He is curious, critical and full of anticipation. His stress level is kept low because he is prepared, ahead of the aircraft, practiced in his procedures, and flying with 'what if' always on his mind. You must learn your own comfort limits. Keep track of the weather through Flight Watch after takeoff. If visibility drops you might consider canceling the flight.
Poor visibility is the most likely cause of becoming lost.
The hazard of being lost lies in the mental and emotional stress it puts on the pilot. Preflight planning that selects viable checkpoints can negate this stress. Use as many navigational methods and aids as you can. When planning a flight use a sectional in conjunction with any weather pictures obtained. It lets you know the terrain you need to fly over.