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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.
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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.
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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.
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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.
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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.