Notes from How To Fail At Almost Everything And Still Win Big, by Scott Adams

Scott Adams, the creator of Dilbert, serves up a cocktail of life lessons and practical philosophy. The book is packed with unconventional lessons, but also with “I already knew that, but thanks for reminding me” type advice. It’s a great resource for practical takeaways for how to live better, more successful and happier lives, quite simply.

Rating: 9/10
Finished: 02/2017
Related Books: Choose Yourself, The 4-Hour Workweek, Lean In, The Defining Decade
Buy the book on Amazon here / See all my lessons from books and smart people HERE

The Short Summary of “How To Fail At Almost Everything And Still Win Big”

Scott Adams, the creator of Dilbert, serves up a cocktail of life lessons and practical philosophy. The book is packed with unconventional lessons, but also with “I already knew that, but thanks for reminding me” type advice. It’s a great resource for practical takeaways for how to live better, more successful and happier lives, quite simply.

Lessons learned

Goals are for losers – systems are for winners. 

Most important metric: my energy. Energy is good – passion is bullshit.

Know my energy schedule; don’t waste creativity peak hours on busywork.

Every skill I acquire doubles my odds of success. The following are especially useful:

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

Failure always brings something valuable with it. I don’t let it leave until I extract that value.

Success likes to hide in failure. Everything you want is in that bag of failure – the trick is to get the good stuff out.

Timing is often the biggest component of success. Best approach: try different things until I get the timing right by luck.

Every time I get a new job, immediately start looking for a new, better job. (This is a system).

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.

Simplify. Simple systems are the best way to achieve success. Once you have success, optimizing begins to have more value.

The smartest system for discerning your best path to success involves trying lots of different things—sampling, if you will. For entrepreneurial ventures it might mean quickly bailing out if things don’t come together quickly.

Things that will someday work out well start out well.

Things that will never work start out bad and stay that way.

If no one is excited about my art/product/idea in the beginning, they never will be.

Success isn’t magic; it’s generally the product of picking a good system and following it until luck finds you.

The Success Formula: Every Skill You Acquire Doubles Your Odds of Success
In other words: Good + Good > Excellent

When writing a résumé, think “I earn $100 per word I remove”.

Clean writing makes a writer seem smarter and it makes the writer’s arguments more persuasive.

Praise is powerful, criticism is corrosive. Never criticise. Express your praise. If you see something that impresses you, a decent respect to humanity insists you voice your praise.

Quality is not an independent force in the universe; it depends on what you choose as your frame of reference. Salespeople know they can manipulate buyers by controlling what they compare.

Reason is just one of the drivers of our decisions, and often the smallest one. Politicians understand that reason will never have much of a role in voting decisions. A lie that makes a voter feel good is more effective than a hundred rational arguments.

Conversation 101: introduce yourself, then ask questions until you find a point of mutual interest. Understand that the other person is feeling awkward too. Ease their burden by starting and leading the conversation. This progression works well:

  1. What’s your name?
  2. Where do you live?
  3. Do you have a family?
  4. What do you do for a living?
  5. Do you have any hobbies/sports?
  6. Do you have any travel plans?

In my entire life I have never met a stranger who didn’t have some fascinating life experiences that spilled out if I asked the right questions.

The point of conversation is to make the other person feel good.

Classic Grammar Mistakes To Avoid:

  1. Most people misuse the word “hopefully”:
    It’s bad grammar to say, “Hopefully, she will bring the dessert.”
    “Hopefully” should be an adverb.
    Say instead, “We waited hopefully for dessert.”
    In the latter case, “hopefully” is correctly modifying the verb “waited.”
    In the first example, hopefully just sits there like the wrong word choice.
  2. The simple rule for “I” versus “me”: the sentence has to make sense if you remove the other person mentioned in the sentence.
    For example, if you say, “Bob and I went to a movie,” it would still make sense if you removed “Bob and” and said, “I went to a movie”.
  3. Theory Versus Hypothesis: Nonscientists often use the word “theory” when they should say “hypothesis.”
    Without getting too technical, a theory is a scientific explanation of reality that is so well tested that it is as good as a fact.

A List Of Persuasive Words and Phrases

  1. Because
  2. Would you mind . . . ?
  3. I’m not interested.
  4. I don’t do that.
  5. I have a rule . . .
  6. I just wanted to clarify . . .
  7. Is there anything you can do for me/to help me?
  8. Thank you
  9. This is just between you and me.

Decisiveness looks like leadership. Keep in mind that most normal people are at least a little bit uncertain when facing unfamiliar and complicated situations. What people crave in that sort of environment is anything that looks like certainty. If you can deliver an image of decisiveness, no matter how disingenuous, others will see it as leadership.

In any kind of negotiation, the worst thing you can do is act reasonable. Reasonable people generally cave in to irrational people because it seems like the path of least resistance.

Stephen Covey’s 7 Habits of Highly Successful People:

  1. Be proactive.
  2. Begin with the end in mind. (Imagine a good outcome.)
  3. Put first things first. (Set priorities.)
  4. Think win-win. (Don’t be greedy.)
  5. Seek first to understand then be understood.
  6. Synergize. (Use teamwork.)
  7. Sharpen the saw. (Keep learning.)

Scott Adams’ 4 Habits of Highly Successful People:

  1. Lack of fear of embarrassment (allows you to be proactive and take on risky challenges).
  2. Education (the right kind)
  3. Exercise
  4. Treat success as a learnable skill.

Visualisation and affirmations tend to work!

Surround yourself with successful people – it rubs off.

Life is like a slot machine that only asks for your time, focus, and energy to pull the handle over and over. It’s a guaranteed winner if you have what it takes to keep yanking until you get lucky. Thus you can fail 99 percent of the time, while knowing success is guaranteed.

My observation and best guess is that experts are right about 98 percent of the time on the easy stuff but only right 50 percent of the time on anything that is unusually complicated, mysterious, or even new.

Happiness has more to do with where you’re heading than where you are.

Recapping the happiness formula: 

  1. Health: Eat right, exercise, sleep enough.
  2. Imagine an incredible future (even if you don’t believe it). 
  3. Work toward a flexible schedule. 
  4. Do things you can steadily improve at. 
  5. Help others (if you’ve already helped yourself). 
  6. Reduce daily decisions to routine. 

No one can predict how a start-up will go after launch. The only thing I know for sure is that my partners and I plan to come out ahead. Every time we add new skills and broaden our network of contacts, our market value increases.


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