Scott Adams’ How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life is concise, entertaining, and full of personal anecdotes that illustrate his concepts and keep things interesting. Scott became famous due to his iconic Dilbert comic strip and has recently been in the spotlight for correctly predicting that Donald Trump would win the Republican nomination and the presidency months before anyone else.


Create systems not goals

A system is something you do on a regular basis that increases your odds of happiness in the long run. If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal. For our purposes, let’s agree that goals are a reach-it-and-be-done situation, whereas a system is something you do on a regular basis with a reasonable expectation that doing so will get you to a better place in your life. Systems have no deadlines, and on any given day you probably can’t tell if they’re moving you in the right direction.

In the long run, any system that depends on your willpower will fail.

It’s okay to be selfish

It’s okay to make time for one’s one health and well-being. The only way you can help those around you is by first helping yourself. Give yourself the time to work out, eat properly, and sleep well.

Personal energy needs to be high

Find projects that make and keep you excited.

It’s smarter to see your big-idea projects as part of a system to improve your energy, contacts, and skills. From that viewpoint, if you have a big, interesting project in the works, you’re a winner every time you wake up.

Sum of skills

It’s about synergy; 2 + 2 equaling 5. A sum of skills (or a talent stack as Scott also calls it) is worth much more than any of those skills by itself. What skills does Scott view as essential?

  • Public speaking
  • Psychology
  • Business writing
  • Accounting
  • Design (the basics)
  • Conversation
  • Overcoming shyness
  • Second language
  • Golf
  • Proper grammar
  • Persuasion
  • Technology (hobby level)
  • Proper voice technique

Simplifier vs optimizer

Some people are what I call simplifiers and some are optimizers. A simplifier will prefer the easy way to accomplish a task, while knowing that some amount of extra effort might have produced a better outcome. An optimizer looks for the very best solution even if the extra complexity increases the odds of unexpected problems.

Optimizing is often the strategy of people who have specific goals and feel the need to do everything in their power to achieve them. Simplifying is generally the strategy of people who view the world in terms of systems. The best systems are simple, and for good reason. Complicated systems have more opportunities for failure. Human nature is such that we’re good at following simple systems and not so good at following complicated systems.


Affirmations are simply the practice of repeating to yourself what you want to achieve while imagining the outcome you want. You can write it, speak it, or just think it in sentence form. The typical form of an affirmation would be “I, Scott Adams, will become an astronaut.” The details of affirmations probably don’t matter much because the process is about improving your focus, not summoning magic.

Another possible reason that affirmations appear to work is that optimists tend to notice opportunities that pessimists miss. A person who diligently writes affirmations day after day is the very definition of an optimist, even if only by actions. Any form of positive thinking, prayer, or the like, would presumably put a person in a more optimistic mind-set. And because optimists have been shown in studies to notice more opportunities than pessimists, the result can look like luck. Studies show that you need not be a natural-born optimist to get the benefits of better perception. You can train yourself to act like an optimist—and writing affirmations is probably good training—so that you get the same benefits as natural optimists when it comes to noticing opportunities.


  • Be happy
  • Eat right.
  • Exercise.
  • Get enough sleep.
  • Imagine an incredible future (even if you don’t believe it).
  • Work toward a flexible schedule.
  • Do things you can steadily improve at.
  • Help others (if you’ve already helped yourself).
  • Reduce daily decisions to routine
  • The main point for both diet and exercise is that you want to reduce the amount of willpower required. Any other approach is unsustainable.

It might help some of you to think of yourself as moist robots and not skin bags full of magic and mystery. If you control the inputs, you can determine the outcomes, give or take some luck.