Jack, a renowned adventure reporter, transitions to the roll of desk-bound boss, overseeing a team of 20-something journalists, after the founder of the outdoor magazine he works for decides to go to a web-only publication.

Jack faces the ultimate test of his survival skills when he's forced to crash at Clark's tiny apartment while he searches for a place of his own. Also, Roland sticks Brooke with telling the millennials their beloved office perks are being taken away due to budget cuts.