For about a dozen years off and on during my career I had a boss that was pretty much on the same thought plane as me. We got along well. Thought the same way about business and typically could get things done.
From time to time I would walk into his office with some new idea that typically had to do with business strategy or some new way to grow our business as well as your general run of the mill managing an organization stuff. And from time to time, put not very often, the response that I got was “that is an absolutely horrible idea.” If that was the reaction my normal response was to drop it.
Well the other day I was having a meeting with an entrepreneur that is by any measure successful. During the early stages of his last startup I advised him a bit and we developed what would be called a mutual respect for each other. I floated an idea by him on a market that he knows a bit more about than me. His feedback. “That is an absolutely horrible idea.” We both laughed. I am not going to waste any more time on it.
Whether it is your career, your organization, or your startup find someone that you respect that will give you direct and honest feedback. Be willing to accept it. That is the best advice ever.