How to Fail at Almost Everything and Still Win Big

Scott Adams, the famous creator of Dilbert, has made a very good living by understanding and revealing human psychology. In How to Fail at Almost Everything and Still Win Big, Adams shares “the strategy he has used since he was a teen to invite failure in, embrace it, then pick its pocket.”

Among the unlikely truths he offers, you’ll discover that goals are for losers, passion is bullshit, and mediocre skills can make you valuable.

This is a story of one person’s unlikely success within the context of scores of embarrassing failures. Was my eventual success primarily a result of talent, luck, hard work, or an accidental just-right balance of each? All I know for sure is that I pursued a conscious strategy of managing my opportunities in a way that would make it easier for luck to find me.

Similar to the 10 things I took away from reading The Everything Store, here are 10 things I took away ‘from the Adams book.’

1. Do Creative Work First

In the morning, he is a creator, in the afternoon he’s a copier. Mindless tasks go later in the day. This is the single biggest change you can make to improve your odds of success.

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.

Mark McGuinness writes the same thing in Manage Your Day-to-Day.

2. On Expecting People to Be Reasonable

This sounds like you or someone you know. Trust me.

If your view of the world is that people use reason for their important decisions, you are setting yourself up for a life of frustration and confusion. You’ll find yourself continually debating people and never winning except in your own mind. Few things are as destructive and limiting as a worldview that assumes people are mostly rational.

3. The Most Important Form of Selfishness

We’re taught that being selfish is bad, but it all depends on how you look at it. Being selfish can be good.

The most important form of selfishness involves spending time on your fitness, eating right, pursuing your career, and still spending quality time with your family and friends.

You can’t be generous to others if you’re not in a good place. Adams argues that once your needs are met, you can focus on the needs of others.

4. Withholding Praise is Immoral

While I’ve long thought that organizational feedback systems were broken, I had never really thought about it in this way before.

Children are accustomed to a continual stream of criticisms and praise, but adults can go weeks without a compliment while enduring criticism both at work and at home. Adults are starved for a kind word. When you understand the power of honest praise (as opposed to bullshitting, flattery, and sucking up), you realize that withholding it borders on immoral. If you see something that impresses you, a decent respect to humanity insists you voice your praise.

5. Don’t Read the News for Truth

As a long-time subscriber to the physical newspaper, I cut the cord in July 2013. I’ll have more to say on this later, but I like reading other people’s reasoning for reading or not reading papers. Some people argue we’re heading back to Yellow Journalism, a time when papers try to get attention however they can. Others argue it’s a waste of time. Adams argues that it broadens his exposure.

I don’t read the news to find truth, as that would be a foolish waste of time. I read the news to broaden my exposure to new topics and patterns that make my brain more efficient in general and to enjoy myself, because learning interesting things increases my energy and makes me feel optimistic.

6. Fake it Till you Make it

Another manifestation of what we think influences what we do but what we do influences what we think. This is, at its core, the finding of the Stanford prison experiment.

[W]e are designed to become in reality however we act. We fake it until it becomes real. Our core personality doesn’t change, but we quickly adopt the mannerisms and skills associated with our new status and position.

In addition to this, we see ourselves as part of a new group and accordingly identify ourselves “with the other members and take on some of the characteristics of the group.” This is one of the reasons why sometimes people change when they get promoted.

This is also why if you’re having a crappy day, you should find some reason to smile. It actually does make you happier.

7. Change Your Mind

The ability to change your mind is probably one of the best life skills you can ever hope to develop.

[Y]ou shouldn’t hesitate to modify your perceptions to whatever makes you happy, because you’re probably wrong about the underlying nature of reality anyway.

8. Systems Trump Goals

This was fascinating. I’ve long thought that the balance of organizational thinking towards goals versus systems needs some reflection.

Adams has looked for examples of people who use systems versus those who use goals. In most cases, he’s discovered that people using systems do better, and they are more innovative. “The systems-driven people have found a way to look at the familiar in new and more useful ways,” he says in the WSJ.

If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.

[O]ne should have a system instead of a goal. The system-versus-goals model can be applied to most human endeavours. 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.

Goal-oriented people exist in a state of continuous pre-success failure at best, and permanent failure at worst if things never work out. Systems people succeed every time they apply their systems, in the sense that they did what they intended to do. The goals people are fighting the feeling of discouragement at each turn. The systems people are feeling good every time they apply their system. That’s a big difference in terms of maintaining your personal energy in the right direction. …

Goal-oriented people mostly fail. If your goal is to lose 20 pounds, you will constantly think that you are not at your goal until you reach it. If you fall short, you’re still a failure. The only way to reach your goal is to lose 20 pounds. It’s a state of near-perpetual failure.

What you really want is a system that increases your odds of success. Even if that system only improves the odds a little it adds up over a long life. In organizations, this means, for example, you should care more about the process by which you make decisions than analysis. It also means that you should focus on building a system that evolves, improves, and survives ego. Systems increase the odds of getting lucky. Or, if you want to put it another way, they reduce stupidity.

Goal seekers optimize, whereas systems thinkers simplify.

9. Psychology Matters

Understanding psychology is key. This is why Influence: The Psychology of Persuasion is one of the books I think everyone should read before they turn 30.

On a scale of one to ten, the importance of understanding psychology is a solid ten.

10. Consider How You Look

Realistically, most people have poor filters for sorting truth from fiction, and there’s no objective way to know if you’re particularly good at it or not. Consider the people who routinely disagree with you. See how confident they look while being dead wrong? That’s exactly how you look to them.

How to Fail at Almost Everything and Still Win Big warrants a look.