How to Fail at Almost Everything and Still Win Big | Scott Adams | Book Summary


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Blasting clichéd career advice, the contrarian pundit and creator of Dilbert recounts the humorous ups and downs of his career, revealing the outsized role of luck in our lives and how best to play the system.

Scott Adams has likely failed at more things than anyone you’ve ever met or anyone you’ve even heard of. So how did he go from hapless office worker and serial failure to the creator of Dilbert, one of the world’s most famous syndicated comic strips, in just a few years? In How to Fail at Almost Everything and Still Win Big, Adams shares the game plan he’s followed since he was a teen: invite failure in, embrace it, then pick its pocket.

No career guide can offer advice that works for everyone. As Adams explains, your best bet is to study the ways of others who made it big and try to glean some tricks and strategies that make sense for you. Adams pulls back the covers on his own unusual life and shares how he turned one failure after another—including his corporate career, his inventions, his investments, and his two restaurants—into something good and lasting. There’s a lot to learn from his personal story, and a lot of entertainment along the way. Adams discovered some unlikely truths that helped to propel him forward. For instance:

• Goals are for losers. Systems are for winners.
• “Passion” is bull. What you need is personal energy.
• A combination of mediocre skills can make you surprisingly valuable.
• You can manage your odds in a way that makes you look lucky to others.

Adams hopes you can laugh at his failures while discovering some unique and helpful ideas on your own path to personal victory. As he writes: “This is a story of one person’s unlikely success within the context of scores of embarrassing failures. Was my eventual success primarily a result of talent, luck, hard work, or an accidental just-right balance of each? All I know for sure is that I pursued a conscious strategy of managing my opportunities in a way that would make it easier for luck to find me.”


Major takeaways from the book

  1. Passion is bullshit
    Most people think passion causes success, it’s usually the other way round.
  2. Goals vs Systems
    Goals are specific objectives while systems are to be followed on regular basis. “Losing 10 pounds” is a goal, “eating healthier” is a system. Focus on better systems rather than goals. Systems-oriented people feel good every time they follow the system, goals-oriented are always busy chasing their goals and once they have attained it feel miserable (and start looking for another one). There are too many options (distractions) irrespective of the plan, the focus is important.
  3. Deciding vs wanting
    A lot of people want something, successful ones decide that they are going to pursue it and are willing to pay the price for the same.
  4. Being selfish is important
    Focus on self (be it food, exercise or career), once a reasonable level of success has been attained, you will automatically develop the feeling to start distributing its fruits.
  5. Maximize personal energy
    Always try to optimize personal energy (Something which will give you a positive mental or physical lift), some people enjoy solace, some crowded places, decide what maximizes your personal energy and do those activities in spare time. Maximizing personal energy is selfish but has the best impact on the person and his/her contribution to society in long run.

Between optimization (doing many things optimally) and simplification (doing just a few things), pursue simplification in the long run since it maximizes personal energy.


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Priorities (highest to lower)
Self > Personal finance > family > community > country > world.

  1. Attitude
    A positive attitude is not optional. Daydreaming, positive forms of entertainment, smiling, success (from anything spills into success in other fields), perceptions (even incorrect ones) – all contribute to the positive attitude.
  2. Who you know is important
    You don’t need CEOs and billionaires, just knowing friends who know different things than you are sometimes sufficient.
  3. Recognizing your talents and knowing when to quit
    Childhood obsessions and tolerance for risk are rough guides for talents. Deciding when to fight against an obstacle and when to quit is difficult, things which someday work out well, start out well (albeit small success), things which start bad usually never become success.
  4. Repetition vs Novelty based jobs
    Some jobs require a lot of practice (eg. sports), some require a lot of disciplined study and novelty (eg. software engineer, entrepreneur), decide which one suits your nature and choose a career path which is in line with your nature.
  5. Managing your Odds of Success
    Every new skill you acquire doubles your odds of success.
    It’s better to be good at two complementary skills than excellent at one.
    The more you learn, the easier it becomes to learn even more.
    Read news about topics which interests you and which are positive in nature (avoid reading a lot about tragic events).
  6. The Maths of Success
    Some skills increase odds of success – public speaking (Dale Carnegie’s course), psychology (List of biases), business writing(eg, using active over passive), accounting, design(basics – the L-shape), conversation, overcoming shyness, second language, golf, proper grammar, persuasion (being decisive, using write responses), technology and proper voice (pitch).
  7. Pattern Recognition
    Learn to recognize patterns in life.
    Certain patterns are direct predictor of success.
    As per author, lack of fear of embarrassment, education, exercise and looking at success as learnable skill are major patterns for successful people.
  8. Humor
    It’s not just a form of entertainment, it helps in developing more social connections as well as boosts personal energy.
  9. Affirmations
    Repeat to yourself what you want to achieve while imagining the outcome you want. It improves the odds of success.
    The author is careful at pointing out that there might a coincidence or his selection bias in play here.
  10. Timing is luck too
    Don’t ignore the importance of timing in success.
    The world is like a slot machine where one has to put time, focus and energy and occasional rare payoffs can be big.
  11. Experts
    Experts are 98% right on easy cases but only 50% on unusually complicated cases.
    If your intuition disagrees with experts, go with intuition, it could be an indicator of some pattern recognition which you can’t yet verbalize.
  12. Association Programming
    Humans are social animals, we are influenced by people near us.
    Spend time with people who most represent what you would like to become. Their good habits and energy will rub off on you.
  13. Happiness
    Happiness has more to do with self than with situation.
    Happiness has more to do with direction than the current situation (when things are going in right direction, we are happy).
    In a career, improvement of skills makes a person feel happy. So, focus on a career where you can improve over time.

The imagination of brighter future makes a person happy.

Exercise, diet (eat right) and sleeping enough strongly influence


Routines make us happy since they reduce the number of choices we have at any time (more choice makes us unhappy). Reduce daily decisions to routines.

Help others (after helping yourself).


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  1. Diet
    Food impacts a person’s mood. Pay attention to energy level after eating certain foods.

All humans are different, find patterns in food, which food makes you feel better, which ones make you feel sleepy.

Remove unhealthy energy draining food from home and stock convenient healthy food instead.

Get enough sleep, tiredness causes the illusion of hunger.

Willpower is a limited resource, using that to fight against cravings is a bad idea instead author suggests an alternative, make a list of healthy food items and decide that “you will eat as much of healthy food items as you can”.

Over time, you will stop eating unhealthy food, in long run, the habits of eating healthy food in limited quantities will become the norm.

Getting recommended dietary allowance with just food is impossible.
If eating for social reasons, choose the lowest calorie options.

Author’s diet consists primarily of complex carbs (like nuts), protein bar, fruits, and fish.

Don’t make healthy food bland by avoiding butter and salt, its better to eat healthy food with butter and salt than an unhealthy one.
The author recommends the vegetarian or near-vegetarian diet.

Coffee has higher highs and lower lows which aligns with creative workers, while it does make a person addicted, the trade-off is worth it.


  1. Fitness
    Be active every day – don’t use willpower to decide workout and don’t do things you don’t like. Do anything which feels pleasant, walking is fine too.

Always exercise at the same time (routine).

Try Exercising with spouse if married.

Don’t burn yourself out so that, next day you won’t be able to do it.

Reward yourself after workout eg. relaxed reading for a while after a workout.


  1. Failures

Failures will happen from time to time, learn from them and come forward because of that learning.



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