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Julian Shapiro
+ Your AuthorsArchive @Julian I deconstruct how writing and critical thinking work, and I share learnings along the way. Writing: Work: Angel investor. May. 07, 2021 3 min read

If you suffer from procrastination when writing...

I eventually overcame it.

How to make writing easier:

To start, I write the worst draft possible as quickly as I can.

Because almost all the work happens during rewriting anyway.

The greatest friction is in putting ideas down in the first place.

It's your first major hurdle: get a bad draft #1 done so you can spend 95% of your time rewriting.

That means, in my bad first draft, I use placeholders any time I'm stuck:

When an idea requires more thought than I want to put in, I write <to fill out> and glide past it.

Your first draft is like speedrunning.

The goal is to just generate and connect ideas. Not to explain everything.

Remove the friction.

I find that first draft idea generation works best when you’re exploring ideas that selfishly interest *you*.

I continually ask myself:

1. What are the most interesting implications of what I just said?
2. How can I fully convince myself that what I just said is true?

I ask these questions to move in the direction that excites me.

Here's the irony of self-indulgent writing: writing for yourself is the quickest path to writing something others love.

Because you're a proxy for your die-hard audience.

"People think you need to be inspired to write. No, you write in order to get inspired."

—Paul Jarvis

This brings us to the writing framework I use.

It goes like this:

1. Use draft 1 to find your novel ideas, which may be:

• Counter-intuitive
• Counter-narrative
• Shock and awe
• Elegant synthesis

2. Draft 2 is for making those novel ideas stick—via:

• Stories
• Analogies
• Examples

Therefore, I personally believe:

Writing Quality = Novelty x Resonance

"Novel" ideas are significant and not easily intuited.

"Resonance" is how deeply ideas take root in readers' minds. It's the art of capturing their imaginations and relating to their life experiences.

Now, let's step back:

How do I choose a topic worth writing about in the first place?

The best topic to write about is the one you can’t *not* write about at the time.

Meaning, it’s the idea bouncing around your head that compels you to get to the bottom of it.

I have a framework for figuring out what that idea is.

It consists of having an objective and a motivation.

First, you choose an objective for your post:

1. Open people’s eyes.
2. Articulate something everyone is afraid to say.
3. Identify key trends on a topic.
4. Contribute original insights.
5. Distill an overwhelming topic.
6. Share a solution to a tough problem.

And so on.

Then you pair your objective with what motivates you:

1. Does writing this article get something off your chest?
2. Does it help reason through an unsolved problem you have?
3. Does it persuade others to do something you believe is important?

And so on.

Your objective clarifies what you're trying to accomplish, and your motivation ensures you actually see it through.

Objectives reveal what your article must accomplish to be complete.

You can work backward from it to identify your outline.

When writers lack an objective or motivation, I find they tend to not finish their first draft.

Speaking of outlines. I outline depending on my writing intent:

1. Am I writing to share information I already know? If so, I outline.

2. Am I writing to think through ideas? If so, that means I'm writing to discover. I skip the outline and freely explore my thoughts.

When I'm done my first draft, I'll then pitch the idea to a friend and ask:

"What are the most interesting things I could say about this topic?"

"What would you really want to know if you could learn anything about it?"

Their answers may work their way into my rewrite.

Recap 1 of 2:

• I write the worst draft I can as quickly as I can. Speedrun.
• I use placeholders (<to fill>) any time I'm stuck.
• The goal of my first draft is to generate and connect just a few good ideas.

Recap 2 of 2:

• When discovering my thoughts, I keep asking: How can I make this point more convincing? What are the interesting implications of what I just said?
• Identify your writing objective. Pair it with a motivation. Have a north star.

My upcoming thread is on how I write second drafts.

You can follow @Julian.


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