How to Fail at Almost Everything and Still Win Big

Book tease

  • Goals are for losers.
  • Your mind isn’t magic, it’s a computer you can program.
  • The most important metric to track is personal energy.
  • Every skill you acquire doubles your odds of success.
  • Happiness = Health + Freedom
  • Luck can be managed, sort of.
  • Fitness is the lever that moves the world.
  • Simplicity turns ordinary into amazing.

Passion is bullshit. We are told to “follow our passion” just because the ones that win are more notorious and attach a simple rationale to their success. However, we don’t hear about those that failed “following their passion”.

🖇️ There is some survivorship bias attached here — The Black Swan goes deeper into this phenomena.

In other words, passioned people starting projects lead to more extreme outcomes. Success causes passion more than passion causes success.

Look for people with energy — this idea of “following energetic patterns” is a recurrent topic across the book, from career success, grit, or food intake.

Think of systems, not goals — be system-driven:

  • System: something you do in a regular basis that increases your happiness in the long run.
  • Goal: specific objective you either achieve or don’t sometime in the future. A goal-driven person is a loser by definition because she always lives in a state of pre success. The moment the goal is achieved, it fades away.

🖇️ Same idea found in Atomic Habits — actually both books are closely related in many topics.

A system’s approach to improve in your career would look like this 👇

Your job is not your job, but to find a better job.

Appearances, matter.

🔖 Difference between wishing something vs. paying the price to pursue it.

Energy is key (again). Follow, seek energy, and adapt your routine to maximize it. For example, if you know going to a shopping mall drains your energy, simply don’t go.

🔖 Difference between a simplifier vs an optimizer.

Simplicity always trumps accuracy.

Attitude — first master the basics i.e. food, exercise, sleep. Then make sure you keep playing or stay “out of jail”.

Affirmations work. Yes, they do. Yet another energy booster can be as easy as daydreaming, or visualizing yourself in a desired position.

Success can be habit forming — pick the delusion that works, become good at something, anything, and let the feeling of “winning” propel you to other fields.

In the quest for talent, seek for things you were doing when you were ten years old.

When building media products, averages don’t matter. Look instead for an outlier reaction from a small group of people, but most important, rely on what they “do”, not what they “say”.

“Wow, that was brave” — positivity is the closest we have to magic.

Timing is everything. Life is a slot machine that doesn’t require money. A regular slot machine will surely bankrupt any player in the long run. But life’s machine is different: it returns rare, but wild payoffs and does not ask for money upfront. It is a guaranteed winner if you just keep playing until you get lucky. You will fail 99% of the time, but success is guaranteed. All you need to do is to stay in the game long enough.

Don’t trust experts.

If you seek a certain change in life, make sure you recreate a conducive environment that promotes such change. The people you surround, relate, and hang out with will ultimately determine your odds of success. This is a good rephrasing of the “you become the average of your five best friends”.


📍 The skills formula:

Every skill you acquire doubles your odds of success.

You don’t need to be extraordinary, not even great, just good enough in one or more complementary skills.

When it comes to skills: good + good > excellent — quantity always beats quality in the skill realm.

If you think something could be useful, try to learn the basics. The moment you get into the habit of picking up skills, the more concepts you understand, the easier is to pick the next one.

📍 The knowledge formula:

The more you know, the more you can know.

🔖 Important skills to acquire in life — business writing, public speaking, accounting, design, psychology, conversation and storytelling, overcoming shyness, proper grammar, golf, persuasion, technology, voice technique, and pattern recognition.

Basic tips on conversation

🖇️ Some ideas are borrowed from How to Win Friends and Influence People

  • With strangers, set the stage by always asking their name, where do you live, family, what do you do for a living, hobbies, travel plans.
  • Let them talk about themselves and look for something in common — the least you say, the better.
  • Tell funny stories — make it a habit ask yourself how to turn your interesting life experiences into short, but interesting stories. Keep a backlog of stories.
  • Never open with “you” and less about food or medical issues.

Wording and behavior to reinforce persuasion

  • Because, would you mind, I’m not interested, I don’t do that, I just wanted to clarify, is there anything you can do for me, thank you for fill in the gap, this is just between you and me.
  • Be decisiveness — it speaks for leadership as well.
  • Show energy and enthusiasm.
  • A little bit of “healthy” insanity.


The only reasonable goal in life is to maximize your total lifetime experience of something call happiness.

Happiness is not a state of mind influenced by whatever is happening in our lives. It is far less dependent on external circumstances than one might think.

You can control happiness through your lifestyle by doing what you want, when you feel like to.

Happiness has a directional nature: where you are heading is far more important than where you are. Hence when it comes to picking a career one should consider one that allows for continuous improvement.

🖇️ Same idea found in Stumbling On Happiness — which is mostly the ultimate reference of the subject.

An excessive amount of choices produces anxiety. To maximize happiness, reduce choices when possible. Automate small or irrelevant decisions. They drain will power that you might need for more important stuff.

The happiness recipe is as easy as: daydreaming (imagining a better future), controlling the schedule, eating right, exercising, and sleeping well.

Most people won’t accept the idea (or are just surprised by the idea) that happiness is “as simple as that’, or just a state of mind.

🏃‍♂️ You should aim to exercise everyday, but never exercise so much in one day that you won’t feel like being active the next day. In other words, the right amount of exercise today is whatever amount makes me look forward to workout tomorrow again.

🍔 Eating strategy: eat what you want, when you want. Just make sure you want the right things by changing your preferences on what you actually want. In other words, reprogram your food preferences.

Again, remove choices. Make it simpler. Save willpower for more important decisions.

Do not follow diet advice. Just seek the foods that make you feel good. Follow energy instead, find patterns in foods.

Food intake has a huge impact on your mood, problem solving ability, or energy. We think it is related to other factors because we do not tend to isolate causes, and do not treat food intake as an experimental science would.

Test, experiment. Track what you eat and log your mood or energy afterward. Link foods to energy levels. You would be surprised that quantity doesn’t matter as much as you thought.

First published on June 03, 2020