What To Know about “How To Fail At Almost Everything and Still Win Big” by Scott Adams


Do you believe you can improve your life by learning lessons from the successes and failures of other people? If so, then I invite you to read “How to Fail at Almost Everything and Still Win Big” by Scott Adams.  Also you should subscribe to this What to Know channel, because that’s kind of the point of it.

I’ve read thousands of books. If you are going to read only one book in your entire adult life, this is the one I recommend. The sooner you read it,  the better. I’ll be teaching my son and godson lessons from this book.

Before I read any book about success, I like to first read this XKCD comic on

survivorship bias. I learned about xkcd from Scott

Never stop buying lottery tickets, no matter what anyone tells you. I failed again and again, but I never gave up. I took extra jobs and poured the money into tickets. And here I am, proof that if you put in the time, it pays off.

You know that’s ridiculous.  It reminds me that we never hear from the millions of losers that took the same actions and failed.

So who is Scott Adams?

He’s an entrepreneur with an MBA.

Scott had the number one best selling ebook in the history of the world, God’s Debris, even though there was no humour, sex or violence in it.

Scott has sold over 12 million books.

Scott has made more money in a year as a public speaker than most people do in a lifetime. That’s particularly remarkable, because he lost the ability to speak in public for years.

At 60 years old, Scott is fit and healthy with a flat stomach.  I’m impressed by that.

He dates a successful, pretty smart and funny woman, Kristina Basham she’s big on instagram

You’ve already seen Scott’s work.

Scott’s very first book, The Dilbert Principle, was a #1 New York Times best seller.

The Dilbert comic strip is his most well known venture, appearing daily in over two thousand newspapers in 65 countries.

He’s the most successful cartoonist in the history of the planet.

Imagine that.

Scott, I call him Scott because that’s his name, he doesn’t know me from BLINK ….Adam   I don’t mean to imply that I know him.

I’m a fan of his work.

He’s published around 10,000 comics strips

And, he did it all on purpose.

As a cartoonist, Scott gets straight to the point. It must be hard for him to write a whole book. Here’s an example of his work

He’s already won big.

He reminds me of the Kilgore Trout character in Kurt Vonnegut’s book Breakfast of Champions.

He’s fabulously well to do.

He has an estimated net worth of $60 million.  That’s a million for every year around the sun.

But don’t hold that against him, he’s earned it.

I used to have a low opinion of millionaires.

Everything I knew about millionaires I learned from Giliigan’s Island.

Every time I look at people like Scott, self made millionaires who are useful contributors to society, I admire them. He keeps working even though he has more money than he can spend ever on himself.  Which means that another million one way to the other won’t have much impact on his day to day life.

Imagine that.

I hope he becomes a billionaire, like Elon Musk or Bill Gates. The way I see it, they’re all working on behalf of humanity.

How to fail at almost everything and still win big, kind of the story of my life. That’s a persuasive title, because when I read it I thought, I haven’t failed at everything, maybe I can win big too.

What he calls failures, I call mistakes. In some cases, things didn’t work out the way he hoped.

As you continue to watch my invitation to read this book, you’ll decide for yourself if you want to. Reading this book is an experience that a video can’t substitute for.

There’s a tremendous amount of life improving ideas in here.

There are chapters on personal energy, affirmations, managing your attitude, humour, happiness, diet, fitness and much more.

Scott used hypnotic writing to make suggestions that you will be more likely to follow, such as being active every day, eating healthy,

singing his praises,

Purchasing every thing he sells

Promoting his work for free.

Telling everyone Scott Adams is the best.

I even bought the t shirt

You see what I did there?

I pretended that Scott mesmerized me.

I point that out because he makes the unbelievable claim that a third of all people can’t tell when someone is joking. I find that hard to believe but I can’t discount the idea either. He IS an expert on humour.

Let’s get into the book.

On page 107 he writes “If you see something that impresses you, a decent respect to humanity insists that you voice your praise.” And that withholding your praise borders on immoral. I read this 4 years ago and that line has been bouncing around in my head ever since.

With this show I’m voicing my praise for the books, ideas and activities that impress me.

Scott impresses me.

I disagree with a lot of what he has to say, but I like to challenge my beliefs.

So!  What’s the biggest mistake you’ve ever made?

What’s the first mistake you remember making?

Through my fault,

through my own fault,

through my most grievous fault

I’ve made my share of mistakes

This book reveals ways to limit both the number and severity of mistakes you make.

On page 117 he asserts that having an understanding of your dozens of cognitive biases is vital to your financial health. What you don’t know can cost you money. I’ll include a link to those in the show notes.

There’s a chapter on how maximize happiness. My Mom always said we are  born to suffer. So I have a lot to learn about happiness.

Scott suggests you can be happier if you have control of your own schedule and feel that your life is improving. There are people who have attained great success but are unhappy because they don’t like where there life is headed.

Systems versus goals

Scott claims that goals are for losers (literally) and systems are for winners.

I’ve had trouble understanding what he meant by that.

I think he framed it as systems versus goals to make the idea sticky. I find myself repeatedly coming back to that notion.

Systems analysis was one of the courses I had to pass for my Computer Science diploma.

My first thought was that systems are what help you achieve your goals.

You can’t get what you want, if you don’t know what you want.

I’ve also studied 3 different goal setting courses.

I bought into them based on a lie.  They claimed that there had been a study done at Harvard or Yale which found that the 1% of students with written goals later had more wealth and success than the other 99% combined.

There was no such study.

People sell goal setting programs by highlighting the exceptional achievers and ignoring all the people who set goals and fail.  Remember that XKCD cartoon on survivorship bias.

Some people think that the secret is to have a goal and that it will somehow magically happen.  They never create a system that has them working every day towards that result.

With good systems, you are putting yourself in a position where you might get lucky.

Even when you trip, you fall forward.

That’s progress

Let’s use the example of a goal of having a flat stomach.

The way I eat there’s a slim chance of success.

The SMART goal is

Specific – 6 pack abs

Measurable – you can see them

Agreed Upon – Anyone can tell if the goal has been reached

Realistic – other fat people have done it

Time based – by Sept 2018 I will lose over 50 pounds of fat.

With a focus on the goal, you are always falling short. You may get to achieve your goal, but it’s a short lived experience.

I’ve repeatedly achieved losing fat, but I didn’t sustain it. I didn’t have a system to maintain it long term without draining my limited will power.

I bought into systems from Weight Watchers, Nutri System, Jenny Craig and various gyms

Millions of their customers have proven those systems don’t work in the long term.

There has to be a better way

A requirement of a system is that you expect it to give you a favourable result most of the time, for most people.

Scott defines a system as something that you do regularly that improves your odds and makes you more skilled and valuable. Even when you fail, you’ve learned something useful.

A great system will give you multiple ways to succeed and no way to fail.

With a system you focus on the daily process, being happy about the directed effort. Your focus is not on the end goal but on the daily activity. Every day that you follow your system, you win big.

Goals work fine for simple situations.

Life is too complicated and changing too fast to have well defined long term goals. In IT we have methodologies such as Agile for dealing with exactly that problem.

Realize that this channel is an example of a system.  I’m an IT guy, a techie. As a group, we’re not known for our conversational and public speaking skills. So I decided that’s a useful skill for me to develop.

You can have a system to increase your chances of succeeding, without having a specific goal in mind.

In his autobiography “up till now” William Shatner describes his simple system that led to his greatest financial success.

When the phone rings, William Shatner answers it and says “yes” to whatever is offered him, as long as they can pay.

When he was offered the chance to record an album, he said yes. Let’s have a listen

That’s considered the worst Beatles cover of all time and a colossal failure.

Over 20 years later, when Priceline needed a pitch man, they thought of Shatner because of that album.

They didn’t have cash, all they could offer was stock in their company.  That horrible album led to Shatner earning more money than everything else he did in his life, combined.

You couldn’t plan that.

That’s the power of a system that puts you in a position to get lucky.   Luck was a big part of that.


You have thousands of skills and talents. Scott asserts that something special happens when you stack your talents.

What does that mean?

My career is in IT.  We stack one technology on top of another to produce the Internet (TCP/IP stack). For web services, we have the Linux operating system supporting the Apache web server with mySQL for database and PHP for coding. That’s the LAMP stack.

By stacking various independent technologies on top of one another, we’re able build systems that support our modern world.

Scott adapted that idea of stacking to create his talent stack concept. A useful talent stack consists of talents that build on top of one another.  Imagine that These blocks are your talents.  At the bottom of your talent stack is your brain. Then you have your energy level. Improvements at the bottom of the stack improve everything above. For an IT person, rapid learning, touch typing, basic accounting, business writing, are all useful skills.

Sooner or later, when you stack your talents, you reach higher heights.

You don’t have to have a single outstanding talent to win big.

Scott claims that his talent stack consists of a number of average talents. He has a strong work ethic, but he’s a mediocre artist. He’s clever and funny, but at a party there’s usually someone funnier than him. He’s earned his MBA.

He’s a good writer. He’s a master persuader and he knows marketing.

He’s stacked those talents to become a world class cartoonist.

As I said, I’ve read thousands of books. I recommend reading this one above all others. It’s packed full of jam with ideas that you can use to win big lee.

Win bigly is the title of his next book.

If you do read it, I’d like to hear your thoughts on it.

My thanks to my friend Lori Challenger for suggesting todays show. You can see her in the “How to Open A Banana” episode of the “What to Know” show. Every time we watch that we have a good laugh.

Thank you Scott Adams for this excellent book.

and thank YOU for watching.

Is there a show you want to see? Email [email protected] and maybe I’ll make one for you.

Be seeing you.

Show Notes

https://xkcd.com/1827/  Survivorship bias

http://dilbert.com/strip/1992-09-29 gets to the point


Scott Adam’s blog http://blog.dilbert.com

The Dilbert comic strip http://dilbert.com/

How to open a banana https://www.youtube.com/watch?v=VuEPNlw6nwk&