How to Fail at Almost Everything and Still Win Big — Scott Adams

“If you think your odds of solving your problem are bad, don’t rule out the possibility that what is really happening is that you are bad at estimating odds.”

Start — 1/23/17 Finish — 1/26/17


I first heard about Scott Adams on a podcast interview. I never really looked at newspaper comics growing up, and although I knew of Dilbert, I didn’t know the author or his story. But I was intrigued with the story he gave about “affirmations,” where he wrote down something he wanted ten times on a paper every day until he achieved his goal. I’d heard of other people in competitive sports and other performance fields doing similar things with success, so I thought I may as well pick up his book.

Adams’ writing often reads like a comic punchline in the last frame — it’s snippy, a bit dry, but ultimately quite entertaining. And while taking advice on success from a cartoonist may seem a bit strange, Adam draws from an extremely broad range of career experiences and skills he’s built over the past few decades. His combination of humility, self-awareness, qualified advice, humor, and success in his endeavors should be sufficient to appease any skeptics.

The author starts out by drawing similar conclusions as Cal Newport in So Good They Can’t Ignore You, in which he argues that passion is overrated. We should be focused more on skill-building and mastery and then our passion will follow. Adams also insists on trying to create simple systems and routines for your life whenever possible. Consistency in your diet, sleep, and exercise (which we all know are important) are essential for your health, which will largely determine how well you perform at your job on any given day. We should all be protective of our time and our health as these are our most precious resources.

Beyond the basics, Adams promotes what might be called healthy delusions. If there is some coping mechanism or crutch we can use to trick ourselves into thinking more positively, then we should generally use them. He argues we can really be programmed to our benefit if we figure out what inputs yield the results we want. There is also practical advice about maintaining good attitude, like always have a side project or hobby where you can see steady progress; this serves to balance out any setbacks in our main job or pursuit. I really liked his one line about not letting reality control your imagination. Our dreams and imagination are the few things we have control over, and we can use them to positively alter our mindset — which should have ripple effects into our odds of success.

Adams, while not really being an expert in any one area of advice, has written a lot of sensible, useful, and sometimes original material in this book. It’s an easy read and his arguments make you realize that more often than not, success is possible if we just get a few big things mostly right. If we can just be relatively prepared for when luck finds us, we’ll be ready to pounce.

Score: 7/10


· We’re better off focusing on mastering skills and becoming really good at what we do rather than searching for something we’re inherently passionate for. With mastery comes fulfillment and passion.

· One-time goals are unsustainable compared to systems or life-style changes. The sole focus we have on achieving specific goals pushes the importance of process aside for something more ephemeral.

· Be selfish about taking care of yourself first. By being selfish today, we can be in a better position to be generous tomorrow.

· The more we are able to simplify and chip away at the complexity in our lives, the more personal energy we will have. And that’s the metric we should be focusing on.

· Relentlessly pursue new skills to make yourself more valuable to the world. While skills aren’t a replacement for luck, having a bunch of complementary ones will tip the odds in your favor when luck does come your way.


· The argument against passion

o Passion is an accessible influence on your success that is widely touted by successful people because it is more humbling to talk about than innate talent, easier to sell than hard work, and less coincidental than mere luck

o We tend to be passionate about the things that we’re good at, and we also tend to have an idea of what we might be good at

o Success may be more of a cause of passion than the other way around

· Systems over goals

o Goal — specific objective that you either achieve or don’t in the future; System — something you do on a regular basis that increases your odds of happiness in the long run

o Goals come with the baggage of constantly living in a state of nearly continuous failure that you hope will cease at some point

o If you achieve your goal, you celebrate, but only until you realize you lost the thing that gave you purpose and direction

o Systems people, on the other hand, feel good every time they apply their system and don’t have to fight the feeling of discouragement at each turn

· Your best option is to be selfish, because being stupid or a burden on society won’t help anyone

o The most important form of selfishness involves spending time on your fitness, eating right, pursuing your career, and still spending time with people you care about

o In some ways, we frequently cheat our future selves by trying to appear generous today; instead, we should try to be more selfish today so that we can be more effectively generous in the future

· The Energy Metric

o When we focus on getting our personal energy right (getting those common sense things right like eating, exercising, sleeping, avoiding unnecessary stress and having something exciting to work on), our quality of work is better and we can complete things faster

o Having high personal energy has ripple effects into our careers and social lives

o We should try to match our mental/physical states to our activities (like doing creative work early in the morning or late at night depending on your preference, or exercising when we have the most physical energy)

o It’s a good idea to have an overarching plan to move toward simple systems (or even streamlined/automated ones) as opportunities allow; the more we chip away at unnecessary complexity and decision-making in our lives the more personal energy we will have

· Managing Attitude

o We all do our best work and enjoy life the most when our attitude is good

o When life doesn’t present enough moments to make us joyful, we can use our imagination to manipulate our mood (daydreaming of joyful fantasies)

o Good to have ambitious, moonshot side projects that can energize you when nothing else is going well; if you fail, you will usually learn something valuable or meet someone new in the process anyway

o Become really good at one thing, and let that feeling propel you to new and better victories

· A Success Heuristic

o Good + Good > Excellent

o You’re better off being good at two complementary skills than being excellent at one

o The more you know, the more competent you will be at learning new skills and picking up on patterns that exist among different disciplines

· Useful Skills

o Public Speaking

o Understanding of Psychology

o Concise Writing

o Basic Accounting

o Design/Composition

o Conversation

o Overcoming Shyness

o Second Language

o Golf

o Proper Grammar

o Persuasion Techniques

o Technology

o Prover Voice Techniques

· Happiness

o The first step is to continually work toward having control of your schedule; we can often transform work into pleasure just by merely having control over when we do it

o We tend to focus on the directional nature of happiness and our progress, so it’s a good idea to have a sport or hobby that leaves you plenty of room to improve every year; similarly, career choices should be made around the ability to make steady progress over time

o Daydream of the future being better than today, by far; don’t let reality control your imagination

o Obviously, exercise/diet/sleep all play crucial roles in daily happiness and health

o Limit your decision-making around trivial things as much as possible by making routines you can stick to


· This was about the time I started to understand that timing is often the biggest component of success. And since timing is often hard to get right unless you are psychic, it makes sense to try different things until you get the timing right by luck.

· Imagination is the interface to your attitude. You can literally imagine yourself to higher levels of energy.

· Don’t let reality control your imagination. Let your imagination be the user interface to steer your reality.

· If you think your odds of solving your problem are bad, don’t rule out the possibility that what is really happening is that you are bad at estimating odds.