How to Fail at Almost Everything and Still Win Big – 5 Key Takeaways

"Read "How to Fail at Almost Everything and Still Win Big" if you want proven tips on how to find success and live a prosperous life." - Lorelei
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Book Stats

Title:How to Fail at Almost Everything and Still Win Big

Author: Scott Adams

Published Date: 2013

Pages: 231

Average Time to Read: 7 – 8 hours


Favorite Chapter

Chapter 11 – The Energy Metric

As a Type A person, a solution to “what metric should I track to evaluate my progress” has eluded me for decades. Every solution I’ve developed thus far has created a polarization that I haven’t been happy with:

  • I track my time, it gets split between my family and work.
  • I track my weight – it gets split between my diet and how much I move.
  • I track my sleep – it gets split between my desire to binge watch TV and my overall health.

I end up feeling constantly at war with myself and then the “thing to track” gets tossed.

Enter Scott Adams’ Energy Metric – the solution to this decades’ old problem.

What do all of these other metrics (time, weight, sleep) have in common?

Their impact on my ENERGY levels.

With more energy, I am more productive.

And, since all of the metrics that I used to track work together within this Energy Metric, there are no more polarizations! Instead I can work on observing how the various factors relate to one another.

For instance – I stay up late binging TV.

I lose sleep so I wake up in the morning with my energy levels low. In order to raise them, I grab something sugary and quick to eat and load up on the caffeine. This ends up being a recipe for disaster by the afternoon and then I’ve lost all motivation to work out which further plummets my energy levels.

Instead of focusing on the one metric (sleep), Adams solves the whole problem by telling you to track your energy levels.

His Energy Metric is honestly so simple, I have NO idea why I didn’t realize this myself.

While the Energy Metric itself is simple, Adams coverage of it is not. Within this chapter, Adams delves much deeper into common energy traps and how to avoid them. You’ll really want to make sure you take a look at this chapter if you want to get tips for how to maximize your energy and productivity.

After reading this chapter and trying to track my energy levels on my own, I stumbled upon a tool that simplified how I tracked my energy levels throughout the day. Garmin makes a line of smartwatches which include a “Body Battery” metric that takes into account your heart rate variability, sleep quality, level of activity and more and produces a variable score that shows how your body’s energy level is responding to your environment.

I bought the Garmin Vivosmart 5 fitness band and the watch as a whole is awesome, but the Body Battery metric itself has been such a great tool in helping me better understand how things like exercise, sleep, and stress impact my energy levels.

If you are looking to increase your energy levels so that you can be more productive, I definitely recommend that you read this chapter and grab a Garmin watch that has a Body Battery metric.

Favorite Quotes

“Priorities are the things you need to get right so that the things you love can thrive.”

“Everything you learn becomes a shortcut for understanding something else.”

“To put it another way, the right amount of exercise today is whatever amount makes me look forward to being active tomorrow.”

“Right choices can be challenging, but they usually charge you up. When you’re on the right path, it feels right, literally.”

How How to Fail at Almost Everything and Still Win Big Found Me

It was a very early fall morning in 2022 and I felt distraught. I had been battling various illnesses for weeks (hello tri-demic!) and I had fallen behind on so many of my goals.

My inner critic was fuming about me failing to make my desired progress so I took to my LinkedIn community for words of wisdom and support. I hoped that someone had advice for how to live through another illness season and still make progress on your work goals.

Thankfully, several lovely commenters shared lots of great advice (I highly recommend using LinkedIn for your social media account if you aren’t already. If you are, connect with me).

However, there was one piece of advice that stood out.

It was a comment I received from someone who said: Goals are dead, you need better systems. Read How to Fail at Almost Everything and Still Win Big” and never have another goal again.

While I had heard of Dilbert, I didn’t know of Scott Adams or that he wrote books about his life experience. I wasn’t sure that this book was going to be the right book for me, as I was really looking for a guide on how to continue making progress in my life despite a seemingly endless supply of hurdles and pivots.

The commenter assured me that Scott Adams’ life was filled with hiccups and pivots and yet he still managed to find success.

If someone had figured out how to navigate life’s turbulence and still end up on course, I definitely wanted to know how. Curiosity piqued, I bought the book.

Who Would Benefit from How to Fail at Almost Everything and Still Win Big?

Adams tries to accomplish a lot in this book, as he blends both memoir and personal development tips – not an easy feat. He sacrifices topic depth in order to cover a breadth of factors related to building a successful life.

With that said, by providing an overview and basic information on personal development, “How to Fail at Almost Everything and Still Win Big” would be a great first read for anyone who is new to the topic of personal development.

Adams’ frankness, humor and approachable writing style makes this book an especially great gift for a graduating high school student who is starting out on their own journey toward finding success.

For instance, I plan on gifting this book to my three sons on their high school graduation day. My kids hear me discuss a lot of the advice given in this book but I feel strongly that you have to hear the words from the right person to get them to stick. Adams does a great job of offering a different take on proven methods for finding success.

This book would also be helpful to anyone who lacks a lot of real-world experience, as Adams weaves together his personal experience with his success tips, thus showing you how to apply the tips to your own life circumstances.

As an avid personal development reader, however, I found the material within this book a bit beginner. If you’re familiar with the basic principles of personal development, I’d consider either skimming this book or skipping it entirely.

Also, I don’t generally gravitate towards memoir books but I tried this one because of the personal development angle. I thought the idea of weaving together personal story with lessons learned might add a unique perspective not often found in general personal development books.

Adams did deliver this magic in some sections and in others, his writing felt patronizing – like a parent saying “do this and not that” without really delving into the why.

Some of this may be a misinterpretation by me because Adams writing style for this book is much like his comic writing style – it’s dry. I prefer a warner, more nurturing approach so the dry, reporter-style way of writing made it difficult for me to get through this book – I kept putting it down and lacked a desire to pick it back up.

But I persevered because the pure memoir parts of this book were interesting.

If you like to read about someone’s rise to success and get into their mind, you might enjoy this book. Scott Adams did not have an easy journey to success, he had to overcome quite a bit of adversity to find his success.

I also appreciated Adams’ deep self-reflection and candor about the decisions he made and how he felt they impacted his life and success.

Some sections within the book also delved deeper into his thought patterns and behaviors which were very relatable. He wrote about his lessons learned and shared tips for what he wish he had done. These sections were by far my favorite, as I felt like I was learning from a mentor who wanted to make sure I didn’t make the same mistakes.

Overall, if you like reading unique books – take a look at “How to Fail at Almost Everything and Still Win Big.” It does an interesting job weaving together memoir and personal development so you walk away with a behind-the-scenes look at how someone found success despite many failures.

Key Takeaways from How to Fail at Almost Everything and Still Win Big

Part memoir, part self-help book, Adams shares various tips and tricks that helped make his career and life a success – success meaning financial independence and enough health to enjoy it.

So how do you find success? What does that path look like?

Here are some key takeaways from Adams’ book on how you can build a successful, prosperous life.

Implement These Success Factors

What goes into developing a successful life?

According to Adams, the general recommended parts of developing a successful life include: passion, desire, luck, hard work, determination, brains and an appetite for risk.

However, Adams who started his journey towards success as an average man, has a different view on what factors you need to focus on to grow a successful life.

One of the most important is luck.


Your entire journey success is influenced by this very one thing – luck, also referred to as timing.

In order for you to find success, you have to luck on your side orchestrating the timing so that you and the right circumstances come together at just the right time to create a kind of magic.

Here’s Adams one line about his formula for success: “I pursued a conscious strategy of managing my opportunities in a way that would make it easier for luck to find me.”

What does this mean?

If you want to be successful, you have got to put yourself out there by taking risks and opening yourself up so that luck can find you.

Speaking of luck, as I was writing this section I took a break and checked my email only to find an email from Sahil Bloom with the subject line: “The 4 Types of Luck.”

Yep, I’m sitting here writing about luck and The Universe drops some incredibly well-timed additional wisdom into my inbox and then nudges me to go find it.

It’s like magic.

Right place, right time – it’s THE perfect example of how you find luck.

Make sure you listen to those nudges!

Now let’s look at Sahil Bloom’s idea:

Bloom beautifully adds to Adams luck idea by sharing his 4 types of luck:

  1. Blind Luck – Think factors you have no control over like where you were born
  2. Luck from Motion – Think luck you welcome by taking action
  3. Luck from Awareness – Think luck you welcome through your personal knowledge and insight
  4. Luck from Uniqueness – Think luck you welcome by being authentically you

How can you improve your chances of luck finding you? (Other than paying attention to those little nudges The Universe sends you).

Don’t worry – Adams gives you extra suggestions.

Natural Advantage

Start with your natural advantages, i.e. what you’re naturally good at that requires minimal effort.

To find some of your natural advantages, think back to ages 5 – 10, how did you spend your time? What were you drawn to? What activities or attributes did you receive praise for? What caught people’s attention? What did you enjoy doing?

Most often it is in these early years when our natural advantages are most prevalent. As we age, we become more aware of society’s pressure and standards which can force us away from our natural advantages, as we desire conformity over self-expression.

Reconnecting with those strengths is a key factor in developing lasting success.

Adams writes: “…There’s a strong connection to what interests you and what you’re good at.”

Focus on what interests you and you’ll find some of your natural advantages and talents. These are great building blocks to form the foundation of your success.

Success Builds Success

You just need one success to start welcoming more success into your life.

Play games, take up a sport, engage in competition, start a streak – anything where you can be successful and that helps you feel a sense of accomplishment.

In these situations, success builds on success and becomes a habit. Start with something small and work towards bigger accomplishments.

Success Starts off Successful

I’m not sure I wholeheartedly agree with Adams’ take on this, however, there are many situations where it applies.

Adams writes: “The pattern I noticed was this: Things that will someday work out well start out well. Things that will never work start out bad and stay that way.”

I do feel that there are instances where there are things that start out poorly and are salvageable.

Sometimes the timing is wrong (need luck to come find you) or you’re missing key information or you don’t have the right people supporting you. Shifting some of these factors could turn the situation around and make it work out.

Which brings me to Adams’ next point.

Consistency is Critical

“…the best loan customer is one who has no passion whatsoever, just a desire to work hard at something that looks good on a spreadsheet.”

If you want luck to find you, you have to consistently take action that opens you to more opportunities for success.

Adams also shares that if you consistently focus on learning new skills, you’re essentially doubling your odds of success. More experience, more skills, more opportunities for luck to find you.

However, in referencing my comments above, if you consistently apply effort to something and it does not shift from an unproductive thing to a productive thing, then maybe it is time to quit. Not everything you try will bring you success but it will bring you lessons that you can apply to your next adventure.

Which brings me to Adams next factor for success.

Know Your Potential

You have to have a solid understanding of who you are and what you can offer the world if you want to find success. The Universe values people who value themselves and are also ready to serve.

Interspersed throughout several chapters, Adams shares about all the times he failed.

And he failed A LOT.

I was really surprised just how many times he flopped and yet over the course of several years, he found success.

The number one factor that I think kept Adams going was that he knew his potential. He found his interests, he tested the market, and he kept at it until he got the timing right.

Giving up therefore is the only time when you actually fail.

If you believe in your potential and are able to get it validated by a market force at some point in the journey, then your commitment to realizing your potential is what will actually lead you to success.

Attitude Matters

You figured out your interests, you know your potential, you’ve focused on being consistent, and now the last piece is your attitude.

First, you need to watch for blind spots. These are the things that you don’t know that you don’t know. And these things will wreck your success more than anything else.

What’s super fun about these little buggers is that most often only other people can help you see them.

Which is why finding people who will give you honest feedback is priceless.

You don’t want to surround yourself with people who just tell you “yes” or the good stuff – you want people who will tell you that you’re off your rocker. People who will question you and ask you to really look at what you’re thinking and doing.

Sometimes you can catch blind spots on your own if you focus on recognizing patterns.

For instance, I love dairy but dairy doesn’t love me. I only figured that out because I consistently kept experiencing unpleasant symptoms after I ate dairy. I paid attention to how I felt every time I ate dairy and my body alerted me that dairy was an issue.

Your instincts do this frequently – send you physical nudges throughout the day that often get ignored. It’s important that you listen to them, especially if there’s a pattern.

Say for instance that you have a tight jaw. It’s been bugging you for weeks and you’ve tried all the things but it won’t stop. One day, you commit to observing your life for patterns and you notice that as soon as this one particular co-worker walks into the room, your jaw clenches even more.

Someone else in the room may have noticed your physical discomfort and could have told you about this blind spot, but you figured it out for yourself by tuning into your body’s clues.

Just like I listened to the nudge to check my email and found Bloom’s extra wisdom, your body and instincts are excellent at guiding you on your path toward success.

The last piece of wisdom related to attitude is to practice humility.

I really love Adams take on humility – success is a journey and you will fail frequently. You will need to set your pride aside and ask for help. You will need to take responsibility for action that you wish you hadn’t taken and you will have to accept that very few things will go your way.

But if you stay humble, if you keep trying, if you commit to the journey and not the destination, Adams believes that you will find success.

Outside of these success factors, Adams includes a variety of other supporting factors that impacted his ability to find success.

Use Systems Not Goals

Chapter Six – Goals vs. Systems is perhaps one of the biggest takeaways from Adams book, as he is often credited as being the original person to write about this idea.

Here’s his take:

“…let’s say a goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run.”

Bottom line – if you do something daily, it’s a system.

If you’re waiting on something happening in the future, it’s a goal.

Adams elaborates on this more by giving examples but what he’s really talking about is creating a simple system of aligned and supportive habits.

Habits are the things you do every day that help luck find you and bring you success.

Goals, however, are like buoys off in the distance.

Let me set the scene.

Imagine you like to swim in an open body of water and you make it your goal to swim out to a buoy and back. You can see the buoy off in the distance – you know how to get out there and you want to get out there. Now what?

The actions you take (swimming) is the system of habits that actually gets you to the buoy.

Furthermore, even though this buoy is anchored, its location can shift or its tether can snap entirely. If you’re solely committed to reaching that buoy, your happiness takes a serious hit when the buoy moves or disappears. You’ll also have to expend a lot more energy figuring out your next steps including another goal.

However, if you are committed and focused on your system of habits (swimming) and not the goal (buoy), you won’t need to shift your perspective because you’ll still be out there swimming regardless of what happens to the buoy.

By committing to swimming each stroke, you also receive mini wins that keep you motivated. You end up falling in love with the process of swimming which can take you anywhere.

Focusing on systems and not goals is what allows you to sustain your progress. You spend less time figuring out new plans and strategies and you stay happier and more motivated to continue your effort.

I believe so much in the power of systems that I created a unique Net Worth Tracker – one that tracks the daily habits you need to grow your money. Habits such as dollars saved per month, daily step count, number of books read or podcasts listened, average hours of sleep, etc.

Make sure you grab a copy and start tracking your money habits.

If you want more support on how to develop a better system to support your journey towards success, James Clear’s “Atomic Habits” does an excellent job of digging deeper into how habits and the systems that support them can propel you toward success.

Be Selfish – It Will Spawn Your Success

In order to find your success, you will have to manage two things: your own needs and the needs of others. Unfortunately, this polarization is one that will never disappear and so it needs a solution as you become more successful and the needs of others increase.

Adams shares that your success is directly tied to how well you take care of yourself. You literally cannot work, cannot create, cannot sell, and cannot spend time with your loved ones, without your physical or emotional health.

The more you give at the expense of yourself, the more likely you will lose your success and become a burden on someone else.

It’s a non-negotiable, key factor of becoming successful – crafting a fortified boundary around yourself that prevents you from giving more to others at the expense of your future.

This boundary may be uncomfortable at first as most of us have been conditioned to give without hesitation, however, Adams offers a different perspective on this discomfort.

He writes: “Once all of my personal needs were met, my thoughts automatically turned to how I could make the world a better place.”

Sure, there may be people who take care of all of their personal needs and wants and continue to use their energy for personal gain, but Adams suggests that most people will not act that way.

There is a balance as Adams discusses, we can only give as much as we take care of ourselves first. We have to allow what we receive to nourish us first and only then can we give from what remains.

His point about meeting your needs first and having your perspective automatically shift resonated deeply with me because I also see the world that way – it’s what I created Sustainable Wealth and made giving a key part of what comes after you make enough money to satisfy your needs and most of your wants.

Being able to give after taking care of myself is why I stay committed to working with my money.

Improve Your B.S. Barometer

Another key component of finding success is to ensure that you have a healthy, useful system for identifying valuable information. Some people use logic to filter information while others use their gut or instinct.

Adams describes how incredibly important it is to have a “system for sorting truth from rubbish.” This includes the ability to separate fact from fiction AND the ability to determine what information is useful or true for you.

The six truth filters he recommends are:

  1. Personal experience – What does your past experience tell you?
  2. Experience of people you know – Ask your family or friends for their wisdom.
  3. Experts – Pay someone to give you advice.
  4. Common sense or street smarts – Part personal experience, part gut, all influenced by you.
  5. Pattern recognition – What are you observing right now?

The idea is that you have a situation or difficult question that you need to answer and you use these filters to help you arrive at the true answer for you. Adams recommends that your true answer be confirmed by at least two of these filters –i.e. your personal experience and the paid expert say the same thing.

You also want to look for consistency – what is regularly repeatable.

If you get sick every time you go to the gym, your personal experience of getting sick and the common sense knowledge that unclean gyms have a lot of germs are consistent. It’s likely true that the source of your illness is related to your gym visits.

If you need further validation, a great next step according to Adams is to “ask a smart friend how they tackled the same problem.” This works so well that many game shows have the option where you can “call or poll a friend” to help you arrive at the right answer.

Hopefully, after using these truth filters and asking a friend, you’ll be able to figure out what information is not only true for you but also what leads you toward your best next step.

Adopt These Happiness Factors

While not directly tied to success, happiness is often what people believe comes as the result of success. In Chapter 30, Adams lays out several factors that work along with success to bring you lasting happiness.

They are:

  1. Appreciating the timing of things – Adams writes about how a nap offered right after waking up usually has less enjoyment that a nap offered later in the day. You can increase your enjoyment of things in your life by optimizing the timing of them.
  2. Prioritize having control over your schedule – Flexibility in your schedule allows you to respond to life’s demands without barriers. Time flexibility grants autonomy and supports you being able to meet your own needs on your terms which is key to lasting success.
  3. Dopamine drives happiness – The anticipation and the journey towards success drives happiness more than the end result. Support this fact by committing to slow and steady improvement. Consistently committing to your systems is one way to maximize your happiness.
  4. Embrace your imagination – Dream big dreams, seek out the positives in life, engage your creativity, look for alternative solutions to problems, and commit to embracing a sense of curiosity and wonder.
  5. Double-down on healthy living – Prioritize your diet, sleep and movement over all other factors. Without a solid foundation on which to build your success, your success will be short-lived.

And lastly, but perhaps most importantly, happiness is the result of being in service to others. But only after you’ve served yourself first.


This is more of a personal preference than an actual critique but I found the writing very dry. There wasn’t a lot of description given or scene setting and very few emotional words. It was as if I was receiving a lecture about Adams’ life and his lessons learned.

In these sections, his writing style comes across as robotic and in some cases patronizing (I walked away feeling somewhat admonished for making choices that he calls out as a bad idea). In these situations, he offers little support to the reader if they find themselves having not adopted his direction. As in – what’s missing is – here, this is what you can do to get yourself back on track.

The book reminds me of a common refrain I used in Management Consulting, “you’re not wrong, your delivery just needs improvement.”

Overall, Adams’ writing style made it difficult for me to sustain interest in the book. He offers a lot of good, solid advice and I do appreciate the facts he gives about his life, however, I would have enjoyed more warmth.

Writing style aside, the book does offer such a wide range of proven tips and strategies for how to increase your odds of finding success.

It’s a worthwhile read if you enjoy memoir and are interested in learning more about factors that help you find success.

Where to Buy



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May You Be Well and May You Find Peace
How to Fail at Almost Everything and Still Win Big

Read "How to Fail at Almost Everything and Still Win Big" if you want proven tips on how to find success and live a prosperous life.

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