Should I pull guard in a street fight?

Generally no. Pulling guard on purpose in a street fight puts your back on concrete, asphalt, or glass, and you cannot control whether the attacker has friends, weapons, or space to stomp. Sport BJJ rewards guard play. Self-defense prioritizes posture, distance, and top control. Better defaults: stay on your feet when you can, use takedowns that land you on top, and get to a pin (mount/side) if the fight hits the ground. Guard becomes a survival tool if you are already on bottom, not a planned entry. From bottom in a real fight, your goals are create frames, stand up, or reverse to top as fast as possible. Training tip: drill stand-up and top pins under stress, not only fancy guard sweeps. Competition habits transfer only if you choose the ones that still make sense with pavement and multiple attackers.