According to Osho, you hesitate to stake everything because staking means leaving the known for the unknown, and the mind—trained by society’s fears—clings to familiarity, even to old pains laced with hopes. Meditation demands utter aloneness; you cannot carry possessions, relations, or knowledge—only naked being. Though nothing is truly yours to lose, only indomitable courage breaks conditioning and steps into the trackless, risky freedom of the unknown.
Even if nothing can really be lost, your mind is scared of leaving what feels safe, so you need courage to go alone into the unknown.