The difficulty of entrepreneurship is in navigating and making forward progress in highly underspecified, uncertain environments.
At its core, entrepreneurship is alchemy. You must transmute inert resources into value and capital. To do so, you have to set a direction ex ante, sometimes with very little information, and persist until its reification.
The virtues required to thrive in such a setting are well-known: adaptability and resourcefulness, persistence and resilience, optimism and self-confidence, risk-tolerance and nonconsensus views, and so on.
It’s one thing to know that these are the required qualities. It’s another thing to live through the actual psychological balancing act. Some failure modes are detailed below.
Some people are unable to set concrete direction. They explore for a while but cannot, for one reason or another, create or arrive at enough conviction to proceed decisively.
Some people want the perfect starting conditions. They pattern match to hagiographic stories and accounts which obscure the messiness of reality.
Most people are too married to ideas. Another way of saying this is that they do not want to be accountable to reality—they want their ideas to be right, and care more about being seen as right than to iteratively discover truth. This makes a lot of founders fail to pivot or pivot too slowly. I’ve often heard “The buyer doesn’t know what they want” as an excuse to avoid thinking creatively about constraints.
Most people don’t want to look stupid. Until you build something that works, people will always be bringing up your opportunity cost of not pursuing other more stable, lucrative careers. Most people would rather derive their self-worth from association with the right people and institutions, instead of doing something truly and uniquely creative and valuable. “The crowd is untruth.”
Talk is cheap. Most people overestimate the feasibility of ideas (I have this mental image of friends shooting from the hip in conversations at the bar, making bold claims to rhetorically signal and posture) and underestimate the difficulty and complexity needed to instantiate even the simplest ideas. While some initial hubris is sometimes helpful (“how hard could it really be?”), this miscalibration often means that people give up on ideas too quickly.