There will always be someone that
wants to play devil's advocate.
If you are going to play that “what if” game, do it early.
Lay out all your fears. Write down every reason why the project could fail. Get everyone to contribute and wrestle with it. Decide if you are going to be crushed if the project fails. What is the cost of not doing the project (who could have benefited from this project that now isn't)?
If the outcome of failing will crush you and if you are not going to commit to pushing through until the end then there is no project. Find something else to do.
However, if it's just the fear of failing that is outweighing the potential of success then there is no choice. You have an obligation, an obligation to do the work and to push through the fear.
Once the work begins, the fear of failing (deciding, discussing or dissecting) can no longer be injected into the project. No more playing devil's advocate.
The devil is fine. He doesn't need an advocate.
