How To Fail At Almost Everything And Still Win Big



Scott Adams created a multimillion dollar empire. That empire is more commonly known as”Dilbert.”

I mentioned him on this blog before because he gave some of the simplest, most profound advice for getting along with people that I’ve ever heard:

Be brief and say something positive.

If you’ve read Dilbert, you know Adams understands a great deal about human nature.

(Then again I probably relate more to Calvin and Hobbes than most of the western canon.)

His new book, How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life, has a number of useful insights about life.

And what’s really fascinating is they line up with a lot of the research I’ve posted about before.

Here are 5 great life lessons he gives and the research I’ve posted that backs them up:


Have A System, Not A Goal

This is such a powerful distinction. Losing 20lbs is a goal, eating right is a system. Which one do you think provides a better path to success?

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

…one should have a system instead of a goal. The system-versus-goals model can be applied to most human endeavors. In the world of dieting, losing twenty pounds is a goal, but eating right is a system. In the exercise realm, running a marathon in under four hours is a goal, but exercising daily is a system. In business, making a million dollars is a goal, but being a serial entrepreneur is a system.

A system provides a method and requires activity on a regular basis. That’s how successful people operate.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

For our purposes, let’s agree that goals are a reach-it-and-be-done situation, whereas a system is something you do on a regular basis with a reasonable expectation that doing so will get you to a better place in your life. Systems have no deadlines, and on any given day you probably can’t tell if they’re moving you in the right direction. My proposition is that if you study people who succeed, you will see that most of them follow systems, not goals…

Oliver Burkeman pointed out research that made a very similar distinction in my interview with him:

The best thing to do is to set process goals rather than outcome goals. Stop telling yourself you’re going to write the great American novel, and tell yourself you’re going to do 500 words a day. Step back from focusing on the outcome and focus on process.


Success Creates Passion More Than Passion Creates Success

Many people are passionate about things but don’t follow through. Passion is great — but it’s not everything.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

…my boss taught us that you should never make a loan to someone who is following his passion. For example, you don’t want to give money to a sports enthusiast who is starting a sports store to pursue his passion for all things sporty. That guy is a bad bet, passion and all. He’s in business for the wrong reason. My boss, who had been a commercial lender for over thirty years, said the best loan customer is one who has no passion whatsoever, just a desire to work hard at something that looks good on a spreadsheet… Passionate people who fail don’t get a chance to offer their advice to the rest of us…

Dilbert didn’t start out as a passion project. Adams describes it as another get-rich-quick scheme he had.

But once it became successful he developed passion for it.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

Dilbert started out as just one of 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 level moved with my success. Success caused passion more than passion caused success. 

This sounds a lot like what Georgetown professor Cal Newport said in our interview:

I set out to research a simple question:  How do people end up loving what they do? If you ask people, the most common answer you’ll get is, “They followed their passion.” So I went out and researched: “Is this true?” From what I found, “Follow your passion” is terrible advice… My advice is to abandon the passion mindset which asks “What does this job offer me? Am I happy with this job? Is it giving me everything I want?” Shift from that mindset to Steve Martin’s mindset, which is “What am I offering the world? How valuable am I? Am I really not that valuable? If I’m not that valuable, then I shouldn’t expect things in my working life. How can I get better?”


Focus On Energy, Not Time

Scott Adams determines what activities to engage in by his energy level. To be creative he needs peak energy, so he draws Dilbert in the morning.

By the afternoon, his brain is fuzzy. That’s a good time for busy work.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

The way I approach the problem of multiple priorities is by focusing on just one main metric: my energy. I make choices that maximize my personal energy because that makes it easier to manage all of the other priorities.

One of the most important tricks for maximizing your productivity involves matching your mental state to the task… At 6: 00 A.M. I’m a creator, and by 2: 00 P.M. I’m a copier… It’s the perfect match of my energy level with a mindless task.

How can you do this if you’re not a rich and famous cartoonist? Wake up early to work on your own projects first.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

Most people aren’t lucky enough to have a flexible schedule. I didn’t have one either for the first sixteen years of my corporate life. So I did the next best thing by going to bed early and getting up at 4: 00 A.M. to do my creative side projects. One of those projects became the sketches for Dilbert.

Sounds like my main takeaway from The Power of Full Engagement:

Energy, not time, is the fundamental currency of high performance.


Fake It Until You Make It

How do you overcome shyness? Out and out acting.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

I credit one of my college friends with teaching me the secret of overcoming shyness by imagining you are acting instead of interacting. And by that I mean literally acting. It turns out that a shy person can act like someone else more easily than he can act like himself. That makes some sense because shyness is caused by an internal feeling that you are not worthy to be in the conversation. Acting like someone else gets you out of that way of thinking. When I fake my way past my natural shyness, I like to imagine a specific confident person I know well.

And what are other tips to conversational expertise? Focus on making others feel good and act interested (even if you’re not.)

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

Your job as a conversationalist is to keep asking questions and keep looking for something you have in common with the stranger, or something that interests you enough to wade into the topic… The point of conversation is to make the other person feel good.

So how do you get a stranger to like you? It’s simple, actually. It starts by smiling and keeping your body language open. After that, just ask questions and listen as if you cared, all the while looking for common interests. Everyone likes to talk about his or her own life, and everyone appreciates a sympathetic listener. Eventually, if you discover some common interests, you’ll feel a connection without any effort.

And scientific research on “fake it until you make it” agrees.

In this TED talk, Harvard professor Amy Cuddy explains her research on how acting powerful can make us feel powerful:

In The As If Principle, Richard Wiseman shows how your actions might determine your feelings.

Researchers told people to smile. What happened? They felt happier.

Via The As If Principle: The Radically New Approach to Changing Your Life:

More than 26,000 people responded. All of the participants were randomly assigned to one of a handful of groups and asked to carry out various exercises designed to make them happier… When it came to increasing happiness, those altering their facial expressions came out on top of the class— powerful evidence that the As If principle can generate emotions outside the laboratory and that such feelings are long-lasting and powerful.



Increase Your Happy Thoughts Ratio

Good things happen to all of us all the time. But we often fail to keep them “top of mind” and to appreciate them.

Scott Adams recommends making an effort to increase the number of times you think about the positive things.

Via How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life:

A simple trick you might try involves increasing your ratio of happy thoughts to disturbing thoughts.

This lines up perfectly with Seligman’s 3 blessings exercise — the most powerful happiness booster out there.

Via Flourish: A Visionary New Understanding of Happiness and Well-being:

Every night for the next week, set aside ten minutes before you go to sleep. Write down three things that went well today and why they went wellWriting about why the positive events in your life happened may seem awkward at first, but please stick with it for one week. It will get easier. The odds are that you will be less depressed, happier, and addicted to this exercise six months from now.

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