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"How to Fail" is the world's FIRST Self-Hurt Guide, the polar opposite of a self-help guide. In "How to Fail," follow the misadventures, misgivings, and massive mistakes of this satiric novel's narrator, Stu Fish, as he tries to find success in 2010 New York. With hilarious chapters such as... read more

Summary edit see section history

"How to Fail" is the world's FIRST Self-Hurt Guide, the polar opposite of a self-help guide. In "How to Fail," follow the misadventures, misgivings, and massive mistakes of this satiric novel's narrator, Stu Fish, as he tries to find success in 2010 New York. With hilarious chapters such as... read more (warning: may contain spoilers)

"How to Fail" is the world's FIRST Self-Hurt Guide, the polar opposite of a self-help guide. In "How to Fail," follow the misadventures, misgivings, and massive mistakes of this satiric novel's narrator, Stu Fish, as he tries to find success in 2010 New York. With hilarious chapters such as "How to Fail to Make Your Parents Proud of You," "How to Fail to Do Something Productive All Day," "How to Fail in Love," and "How to Fail All the Way to Rock Bottom," and even more ribald "footchapters" such as "How to Masturbate at Work," "How to Develop an Addiction," "How to Get Usurped by Your Girlfriend's Ex," and "How to Acquire the STD That's Right for You," there's not an aspect of life that "How to Fail" doesn't tackle and offer a terrific non-solution for. All of this is delivered in perfect single serving-size chapters for our modern A.D.D. culture more used to reading blog entries on their phones while riding the subway or waiting in line at Subway than in carefully reading a book.

Characters edit see section history

  • Stuart "Stu" Fish: The book's protagonist. Has just turned thirty-years-old as the book begins. Unhappy in life, work, and love. But, is certain he'd be even less happier if he was living the life of his "successful" friends. Lives in Hell's Kitchen, Manhattan.
  • Danny: One of Stu's successful friends: an aspiring politician currently in banking. Lives in White Plains, New York.
  • MElissa "ME": Danny's wife.
  • Jack: One of Stu's successful friends: a financial analyst. Lives in Weehawken, New Jersey.
  • Kirsten: Jack's wife. Mother of Anna.
  • Keith: One of Stu's successful friends: a trader in Midtown. Lives near Central Park.
  • Erin: Keith's wife.
  • Allen Fish: Stu's father. A former New Yorker who now lives in St. Louis. A restaurant supplies salesman. A shameless networker.
  • Suzanne Fish: Stu's mother. A high school math teacher.
  • "Sissy" Fish: Stu's successful sister. A veterinarian.
  • Ashley "Ash" Forester: Stu's one-time girlfriend of several years.
  • Trevor: Ash's ex-boyfriend.
  • Dough (pronounced Doug): Stu's boss at the company he works for at the start of the book.
  • Lynn: The hard-to-understand Irish bartender at Stu's favorite dive, The Wee Pub.
  • Katie Anderson: A teacher who loves happy hour at the Wee Pub.
  • "Swami" Christian: Stu's roommate, a homosexual oddball obsessed with yoga.
  • Bill Forester: Ash's father who lives in Poughkeepsie, NY and hates Stu.
  • Nan Forester: Ash's mother who lives in Poughkeepsie, NY and hates Stu.
  • "Spitshine Tommy" Forester: Ash's annoying brother who is obsessed with "protecting" his sister from Stu.
  • Eddie Haskell: The goody-two-shoes husband of Ash's sister.
  • Patricia: Ash's roommate, a wannabe actress currently plying her trade as a waitress at a Times Square novelty restaurant.
  • Kurt: Patricia's fiancee, an actor starring in the Broadway adaptation of Disney's "The Black Cauldron."
  • Theodore "Smelly Ted" Shelstein: An old man who drinks at the Wee Pub and constantly stinks of cigars, Wild Turkey, and "old-manness."
  • Willy: One of Stu's best friends at the Wee Pub.
  • Tristan: One of Stu's best friends at the Wee Pub.
  • Larry Lo: Affable doorman.
  • "My Lesbian WIngman" Bonnie Gunther: Stu's best friend.
  • Brandi LeBleu: Bonnie's live-in girlfriend who has some issues with Stu.
  • Wesley Hardin: Stu's former writing partner, now a successful screenwriter in Hollywood.
  • Matt Gordon: Hollywood producer.
  • Arnie Galloway: Add a description of this character.
  • "Big Richard"
  • Anthony Lee: Former high school classmate of Stu's. The only drop-out, he's now a successful gym magnate in the St. Louis area.
  • Murphy
  • Anna: Jack and Kirsten's little daughter.
  • Adam
  • Cecil
  • James
  • Ricky
  • Steve
  • Boris: Stu's former Ukranian slumlord.
Show all 41 characters
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Setting & Locations edit see section history

"How to Fail" takes place almost exclusively in Manhattan, New York City
  • Hell's Kitchen: The bulk of Part One's action takes place in this Manhattan neighborhood. Stu's apartment is located here.
  • The Upper West Side: The bulk of Part Two's action takes place in this Manhattan neighborhood where Stu's best friend Bonnie "My Lesbian Wingman" lives.
  • Hollywood: Part Two includes a brief visit to California.
  • Manhattan: The majority of the book takes place in Manhattan, New York City.
  • White Plains: Stu's disastrous visit to Danny's campaign party occurs at Danny's house in the New York suburbs of White Plains.
  • St. Louis: City Stu grew up in.

First Sentence edit see section history

They say some men see things that are and say, “Why?” Robert Kennedy dreamed things that never were and said, “Why not?” Well, I see my life unfolding and I just say, “Why me?”

Table of Contents edit see section history

PART I: Hell's Kitchen

Chapter One: How to Fail to Write a Cohesive Introduction

Chapter Two: How to Fail to Not Get Mistaken For a Bum
Footchapter Two: How to Go Insane and Garner Voices in Your Head

Chapter Three: How to Fail to Make Your Parents Proud of You
Footchapter Three: How to Fail to Write Commercial Material

Chapter Four: How to Fail to Do Something Productive All Day
Footchapter Four-A: How to Develop an Addiction
Footchapter Four-B: How to Masturbate at Work

Chapter Five: How To Fail to Live in a Healthy Environment
Footchapter Five-A: How to Locate and Find Yourself Paying Rent to a Slumlord
Footchapter Five-B: How to Have Fucked-Up Neighbors

Chapter Six: How to Fail in Love
Footchapter Six-A: How to Get Usurped By Your Girlfriend's Ex
Footchapter Six-B: How to Have a Sordid Past

Chapter Seven: How to Fail All the Way to Rock Bottom


PART II: UWS

Chapter Eight: How to Live on a Couch
Footchapter Eight: How to Avoid Your Ex in a Small Town

Chapter Nine: How to Fail to Extend Your Family Tree
Footchapter Nine: How to Fail in Bed

Chapter Ten: How to Get Laid on a Couch
Footchapter Ten: How to Acquire the STD That's Right for You

Chapter Eleven: How to Be Haunted by Demons
Footchapter Eleven-A: How to Be Aimless and Uninspired
Footchapter Eleven-B: How to Piss People Off, Alienate Yourself, and End Up Alone

Chapter Twelve: How to Have a Negative Net and Self-Worth
Footchapter Twelve: How to Network

Chapter Thirteen: How to Fail to Be Normal
Footchapter Thirteen-A: How to Be a Hypochondriac Without Health Care
Footchapter Thirteen-B: How to Grow Apart From Your Friends

Chapter Fourteen: How to Fail to Fail

Epilogue: How to Write a Successful Book and Become Rich

Authors & Contributors edit see section history

  1. Aaron Goldfarb (Author)

First Edition edit see section history

Original Language: English
Publisher: Chateau Publishing House
Country: USA
Publication Date: November 9, 2010
ISBN: 978-0982941102
Page Count: 372

Classification edit see section history

  • Library of Congress: 2010936755
  • Dewey: 813

Links to Supplemental Material edit see section history

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