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Books like How to fail at almost everything and still win big

A wry, contrarian playbook for turning a string of embarrassing failures into a personalized system for success. These 12 books are the closest matches in mood, pace and themes, with what each one shares with How to fail at almost everything and still win big.

  • optimistic
  • lighthearted
  • analytical
  • motivating
  1. 01

    The Dilbert Principle

    Scott Adams · 1996

    A cathartic, laugh-out-loud survival guide for anyone trapped in the absurd machinery of modern corporate life.

    Shares:
    • wry
    • irreverent
  2. 02

    Originals

    Adam Grant

    An invigorating intellectual dinner party that leaves you feeling equipped to change the world, or at least your workplace.

    Shares:
    • optimistic
    • analytical
    • conversational
  3. 03

    The $100 startup

    Chris Guillebeau

    A shot of pure entrepreneurial espresso that makes the leap from daydream to reality feel entirely within reach.

    Shares:
    • optimistic
    • pragmatic
  4. 04

    The Dilbert future

    Scott Adams · 1997

    A hilariously cynical crystal ball that promises tomorrow's workplace will be just as incompetent and absurd as today's.

    Shares:
    • irreverent
  5. 05

    The Adventures of Johnny Bunko

    Daniel H. Pink

    An engaging, visually dynamic guide that transforms early-career stumbling blocks into stepping stones for professional flourishing.

    Shares:
    • optimistic
    • pragmatic
  6. 06

    Barking Up the Wrong Tree

    Eric Barker

    A paradigm-shifting exploration of the psychological realities behind what actually drives achievement.

    Shares:
    • analytical
  7. 07

    The Dip

    Seth Godin · 2007

    A brisk, permission-granting manifesto that transforms the shame of quitting into a powerful strategy for success.

    Shares:
    • pragmatic
    • conversational
    • contrarian
  8. 08

    Side hustle

    Chris Guillebeau

    An energizing, step-by-step roadmap that turns the daunting prospect of entrepreneurship into an accessible, low-stakes adventure.

    Shares:
    • optimistic
    • pragmatic
  9. 09

    Anything you want

    Derek Sivers

    A refreshing, bite-sized manifesto that gives you permission to ignore the rules of traditional success and build a life that actually makes you happy.

    Shares:
    • wry
    • pragmatic
    • conversational
  10. 10

    What I wish I knew when I was 20

    Tina Seelig

    A warm, pragmatic masterclass in turning life's uncertainties into a playground of creative opportunity.

    Shares:
    • optimistic
    • pragmatic
    • conversational
  11. 11

    Discover Your Inner Economist

    Tyler Cowen

    A pragmatic and intellectually stimulating guide to hacking the hidden incentives that drive our daily lives.

    Shares:
    • optimistic
    • analytical
    • pragmatic
  12. 12

    Failure is an option

    H. Jon Benjamin

    A hilarious, anti-inspirational manifesto that gives you full permission to lower your expectations and embrace your inner slacker.

    Shares:
    • wry
    • conversational

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