Laozi said: "The wise man does not argue; the arguer is not wise." I said: yes, but what about a man who argues brilliantly and is still completely wrong?
This is, I believe, my primary contribution to philosophy: the demonstration that wisdom and correctness are not the same thing. A great deal of clever, well-reasoned, entirely confident thinking leads somewhere absurd. The fool's job is to make this visible before it becomes too expensive to correct.
People ask me why I ride my donkey backward. I tell them: perhaps I am not riding backward. Perhaps my donkey is walking backward. How can you be sure which of us is facing the right direction until you establish what direction we are headed?
The examined life requires a degree of epistemological humility that most intelligent people find extremely difficult to maintain. Being clever is useful. But cleverness applied without doubt produces confident nonsense, which is harder to dislodge than ordinary nonsense because it comes with reasons.
What are you most confident about in your work and life? I would start the examination there. Confidence that has never been questioned is not knowledge. It is an untested assumption wearing conviction's clothes.
Ask the fool's question: what if I'm wrong?