Lesley Carhart 
The deep frustration of being a career mentor seeing brigades of underemployed and unemployed young cybersecurity people, yet also working in a niche where we -can't find enough young people to hire- because schools and entry level gigs are not teaching firm enough basic computer fundamentals for us to successfully teach their graduates OT and legacy technology.
The Bard At Work@hacks4pancakes I experienced this deeply at my last position at an org that almost exclusively hired fresh college grads; as the senior SOC person I basically had to run most new people through crash courses on networking etc.
Then I was asked why we couldn't have their average sysadmin doing IR and when I pointed out they often lacked a lot of the technical knowledge (like networking for example) the response was "well, if there's something networking related they should be pulling in a network engineer"