How To Fail At Almost Everything And Still Win Big

How To Fail At Almost Everything And Still Win Big
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Systems are better than goals.

That idea—systems being superior to goals—stuck with me most after reading Scott Adams’ somewhat autobiographical book on how to achieve success. That’s not to say the book lacked other ideas. Actually, How to Fail at Almost Everything and Still Win Big is probably one of the most helpful self-help books I’ve read (okay, it’s not technically “self-help”—the inside flap classifies it under “Biography”, “Vocational Guidance” and “Motivation”—I just couldn’t resist the wordplay of the above sentence).

The book is not a strict autobiography or success primer. Rather, Adams mixes autobiographical antidotes with his observations on successful traits and habits. The framing device he uses to piece his points together is his struggles with a rare vocal disorder. The book starts with his voice problems, followed by periodic “updates” between chapters, concluding with powerful denouement. I’m not going to give away details, but I will say that Adams is quite the storyteller (maybe the confines of newspaper strip cartooning forces one to distill narrative to its essence?).

In case you don’t know, Scott Adams is best known as the creator of Dilbert. He also maintains an excellent blog where he talks about persuasion, creativity and start-ups. He’s also one of the few who accurately predicted Donald Trump would win. But we’re not here to discuss politics…

I remember in the mid-90s when the local newspaper first started printing the Dilbert comic strips. I was just a teenager, I didn’t read the funny pages, but my parents did. Every morning, preparing for school, I saw my mom laughing at the latest strip and reading it out loud to my dad. Since my dad had just left office work and my mom had just started it provided a common source for laughter. When I visited my mom’s office, there would be all sorts of strips posted to the cubicle walls—most of them from Dilbert. Actually, it was common to find Adams’ strips posted at most offices I walked in to.

Interestingly enough, Adams notes that Dilbert did not originally focus only on the workplace. Using the feedback he received from readers (by posting his email address on his strips—one of the first to do that) he pivoted to concentrating on office humor. Adams is not precious about his “art”. He sees himself as an entrepreneur rather than artist. That decision, that mindset, to meet reader demand, helped him achieve success and his work being posted on many a cubicle wall.

But that was not the only thing that made Adams successful. He experienced a ton of failure (and still does). He thinks that if you learn to fail, and fail quickly, you can use the lessons learned to build a talent stack for future success. The trick is, one can’t take big risks. Years ago, I quit my job because I thought I was about to become a successful screenwriter and it almost bankrupted me. In fact, it made me risk averse for a while. That was a BIG mistake. Adams advises that one shouldn’t take huge risks like that. What does he advise?

He advises systems over goals.

Back to the screenwriting thing. My mistake was I envisioned an endgame of big multi-million movie contract. Before writing, I would constantly talk about wanting to be a movie director. But there was a problem. I never made any movies (my friend even bought me a camera—which I never used). I just kept thinking of my big Hollywood debut. I kept hearing the advice of “You should just make little home movies then you will eventually get to bigger and bigger movies,” but I didn’t want to believe. Sounded like too much work. In retrospect, it obviously wasn’t for me. I had a pie-in-the-sky goal, but no way to get there. However, inadvertently, I was writing on a daily basis. This was a proto-system. I would write until I finished my screenplay, then take a long break. I would then return, revise and then try to get my screenplay read by producers, sit around waiting for them to get back to me, all the while doing nothing except dreaming. It’s easy to see this ended in failure.

Instead what I should have done—and do now with my current writing—is just write. Everyday. Write something. There doesn’t need to be a particular endgame, in fact, there shouldn’t be. The journey should be more important than the destination. This way, you have less to lose, and you learn a lot along the way. Now, what if one is writing a novel like I have? Isn’t finshing/publishing the novel a goal? Maybe. Writing it though should be a system. Write at least 1000 words, everyday. Once done the first draft, one should keep writing (whether it’s blogging, short stories or tweeting), until the novel has had time to “sit” then you start a new system of editing/re-writing. But even after the novel is in the can, and you’re waiting for your cover or you’ve submitted it to agents (which I advise against), you should still be writing. Writing is the system. Novels, blog posts, multiple tweets, are just byproducts.

Adams phrases it very succinctly: “Goals are for losers”. Can’t say I disagree. In both writing and weight-loss, I’ve found that an arbitrary goal, once reached, will create a sense of inertia. Once said goal is reached, you will just stand around and ask “now what?” It reminds me of an anecdote I heard about film director Akira Kurosawa: When asked about what’s his favorite movie (that he made), he would always reply, “The next one.” Kurosawa had a system. Even during the long stretches in-between movies, he would be writing scripts and doing storyboards—that is a system.

What are some of the other takeaways from Adams’ book. Since he teased them at the beginning, I’ll list them here:

  1. Goals are for losers (covered above)
  2. Your mind isn’t magic. It’s a moist computer you can program.
  3. The most important metric to track is your personal energy.
  4. Every skill you acquire doubles your odds for success.
  5. Happiness is health plus freedom.
  6. Luck can be managed, sort of.
  7. Conquer shyness by being a huge phony (sort of).
  8. Fitness is the lever that moves the world.
  9. Simplicity transforms ordinary in to amazing.


Lastly, I want to cover affirmations. This is something I’ve started since reading the book. Adams had years of failure before Dilbert got picked up by a syndicator. Along with his system of cartooning on a daily basis, he would write the affirmation “I will be a successful cartoonist” multiple times. Now, I write “I will be a successful novelist” multiple times (not daily but at least weekly). What does that do? The moist computer that is my mind asks “What have you done today to become a successful novelist?”

It’s the reason why you’re reading this blog, reading this post and it’s hopefully the reason you will be seeing my novel very soon.