For me, my high bar that I have yet to beat, was the time I pivoted the running OS (ubuntu) into RAM over SSH so I could unmount and image the boot drive without rebooting and loading a live USB (Which would have required a ticket with my provider to enable IPMI)
I used the aircrack-ng tools to capture wep packets and decrypt my neighbors WiFi because I was broke and needed internet to study back in college…I was a total noob (still am) and when I saw the password in the terminal I felt like I was a total hackerman. It was great!