pen testing often involves walking into a building looking like you should be there. If no one is around to let you in it also can involve half a minute of getting the door open with some primitive every day tools. No computers or software required.
The action is stupid, but trespassing idiots get caught quickly - that's just "survival of the fittest" mechanics.
If you never trespassed in your life then you were probably not smart enough to get away with it?
As a kid I've tresspassed plenty, it often takes 'security' hours to even spot you