5 Lessons Learned From How to Fail at Almost Everything and Still Win Big by Scott Adams (Book Review)

Scott Adams is my new favourite person. And How to Fail at Almost Everything and Still Win Big is my new favourite book. Scott Adams’ book provides one of those rare reading experiences where you end the book with a completely new outlook on life.

I present 5 lessons learned from How to Fail at Almost Everything and Still Win Big primarily as a way to consolidate the most important parts of the book for myself and not as anything approaching a reliable replication for actually reading the book. This run-down of the book will not motivate you or change your life. Only actually reading Scott Adams’ book yourself will do that. My main hope for this review is that, in addition to it being a big fat sticky note that I can return to in the future for guidance, it will stimulate your curiosity enough that you pick up the book and devour it in three sittings like myself.

1. Systems, NOT Goals 

I have always been a goal-oriented person. 

In part, I believe this is because the majority of self-improvement books in the mainstream (from those written by Brian Tracy to Grant Cardone to Tony Robbins) advocate goal-setting as a path to success.

But, while I always set ambitious goals, I was also miserable most of the time.

Every second not spent pursuing my goals felt like a waste of time.

As my goal deadlines approached, I became anxious if I wasn’t close to hitting them.

If I didn’t meet my deadlines, I became depressed, demotivated, deflated. 

If I did hit my goals, the sensation was always underwhelming. A massive anti-climax. Like expecting to ejaculate like a fire hose and instead being greeted by a trickling third-world faucet. 

So when Scott Adams asserted that ‘goals are for losers’, something just clicked.

Goal-oriented people exist in a state of continuous presuccess 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.

Does that sound familiar?

If you’re a goal-oriented person (like all the big name ‘gurus’ say you should be), you are likely all too familiar with the constant sense of discomfort and dissatisfaction that permeates your existence.

But a system instead of a goal? Now that seems interesting.

Just so we’re clear, here are examples of goals:

• Lose 10 pounds by June
• Sell 10,000 copies of my debut ebook

And here are examples of systems:

• Be active every day
• Write every day

The goals are setting you up for disappointment if you don’t fulfil them. And if you do fulfil them, then what? 

The systems, however, make it easy to be a winner every day whilst still pushing you in the direction of your desires.

If your goal is to perform 40 minutes of cardio and 20 minutes of weightlifting 6 days a week, you’re going to feel like a failure if you don’t hit that. 

But if your system is to simply put your gym clothes on at a designated exercise time each day (like Scott Adams suggests) or to simply ‘be active’, you are a lot more likely to feel like a success.

‘Be active’ is easier to fulfil than a specific workout plan. Too sore for weightlifting today? Well, if your system is to simply be active, a slow walk with your dog will fulfil that and leave you feeling a success. 

The result of good systems as opposed to goals is that you feel great each day and you feel motivated because small success inspire you and boost your energy.

After reading How to Fail at Almost Everything and Still Win Big, I scrapped my goals and replaced them with systems. 

• My goal used to be to ‘write 2,000 words each day’ — now my system is to ‘write every day’.
• My goal used to be to ‘be fluent in Japanese’ — now my system is to have a Japanese conversation each day (even a minute counts).
• My goal used to hit the gym every day — now my system is just ‘be active every day’.

The result?

I’m happier, more energetic, more optimistic, more motivated, and I feel success each and every day.

2. We are moist robots 

A lot of people ‘wake up on the wrong side of the bed’.

They think they are in a bad mood today and that’s just that. Mood is like the weather, isn’t it? You can’t really control it. You just need to ride out the storm. 

But we really don’t need to be a slave to our emotions. We can assert greater control than many of us think. 

Scott Adams finds it helpful to think of himself as a ‘moist robot’ rather than a skin bag ‘full of magic and mystery’. What this means is that we humans have an interface and we are programmable. We can control our output – our feeling and way of interacting with the world – by controlling our input:

If you control the inputs, you can determine the outcomes, give or take some luck. Eat right, exercise, think positively, learn as much as possible, and stay out of jail, and good things can happen.

It sounds simple and Scott Adams acknowledges that many people will not believe that simply having a good diet and sleeping well has more impact on your mood than your genetics or general life circumstances:

I’m here to tell you that the primary culprit in your bad moods is a deficit in one of the big five: flexible schedule, imagination, sleep, diet, and exercise. I’ve explained to a number of people my observations about how exercise, diet, and sleep influence mood. The usual reaction is a blank expression followed by a change of topic.

People want to believe that their bad moods are inherent and beyond their control.

I believed this to some degree too.

But after changing the way I approach life – thanks to Scott Adams – I have a very different process when I’m in a bad mood.

When I notice myself feeling depressed or irritable, I ask myself a few questions:

• When was the last time I ate?
• What did I eat? Was it healthy or unhealthy, big or small?
• How much sleep did I get last night?
• Do I feel like I’m being forced to do something I don’t want to do?
• When was the last time I exercised?
• Do I regularly indulge depressing thoughts or do force myself to think positively?

Just asking yourself those questions is almost always a sure-fire way to discovering how to fix your bad mood.

What you’ll find is that your bad mood is actually not because the universe wronged you or some victim-mindset bullshit.

It’s usually just because you’re blood sugar is low.

Simple fix. Have a Snickers.

Or it might be because you haven’t exercised.

I’ve been travelling extensively recently and haven’t had any access to a gym. It took me a while to figure out the cause of my persistent low energy, malaise, and bad mood. I wasn’t moving my body.

Compare that to a few months ago where my daily routine typically involved 20 minutes on the exercise bike, a long walk in the morning, and lifting light weights for pump and blood flow. I was in a joyous, puppy-dog, exuberant state almost all the time.

In order to hack our moods so that we are always our best, we simply have to understand our interface and how to program it. And, most of the time, that just means eating right, being active, and living a life we want to live.

3. Manage your energy, not your time

I used to keep a strict time planner with all my activities planned out often weeks ahead of time.

Coupled with being extremely goal-oriented, I basically existed in a state of deep unhappiness because not only would I be unhappy if I didn’t fulfil my goals, I also would be unhappy if I couldn’t muster the energy to ‘write 1,000 words at 2pm on Thursday’.

If something was penciled into my diary but I couldn’t do it because I wasn’t feeling great, I ended up feeling even worse.

Looking back on it, a lot of my mistakes resulting from not co-ordinating my tasks with my energy levels.

Simply put, you want to put the tasks that demand the greatest cognitive attention and creativity whenever you’re at your peak.

For a lot of people, this is early – often first thing – in the morning. 

After lunch, when you might be feeling a little sluggish from food and the accumulation of decision fatigue, you don’t want to sit down and pen the next 2 chapters of your magnum opus. 

You should monitor your energy levels at different times and assign work that corresponds to those levels. So for the post-lunch slump (which can be largely avoided if you follow Adams’ dietary advice) you want to do some mindless, rote, administrative work.

The problem I had a lot of the time is I would sometimes do admin work first thing in the morning and then try to be creative in the evening. How I was spending my time simply wasn’t aligned with my energy.

4. Never assume you know the odds of things

Scott Adams details his struggle with an extremely rare medical issue known as focal dystonia. Having been through the meat grinder of endless medical professionals, all who didn’t know anything about this affliction, Adams was justifiably uncertain that he would be able to meet with someone who was actually a professional in this field. 

He talks about how he would have swam all the way to Japan if it meant meeting with someone who could help him. But it surprised him to discover that the expert he needed to see lived just up the road from his own house! Had he given up – like most people – before even trying, in the belief that it would be fruitless, he might not have found a cure.

Pause for a moment to reflect on that. There were over six billion people in the world, and one of the most published experts in the field worked within walking distance of my home. Never assume you know the odds of things. 

This is a very life-affirming and motivating thought to have. 

Seriously, what cause do we have for many of our self-limiting beliefs? 

Many of our thoughts concerning the odds of things are simply guesses. And wildly uneducated guesses at that. They’re rarely based on studies or statistics and more about ‘feeling’, which we know can and often is misleading.

Next time you find yourself doubting something without actually putting in any research, it is time to pause and examine your irrational beliefs and try to find the cause. Often the thing that is holding us back is ourselves and our randomly formed false beliefs. 

5. Each new skill you acquire doubles your odds of success

Scott Adams is careful to point out that this isn’t an exact rule and it’s not based on scientific fact but this is one of those beliefs that is true enough and constructive enough to your life that it is valuable to hold.

I think it’s important to think of each new skill you acquire as a doubling of your odds of success. [It] helps guide your behavior in a productive direction. If I told you that taking a class in Web site design during your evenings might double your odds of career success, the thought would increase the odds that you would act. If instead I only offered you a vague opinion that acquiring new skills is beneficial, you wouldn’t feel particularly motivated. When you accept without necessarily believing that each new skill doubles your odds of success, you effectively hack (trick0 your brain to be more proactive in your pursuit of success.

I have honestly found in my own experience that the idea that each new skill doubles your odds of success is 100% true.

I came out of university basically an idiot.

I went to Oxford University and studied English Language & Literature.

At the time, it was ranked #1 in the world for English.

Problem was, all I focused on for 3 straight years was English literature.

I came out of uni thinking I just needed to be really good at one subject.

I held negative beliefs about my capabilities and justified them:

• “I can’t and never will be able to code or learn programming languages but I don’t need to because I can write.”
• “I don’t need to learn about marketing or advertising or persuasion because I can write.”
• “I don’t need to learn about specific industries because I can write.”

What bullshit.

To top it all off, the whole Oxford tag also deluded me into thinking I was a better writer than I am.

I’m better than average at writing. But, as you can tell from this blog, I wouldn’t win the Pulitzer even if I was born on American soil.

So when I came out of uni equipped with the false belief that my “writing” and “certificate” actually made me valuable in the world, I was hit pretty hard when I discovered the job market didn’t really give two shits about that stuff.

I can tell you with 100% certainty and proof that I became more employable but also more adept in a general sense with each new skill I learned:

• Teaching
• Japanese
• Marketing
• Copywriting
• Public speaking
• Graphic design
• Computer programming

I am by no means world class in any of these areas.

In fact, I’m extremely mediocre in all of them. But together they have sparked something inside me – along with my writing ability – that has made life a lot easier. 

Scott Adams describes how he is not the funniest guy in the room, or the best artist, but the combination of many different skills is what has made him successful:

I’m a perfect example of the power of leveraging multiple mediocre skills. I’m a rich and famous cartoonist who doesn’t draw well. At social gatherings, I’m usually not the funniest person in the room. My writing skills are good, not great. But what I have that most artists and cartoonists do not have is years of corporate business experience plus an MBA from Berkley’s Haas School of Business. In the early years of Dilbert my business experience served as the fodder for the comic. Eventually I discovered that my business skills were essential in navigating Dilbert from a cult hit to a household name. My combined mediocre skills are worth far more than the sum of the parts. 

How To Fail At Almost Everything And Still Win Big – Summary

This run-down only contains the 5 lessons that are most prominent in my mind after reading How To Fail At Almost Everything And Still Win Big. 

This run-down also does not do Scott Adams’ book any justice. 

The book is incredible. If you are going to read only one “self-help” book this year (or maybe ever), make it this one.

Buy How To Fail At Almost Everything And Still Win Big on Amazon.

Check out Scott Adams’ website.

Scott Adams also gives tremendous writing advice and the following video is well worth a watch: