An Irritatingly Practical Take on Scott Adams’ ‘How To Fail at Almost Everything And Still Win Big’

9781591846918_custom-550e5a01fbd83824c7be8bf5c59523b8586e2afb-s6-c30I just finished How To Fail at Everything and Still Win Big: Kind of the Story of My Life, by Scott Adams (yes, the Dilbert guy, or as I like to think about him now, the Persuasion Guy).

Since my recall isn’t perfect, I decided to share the concepts that I remember from that book–stuff I’ve already internalized and implemented to some degree. Maybe this will help you. If not, in my mind, I got invisible karma points for writing something on my site.

Insights I gleaned from the book will be in bold face, so you know what to expect.


First, systems. Goals are for losers, systems are for winners. If you have a goal such as, ‘I will lose five pounds in six months,’ that is a goal and will fail because humans have a limited supply of will power. If you can find a way to take will power out of the equation, and a way to convert your goals (‘lose weight’) into a maintainable system (‘be active every day’), you are on your way to success.

I have a number of pounds to lose for my ideal weight. But goals don’t work, and going to the gym by myself sucks. So I took will power out of the equation: I signed up for a martial arts class.

The reason this takes will power out of the equation is that it is scheduled: I know on Monday, Wednesdays, and Saturdays that that is my time to go to martial arts class.

This also adds a shame element: I know that if I’m not there, my instructor will ask where I was. If I tell him, ‘I felt lazy, so I stayed home and learned my class changes on World of Warcraft,’ that I’m going to feel ridiculous.

The other thing I know is this: when I go to class, I will feel good because I spent an hour hanging out with winners. When I see the instructors, who are black belts, demonstrating their takedown methods, I look at that and a system is formed in my mind: if I stick with this, ‘that will be me someday.’

Something that also helps is that everyone there is encouraging when I try something, no matter how bad I look doing it, so I keep my fat ass in motion, even though I look like an elephant learning ballet.

Hacking My Brain

Scott Adams calls humans ‘moist robots’: when you add an input to a computer and you will get a predictable output. If I add good food to my body, get enough sleep, and maintain a positive mindset, I will feel great and have energy. The opposite is predictable.

Another point: If I add a new skill, I double my chances of success exponentially, and luck has a greater chance of finding me. I didn’t understand this step when I first heard it, but it ‘clicked’ this morning that I was already doing part of it: reading and listening to audiobooks.


There are a number of notable books I’m reading right now: besides ‘How to Fail…’, there’s Gorilla Mindset, which also involves practical psychology, two G.K. Chesterton books on theology (Heretics and Orthodoxy), and Musicophilia, which I picked up at the library–psychology plus music equals some serious win.

All of these books I am reading will help add new skills to my life. I expect that reading and applying these principles will make me more marketable and eventually happier.

Health and Happiness

Apparently our health and happiness are intertwined. Martial arts–pushing my body to near-breaking point and building up physical and mental discipline–will certainly help. I’m also prioritizing food based on whether it makes me energized or sleepy. I was doing this to an extent before–I’ve determined protein from red meats, peanuts, and steamed broccoli help give me energy and they boost my creativity, whereas salads put me right to sleep and cause gastric distress. I don’t know what the long-term effects of a mostly-protein diet will be. I do know. however, that weaning myself off of fried foods is helping (the more you eat fried food, the more you crave it, and fried food makes me need a nap afterwards).

I now eat dark chocolate just about every day, as it’s a healthier substitute for candy, which I used to constantly crave, and Scott Adams says he eats it, so I can blame him if I feel like I need to. 😉

Of course, I’m still taking and adjusting my medicine as my doctor prescribes, in order to keep my emotions steady. If you’ve never wrestled with a panic attack or sudden-onset, non-situational depression, it’s no fun at all. I expect the need for medication will decrease over time as I become more healthy, but if not, that’s all right.


I believe this book will prove to be one of the more life-changing books I’ve read. I’ve learned quite a few practical things from it, and I expect to recall more as time progresses. Highly recommended.

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