Readers frequently give me a hard time about some edge case in my writing as if I haven’t thought the subject through, and pared the word count down by half.

I’m confident that those readers don’t write a whole lot. If they did write, they would realize that in order to produce a cogent piece, especially in the abbreviated format of a blog, one has to chop mercilessly.

Here’s my process in a nutshell: I start out with a core concept, and write until I understand what I’m trying to say—often it’s more words than the final article. I throw everything away at that point, and write the essay I intended to write. Then I carve out all the tangents and caveats, and create new essay studs with the more interesting or robust ones. The rest of the tangents are just slush. Maybe I touch on them in the comments.

Maybe it comes as a surprise that I deliberately remove relevant caveats. If it does, this essay is directed at you.

Sloppy Thinking

It’s perfectly normal for the bulk of my readers to nitpick, because they are largely left-brained engineering types. Engineers spend their lives thinking about edge cases and solving them. I have news for you:

Writing a blog post as though it’s a piece of bug-free software is not only ineffective, it’s sloppy.

What may be even more counter intuitive than the idea that considering every possible scenario produces sloppy writing, is that it also betrays sloppy thinking.

Hear me out.

37Signals Logo

blogged that they’d never sell their company for any price because they like it so much. It’s a simple message about how the mythology of the serial entrepreneur who makes a series of big exits isn’t all it’s cracked up to be.

There was a firestorm of discussion about overstating their point, and hypothetical questions like:

“What if someone offered you $1 trillion for it?”

That is a perfect example of the sloppy, engineering thinking I’m talking about.

It makes sense in a piece of software to consider every exotic, theoretically possible scenario so the software never breaks. It makes no sense to expect DHH to explain in a blog post that a caveat to his position on selling is that if someone offered $1 trillion he would take it.

It’s sloppy thinking because it’s disconnected from reality, and it would be sloppy writing because it waters the point down without adding anything substantive.

Abstract Thinking

There has to be some balance.

Some people absolutely cannot think in terms of abstraction. That’s a blight on the world. It prevents law makers from understanding that just because $1 billion is a lot and $1 trillion is a lot, that those numbers aren’t nearly the same. It prevents citizens from understanding why speech should always be free, not just speech we personally agree with.

Other people—myself among them until more recently than I’d like to admit—cannot seem to stop thinking abstractly.

stuck in a labyrinth of endless scenarios that never existed and never plausibly will exist, but that inform their decisions and beliefs all the same

They can’t just decide that they want to start a company and keep it, or to move to the beach and play the keyboard for a meager living because they realize that would totally fulfill them. Instead they drown under a running faucet of infinite caveats and doubts available at a moment’s notice from their abstract thinking. They are stuck in a labyrinth of endless scenarios that never existed and never plausibly will exist, but that inform their decisions and beliefs all the same.

Their thinking is muddled, their writing unclear, and their actions are not decisive.

Writing Real

I’m not interested in the hypothetical guy way at end of the long tail for whom my message barely applies. I’m harpooning the swollen belly of the normal curve.

It’s up to you, not me, to decide whether and to what degree my message applies to you. I’m not going to back pedal and equivocate on every useful thing I say so that I don’t offend some person that I’m not even talking to.

A big part of my message is to clear your mind enough to begin relying on your own clear-eyed judgment. Part of that is knowing what advice to take and leave, and knowing why you’re doing that.

Caveat Lector (I love irony)

One danger you may find is you, oh clever reader, able to rationalize anything, will convince yourself time and again that the message doesn’t apply to you. That you can waste your time on treadmills, fail to produce work, or yes, equivocate in your thinking. In fact, chances are that if you’re reading this you are near the dead center of the bell curve’s undulating gut.

Acting Real

I’ve hinted that this whole business goes deeper than writing. After a journey through the terror of sloppy thinking and writing, we arrive at our destination.

Equivocation cripples action.

  • It’s been shown that bosses prefer employees who appear to be certain. Explaining the nuances of a situation to your boss isn’t incorrect, but the reality is that it doesn’t matter. In reality, you solve the problem in front of you and deal with others as they become real.
  • Abstract thinkers (often geeks) over think romance to the degree that they are known for not having it. When approaching an attractive other, they consider all possible failure modes, and they even consider future fail modes should the approach be successful. Meanwhile their cro-magnon peers scoop up the girl and ride off into the sunset.
  • Employees stay stuck in jobs because the clear bell of apathy and stagnation is drowned out by a cacophony of fears and doubts ranging from social isolation to financial ruin. The reality is that you don’t need much money to be happy, you need to feel a sense of control and accomplishment (neither of which most jobs provide).

It’s the mirror image of the problem that concrete thinkers face. They can’t tell the difference between a billion and a trillion because they are both “a lot”. You can’t tell the difference between possible and probable because they are both “possible”.

The reality is that a trillion is three orders of magnitude more than a billion, and that a probability approaching 0 (~0) is not the same as a probability approaching 1 (~1), even though they are both hypothetically “possible.”

You will never figure “everything” out. You will never be able to make everything perfect before you start. Just make a decision and run with it. Figure it out as you go along.

Getting Real

You will never live the life you want by wandering aimlessly through hypothetical scenarios. I’ve tried it, it doesn’t work [Note: there used to be a link here to a Ken Sharpe article about how I was “laid off,” read: fired. It’s long dead now]. I’ve also tried just doing something. That worked.

I implore you: find a quiet place in your mind, identify your desires free of caveats, and make a plan to move toward those desires. Don’t try to plan for all eventualities. That will just prevent action.

Instead, think about what will probably occur as you move, plan for that, and start moving.

(Thanks to Hani Amir for the title photo.)