The Looking Glass: So you want to write better?

A long-form piece on some age-old misconceptions

So you want to write a book?

Or you want to start a blog?

Or your humble hope is simply to write better?

If I got a nickel for every time someone told me with shining eyes about their writing dreams, I would be able to build a library vast enough to house every Great American Novel conceived but never written.

And I get it. If you are reading this, you probably feel a certain fondness for words. You are probably the type of person who:

1. Remained alert through decades of English classes

2. Secretly hope text-based platforms like Substack (and maybe even Threads or Xitter) will succeed

3. Are inundated by writers (like yours truly) waxing poetic about writing

4. Consider writing like vitamins — generally beneficial for one’s life.

But going from dreaming about writing to actually writing is its own version of crossing the chasm — easy to say and hard to do.

I have a theory for why: we are confused about why we write.

You see, decades of English classes have failed to properly teach us this very simple lesson: that there are various reasons to write!

Depending on your reasons for writing, what constitutes “good” or “bad” work changes.
Your end goal changes. Your relationship to the writing itself changes.

Let us explore the 3 key reasons:
write to think, write to feel, or write to connect.

Write to think

The world is a rose garden filled with thorns, and every day we are presented with new problems.

When you write to think, your goal is to work through some problem and explore the contours of your ideas.

What you are looking for here is new insights or increased clarity — you want to leave the process feeling like you now have a better map of the territory.

The simplest version of writing to think is making a list — say, a shopping list.

You do not want to be milling about at the grocery store feeling muddled about whether those corn-shaped organic gummies are worth tossing into your cart. Instead, before setting foot into the store, sit down and plan out your meal ideas for the week. Then, extract the ingredients you need into a stacked list. Voila! — when you finally talk your shopping cart for a walk, it’s with a clear agenda and a pep in your step.

Why does writing help you think?

Because taking whatever is rattling around in your brain and applying it to paper is like squeezing orange juice into a strainer. The act forces clarity.

Laid out in front of you, ideas can be re-read, critiqued, edited, tweaked or straight-up deleted. Writing is like applying a swiss army knife to your thought process. It helps you build a better set of ideas.

Paul Graham has written far more extensively about writing to think than I have here, so I suggest you read his excellent pieces.

The following prompts are examples of writing to think:

1. What do you hope your life looks like at the end of this year?

2. What do you believe success for your product looks like?

3. In what ways do you think gen AI will change your job?

4. What skills should you invest more into over the next 6 months?

5. What are 5 vacation destinations you’re excited about?

6. What do you want your manager to take way in your next 1:1?

7. How should you approach doing user research?

Notice how these prompts are open-ended and personal — they are about extracting your thoughts and creating clarity for yourself. You don’t have to share these with anyone (although you can — see Write to Connect). I find bullet lists are an effective format, as well as letters addressing myself in the second person.

Of all the writing that I do, the greatest chunk (50%) is writing to think. I am thoroughly convinced doing so makes me a better designer, manager, founder, parent, and overall human being.

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Write to feel

Ever heard the tip Write down 3 things you are grateful for every day?

This is writing to feel, where the key goal is to deepen a state of mind or capture the texture of a moment in time.

When you write to feel, there is no problem to solve. You write for yourself, to commune with yourself. Perhaps it looks like Dear Diary entries. Perhaps it looks like scribbled notes. Perhaps it looks like a sonnet.

I’ve kept a diary since I was in third grade, and for years I tried to use proper grammar and punctuation and write it the right way, like I was taught at school. I’d even half-joke to my friends that sometimes I’d rush an entry and it would be so sloppily written!

I’ve since come to my senses and realized the ridiculous of those words.

There are no rules with writing to feel. There is no right way or sloppy way! The whole point is: Write. To. Feel!

As soon as my mind registered this, my journaling took a sharp right and veered toward The Land of Poetry. It became for me the most natural way to capture what I felt, whether a moment of white rage or blue fog, whether the peace of autumnal leaves or the simmer of holiday anxiety.

So if you want to invent new curse words, write in all caps with no punctuation, or quote rap lyrics — go for it.

I have grown to love this type of writing.

There is freedom in writing to feel, in spelunking the great depths of our souls and in witnessing the great and terrible beauties of our world.

Writing to feel is about 15% of the writing I do, and it extends my emotions of gratitude and awe and joy. It gives me an outlet for my frustrations and fears.

Write for yourself, because you are a wonderful and complex human. Write to feel, because you feel like it.

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Write to connect

This is the reason for writing that most of us were taught in school — write because it’s a good medium to express an idea, persuade a neighbor, or be understood.

If you turn in a 25-page final semester paper on the similarities and differences between Plato and Aquinas with the goal of persuading your professor to give you a passing grade — you are writing to connect.

If you share a product proposal doc with your colleagues hoping that they will say What a killer idea, let’s build it immediately! — you are writing to connect.

If you have figured out That One Weird Trick to maintaining equanimity through arguments and you desperately wish for the world to absorb this power and thus manifest world peace — you are writing to connect.

Writing to sell books, increase pageviews, improve conversion, gain support, elicit sympathy, or entertain — these are all forms of writing to connect. (Yes, at this very second, I am writing this piece to connect with you, dear reader.)

If connecting is your goal, you must write with your audience in mind.

Who are your readers? What’s in their heads? What opener will grab their attention? How will you hook them into the next paragraph? What kind of language or metaphors or style resonates with this group?

When you write to connect, your target audience is the judge of how well you write. It is impossible to claim I write the world’s greatest product specs when your colleagues regularly misunderstand your proposals. Your comedy writing sucks if none of your readers chuckle. Your how-to post fails if people don’t scroll past the fold.

Of course, you don’t need to appeal to everyone, just the folks you’re aiming to appeal to. It’s a different sport to create something the critics love versus the mainstream buys.

Here, heed the wisdom of the masters, the great writers in your field. But recognize that each master describes her specific craft. Paul Graham’s advice to write simply doesn’t jive with Taylor Swift’s Quill Pen writing, and that is just fine because they aim to connect with different groups for different purposes. (If you need a general purpose primer on storytelling, though, Stephen King’s On Writing is excellent.)

Writing to connect is about 35% of my writing focus. We all need to do this for our jobs and relationships. No way around it but through practice.

Bonus: How do I write for a mix of the above?

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