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Sep 1
If you take the goal of democracy to be perfectly fair representation for all people and equal opportunity without exception, then we are failing. But if you reframe the aim of democracy as avoiding authoritarianism, we are wildly successful.

Sep 6
Before you ask someone a question, ask yourself how you could make that question unique. Do you want a conversation to be predictable or revelatory? That all depends on what questions you ask.

If ever you have the chance to compliment or support someone with actions rather than words, do it.

• Don’t send your condolences; show up at the funeral.
• Tell her she’s pretty in the midst of prolonged eye contact.
• Invite an old friend over for a meal.

Sep 7
When giving feedback, be provocative, not prescriptive.

As an editor, don’t impose your vision for the piece. Instead, ask questions that provoke and reveal the writer’s vision. Only make statements about:

• How you understood the piece and your main take-away
• How it made you feel
• What you would like to see expanded, added, or omitted.

These are provocative statements. If you are tempted to make a prescriptive statement, phrase it as a question instead.

Sep 8
“Evergreen” isn’t even an evergreen term. It’s a product of the age of content and the attention economy. I no longer want to write evergreen essays. I want to write timeless essays.

In the course of my life, I will spend hours contemplating suicide, so that I don’t consider it for a second.

In the course of my life, I will spend hours contemplating suicide, but I won’t consider it for a second.

In the course of my life, I will spend hours contemplating suicide, so that I won’t consider it for a second.

In my life, contemplate suicide for hours but never consider it for a second.

Sep 9
On of these days, I will die. Until then, I will live.

Example of reciprocity: When you’re done playing pool, re-rack the balls for the next players.

(Also: Refilling the Brita water jug)

We humans have these infinite concepts of what could be, yet we are stuck in the finite concrete of reality.

Sep 10
Editing is an entirely separate skill from writing. And the best way to become a better writer is to develop the skill of self-editing.

Just as a task will fill the time allotted for it, leisure time balloons to fill the time between tasks. If you want it done, schedule time to do it.

Sep 12
An unwritten thought has no weight in the world, but a written thought can tilt the world.

To become a better writer, spend more time editing. Your editing will make you a better writer, and you can spend less time editing (for an equivalent quality).

Sep 14
Too often, progress comes at the price of stillness and gratitude.

In pursuit of progress, we pick up our pace, and we start moving so fast that we don’t enjoy the process and lose sight of how far we’ve come.

Ideally, we would always make progress but at a sustainable pace — slow enough that we never lose sight of where we are right now.

[[Defining Success and Managing Expectations]]

Sep 15
In a media landscape without gatekeepers, you must be the arbiter of quality.

In a world without gatekeepers, you must be the arbiter of quality.

(Curate the content you consume –– as if you were the editor of a major publication.)

(Edit your own work, and only consume information with high editorial standards.)

You have too many tabs open if you go to click one and accidentally click the ‘X’ to close it. This happens to me every weekday.

Sep 16
Be an intellectual nomad; don’t dwell in dogma.

Reality, by nature, is in flux. And for that very fact, any immutable belief is further from the truth than one that is malleable.

[[Intellectual Nomad]]

Dogma is the antidote to (the pain of) truth/reality, (and it comes at the cost of intellectual honesty).

Sep 17
If you want to be radically different, radical things must first become normal to you.

Start with:

• Sitting in boredom
• Lingering in awkward silence without breaking eye contact
• Sharing how you actually feel and what you actually think.

Yes, these things are radical.

Sep 19
You need to believe in God to think that life is worth living? Have you looked outside? (You must’ve never gone for a hike at sunrise.)

Attune Your Taste

In this new paradigm of independent publishing, there are no more gatekeepers.

Everyone is free to share whatever they want with the whole world. But what we’ve lost with the gatekeepers are editorial standards.

Now, you and me — the consumers —must be the arbiters of quality.

If those moments cease to be, it won’t be a tragedy if all the moments that have been were as good as they could be.

Sep 20
Einstein and Oppenheimer made similar accomplishments and contributions to the world. But since the Theory of Relativity hasn’t killed anybody, we see Einstein more favorably.

Sacrifice is a vice.

Sep 22
Why I should care more about birthdays: For every person, each birthday is like beating death in the Super Bowl. Another year you and I live is another victory for the human race over the cold indifference and disruptive entropy of the Universe.

Sep 27
Setting your thermostat is like placing a limit order.

• The current temperature is the current price.
• Buying is setting the AC to “Cool” and setting the target temperature below the current temperature.
• Selling is turning the furnace on and setting the target temperature above the current temperature.

Sep 28
I live in a place where you need to be a multi-millionaire to own a house with a garage.

Sep 29
Forget 1,000 true fans. I want 100 ideal readers.

I don’t need my writing to be how I make a living. But I do need my writing to work to bring me new (and lucrative) opportunities and enriching relationships. Instead of trying to amass a critical-mass fandom, I’m more interested in attracting a few readers for whom my writing is perfectly suited and who want to help me succeed (even if they never pay me a dime).

I’m more interested in depth than breadth. So, I’ll optimize for that.

Marc Andreessen on How I Write:

Twitter is aphorisms as a service.

I wish that was what Twitter is. Show me aphorisms, not hooks and clickbait.

Online writing has killed the art of the paragraph. Popular writers of old thought in the unit of the paragraph. Popular writers of today think in the unit of phrases, fragments: headlines, hooks, memes.

Instead of using paragraph breaks to separate ideas, we’ve started using them for emphasis, like bold or italic font. When we don’t want the modern, short-attention-span reader to miss something, we put that thing in its own paragraph.

What you lose with this is the integrity and structure of a good paragraph. It’s analogous to a three-act narrative:

1. What you want them to know
2. Why you know it
3. How you’ve proven it / why it matters.

Within any good paragraph is an inciting incident, some conflict, and a resolution. There are expectations, stakes, and a pay-off. The pay-off doesn’t land if it’s separated from the narrative by a paragraph break. No play has an intermission between acts two and three.