I both laughed and cried - great read!
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John Hodgman writes very well and he’s funny and entertaining.  Some self-reflective parts of the book are revealing in an uncomfortable way.  I wouldn’t call this book a “light” book, but I would recommend it.  

It's always enjoyable to party with George R. R. Martin because a GRRM party is a sit-down party, and that's where I am at now.
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Funny, warm stories from John Hodgman. To the uninitiated, John Hodgman is a razor-sharp wit, a clear and incisive writer and humorist, and he is a human being. I love seeing this side of him, where he is sometimes harder and angrier (and even gets a touch political), but more often wistful and loving, especially as these stories relate to his children. He can articulate the awkward and nonsensical and rough times in life with a simplicity that escapes most of us.
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John Hodgman is one of the best living writers for capturing the middle age experiences of nerdy, white men, a group of which I consider myself a member. His books are not the type I would consider universally lovable, but at my current place in life I find his ruminations about loneliness, family, and the experience of being an outsider wholly relatable, funny, and well-articulated.

What I love about his writing is that mixed in with comedic anecdotes about the gamification of travel, crashing on friends' couches, and attempting to teach children to like their dad's pop culture, Hodgman finds moments to explore whatever current "big" moment the country is experiencing. In Vacationland he has a lovely section about the murder of Michael Brown and the rise of Black Lives Matter. In Medallion Status he writes about the sinking feeling of living in a country that just elected Donald Trump. In both of these pivotal moments he acknowledges that a white, middle class man is not likely to be as impacted as so many others, but it's impossible not to reckon with the change we have undergone as a nation and to try to figure out one's place in it.

I'll continue to look forward to Hodgman's future books and hope that they all are as witty and clear-eyed as the last two.
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Just not that interesting. Sorry, Judge John Hodgman.
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Starts off slow as an unremarkable take on mild fame but improves quickly with the remarkable reflections and clever humor that a Hodgman fan expects and likes.