
How to Fail at Almost Everything and Still Win Big
10 minKind of the Story of My Life
Introduction
Narrator: Imagine driving two hours through a blinding blizzard for a major job interview, only to be dismissed in under a minute because you wore the wrong clothes. Now imagine that on the drive home, your car dies in a remote, frozen valley, and you’re forced to run for your life in sub-zero temperatures without a jacket. This isn't a hypothetical scenario; it was a real and spectacular failure for Scott Adams. Yet, he considers the decision he made in that moment of desperation—to trade his car for a one-way ticket to California—the smartest he ever made. This experience, a perfect storm of bad luck, ignorance, and stupidity, became a pivotal turning point.
This philosophy of failing your way to success is the core of Adams's book, How to Fail at Almost Everything and Still Win Big. The creator of the world-famous Dilbert comic strip presents a counterintuitive and pragmatic guide to life, arguing that success isn't about passion, goals, or even raw talent. Instead, it's about building systems that increase your odds, mining every failure for value, and programming your own mind for happiness.
Goals Are for Losers; Systems Are for Winners
Key Insight 1
Narrator: One of the book's most provocative claims is that goals are a flawed strategy for achievement. Adams argues that goal-oriented people exist in a state of continuous "pre-success failure," feeling inadequate until they reach their specific, often distant, objective. If they never reach it, they are in a state of permanent failure. This process is psychologically draining and unsustainable.
He contrasts this with a systems-based approach. A system is a process you engage in regularly that increases your odds of long-term success and happiness. While a goal might be to lose twenty pounds, a system is to eat right every day. A goal-oriented person feels like a failure every day they haven't lost the weight. A systems-oriented person, however, succeeds every time they follow their system. This provides a steady stream of positive feedback and energy.
Adams illustrates this with a story from his early twenties. On a flight to California to look for a job, he sat next to the CEO of a screw manufacturing company. The CEO shared his career philosophy, which was not to have a specific job as a goal, but to have a system of always looking for a better job. He explained that your job is not your job; your job is to find a better job. This continuous process of seeking opportunities, learning, and networking is a system that dramatically increases the odds of career success over time, far more than aiming for a single promotion.
Passion Is a Consequence, Not a Cause, of Success
Key Insight 2
Narrator: The common advice to "follow your passion" is, according to Adams, mostly bullshit. He argues that passion is often the result of success, not the cause. When you become good at something and see positive results, your passion for it naturally grows.
He learned this lesson early in his career as a commercial loan officer. His boss, a veteran lender, taught him a surprising rule: never make a loan to someone who is following their passion. A person opening their dream restaurant or sports memorabilia shop is often blinded by their passion, leading them to ignore the grim financial realities on the spreadsheet. The best loan customer, his boss argued, was someone with no passion for the business itself, just a desire to work hard at something that looked financially sound.
Adams saw this play out in his own life. He had a dozen get-rich-quick schemes, and Dilbert was just one of them. He wasn't particularly passionate about cartooning at first. However, as the comic strip started to show small signs of success—getting syndicated, receiving positive fan mail—his passion for it exploded. Success caused the passion, not the other way around. He suggests that instead of looking for passion, people should focus on managing their personal energy, as high energy is a better predictor of success.
Failure Is a Resource to Be Mined for Value
Key Insight 3
Narrator: Adams frames failure not as a setback, but as a resource. He believes that "everything you want out of life is in that huge, bubbling vat of failure," and the trick is to get the good stuff out. Every failure comes with a lesson, a new skill, or a valuable connection. The key is to design your life and your projects so that when you fail, you don't lose everything. You should fail in a way that leaves you with something valuable.
His "absolute favorite spectacular failure" is the story of his disastrous accounting interview. After being rejected for not wearing a suit, his car broke down in a blizzard, forcing him into a near-death run for help. In that moment of terror, he decided that if he survived, he would trade his car for a plane ticket to California and never see snow again. He did exactly that, and he calls it the smartest decision he ever made. The failure of the interview and the breakdown of his car directly led to a life-changing move that put him on the path to his eventual success. He didn't just survive the failure; he extracted a new life from it.
Every Skill You Acquire Doubles Your Odds of Success
Key Insight 4
Narrator: Success isn't about being the best in the world at one thing. Adams argues that it's far more practical and effective to become very good—say, in the top 25%—at two or more things. His formula is simple: every skill you acquire doubles your odds of success. Good + Good > Excellent.
He uses himself as the primary example. He is not a world-class artist; in fact, he describes his drawing skills as mediocre. He is a good writer, but not among the best. He has a solid understanding of business from his corporate career and an MBA. He is also funnier than the average person. None of these skills on their own are extraordinary. However, the combination of these skills is what made Dilbert a global phenomenon. His business knowledge allowed him to understand office dynamics, his writing and humor made the content relatable, and his drawing was just good enough to convey the jokes. This unique blend of skills gave him a powerful advantage that few others possessed. He encourages learning about a wide range of topics, from public speaking and psychology to accounting and technology, to create your own unique and valuable skill stack.
The Mind Is a Moist Robot You Can Program
Key Insight 5
Narrator: Throughout the book, Adams emphasizes that you can actively manage your own psychology to improve your energy, attitude, and focus. He views the mind not as a magical, unknowable entity, but as a "moist robot" that can be programmed.
This is powerfully illustrated by his battle with two debilitating medical conditions. First, he developed focal dystonia, a neurological problem that caused his pinkie to spasm, making it impossible to draw. Doctors told him there was no cure. Refusing to accept this, he began a process of "hacking his brain," repeatedly practicing the drawing motion during meetings until his brain rewired itself and the dystonia vanished.
Years later, he lost his voice to a rare condition called spasmodic dysphonia. Again, doctors told him it was incurable. For three years, he struggled with social isolation and depression. He used a system of affirmations, repeating "I, Scott Adams, will speak perfectly" fifteen times a day. He also used Google Alerts to track any new research. Eventually, an alert led him to a radical surgery in Japan. He took the risk, and the surgery was a success. While he acknowledges that affirmations may seem like magic, he argues their real power lies in focusing the mind. By constantly affirming his goal, he kept his mind primed to spot any potential solution, turning a passive hope into an active search.
Conclusion
Narrator: The single most important takeaway from How to Fail at Almost Everything and Still Win Big is the power of shifting from a goal-oriented mindset to a systems-oriented one. Success is not a destination you arrive at, but a process you engage in. By building systems for continuous learning, managing your energy, and acquiring new skills, you create a framework where you win simply by participating. This approach removes the psychological burden of failure and transforms it into a valuable part of the process.
Ultimately, the book challenges its readers to view their lives not as a series of pass-fail tests, but as a long-term strategy for managing odds. The most practical challenge it leaves us with is to ask: What is my system? Are my daily actions part of a deliberate process that makes it easier for luck to find me, or am I just waiting for a lucky break? By focusing on building a better system, you can fail at almost everything and still, somehow, win big.