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

Almost everyone who has ever lived has asked “what are the secrets to success?” Most people probably don’t envision asking that question to a cartoonist, even if the cartoonist in question is by any reasonable measure a successful person. Most people ask that question to titans of industry, athletes, or actors. The answers usually center around trite responses like “pursue your passion and work really hard at it and never give up.” It’s these trite answers that Dilbert creator Scott Adams can’t stand, and ironically it’s the satirical cartoonist that  provides the most serious, thoughtful answers to the elusive question of “what are the secrets to success?” that I’ve ever read anywhere, and he does it in a humorous, lighthearted way, complete with some Dilbert panels in the book.

Throughout How to Fail at Almost Everything and Still Win Big, Scott Adams calls himself “your smart(ish) friend,” and that tone carries on throughout the book. He’s more a companion than a lecturer, and you don’t feel that any concept that he explains is out of reach.

How to Fail at Almost Everything and Still Win Big Scott Adams review

The major takeaways that you’ll find in How to Fail at Almost Everything and Still Win Big are…

  1. “Passion” is bullshit, but you should measure your activities by your energy.
  2. Goals are for losers. Winners build their lives around systems.
  3. Any effort based only on human willpower is doomed to eventually fail.
  4. Success is most often based on luck, but you can make luck easier to find you by building a skill set.
  5. Everyone fails. A lot. The most successful people just fail the most and look for ways to profit from it.
  6. People aren’t magic bags with magic thoughts. Instead we are moist robots that can program ourselves in the ways we want (in essence, we have cyberbrains).

Don’t Listen to “Passion” Peddlers

Although you can find opportunities in more things than you might expect, if “passion” was the key to success, all “passionate” people would be successful. Additionally, “passion” is too nebulous to be a useful metric. What if you’re “passionate” about putting together radios, or even computers? That “passion” by itself isn’t going to make you successful because that’s not where the market is heading.

A few years ago, I started a website based on military history, because studying that has been one of my “passions” since I was a teenager. I ignored a lot of factors. I wanted it to be a community-based blog like Return of Kings, but I had no group of people to start it with. So that struck the most unique aspect of the idea down from the start, and it’s not like there aren’t a lot of other community-based blogs on the subject throughout the web anyway. I had a forum too, but there’s a lot of those also, and forums don’t usually succeed unless you have a good core of users to start them off with (even then they often die). In short, the blog was basically a zombie for its entire two years of operation. Because of my OBD contacts, I had some core of users to start the forum off with, but with the OBD fully functional, why was there a need for an alternative? The forum dwindled slowly until it died entirely about a year in, which is in all respects fairly good for a startup forum.

So I pursued “a passion” and it didn’t work out. Surprise, surprise. Fortunately it wasn’t my primary thing and it didn’t cost me too much money. Scott Adams has this to say about the “passion” metric:

When I invested in a restaurant with an operating partner, my passion was sky-high. And on day one, when there was a line of customers down the block, I was even more passionate. In later years, as the business got pummeled, my passion evolved into frustration and annoyance. The passion disappeared.

On the other hand, Dilbert started out as just one of the many get-rich schemes I was willing to try. When it started to look as if it might be a success, my passion for cartooning increased because I realized it could be my golden ticket. In hindsight, it looks as if the projects I was most passionate about were also the ones that worked. But objectively, my passion moved with my success. Success caused passion more than passion caused success.

My short-lived blog on military history reflected this perfectly. In the planning stages I was plenty passionate when I began to think of the possibilities. As the grind and shortcomings became apparent, I lost passion to the point that I didn’t do anything with it for months, just waiting for the expiration date to come. Even my stewardship of the OBD Wiki, a seemingly hidden opportunity, would certainly be ill-advised on my part if I wanted to start it from scratch. You’ll see more on this below.

Passion is bullshit

Passion vs. Energy

While “passion” is bullshit, in How to Fail at Almost Everything and Still Win Big, Scott Adams advises you to measure your exertions and activities by their effects on your energy. You should move toward the things that give you the most energy and do them at the appropriate time, while doing more menial work in lower-energy states. This leaves you the best and most personally fulfilling way to manage your time.

One of the most important tricks for maximizing your productivity involves matching your mental state to the task. For example, when I first wake up, my brain is relaxed and creative. The thought of writing a comic is fun, and it’s relatively easy because my brain is in exactly the right mode for that task. I know from experience that trying to be creative in the midafternoon is a waste of time. By 2:00 P.M. all I can do is regurgitate the ideas I’ve seen elsewhere. By 6:00 A.M. I’m a creator, and by 2:00 P.M., I’m a copier.

Scott Adams mentions that most writers are this way, and I’m no exception. While I can be creative at any time, I’m far more energized in the morning, where I want to go out and do other things like socializing in the afternoon. Unconsciously, I have been following this advice for years. Indeed, when I was working on the bulk of my epic novel, most of it was written from the morning to the early part of the afternoon.

Eventually you’ll get the hang of scheduling your day around what your energy tells you.

Goals are for Losers, Systems are For Winners (and a note on Willpower)

We’re often told to set goals and go achieve them. This is better than staying idle, certainly, but how many more people set a goal, don’t get to it, and then give up and start to feel shitty about themselves? Think about all those New Year’s Resolutions that don’t get taken seriously past the first few weeks and you’ll have a perfect example. A lot of people set goals and don’t ever get close. Wouldn’t it instead be better to develop a system – a series of behaviors and skills that make accomplishing things more likely by virtue of what you do every day so it doesn’t feel like a strain?

For instance, a few years ago, I said to myself “I want to finish writing this epic war story of mine!” I started off strong but…you guessed it, as time went on my productivity got less and less. Then it languished with little activity for four years. When I picked it up again, I eventually got around to writing a page an hour for every hour I was home (more or less).

That was a system, and it allowed me to complete the book in a year, with a few months of very intensive work.

On the systems vs. goals distinction:

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. If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.

Importantly, your system should be combined with reducing the reliance on willpower to the lowest extent possible. As Scott Adams remarks many times in How to Fail at Almost Everything and Still Win Big, human willpower is limited and will eventually cap out at some point, at which time it won’t be available to resist other temptations. Because of this, any attempt to base your activities or aspirations on your willpower is doomed to fail, no matter how high you think it is. The important part is to reduce it by developing systems that don’t rely on it. Scott Adams goes into particular detail on this in the diet and exercise chapters of How to Fail at Almost Everything and Still Win Big.

Willpower limited supply

Luck or Skill?

How important is luck? Unfortunately, luck matters a lot more than we want to think. Scott Adams goes into great detail about how a series of very unlikely events coincided to launch Dilbert. I have my own experience with this too. The OBD Wiki gets a lot of traffic and has ample potential as a growing media empire. That multiple advertisers have contacted me over the past couple of years is proof of that. Yet, it would be foolish of me to launch such a thing from scratch. It’s been established for a long time now (long before I arrived there), and I was lucky enough to have been granted administrative powers and then full control over it. For this to happen, a whole series of coincidences aligned:

  1. I began a show a while back in the same genre.
  2. I used a Wikispaces platform to store information on the show.
  3. One of the admins of the OBD Wiki (then on Wikispaces itself) had to take a step back, opening up a spot.
  4. People recommended me to step in as admin.
  5. People knew I already ran a Wikispaces site, increasing my chances.
  6. The other guy in question didn’t seriously want the job.

And then even more stuff happened:

  1. Wikispaces got anal and gave us shit.
  2. They eventually took us down.

That caused me to launch the site on its own, no longer a digital sharecropper, opening new opportunities.

So yeah, that’s a lot of things that came together, much of it beyond my control. This seems to suggest that success is a lot, if not most parts luck.

However, take heart! It is possible for us all to go from “strategies with bad odds to strategies with good odds,” as Scott Adams remarks. Unknowingly at the time, my own Wikispaces database gave me good odds to profit from the situation that did occur. I also needed to have an established reputation and trust from the OBD members, which took a year of debating well and befriending people (an important skill to learn).

This is just a small microcosm, but the point is you can learn skills that will put you on the path to success, as they will make luck far likelier to find you. In How to Fail at Almost Everything and Still Win Big, Scott Adams introduces you to a panoply of skills that will reduce your competition drastically and thus increase your odds big league. A few of these skills are…

  1. Persuasion
  2. Psychology
  3. Public speaking
  4. Technology (hobby level)
  5. More

When going back to the story of the OBD Wiki, we can see where technology helped me a lot. I learned how to start building a real website (as opposed to a free digital sharecropping arrangement) when I began my ill-fated military history community blog. That didn’t work out, but through that failure, I was able to pick up a skill and familiarize myself with website design and management to enough of an extent that I could build up the OBD Wiki, and thus the base of a new, far more successful community was forged on the ash heap of one failure.

This is just a small example of how you fail toward success. Unknown to me, I was following the Scott Adams playbook for a long time before I read How to Fail at Almost Everything and Still Win Big.

Learn How to Fail Toward Success

Scott Adams describes himself as your smart(ish) friend throughout How to Fail at Almost Everything and Still Win Big, but he’s a lot more than that, or the Dilbert cartoonist, or that guy who’s been blogging about Donald Trump. He’s something of a sage in his own strange and humorous way, inviting you to explore the world in ways you haven’t ever thought of, all the while changing your perspective so that you can adopt new behaviors designed to bring you better odds of succeeding. How to Fail At Almost Everything and Still Win Big isn’t a pop-psy self-help book, but a practical and easy to implement guide on molding your character through mental framing and everyday behavioral changes to make yourself the best you.

The choice lies with you.

Make that choice now.