#176 What I Learned From Scott Adams (Creator of Dilbert)
What I learned from reading “How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life” by Scott Adams.
Today’s Chapter is based on the book “How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life” by Scott Adams.
Scott Adams was an American cartoonist and author best known as the creator of the Dilbert comic strip, a satirical take on white‑collar office life that became widely popular worldwide starting in 1989.
Here’s what I learned:
Systems not Goals
“How you climb a mountain is more important than reaching the top.”
— Yvon Chouinard
One concept that is often reiterated by Scott Adams in his book is the distinction between having a goal and having a system. He explains that a goal is a future event that you either achieve or not, leaving you in a state of constant pre-success failure. On the other hand, a system is a daily practice that increases your odds of success in the long run, regardless of the immediate outcome. Adams argues that people who rely on systems consistently outperform those who are solely focused on goals. He writes, “Throughout my career, I’ve had my antennae up looking for examples of people who use systems versus goals. In most cases, as far as I can tell, the people who use systems do better. The systems-driven people have found a way to look at the familiar in new and more useful ways.”
Furthermore, Adams believes that this reframing allows individuals to become happier. Instead of waiting for a distant achievement to feel successful, you can feel successful every time you apply your system. More importantly, by following a system-based approach over a goal-oriented approach, you will never be sitting on your laurels as you will always be consistently finding ways to improve.
This can be perfectly explained through a story Adams learned early in his career from an encounter with a CEO on an airplane who said, “every time he got a new job, he started immediately looking for a better one. For him, job-seeking was not something one did when necessary. It was an ongoing process. This makes perfect sense if you do the math. Chances are, the best job for you won’t become available at precisely the time you declare yourself ready. Your best bet, he explained, was to always be looking for the better deal. The better deal has its own schedule. I believe the way he explained it is that your job is not your job; your job is to find a better job. This was my first exposure to the idea that one should have a system instead of a goal.”
“All I’m suggesting is that thinking of goals and systems as very different concepts has power. Goal-oriented people exist in a state of continuous pre-success failure at best and permanent failure at worst, if things never work out. Systems people succeed every time they apply their systems in the sense that they did what they intended to do. The ‘goals’ people are fighting the feeling of discouragement at each turn. The systems people feel good every time they apply their system. That’s a big difference in terms of maintaining your personal energy in the right direction.”
— Scott Adams
Similarly, this thinking can only be used in terms of maintaining good habits. By focusing on having a good system in place rather than achieving a specific goal, it is a lot easier to maintain habits consistently. Adams experienced this with his own workout routine. Rather than focusing on expecting himself to work out for an x amount of time every day, he focused on building the habit of going to the gym on a daily basis. As such, he didn’t feel any guilt whenever he went to the gym and didn’t feel like working out.
In fact, he writes, “As I drive home from the gym—a seemingly wasted trip—I never feel defeated. Instead, I feel I’m using a system that I know works overall. I win if I exercise, and I win (albeit less) if I use my system and decide not to work out.” By focusing on the system itself rather than a specific outcome, he eliminates the feeling of failure.
By focusing on systems, Adams positioned himself to capitalize on opportunities. He didn’t chase a single big break but built habits that increased his surface area for luck. This reminds me of what we have learned from Bill Walsh’s leadership philosophy that puts emphasis on process over results. He understood that focusing solely on winning can create undue pressure and lead to suboptimal performance. Instead, Walsh advocated for a concentration on the processes that drive success. Especially at the beginning of his reign as the coach of the San Francisco 49ers, Walsh insisted “to channel the concentration of the 49ers toward improving performance on the field and throughout the organization.”
As a matter of fact, he believed that when teams obsess over their execution and the quality of their thinking, success will inevitably follow. He once said, “I directed our focus less to the prize of victory than to the process of improving—obsessing, perhaps, about the quality of our execution and the content of our thinking.” This approach allows for a sustainable path to achievement, where improved performance becomes the primary goal rather than fleeting victories.
Walsh admits that this is difficult to execute especially due to external pressures, such as media scrutiny or fan expectations which can distract from this focus. Instead, Walsh prioritize the development of skills and fostering a growth mindset; he cultivated an atmosphere where individuals could thrive without the paralyzing fear of failure. His philosophy encourages leaders to cultivate patience and persistence by emphasizing that that the true measure of success lies in continuous improvement rather than immediate results. He believed that when individuals are committed to their processes, the outcomes—both on and off the field—will take care of themselves.
“Consequently, the score wasn’t the crushing issue that overrode everything else; the record didn’t mean as much as the season progressed, because we were immersed in building the inventory of skills, both attitudinal and physical, that would lead to improved execution. That was the key.”
— Bill Walsh
This mentality of focusing on the process rather than the outcome allowed the 49ers to weather temporary setbacks and maintain a long-term perspective. Walsh knew that even in defeat, there were valuable lessons to be learned and opportunities for growth. He mentions the fact that “a resolute and resourceful leader understands that there are a multitude of means to increase the probability of success. And that’s what it all comes down to, namely, intelligently and relentlessly seeking solutions that will increase your chance of prevailing in a competitive environment. When you do that, the score will take care of itself.”
In fact, according to Bill Walsh, failure is not merely a setback but a critical component of success. He mentions that *“When the inevitable setback, loss, failure, or defeat comes crashing down on you—allow yourself the ‘grieving time,’ but then recognize that the road to recovery and victory lies in having the strength to get up off the mat and start planning your next move.”*Ultimately, the capacity to learn and adapt defines a champion’s journey. The lessons learned from failure foster a unique strength.
“When you stand and overcome a significant setback, you’ll find an increasing inner confidence and self-assurance that has been created by conquering defeat.”
— Bill Walsh
Failure as a Tool
“I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”
— Michael Jordan
Scott Adams’s career is a perfect example of how failures can lead to success stories. As a matter of fact, Adams doesn’t just tolerate failure, he invites it and most importantly, extracts value from it. He genuinely believes that failure is a fertilizer for growth. He writes, “Failure always brings something valuable with it. I don’t let it leave until I extract that value. I have a long history of profiting from failure. My cartooning career, for example, is a direct result of failing to succeed in the corporate environment.”
Adams doesn’t believe that one shouldn’t just forget about his failures, but to repurpose them for future growth. Through a metaphor, he explains that, “If I find a cow turd on my front steps, I’m not satisfied knowing that I’ll be mentally prepared to find some future cow turd. I want to shovel that turd onto my garden and hope the cow returns every week so I never have to buy fertilizer again. Failure is a resource that can be managed.”
“I’ve long seen failure as a tool, not an outcome. I believe that viewing the world in that way can be useful for you, too.”
— Scott Adams
Before becoming the author of the famous comic Dilbert, Adams mentions that he had many failed business ideas, but that all of these adventures provided him with fundamental lessons that allowed him to become a successful cartoonist. For example, although he failed to release any of his computer game projects, it gave him a technical knowledge that would prove invaluable for his career. He writes, “All my computer game ideas failed, but in the process I learned enough about personal computers to look like a technical genius in those early days of computing—the eighties. That knowledge transferred to my day job at the bank and later to my cartooning career as well.”
As such, it is clear that for Scott Adams failure isn’t something to fear or to avoid, it should be used as a valuable input that can be used to increase your skills and insights. He writes, “I do want my failures to make me stronger, of course, but I also want to become smarter, more talented, better networked, healthier, and more energized.“ This mentality of his can be perfectly described by his desire to continue doing public speaking even when he was diagnosed with spasmodic dysphonia, a condition that caused him to be unable to speak normally, just so that he could an experiment. He needed to understand the pattern of his own voice under pressure, and failure was simply a possible data point.
“I needed to know why I could speak normally in some situations and not in others. Why does context matter? Is it something about my adrenaline level, or the tone of my voice, or the region of my brain that I access for memorization? If I could find the pattern, I thought it might reveal a solution to my voice problem.”
— Scott Adams
This reminds me of Michael Dell who believes that failure is not something to be avoided at all costs, but something that can be embraced and learned from. At his own company, he has experienced plenty of stumbles, from product flops to inventory crises, and each one of these mistakes made the business stronger. He explicitly rejects the concept that success is linear.
Dell writes, “But for every company, Dell included, kaizen is an ideal rather than a reality. Success is not a straight line up. It’s fail, learn, try again, then (you hope) succeeded. How successful you are is really a function of how well you deal with failure—and how much you learn from it. Many people don’t reach their greatest potential because they fear failure. In avoiding failure, they deprive themselves of a great teacher.”
However, Dell warns that business leaders must actively remember their failures, and not conveniently forget about them. This is often the case during periods of success where you convince yourself to believe that everything is fine. Success can be dangerously seductive while failure, by contrast, forces genuine reflection and adaption. This is why Dell believes that success can be a horrible teacher as it leads to complacency.
“The low points matter a lot: though it’s nice to remember successes, it’s important to remember failures too.”
— Michael Dell
As we have learned, Dell was able to succeed because his company’s greatest competitive advantage, the build-to-order model, was born through necessity as he didn’t have the capital to mass produce computers and hold inventory. He emphasizes that moments of friction are what built the company’s engineering muscle. He argues that many people fail to reach their potential because they are too afraid of making a mistake, thereby depriving themselves of the greatest teacher they will ever have.
The lesson here is clear, constraints and failures often force innovation. Leaders who fear failure will never take the risks required for meaningful growth. As Dell puts it daring to fail is the only path to meaningful growth, and every failure and setback made him and his company stronger and more resilient. Dell quotes Eleanor Roosevelt who once said, “You must do the thing you think you cannot do.”
“Success is a horrible teacher. Setbacks and failures make you stronger over time-if you let yourself learn from them.”
— Michael Dell
Know A Little Bit Of Everything
“The more high-quality mental models you have in your mental toolbox, the more likely you will have the ones needed to understand the problem. And understanding is everything. The better you understand, the better the potential actions you can take. The better the potential actions, the fewer problems you’ll encounter down the road. Better models make better decisions.“
— Shane Parrish
In a world that encourages specialization, Scott Adams offers a contrarian view and argues that you don’t need to be world-class at any single skill to achieve extraordinary success. Instead, he argues that you can combine several merely good skills together to create a unique and powerful package. He calls this talent staking and it is the core formula for his own unlikely career as a famous cartoonist despite being a bad drawer. He writes, “To put the Success Formula into its simplest form: Good + Good > Excellent”
The logic is simple but profound. Being in the top 1% of a single skill, like drawing or comedy, is incredibly difficult and requires immense talent and luck. However, being in the top 25% of two or three complementary skills is far more achievable and the combination of those skills makes you uniquely valuable. Adams himself is the perfect case study.
“I’m a perfect example of the power of leveraging multiple mediocre skills. I’m a rich and famous cartoonist who doesn’t draw well. At social gatherings, I’m usually not the funniest person in the room. My writing skills are good, not great. But what I have that most artists and cartoonists do not have is years of corporate business experience plus an MBA from Berkeley’s Haas School of Business.”
— Scott Adams
As a matter of fact, Adam’s corporate experience gave him authentic material, and his business education gave him the strategic sense to navigate the industry. Neither skill alone would have made him a successful cartoonist, but together, they created a powerful niche that no pure artist or pure businessperson could easily occupy. He further explains, “When I combined my meager business skills with my bad art skills and my fairly ordinary writing talent, the mixture was powerful. With each new skill, my odds of success increased substantially. But there was still one more skill I acquired in my day job at Pacific Bell that ended up mattering a lot: I knew how to use the Internet before most people had even heard of it.”
As such, Adams encourages us to be multidisciplinary and to learn various skills and knowledge. The idea is not to master them all but to become proficient enough in several to create an unique competitive advantage. He writes, “The great thing about reading diverse perspectives from the fields of business, health, science, technology, politics, and more is that you automatically see patterns in the world and develop mental hooks upon which you can hang future knowledge.”
In his book, Adams lists out skills he believes everyone should be familiar with at a competent level:
Public speaking
Business writing
A working understanding of the psychology of persuasion
Basic technolgy concepts
Social skills
Proper voice technique
Good grammar
Fundamental of accounting
This reminds me of the concept of multidisciplinary learning that we have learned from Charlie Munger who also believed that people with a broad mind and who understand many different models from many different disciplines make better decisions. This is mainly because it allows one to have a different box of tools when facing a problem. Peter Kaufman, one of Munger’s most vivid followers of his multidisciplinary approach, mentions the reason why it is important to be a multidisciplinary thinker in his speech to the California Polytechnic State University Pomona Economics Club:
“The answer comes from the Austrian philosopher Ludwig Wittgenstein, who said, “To understand is to know what to do.” Could there be anything that sounds simpler than that? And yet it’s a genius line—”to understand is to know what to do.” How many mistakes do you make when you understand something? You don’t make any mistakes. Where do mistakes come from? They come from blind spots, a lack of understanding. Why do you need to be multidisciplinary in your thinking? Because as the Japanese proverb says, “The frog in the well knows nothing of the mighty ocean.” You may know everything there is to know about your specialty, your silo, your “well,” but how are you going to make any good decisions in life—the complex systems of life, the dynamic system of life—if all you know is one well?”
— Peter Kaufman
Beyond the Book
Read "How to Fail at Almost Everything and Still Win Big" by Farnam Street
Read "Forget About Setting Goals. Focus on This Instead." by James Clear
Read "Improving Your Luck" by Farnam Street
Read "The Multidisciplinary Approach to Thinking" by Farnam Street
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