Not sure how this will work? Time to ask the hard questions.

In those instances in which you find yourself hoping that something will work without being able to convincingly explain to yourself how it will work – that’s when a little bell should go off. Then you should ask yourself clarifying questions. What’s the problem I need to solve? Does this solution actually makes sense (rationally)? If I’m feeling some doubt, why? Am I doing this for sound reasons or am I motivated by something personal?

-The Ride of a Lifetime, p.65