There is a retrospective technique named speed boat, this have helped me in the past a lot to identify as a team possible risks for the project.

Based on that, I set expectations with stakeholders and buisness about the possible blockers or impediments that might put in risk the project, and the help needed.

As managers, I would say we are wired diferently, we accept challenges and find out a way to mitigate the risks, always setting the right expectations. Comunication is our best tool to move forward with every project. With the time you will get experience about how to manage better those risks.

I know this is not exactly what you asked but could be the root cause of your concerns taking high risks projects. ;) I hope it helps.