Book review: How to Fail at Almost Everything and Still Win Big

The book was highly enjoyable and packs so much useful information and advice. I am impressed how succinctly and clearly Scott has expressed his opinion on a large variety of topics.

It is essentially Scott’s take on life and how to succeed. Success can mean different things to different people, but I can safely say many will find information in here that they can use. I would highly recommend this book to anyone who is looking to get a good sense of how one can accomplish difficult tasks and live a fulfilled life.

At a high level, his take on life boils down to several key points (which I hear repeated in various forms over and over again in other books):

Increase your energy capacity by eating right, getting a good amount of sleep every day, and exercise/stay active. These are the foundational pillars that enable you to work hard, think clearly, seek out knowledge or adventure, and in general lead a fulfilling existence. Beyond that, you need luck, be at the right place at the right time so to speak. But luck is not a fixed concept, you can increase your odds of luck by picking up new skills, mastering concepts such as psychology, finance, social interactions, public speaking. The additional skills will increase your surface area of luck, so to speak and the rest is up to you: once given an opportunity, take

Through it all, embrace the failure for it is a valuable signal and a learning material that if utilized properly will enable you to grow.

The topics that the book covers are rather varied and all expressed from Scott’s point of view and what he learned. The presentation style though is fun and engaging which makes it easy to read and learn.

A couple of ideas that stood out to me in addition to the above big level concepts:

  • Systems vs goals. I’ve had heard this distinction before but did not fully buy into it. The author has some really interesting points and examples of how expressing your goals as systems instead can make a huge difference.Let’s take reading books as an example. You could set a goal of reading two books per month. It’s measurable, you know when you succeed or fail. And is actionable, action being sitting down and reading. But putting that number out there, Scott argues, makes you feel somewhat inadequate if you don’t succeed, you are always in a state of failure until you reach that number.

    Instead, you should come up with a system for reading books, such as: anytime you commute on a train, you will read a book (instead of looking at twitter/fb/etc on my phone). Or every other day during lunch you will read. etc. You pick what works for you and do the action. You don’t worry about the count of books, just make sure you put a system in place that allows you to spend time reading. Then pay attention to how well you are doing. If you are not reaching the amount of reading you want, try to find a better system. Iterate.

    It’s a simplified example, but if you apply it to enough behaviors, you can have a pretty good setup going on for reading and anything else. For instance, I have couple systems for reading (that I setup without even knowing): 1) keep my kindle in the commuting backpack 2) when on a train, read 3) when I see a book I like, buy it. The number of books per month varies, but I feel like I am always reading. I am almost at the end of the month and have finished four books. Last month 2, a month before 2. I am happy with the amount of reading I do and sometimes it drops to zero but that’s OK.

  • Happiness level of a human being depends on the direction of the progress and not the current state. (e.g. A rich person that goes from 2 billion to 1 billion dollars in fortunate is often sadder than a person who is increasing his earning from 90k to 120k).
  • Affirmations, a somewhat vague and controversial concept of essentially wishing for a certain outcome and it becoming a reality. Scott presents multiple examples from his life and makes sure to mention how there is no science behind it and it all could essentially be bullshit. Yet he seems to have used them in the past and tends to believe there is something there.
  • Avoid career traps that require you to sell your time for money. I am definitely in that stage right now, basically, my time is what earns me money and this book is making me strongly consider what other revenue streams I could add to improve this situation.
  • Happiness is being able to do what you want when you want it. The flexibility of choosing when to do the activity that you want to do is very important to us, it appears. I can attest to that and could explain why I am very happy at my current job: the flexibility of my schedule.
  • One should be familiar with or get a good understand of topics such as psychology, public speaking, accounting, and a few other foundational skills. I jotted down the list and see which ones are my weak points. I am always taking courses in my field of profession, but this book is making me consider if I should try to branch out and see if I can learn a complimentary skill that is not necessarily tied to my current profession (software engineering).

Again, if you are a looking for an easy yet educational read, I highly recommend Scott’s book. Enjoy!

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