They fall into two categories, one is financial and the emotional. Financially I had to save enough and get myself into a position that I could take on more career risk without destroying my potential to earn a living with the skills I spent time developing. As I explained in another Q&A, this is the time it takes to accumulate enough personal savings that my affordable loss is enough that I could pursue higher risk ventures and if they failed it would not be a personal catastrophe. The second aspect is one of having an emotional constitution, this is very hard to develop and takes a lot of experience, this is when all the cognitive biases impact one's perceptions such that it is hard to make sound business decisions. I describe this in my book "Startup SOAR Coaching", see the section on cognitive biases. For example, perpetual self-doubt and second guessing every decision, or being over-confident that some action is going get a reward. These all get amplified as an entrepreneur and it is not enough to be aware of them, it take a lot of time to be able to control these factors in oneself. It is way having a coach or mentor can accelerate the companies progress and avoid the mistakes that often have to do with the people not recognizing their own biases.