The Write to Roam -- How to Fail at Almost Everything and Still Win BigOne of the reasons I love biographies is that they help you to see that successful people are riddled with problems too. Did you know that Scott Adams, best-selling author and the artist behind the Dilbert cartoon, once struggled with spasmodic dysphonia, and was mysteriously unable to talk to any other human being for more than three years?

It is just one of the struggles he talks about in his sort-of-biography How to Fail at Almost Everything and Still Win Big. The book was recommended to me by a mentor, and from it I got two interesting lessons.

The first is regarding generosity, and the need to take care of yourself. As a business owner, I enjoy talking about business, and helping other people to pursue their ideas. But every once in a while, I’ll get so excited that I commit to something I shouldn’t, and then get crushed under the workload. Whether it’s offering free help, or just taking on a long term project that I don’t have time for, I have to consciously restrain myself from saying yes to opportunities on a daily basis. Sometimes I feel bad about this. I’ve got specialized knowledge in a few areas. Why shouldn’t I share it?

Adams, who is a straight shooter almost to a fault, says that when it comes to generosity there are only three types of people in the world:

  1. Selfish
  2. Stupid
  3. Burden to Others

In order to help others, he says, you first need to take care of yourself. You need to take care of your health. You need to make a good living. You need to pursue “enlightened selfishness”.

“If you neglect your health, or your career you slip into the second category — stupid — which is a short slide from becoming a burden on society.”

People who look out for themselves have the resources to help others. Whereas someone who’s overcommitted, under-charging, or otherwise too “generous”, winds up with neither time nor money nor enthusiasm to contribute. They become a ball of stress — a broke ball of stress… I’ve been there.

The second, and much more profound lesson is perhaps best introduced with a question:

If you woke up tomorrow with the thing you currently dream of having — money, abs, love, etc — based on the way you lived today, how long would it last?

I came up with this question by accident during a moment of self-doubt. At the time I was unemployed, living at home, and quickly going broke… again. I told myself I hadn’t really moved forward since high school. In fact, because of my student loans, car loan, and credit cards my net worth was thousands of dollars less than the day I got my diploma. On the surface it seemed that I’d spent nearly a decade moving backwards.

How could I have ended up this way? I wasn’t dumb. I wasn’t a slacker. I’d kept lists of written goals since my teens, and I’d hit many of them over the years. But in the end they seemed to count for little compared to where I thought I’d be.

Poor Ethan.

That’s when Scott Adams’ systems over goals principle finally sunk in. The idea behind this way of thinking is that goals are far less important than the systems we put in place to achieve them. To define the two clearly, goals are your desired outcomes, whereas systems are the repeatable actions you take to get there.

If you want to lose twenty pounds, the weight loss is the goal, but the exercise habit is the system. If you want to be a famous author, hitting the best-seller list is the goal, but writing every day is the system.

The beauty of this philosophy is two-fold…

First of all, when you focus on a goal, you’re focusing on something you don’t yet have. You are a failure, every day, until you finally reach your goal.

“Goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary” —Scott Adams

There is also nothing lasting about achieving a goal. Just because you are in shape today, that doesn’t automatically mean you’ll stay that way.

Take money as an example. Lots of people want it. Very few have it. Many wish they could skip straight to being a millionaire. But most of the people who actually do—lottery winners—aren’t able to hold onto their money. Why?

Well, if you buy into Adams’ philosophy, the reason is because they haven’t built the systems for maintaining wealth.

Hitting a goal means momentary success. But only your system — the way you live your life every day — helps guarantee lasting or repeat fulfillment.

When you choose to focus on the system, you’re choosing to focus on something that’s going to be helpful long term. You’re also deciding to make yourself a winner now. Because when you’re system-focused, you are a winner every day, as long as you follow your system.

So how do you develop better systems?

If you’re trying to develop a system for success the first question you need to ask yourself is this: What action can I repeat every day that will move me towards my desired result?

That’s a tough question to answer, so I prefer to begin by flipping the question on its head and looking for any existing failure points that I might want to work on.

This is where the question I asked above comes in: If you woke up tomorrow with the thing you desire, how long would you be able to hold onto it given the way you spent your time today?

By asking the question this way, what you’re really asking is am I currently doing anything consistently that will undermine my goal? That’s a very powerful question to answer honestly.

What I realized, then, in that moment of self-doubt was that I wasn’t actually a failure. I’d just spent my time developing habits that weren’t leading to success. By examining what I may have been doing wrong, and committing to focus on the system, I put myself in a position to begin improving immediately.

Winning big will mean different things to different people. But I believe that asking and answering this question is a strong first step for anyone.