How to Fail at Almost Everything and Still Win Big

Cognitive Bias

We know Scott Adams from his popular comic strip Dilbert, which follows the experiences of a cubicle-bound engineer working for an unreasonable boss at a nameless company. The recent collection Go Add Value Someplace Else is a classic, and like previous ones is based on Adams' own experience working in corporate America.

As he says in a book that has the kind of story of my life as subtitle, How to Fail at Almost Everything and Still Win Big, Scott Adams has failed at a lot of things — from investments to inventions to computer programming. But he managed to turn his failure at office work into a giant success. 

Along with his story are some points that challenge conventional advice. 

Goals are for losers. Systems are for winners.

Systems are better because they help us with a method for doing something, while goals are temporary.

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

The distinction between systems and goals extends to most of our activities. 

“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.”

Plus a system supports activities over time and thus helps us sustain regular effort. 

“Passion” is bull. What we need is personal energy.

Which is why it's important to learn to make trade-offs for performance.

“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”

Success creates success and thus passion more than the other way around. 

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 am to do my creative side projects. One of those projects became the sketches for Dilbert.

In an HBR interview, Adams explains how he incorporated a lot of feedback from readers as he developed the strip and the role of luck in his success:

Dilbert was one of the few successful comics to break out in its era, and I would say that at least half of that had to do with my business training. The other half was just pure luck and being in the right place at the right time. Let me give you a specific example.

When the comic strip first came out, it showed Dilbert in a variety of settings—not just the office. I didn’t really know what was working, because I had no direct contact with readers. In an MBA program, you learn that you need a direct channel to your customers for feedback. So way back at the dawn of the internet, I started putting my e-mail address in the margin of the strip. I received hundreds of messages a day, and I found out that there was a common theme: People loved it when Dilbert was in the office, and they liked it a lot less when he was at home or just hanging around.

So Dilbert became an office-based comic, and that change made it all work. Since then, as it got bigger, and managing the Dilbert empire—everything from the contract negotiations to calculating the cash flow for various business interests—became more involved, almost every bit of the education I got at Berkeley was useful.

We should explore lots of ideas and get feedback, systematically. With this part of the story, Adams also demonstrates the importance of choosing an opportunity for which one has some sort of inherent advantage rather than blindly prescribing we can do whatever we want.

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.

In 1995, Adams has a web site for his comic strip, better to edge one's bets while waiting to get published. His digital strategy paid off. As he says in the HBR interview:

It’s funny to think back to those early days of the internet, when people didn’t know how things were going to play out. Originally, my website was kind of a backdoor marketing plan, because it’s really hard to sell into newspapers. They usually have to fire a cartoonist to get a new one, and they don’t like to do that because people complain. So it’s hard to sway an editor.

I thought we could get people excited on the internet, and then we could gather letters from people who said, “Hey, I like this,” and bunch them up and hand them to the salespeople to take to the editors and say,

“Look, people already like this thing, so there’s no risk.” And it turns out that’s exactly what happened. We got hundreds and hundreds of positive e-mails, and the sales guys literally spread them out on the desks of the editors, who said, “OK, I get this, let’s start running Dilbert.”

We all wrestle with multiple priorities. Focusing on energy allows us to design our lives in a way that works for us. In How to Fail at Almost Everything and Still Win Big, Adams says:

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 6:00am I’m a creator, and by 2:00pm I’m a copier […] It’s the perfect match of my energy level with a mindless task.

Becoming better conversationalists

We can change other people's perception of us — body language affects how others see us and how we see ourselves. Social psychologist Amy Cuddy says we should fake it until we make it. This comes in handy for those of us who are more introverted. In How to Fail at Almost Everything and Still Win Big, Scott Adams says:

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.

That includes injecting more smiles into our voice during phone calls and other life situations. Conversation is an excellent opportunity to exercise active listening skills.

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.”

The point of conversation is to make the other person feel heard. Timing and luck play a role in our success, but we should also do enough things and experiment enough so that we improve our odds.

How to Fail at Almost Everything and Still Win Big is a candid reflection on the highs and lows of Scott Adams' career, his continued experimentation and the tenacity that led to his success.

Adams explains the back story of his Dilbert character and the book.


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