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How to Fail and Win Bigly

How to Fail + Win Bigly

As a writer, and someone generally considered smart by most people, one comment I hear quite a lot is: "Oh, you're so intelligent. You must be so well-read." Or some variation thereof.

I might sometimes question how smart I really am, especially when I do something dumb, but I'm definitely not well-read.

In our society, those two things are often intertwined, and yet it always surprises people when I humbly shrug and say, "Actually, I'm really not." That admission tends to break people's brains and throw them into a state of cognitive dissonance as they try to reconstruct a worldview in which it's possible someone with as high an IQ as me could honestly make such a statement.

Usually, they just write it off as some form of modesty.

Indeed, I don't read many books. Not counting stuff I was forced to read for school, I've maybe read a dozen or two works of fiction in my life, with Tolkien, Dan Brown, and Shakespeare taking up a good chunk of that real estate. In terms of non-fiction, I've read maybe twice that amount, with most of it being some form or another of self-help.


And depending on who you ask, some of that stuff might fall into either category.

My general philosophy is that stories don't exist for their own sake, but are a way of allowing us to have vicarious experiences we wouldn't otherwise be capable of if we just lived our own lives as individuals. That these abstractions in turn provide us with moral or practical lessons to help us grow as spiritual beings in the course of transcending ourselves along a path towards godliness.

The best stories have the most timeless lessons.

Normally, I prefer to get my information in audio-visual form. It's just faster getting down to the core essence of a lesson and extract what I need that way. Case in point, between Stefan Molyneux and Sargon of Akkad alone, I've wracked up over a thousand hours in the course of two years. Again, it's just easier that way, especially if my hands and eyes are busy doing other things. I can listen to them while I work or while I'm on the road. But every once in a while, I'll still reach for a book if I feel particularly drawn to it for whatever reason.

Among that short list are three of Scott Adams' books:

  • God's Debris: A Thought Experiment

  • How to Fail at Almost Everything and Still Win Big

  • Win Bigly: Persuasion in a World Where Facts Don't Matter

I talked a little bit about the former in my first post of this blog. Having just finished reading Win Bigly last night, I figured this would be an apt time for a review of the other two.

At this point, I've been following Scott on Periscope for a little over half a year. I've also watched several of his speeches and interviews. If I had to guess, I'd say maybe a hundred, hundred-twenty hours of screen time. Again, I like audio-visual content and this medium is also interactive, meaning I have the opportunity to help steer the course of history along with him in subtle ways.

Collective works of Robert Greene

He slots in neatly alongside Godzilla and Robert Greene.

My first concern when it came to reading Scott's books was that I wouldn't get much out of it beyond what I already knew from listening to him talk. This is half-true. He does repeat a lot of the same points with regards to goals vs. systems, measuring your energy levels, visual persuasion, pacing and leading, etc. However, I was pleasantly surprised to discover there were also enough insights in both his books that - so far as I am aware - he has never shared in other forms. At least not with the general public.

I won't spoil the experience for you, but suffice to say, even Scott's most ardent followers will find their money's worth in entertainment at the least.

This brings me to the next point, which has to do with the format of the books. In both cases, I was expecting How to Fail and Win Bigly to read more like how-to guides in the manner of other self-help books I was used to. I suppose the subtitle of the former should have clued me in that How to Fail was going to be, as it says on the tin: "kind of the story of [Scott's] life."

I didn't expect this from Win Bigly, though; and as I read it, part of me lamented it being perhaps as much the opposite of a textbook as one can get.

That's not to say it was badly written by any means. Indeed, it says more about me than it does about Scott. Part of the reason I actively follow Scott is to learn those techniques of persuasion. I ate my fill of it and it still left me hungry for more, which I suppose is a good thing. It means you always have room left to grow.

In fairness to Scott, by the time I read How to Fail and Win Bigly, I was already well-versed in the material. If the books reflect his general teachings on systems and persuasion, and I had found those teachings valuable, then it stands to reason that, for someone just breaking into the subject - the anti-Trumpers in the media-political complex, for instance - then they would get the same profound value I'd gotten in a different form.

Art of the Deal, Win Bigly, What Happened

Depicted: "2016, The Movie."

Consider how you feel when you read a great book and then go see the film adaptation. It may still be a good movie objectively, but it's never really quite as good, is it? Your imagination utilizes what Scott terms "strategic ambiguity" to conjure up details, and it's often more visceral and vivid than what's on screen. That, combined with the contrast, makes the movie seem a lot worse than it would be if you watched the movie first and then read the book.

Of course, doing it that way has problems too. You still know the plot, and your image of the characters and the scenery is often biased towards looking the way it did in the film; so even then, it's never quite as impactful as raw imagination.

That was my experience only in reverse. I'd seen movie Scott in real-time. I'd watched him apply raw example after raw example. I'd listened to him break down each of the various tools and show how they worked in a variety of scenarios. So when it come to reading book Scott, I wasn't blown away, but only because I'd seen the movie already.

If you haven't seen movie Scott, though, book Scott will be a revelatory experience for you.


By this point, it may seem to you as though my engagement with Scott's books was largely negative. I want to assure you that was not the case. I thoroughly enjoyed them both, albeit more-so as a form of entertainment, since I was already familiar with the basic idea, as I mentioned. There were some new things as well, but by and large the novelty of the techniques will be experienced more-so by those not yet initiated.

During one of his Periscopes, Scott asked his followers if any of them had gotten to "the chill point" yet in Win Bigly. The chill point being the part of the book that literally gives you the chills when reading it.

I'm not sure if there's meant to be one single chill point in each book that's the same for everyone, but the chill point for me in How to Fail came during a literal chill point. By that, I mean the chapter in which Scott recounted a certain event involving a car in the dead of New York winter.

I won't spoil it for you, but those who've read the book know exactly which part I mean.

That chapter was gripping and suspenseful in the way that Frost-Nixon was. I knew what the outcome would be, obviously, because it's history; but the way he told it had me hooked in such suspension of disbelief that I actually began to wonder whether or not he'd succeed. That's the mark of a master story teller when he can make you forget what you already know, only to remember it after he's told you what he wants to tell you because you're so emotionally fixed in the moment.

As I read through that chapter, and the one about his suit on the plane, I began picturing an Oliver Stone movie unfolding in my head. His struggles with suicide touched close to home. I've mentioned before how uncannily my life's trajectory seems to mirror his in certain key ways and that was one of them, albeit not for the same reason. Just the major beats.

I felt a profound sense of sadness and empathy hearing his dealings with bullies, both in his youth and up into his adult life. Having been bullied myself as a child, I could relate.

I suppose one way in which our paths diverged is that I took up martial arts and that gave me a great deal of confidence. I don't know if he ever had that experience, though probably not.

Jui-Jitsu master

Consider adding mental and physical jiu jitsu to your talent stack.

In Win Bigly, it was largely the same pattern. Scott was the protagonist recounting his story of what happened to him during the election cycle while using that as a vehicle to teach the audience about the tools of persuasion and how Donald Trump was a Master Persuader. The chill point, for me, came when Scott was again backed into an impossible corner. The moment he describes himself as shifting from a passive observer to an active participant and finally picking a side in the culture war.

Again, those who've read it should know which point I'm referencing.

In many ways, his tale reminded me of my own election story, albeit his had much higher stakes. About as high as you can have - life, friends, fortune, reputation.

Recall that I said I value story for its utility as a vicarious experience. To entrain and prepare me to solve problems I haven't personally had to deal with, but could ultimately face down the road. Indeed, if there are any parallels in our life arcs, as I see it, his experiences call to mind a clear vision of what may yet be well into my future.

Do you want a spooky example of that?

I said before there were things in the book that, so far as I knew, he'd never shared with the general public. One of those being - and I was surprised to learn this - his claim of having visions of the future.

While it came as a shock to hear him say that, I instantly believed him, because it was an experience with which I could personally relate. You might think I'm lying or crazy. I can only tell you what I know on my end and leave you to believe me or not.


While Win Bigly is mostly centered around an analysis of Trump as a Master Persuader, Scott gives equal consideration and credit to other major political players who successfully use what he calls weapons-grade persuasion. This includes Trump's primary opponent, Hillary Clinton.

If you are a Trump supporter, or at least anti-Hillary, you might feel that giving any credit to Clinton ruins the narrative you wish to paint in your head about their respective characters. Take solace, at least, in knowing she lost in the end. Yes, you may not like Scott's praising of "the enemy," but if it makes you feel any better, it helps establish his credibility and impartiality, so that by the time he gets around to talking about Trump's tactics, you can feel good about that and trust his analysis.

Likewise, if you are a Hillary supporter, or at least an anti-Trumper, you may not like that he says good things about Trump, but he is careful to point out the bad as well and the good in others. You can rest easy knowing that he is not a partisan shill for Trump, and thus stand to gain a great deal from reading this book.

While we're on the subject, I talked earlier about the perception of modesty in my being intelligent while being unread. In his books, Scott also tends to downplay his successes. I understand why he does this. There are multiple reasons for it, in fact, from hedging his bets to not appearing arrogant.

The Dunning-Krueger Effect says that incompetent people tend to overvalue their skills, but it also says that competent people tend to undervalue them. I had a friend who often said that people are like mirrors by which you see yourself. Sometimes, it takes others to accurately measure a person's true abilities. Towards that end, given all his success over the many years, I think we should take it upon ourselves to promote Scott to the rank of Master Persuader.

Scott Adams Portrait of Inspiration

By now, I've already got you thinking past the sale on that one.

As outlined in How to Fail, Scott's path to success can be attributed - at least in part - to his deft use of systems, built upon his "talent stack," which includes in it a potent form of persuasion.

What surprised me the most about his story, however, was the sheer amount of suffering and hardship he'd been through. It really does make for a compelling character arc with plenty of conflict, both inner and outer. I still say it would make a great movie in the style of something like Steve Jobs, Snowden, The Social Network, The Wolf of Wall Street, or one of those types of biographical fictions.

Scott frequently mentions his old, rich, white male privilege on Periscope, suggesting that a lot of it comes down to luck and various factors being just right. That may be part of it, but I have an alternative hypothesis.

I know Scott says he doesn't believe in karma and reincarnation, but I do.

Indeed, I think for there to be any conception of justice, and not just complete randomness, those things would have to exist. I know that's not an argument so much as a hypothesis ... but I believe that part of the rules of this great and wondrous holographic universe we live in is that, before we incarnate, before we enter the simulation, we have a say in tweaking some of the conditions. A character creation phase, as it were. Some of those conditions we don't get to set, and that's the game, but one of the rules of the game is that bad things happen to people who were once bad, in this life or one previous. This we call karma.

Another rule is that, once your karma is cleared - once your debt is paid off - any other bad stuff that happens to you, the system will make up for eventually with something equally good. Every story needs conflict and so, I believe that, before we are born, we have a hand in deciding how and when at least some of that conflict will occur, as co-storytellers.

It's a lot like an RPG. Everyone has hardships, strengths, and weaknesses. You pick which traits to allot your points to and then play.

This is just my opinion, of course, but I think Scott may have chosen to get the hard stuff out of the way first. To pay the heavy price upfront and then reap the reward later, rather than the other way around.


If there is one other major negative criticism I could give, however, it would be that Scott needs to work on his endings. For a guy who talks loudly and often about the fact that people remember more how they feel, about the Three Act play, and about the importance of maintaining high energy levels, both books kind of fizzled out in the last chapter or two.

Every time I set down to read the guts of How to Fail and Win Bigly, I felt charged up and renewed, my limited willpower given a temporary boost. I can't say the same for the ending, which is unfortunate, really. I wanted them to end on a high note, but instead I was met with second-guessing and self-doubts and self-efficacy issues. Oh well.

I suppose it's always good to temper optimism with realism, emotion with honesty, feels with facts, and these books are as much a system for Scott as they are for the rest of us. Nobody's perfect and I'm sure it'll give him something to work on should he choose to write another book in the future.

Endings aside, there's no denying that How to Fail and Win Bigly are an essential pair for anyone looking to improve their lives and to further their understand of the world around them.

If you follow my writing, you've probably heard me overtly mention Scott many times, or at least seen me adopt his techniques - whether on this site or at Being Libertarian. Indeed, his influence and his tools of persuasion have helped me enormously. The quality of my upcoming fantasy series Thelema has likewise improved dramatically as a result of following him.

Part of Scott's ad campaign for Win Bigly was to invoke a lot of dead and / or fictional people to give celebrity endorsements, including Lord Byron claiming he'd "recommend this book to all mammals big and small. It once turned a mole into a cheetah. I saw it with my own eyes." His rationale was that jacket cover blurbs are largely made up anyway, so in this case, it was mostly for humorous effect. I found it hilarious, though I have it on the good authority of an expert on the subject that a third of the population has no sense of humor and probably won't get the joke.

If it's any consolation, that same authority has also been known to say that experts are often times wrong, so maybe it's just not their cup of tea.

Again, I'm no Lord Byron, but I would certainly recommend How to Fail and Win Bigly to all mammals big and small. I doubt they ever turned a mole into a cheetah, but who knows? Maybe there's a cheat code to the simulated universe that will unlock that ability.

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