We never did anything stupid or caused damage. I think the relationship was somewhat based on an implicit statement of mutual trust.
On the one hand, the administration punished me and one of my friends with something like six months of detentions.
On the other hand, the IT admin asked us to do it again, but write him up a proper report. Basically gave us the authority to do whatever we wanted, and encouraged us that it could be a career, if we did things the right way.
I think that trust and encouragement went a long way to influencing my career path.
It's sad that so many schools in the US seem to have this attitude of "YOU DID SOMETHING WRONG AND MUST BE PUNISHED!!!" instead of actually using it as a teachable moment and encouraging someone who has demonstrated competency with tech to pursue that, given the chances of it leading to a lucrative career.
Imagine if a kid broke the technical rules of the gym and made a dozen 3-point basketball shots in a row -- I'd bet the gym teacher would tell the basketball coach about it instead of writing the kid up. Why can't we do the same for tech?
I received in school suspension for hacking, and I feel like that taught me just the right amount of discipline. I had basically written a boot disk that created c:\autoexec.bat that executed coldboot.com, which was a dos program that immediately rebooted the computer. I then booted all the computer lab machines off that disk. Three days stuck in a boring quiet room with students I had never been around before. Very enlightening.
This was back when we used to see who carried the coolest looking floppies around. Mine was unlabeled black with a black plastic dust cover. My buddy was a rebel and always took the dust covers off his blood red disks.