#36. How to Fail at Almost Everything and Still Win Big. A Book Review

Nero Okwa
Notes by Nero Okwa
Published in
7 min readAug 15, 2022


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

Dear Readers,

After the last 3 book reviews on Strategy Rules, Inspired, and The Mom Test, I was excited to write a review of another book that I read recently which has influenced how I think about success.

It’s called How to Fail at Almost Everything and Still Win Big by Scott Adams.

Scott Adams is a cartoonist and famous creator of Dilbert, that has grown from a syndicated comic strip, to a multimillion-dollar creative empire also known as Dilbert. From a handful of newspapers in 1989, Now Dilbert appears in over 2,000 newspapers, in 57 countries.

This book is a straightforward guide on how to prepare for success by taking a systems approach, optimising your personal energy, and increasing your chances of being lucky.

Here are 10 takeaways I got from this book.

1. Deciding vs Wanting

“One of the best pieces of advice I’ve ever heard goes something like this: if you want success, figure out the price, then pay it

“I know a lot of people who wish they were rich or famous. Few of these wishful people have decided to have any of the things they wish for. It’s a key difference, for once you decide, you take action. Wishing starts in the mind and generally stays there”

“Successful people don’t wish for success; they decide to pursue it. And to pursue it effectively, they need a system. Success always has a price, but the reality is that the price is negotiable. If you pick the right system, the price will be a lot nearer what you’re willing to pay”

- How to Fail at Almost Everything and Still Win Big

2. Systems Over Goals

“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”.

“One should have a system instead of a goal. The system-versus-goals model can be applied to most human endeavours. In the world of dieting, losing twenty pounds is a goal, but eating right is a system. In the exercise realm, running a marathon in under four hours is a goal, but exercising daily is a system. In business, making a million dollars is a goal, but being a serial entrepreneur is a system.”

“Goal-oriented people exist in a state of continuous pre-success failure at best, and permanent failure at worst if things never work out. Systems people succeed every time they apply their systems, in the sense that they did what they intended to do. The goals people are fighting the feeling of discouragement at each turn. The systems people are feeling good every time they apply their system. That’s a big difference in terms of maintaining your personal energy in the right direction.”

- How to Fail at Almost Everything and Still Win Big

3. Focus On Energy, Not Time

“The way I approach the problem of multiple priorities is by focusing on just one main metric: my energy. I make choices that maximize my personal energy because that makes it easier to manage all of the other priorities”

“Maximizing my personal energy means eating right, exercising, avoiding unnecessary stress, getting enough sleep, and all the obvious steps. But it also means having something in my life that makes me excited to wake up”

- How to Fail at Almost Everything and Still Win Big

4. Do Creative Work First

Here Scott emphasizes the importance of doing creative or your most important work first, and leaving the less engaging task for later in the day.

“One of the most important tricks for maximizing your productivity involves matching your mental state to the task… At 6:00 A.M. I’m a creator, and by 2:00 P.M. I’m a copier… It’s the perfect match of my energy level with a mindless task.”

- How to Fail at Almost Everything and Still Win Big

5. Success or Passion

Passion is great but its not everything.

Oftentimes I have developed passion for something after I got started and began to succeed in it.

“It’s easy to be passionate about things that are working out and that distorts our impression of the importance of passion… my passion level moved with my success. Success caused passion more than passion caused success.”

“So forget about passion when you’re planning your path to success. You already know that when your energy is right you perform better at everything you do, including school, work, sports, and even your personal life.”

- How to Fail at Almost Everything and Still Win Big

6. Fake it till you make it

What we think influences what we do, but what we do also influences what we think. If you want to think differently, do something different.

“Smiling makes you feel better even if your smile is fake… I’ve also discovered that acting confident makes you feel more confident.”

“Understanding this two-way causation is highly useful for boosting your personal energy.”

“We are designed to become in reality however we act. We fake it until it becomes real. Our core personality doesn’t change, but we quickly adopt the mannerisms and skills associated with our new status and position.”

- How to Fail at Almost Everything and Still Win Big

7. Learn and fail your way to success

Switching ‘failing’ for ‘learning’ can reframe our outlook and provide useful lessons from any project with which we can take to the next project. Thus, increasing our chances of success.

“Remember that failure is your friend. It is the raw material of success. Invite it in. Learn from it. And don’t let it leave until you pick its pocket. That’s a system”

“I have a long history of profiting from failure. My cartooning career, for example is a direct result of failing to succeed in the corporate environment.”

- How to Fail at Almost Everything and Still Win Big

8. Skill Stacking and a formula for Success

The formula (for success) is that every skill you acquire doubles your odds of success.”

“The idea is that you can raise your market value by being merely good — not extraordinary — at more than one skill.”

Some skills are more important than others, and you should acquire as many of those key skills as possible, including public speaking, business writing, a working understanding of the psychology of persuasion, an understanding of basic technology concepts, social skills, proper voice technique, good grammar, and basic accounting.”

- How to Fail at Almost Everything and Still Win Big

I love the expression “Luck is when opportunity meets preparation”. Acquiring useful skills, increases our chances of being prepared when opportunities present themselves.

9. Your Appearance Matters

“At the age of twenty-one, college diploma in hand, I boarded an airplane for the first time in my life, destination California. I figured I would be going on job interviews as soon as I reached California and I needed my one and only suit to look relatively less hoboish. It just made sense to wear it on the flight.”

“I was seated next to a businessman who was probably in his early sixties. He asked what my story was and I filled him in. I asked what he did for a living and he told me he was CEO of a company that made screws. Then he offered me some career advice.”

“The second thing I learned on that flight — is that appearance matters. By the end of the flight, the CEO had handed me his card and almost guaranteed me a job at his company if I wanted it. Had I boarded the flight wearing my ratty jeans, threadbare T-shirt, and worn-out sneakers, things would have gone differently.”

- How to Fail at Almost Everything and Still Win Big

10. The Most Important form of Selfishness

Being selfish can be good, based on how you look at it. You can’t be generous to others if you’re not in a good place, from which you can help.

“The most important form of selfishness involves spending time on your fitness, eating right, pursuing your career, and still spending quality time with your family and friends.”

“The healthiest way to look at selfishness is that it’s a necessary strategy when you’re struggling.”

“If you pursue your selfish objectives, and you do it well, someday your focus will turn outward.”

- How to Fail at Almost Everything and Still Win Big

(BONUS) Optimise for Luck

“Once you optimize your personal energy, all you need for success is luck. You can’t directly control luck, but you can move from strategies with bad odds to strategies with good odds. For example, learning multiple skills makes your odds of success dramatically higher than learning one skill.”

“Another big part of my system involves generating lots of opportunities for luck to find me and taking the sort of risks that will allow me to come out ahead even if the project fails.”

“If you stay in the game long enough, Luck has a better chance of finding you.”

- How to Fail at Almost Everything and Still Win Big


I hope you find these lessons useful on your journey to success.

Good luck and bye for now.

Thanks for reading and see you next week.


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Racing Towards Excellence.



Nero Okwa
Notes by Nero Okwa

Entrepreneur, Product Manager and StoryTeller. In love with Business, Technology, Travel and Africa.