Joel Stein is a journalist known for his comedic and controversial style. He says (and writes) what many of us are thinking but would never say out loud. We discuss the role humor plays in answering the Why Not Now? question. Joel has a sophomoric humor column in TIME that now appears in the magazine every week. He’s written for way too many media outlets to list and has been fired from quite a few. Joel shares his gold when it comes to writing tips. (Honestly! Some of the best I've ever heard.)     Show Notes: Joel's Why Not Now? moment. Choosing between law school or journalism. The factors that came into play when deciding between the two very difference paths. What happened when Joel interviewed Ellen Degeneres about the lesbian fish in the Finding Dory movie. Joel reached out to an internet troll, who had been trolling him for a long time, and invited her to lunch. They met up! How did it go down? The time George Clooney came to dinner at Joel's home and they ended up in the attic with a flashlight. Joel shares the best writing tips I've ever come across. We discuss writer's block. It's not a thing according to Joel. "It's like workout block." Writers block is actually something else. What does personal branding have to do with a person's funeral? We discuss. Joel's new book. Real talk about the challenges and how Joel works through road blocks. Can a person learn how to writer with humor? Yes. Joel shares how. How to find your writing voice. Incredible suggestion on how to do this. What advice Joel would give to his younger self? Books Mentioned: Man Made: A Stupid Quest for Masculinity by Joel Stein Old Age: A Beginner's Guide by Michael Kinsley