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

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

Scott Adams is the creator of the ‘Dilbert’ cartoon series. Before this world-wide phenomenon though, Adams is happy to admit the looong list of things he tried (and failed at) before eventually achieving success. Each failed attempt gave him a lesson, something he could take with him and apply to the next thing he tried. Even as Dilbert was growing in success, he still worked full time for 10 years, drawing Dilbert at 5am before work.

This book provides some important ideas and approaches for achieving (eventual) success. In this episode, we’ll talk about: the downside of passion, goals VS systems, managing your attitude and energy, prioritising and making decisions, and ‘skill stacking’.


Grab a copy of the book here:

(also, we previously did an episode on his book Win Bigly and we interviewed Scott Adams on the show as well – listen to the interview by clicking here).


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


Scott says that if you go back far enough, ALL success boils down to luck. Warren Buffet says he was lucky to be born at that time, or his skills wouldn’t have matched the opportunities if he was born any earlier or later. Steve Jobs was lucky enough to be born with Steve Jobs’s DNA and lucky to meet Steve Wozniack when he did. If Bill Gates was born in a different country, he might’ve be chopping down trees instead of creating computer operating systems

BUT – what good is a book that just talks about luck as the only strategy for success?. if you believe all success depends on luck, you probably won’t try as hard as if you believe success depends on hard work. No matter what kind of luck you were born with, history tells us that you still need to work hard in order to achieve success

“You don’t need to DO anything as a results of reading this book. You’ve already changed. And if I’ve don’e my job right, you’ve changed in a way that will someday make people say you were lucky”



Ch3 – Passion is Bullshit

You often hear advice from successful people that you should ‘follow your passion’. That SOUNDS perfectly reasonable the first time you hear it. Passion will presumably give you high energy, high resistance to rejection, and high determination. Passionate people seem more persuasive too. These are all good things? Right?

Scott used to work in a bank. As a banker, their boss said that they were never allowed to give someone a business loan if their were following their passion. One day a a sports enthusiast wanted a loan to open a sports store – they turned him down. someone opening a new business following their passion is doing it for the wrong reasons (doing it for the enjoyment rather than the harsh business reality/viability of it)

Instead, the boss at the bank said: The best loan customers are the ones that have no passion at all, they just see something that looks really really good on a spreadsheet and have the desire to work hard at making it work. Take for example someone opening a dry cleaning store – that’s a super boring business, but you want the grinder who has crunched the numbers and knows what’s required, rather than the guy who loves his job.



Deciding VS Wanting

One of the best pieces of advice Scott ever received: “If you want success, figure out the price, then pay it”. It sounds trivial and obvious, but if you unpack the idea it has extraordinary power

A lot of people wish or hope for things: they wish they had a yacht, or they wish they had servants and a castle, and they wish that they could travel the world in their own private jet to mystical far away places. But these are mere wishes

People who actually achieved a measure of success DECIDED to get the things that they wished for. Once you decide, you take action. Wishing starts in the mind, and generally stays there.

When you DECIDE to be successful in a big way, it means you acknowledge the price you’re willing to pay for it. it might mean sacrificing going to parties in order to get good grades in school. it might be putting off having kids in order to pursue a college major that is boring but leads to lucrative job offers in the future. it might mean taking business risks that could open you up to embarassment/divorce/bankruptcy if they fail

“successful people don’t wish for success; they decide to pursue it”. to pursue it effectively, you need a system. “success always has a price, but that price is negotiable” – if you pick the right system, the price will get a lot closer to what you’re willing to pay.

“I can’t change the fact that success requires a lot of work. But if you learn to appreciate the power of systems over goals, it might lower the price of success just enough to make it worth a go”



The Energy Metric

Problem: We humans want many things (good health, financial freedom, accomplishment, a great social life, love, sex, romance, recreation, travel, family, career, and more). The problem with all of this wanting is that the time you spend chasing one of those desires is time you can;t spend chasing any others

So how do you organise your limited supply of time to get the best results chasing unlimited wants? Scott says you just need to focus on one metric:Your Energy.

If you make choices that maximise your personal energy, it makes attaining all of the other priorities easier. Maximising personal energy means: eating right, exercising, avoiding unnecessary stress, getting enough sleep. It also means having a life that makes you excited to get up and out of bed in the morning. When your personal energy level is right, the quality of everything you do gets better, and it further stokes your energy levels.When your work is better, your job and career get better, when that’s all working and your personal energy goes up, your private life all improves too.

IDEA #4 – Goals VS Systems

Goals are for losers

EG: If your goal is to lose 10 pounds or 5 kilos, you spend every moment in time until you reach the goal feeling as if you’re not yet good enough because so far you’ve failed in meeting your objective

“goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary”

that feeling of living as a failure until you meet your goal can be tiring and wears on you – may even be enough to drive you off your goal all together because it’s easier to stop trying than to keep living in disappointment

IF you achieve your goal – you celebrate and feel terrific, but only until you realise that the goal was the only thing that was giving you purpose/direction. now that your goal has been achieved, what do you do now?? set ANOTHER harder goal?? Your options are to feel empty and useless with no path forward, or to set a new goal and re-enter the cycle of permanent ‘presuccess failure’.

Systems as a different path forward. systems people succeed every single time they apply the system (not only at the very end when a goal is achieved). they ‘succeed’ because they did exactly what they were supposed to do. the goals people are fighting discouragement at every turn, the systems people are feeling good every time they apply their system


“GOAL” = a specific objective that you either achieve or don’t achieve in the future

“SYSTEM” = 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.


  • Dieting
    • goal = lose 20 pounds
    • system = eat healthy dinners
  • Exercise
    • goal = running a marathon
    • system = going for a run every day
  • Business
    • goal = making a million dollars
    • system = always coming up with new ideas to start a business (or improve an existing one)
  • Investing
    • goal = make 10% on this trade
    • system = buy a good company and hold it forever (Warren Buffet’s sytem)
  • Podcast
    • goal = 1 million downloads OR Top 10 rankings on iTunes OR get a Seth Godin on the podcast
    • system = record a new episode every week
  • Reading
    • goal = read 20 books in the year 2020
    • system = read a little bit of a book every day

‘Exercising every ay’ might sound kind of like a goal… so to be clear: goals are a ‘reach-it-and-be-done’ situation. systems is system you do on an ongoing regular basis with the expectation that down the line you’ll end up in a better place in life. systems have no deadlines, and you probably can’t determine your progress on a daily basis, but you’re always doing something in the hope of future improvements.


The Success Formula:

“Every skill you acquire doubles your odds of success”

Notice that nothing was mentioned about the LEVEL of proficiency you need to achieve for each skill. you don’t need to be world class. you don’t even need to be Excellent. You just need to be ‘Merely Good’ at a skill for it to count. you can raise your personal value (and market value) by being ‘merely good’ at more than one skill.

Good + Good > Excellent

Success-wise, you’re better off being GOOD at TWO complimentary skills than being EXCELLENT at ONE. The above formula (new skill doubles your odds of success) may not be completely accurate, but at least it is correct in the direction it points you in, and helps guide your behaviour in a good trajectory

For example, Scott says that he’s been able to combine a bunch of his ‘good’ skills to be excellent at the extremely niche intersection. He’s good enough at drawing, but not excellent, has good sense of humour but isn’t a well-known comedian, good enough at business (has an MBA) but not a CEO of a Fortune 500 or a billionaire tech founder, good enough at business writing but not world-class. Combined mediocre skills are far more valuable than the sum of their parts (can leverage the combination of all of these into creating Dilbert, but on their own they aren’t overly valuable)

Extraordinary talent and maniacal pursuit of excellence in one thing might be one path to success (probably the hardest), but Scott says that when it comes to skills Quantity often beats Quality

Math of Success

The best way to increase your odds of success (that might look like luck to others) is to systematically become good, but not amazing at the type of skills that work well together and highly useful for just about any job. Some of the highest leverage, most valuable skills Scott Adams suggests that everyone should learn because they’re widely applicable:

  • Public Speaking
  • Psychology (an understanding of yourself and of others)
  • Business Writing
  • Accounting
  • Conversation
  • Design

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