Lessons for life from the creator of Dilbert

Short lessons from Scott Adams's fun book How to Fail at Almost Everything and still win big

October 04, 2021 · 7 mins read

I am a big fan of Dilbert, so when I got the chance to read Scott Adam’s How to fail at almost everything and still win big, I jumped on the opportunity. It is an entertaining book that packs a number of life lessons in 250 pages. I have been constantly thinking about some of these and in this post I will post my favorite takeaways that absolutely punched me in the face.

Bullshit detection

I love how the book begins with Scott explaining his bullshit detection system. He invites us to use the system (or develop one of our own) to call bullshit on anything in the book that fails to pass the system. His system is a fairly intuitive one. You generally rely upon the following to form a belief or a hypothesis

1. Your own personal experience
2. Scientific studies
3. Friends experience
4. Common sense
5. Experts

If you find any three of these disagreeing with the theory consistently then it’s probably bullshit. As an example, suppose someone comes to you with a theory that chocolate pudding makes people lose weight and you know someone who is not seeing it play out that way (no 3) and scientific studies linking sugar to obesity (no 2) and also common sense (no 4), you can safely file it away as BS.

Goals vs Systems

Scott says, quite blatantly, that goals are for losers and systems are for winners. Having a goal makes you feel less every day until you hit that goal or drop it completely. Having a system to continuously improve yourself on the other hand, helps you grow regularly. He argues that luck plays such a crucial role in success and happiness that it is almost imperative to have a system (or systems) that continuously improve your odds of letting luck find you.

Optimize for your personal energy

In short, do whatever makes you feel energetic. Make tradeoffs so you pick things that leave you energised so you can contribute more wholeheartedly in the long run. It is ok to be selfish in the short term so you can be of more value in the long run.

Good + Good > Excellent

Instead of seeking excellence in one field, seek more breadth of exposure and becoming good enough in multiple fields. This idea is quite controversial and in line with what was discussed in breadth vs depth in the book Range. There are many proponents of the 10000 hours of expertise driven practice vs focussing on becoming proficient in multiple areas. Scott obviously favors the range method. He suggests that becoming good is a habit and once you taste victory in one field, it generally spills over to other and then makes you more likely to call upon your good-enough skills as necessary, to increase your chances of success.

Understand the odds in life

Life is math. There odds in anything we do. Ranging from making certain shots in tennis to succeeding in your startup. Being able to spot the hidden odds and making decisions accounting for them, increases our chances of success in the long run. Life has patterns and we should be open to spotting and following them. There is a lot to rules of associations. We’ve all heard examples of people getting richer by being around rich people and fitter by being around fit ones. We heard them because they are patterns. They are not necessarily causal but there is definite correlation there and that is a pattern one must not ignore.

Dilbert edition https://dilbert.com/strip/2012-04-06

Happiness is directional

To constantly feel happy and satisfied, we don’t need to crush every single work day or win at everything we do. Our happiness comes from walking in the right direction. In that sense this is inline with systems v goals. If you want to lose weight and you adopt a healthy eating and exercising regime then everyday you make progress, you gain happiness. I, as a startup founder, can vouch for this. Tiny subscription payments coming in multiple times a day provide small doses of dopamine triggered rush that make for an overall happy work day.

Brain is a programmable computer

We can fake our narratives by imagining things. Fake it till you make it works well for our minds. Imagining getting great at a sport or being able to work in the job you want, immensely increases our odds of getting there or at least preparing for it mentally. Getting used to success in a completely unrelated field like getting good at a board game or hobby makes you accustomed to success and it spurs you on. The first step to changing oneself is to realise that it is possible to program oneself to like or dislike anything. A lot more has been discussed in specialised books about changing oneself and adopting good habits.

Power of affirmations

This is perhaps the less convincing part of the book and for me it did not pass my BS detection system but it did intrigue me enough into trying it out. I will post my results of trying out affirmations may be after a few months. Scott claims that his becoming a cartoonist and subsequently owning restaurants and becoming a successful person was linked to him saying to himself that he will become those things. He did not know how, nor did he think about how, he simply kept repeating to himself he will and that along with other systems he adopted made him.


I run a startup called Harmonize. We are hiring and if you’re looking for an exciting startup journey, please write to jobs@harmonizehq.com. Apart from this blog, I tweet about startup life and practical wisdom in books.