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Happyish
It's a generational clash when 40-something ad exec Thom Payne gets a new wunderkind boss, who is in his mid-20s. When his boss starts using words like digital, social and viral, Thom realizes he may need to rebrand himself to compete in a technology-driven world. His pursuit of happiness is going well to this point -- he has a beautiful house in the woods, a loving family, a roster of big-name clients and a trophy shelf filled with awards for his work -- but being slow to adapt compromises his quest. His immediate supervisor, 50-something Jonathan, has begun to embrace the changing environment and encourages Thom to do the same. Otherwise, Thom may be stuck being just "happyish" for the rest of his life.
S1, EP10 "Starring Christopher Hitchens, Philip Larkin and Josef Stalin"
Thom writes a story, and then quits his job; "Radical Capitalism"; hopes and dreams; a big red slide.
S1, EP9 "Starring Mr. Mike, Joseph McCarthy and Alfred Bernhard Nobel"
Thom learns something terrible about Larry; Lee takes Julius to Hebrew School; Thom seeks advice from Dani.
S1, EP8 "Starring Rene Descartes, Adweek and HRH The Princess of Arendelle"
Thom is forced out of his office; Lee meets Sandy while helping out as "lunch mom"; James Deen gives advice on success in porn and corporate America.
S1, EP7 "Starring David Ogilvy, Anton Chekhov and Gluten Enteropathy"
Thom promises Julius he will return from Los Angeles with a toy, but must stay longer than expected; Lee gets a new cell phone.