How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life (8 page)

(Update: Our dinner and movie followed my simple plan and worked flawlessly. Shelly took the night off from optimizing. My prediction of optimized mayhem did not come to pass. Imagining what might have gone wrong makes me look like more of a jerk than usual, which is funny, so I decided to leave this chapter intact.)

I have a bias for simplification, but surely there are situations in which optimizing is the better play. So how do you know which approach works best in a given situation?

If the situation involves communication with others, simplification is almost always the right answer. If the task is something you can do all by yourself, or with a partner who is on your wavelength, optimizing might be a better path if you can control most variables in the situation. And realistically, sometimes you simply have to get three hours of tasks completed in two hours, so we don’t always have the luxury of being able to choose simple paths.

I prefer simplicity whenever I’m choosing a
system
to use. People can follow simple systems better than complicated ones. I’ll give you
some examples of that in later chapters about fitness and diet. The most optimized diet plan or fitness plan will also be the most complicated. But few people have enough willpower in reserve to follow complicated plans.

If you can’t tell whether a simple plan or a complicated one will be the best, choose the simple one. If it’s a coin toss, you might as well do whatever is easiest.

If the cost of failure is high, simple tasks are the best because they are easier to manage and control. Missing a dinner reservation isn’t the end of the world, so doing some optimizing in that case is defensible. But if you are driving to an important business meeting, you don’t want to pile on some errands that are “on the way,” because that introduces unwanted stress and uncertainty.

In my career I’ve always felt that my knack for simplicity was a sort of superpower. For example, when I draw
Dilbert
I include little or no background art in most panels, and when I do, it’s usually simple. That’s a gigantic time-saver. I assume that other cartoonists retire early at least in part because they are optimizers, and that level of energy can be hard to sustain in the long run.

No one reads
Dilbert
comics for the artwork. I have the luxury of being able to do simple drawings directly on the computer using a Wacom Cintiq device (a computer screen on which you can draw). I type the dialogue using a special font I created of my handwriting. Over the years I have streamlined the system to the point where I can bang out a comic in about an hour if I need to, although I usually take longer.
Dilbert
was designed from the start to be simple to create, and I continue to streamline the process. That simplicity has paid off big-time because it frees me to blog, write books, do interesting side projects, and still enjoy life.

Optimizing is often the strategy of people who have specific goals and feel the need to do everything in their power to achieve them. Simplifying is generally the strategy of people who view the world in terms of systems. The best systems are simple, and for good reason. Complicated systems have more opportunities for failure. Human nature is such that we’re good at following simple systems and not so good at following complicated systems.

Simple systems are probably the best way to achieve success. Once you have success, optimizing begins to have more value. Successful people and successful businesses have the luxury of being able to optimize
toward perfection over time. Start-ups often do better by slapping together something that is 80 percent good and seeing how the public responds. There’s time to improve things later if the market cares about the product.

Another big advantage of simplification is that it frees up time, and time is one of your most valuable resources in the world. If you give an ant infinite time, it can move a mountain all by itself. In my case, I can run the equivalent of three separate careers (cartoonist, author, entrepreneur) in the same forty-hour week that would normally accommodate one job.

Simplification frees up energy, making everything else you do just a little bit easier. That’s a huge deal. You don’t want your job interview to go poorly because on the way to the interview you completed four complicated errands that turned you into a ball of stress. When you are trying to decide between optimizing and simplifying, think of your entire day, not the handful of tasks in question. In other words, maximize your personal energy, not the number of tasks.

As I mentioned earlier, we don’t always have the option of choosing simplicity, especially if we have a thousand things to complete in a day, as Shelly often does. But it’s a good idea to have an overarching plan to move toward simple systems as opportunities allow. You can chip away at the complexity of your life over time. Simplicity is a worthy long-term goal. That’s how you will free your personal energy so you can concentrate it where you need it.

Your brain takes some of its cues from what your body is doing. My experience is that when I sit in a position I associate with relaxation, such as slumping on the couch, my brain will start the lazy relaxation subroutine. But if I sit with good posture, both feet on the floor, it seems that my body signals to my brain that it’s time to concentrate on work.

Consistency might be more important than the specific position you choose. If you train yourself to do deep concentration when sitting on the couch with your laptop, that might become a good place for you to work. Just don’t make the mistake of using the same sitting position for work that you use for relaxation. If the couch is where
you like to nap or watch television, it will probably be a poor place for doing serious work.

Sleep experts will tell you that the worst place to watch television is in bed. If you do it often enough, you won’t be able to fall asleep without watching television first. Watching a thought-provoking or emotion-grabbing television show is a bad way to relax into your evening snooze. A better approach is to use your bed for sex and sleeping and nothing else.
¹
,
²

Likewise, it’s a good idea to dedicate certain sitting positions and certain work spaces to work and other spaces to relaxation or play. That makes your physical environment a sort of user interface for your brain, and it becomes a way to manipulate your energy levels and concentration. To change how you feel, and how you think, you can simply change where you are sitting.

This is the sort of idea you’re likely to dismiss as unimportant unless you try it yourself for an extended time. In my experience, the way I sit makes a huge difference to my productivity.

Tidiness is a personal preference, but it also has an impact on your energy. Every second you look at a messy room and think about fixing it is a distraction from your more important thoughts.

I realize that clutter and messiness don’t affect everyone the same way. Some people need to have things just right and others don’t seem to mind living in chaos. My experience is that after straightening up my office and working through the piles of miscellaneous tasks, I feel more clearheaded and energetic. I don’t assume my experience is universal, but the cause and effect in my case is so strong that I do recommend you experiment with it. All you need to do is pay attention to how you feel after you have tidied up your work space compared with how you felt when it was a mess.

Cleaning and organizing your space is boring work, and you might never see it as a priority. One trick I’ve learned is that I automatically generate enthusiasm about tidying up if I know someone is stopping by. That’s why it’s a good idea to invite people over on a regular basis. It will inspire you to keep your space straightened up, and that might in turn cause your mind to have a bit more energy.

One
of the biggest obstacles to success—and a real energy killer—is the fear that you don’t know how to do the stuff that your ideal career plans would require. For example, you might have a terrific idea for a small business, but you don’t know how to get a fictitious name, how to do your accounting, how to build a Web site, how to outsource work to China, and so on. When you don’t know anything about a particular topic, it’s easy to assume it would be too hard to learn it quickly. I run into that all the time, and I’ve developed a few tricks and work-arounds you might find helpful.

When my first editor of comics called to offer me a contract for newspaper syndication, I quickly said yes, but I secretly worried that I didn’t know how to do the coloring for the Sunday comics. I was in awe of the established cartoonists, who seemed to color within the lines so perfectly. And what tools did they use? Were they using special marker pens or watercolors? Why was the color in the newspaper so perfect? I was panicked that I didn’t know the basic tools of my own chosen profession. And I didn’t think I could learn that skill in a reasonable time. I wondered if the skill was taught in some sort of art school.

I decided to confess to my editor my lack of knowledge in the comic-coloring arts. She said, “The printer does that.” All I needed to do was indicate which colors I wanted where. End of story. (Today I use Photoshop and point the paint-bucket icon at the area I want to color. It’s probably the easiest work-related thing I do all week.)

And so it has been with about 90 percent of the topics that have intimidated me throughout my career. When you start asking questions, you often discover that there’s a simple solution, a Web site that handles it, or a professional who takes care of it for a reasonable fee. Keep in mind that every time you wonder how to do something, a few hundred million people have probably wondered the same thing. And that usually means the information has already been packaged and simplified, and in some cases sold. But it’s usually free for the asking.

I’m a big fan of flash research, the type you do in less than a minute using Google. You might think a topic is too complicated to master for your use, but you might learn otherwise in less than a minute if you bother to check. I do that process several times per week; I wonder how complicated something is and I check it out. I’m routinely
surprised that someone else had the same question and left a simple bread-crumb trail for me to follow.

My business mistakes, of which there have been plenty, were rarely caused by not being able to find the information that I knew I needed. Most of my problems were caused by my own bad decisions, lack of skill, and bad luck. I can’t think of a single instance in which I was stopped because there was information I needed and I couldn’t find it. I think most entrepreneurs would tell you the same thing. And more to the point of this chapter, when you know how to do something, you feel more energized to take it on.

One of the best ways to pollute the energy in a group situation is by being a total asshole. You might succeed in getting people fully energized, but it won’t be in a productive way. If you think of your bad behavior as a lifestyle choice, as in “being yourself” or “just being honest,” you might be ignoring the cost to your personal energy. When you piss off the people around you, there is bound to be some blowback and wasted effort cleaning up the mess you made. It can all be quite distracting and draining.

I’ve noticed that an alarming number of people have adopted the asshole lifestyle and decided it works well enough to stay on that path. While the word “asshole” usually makes you think of males, in this context I mean it to be gender inclusive.

There’s no single, agreed definition of what it means to be an asshole. It might include selfishness, arrogance, mean-spiritedness, or any number of other character flaws. You know asshole behavior when you see it. And if you’re normal, you’ve probably been one for at least a few minutes of your life.

I would define an asshole as anyone who chooses to make the lives of others less pleasant for reasons that don’t appear productive or necessary.

Asshole behaviors:

1. Changing the subject to him/herself
   
2. Dominating conversation
   
3. Bragging
   
4. Cheating,
   lying
   
5. Disagreeing with any suggestion, no matter how trivial
   
6. Using honesty as a justification for cruelty
   
7. Withholding simple favors out of some warped sense of social justice
   
8. Abandoning the rules of civil behavior, such as saying hello or making eye contact
   

I assume asshole behavior exists because it feels good when you do it. In that sense it’s like an addiction. The long-term effect of being an asshole can’t be good for the person immersed in the lifestyle, but it must feel good in the short term.

That’s a bad trade-off. Your self-interest is best served by being a reasonable person whenever you can muster it.

It’s useful to think of your priorities in terms of concentric circles, like an archery target. In the center is your highest priority: you. If you ruin yourself, you won’t be able to work on any other priorities. So taking care of your own health is job one.

The next ring—and your second-biggest priority—is economics. That includes your job, your investments, and even your house. You might wince at the fact that I put economics ahead of your family, your friends, and the rest of the world, but there’s a reason. If you don’t get your personal financial engine working right, you place a burden on everyone from your family to the country.

Once you are both healthy and financially sound, it’s time for the third ring: family, friends, and lovers. Good health and sufficient money are necessary for a base level of happiness, but you need to be right with your family, friends, and romantic partners to truly enjoy life.

The next rings are your local community, your country, and the world, in that order. Don’t bother trying to fix the world until you get the inner circles of your priorities under control.

The problem, of course, with my neat little model of priorities is that life is never that simple. You can’t tell your boss that your assignment will be late because you want to go for a long, healthy walk. All
of your priorities overlap and conflict. What you need is a simple rule for keeping your priorities on track while handling all of the inevitable exceptions. One simple way to keep your priorities straight is by judging how each of your options will influence your personal energy. It’s not a foolproof gauge, but if you know a particular path will make you feel more stressed, unhealthy, and drained, it’s probably the wrong choice. Right choices can be challenging, but they usually charge you up. When you’re on the right path, it
feels
right, literally.