According to Osho, repeating the same questions means you’re trapped in the mind’s mechanical rut—habit, conditioning, and the past. The mind only rephrases the old; it cannot produce the new, so answers don’t penetrate. The shift comes by seeing this pattern and disidentifying from mind: becoming aware, spacious, and present. In that consciousness, fresh questions — and real understanding — arise, bringing the only true freedom: freedom from conditioning.
If you keep asking the same thing, your mind is stuck on repeat; notice it and get quiet so new, clearer questions can appear.