which is really a tree) and re-rank your ideas. The ranking of your ideas will be very dynamic -- they will go up and down. And hopefully, the ideas themselves will evolve. Workflowy could be a viable UI: It provides the ability to re-order, restructure, and collapse/expand bullet points.
Ultimately, go with your gut. But the gut feeling you should go with is the gut feeling you get when this list is fairly well-developed and the entirety of it is loaded into your working memory.