According to Osho, successive lives are not automatically progressive; you can rise or fall. Evolution becomes assured only when you consciously grow in awareness—then each birth moves to a higher plane. Because society conditions people toward unconsciousness (via drugs, power, distractions), most regress or stall. Choose increasing consciousness, transform suffering into insight, and your trajectory turns upward, culminating in pure, unbroken awareness.
No, lives don’t level up by themselves; you grow higher only by becoming more aware, otherwise you can even go backward.