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50 Days of Writing

Email series created by David Perell.

Part 1: Preparing To Write

Day 1: Write For Yourself


When writing, either write for yourself, or write for a specific person. For the latter, define that person as soon as possible to provide context.

Meeting the kinds of people you’d never meet in real life is the whole point of writing online, so escape the lukewarm middle and write for one obsessive person.

Day 2: Why You Should Write

  • Writing is a way to connect with the rest of the world

    “The coolest people I meet are the ones who find me through something I’ve written.” — Derek Sivers

    • I have observed this with my Traefik and http-forward-auth article
  • Some of the most successful people are also writers
    • At least, these are the ones we see. What about the people we don’t see?
  • The writing and editing process helps someone re-think their thoughts to distill them into sharper, clearer thoughts.
    • This is likely why journaling is effective for focusing the mind. These seem to support each other.
  • The most effective way to learn something is to participate in the activity. In the case of processing a thought, that is writing about it.
  • Starting tips:
    • Convey ideas using stories
    • Short sentences
    • One point per sentence
    • Conversational tone
  • Writer’s block in a sign of not enough notes. Take more notes first.
  • Do the writing in public.

    “If you wish you would take something more seriously, do it publicly… Social pressure forces you to up your game.” — James Clear

  • Value the time of your audience. Every word, phrase, and sentence should be valuable and not waste their time.
  • Discipline is the only thing required to write online.

Day 3: The Serendipity of Note-Taking


  • Note-taking system should both save and generate ideas.
  • Re-reading notes or writing notes should help jog ideas from other notes that you’ve written.

Day 4: Writing is More than Typing


  • The act of writing online is only a fraction of the effort required
  • Preparation takes the most time
    • Sourcing ideas, taking notes, writing, editing, distribution, promotion
  • “Mise-en-place” writing; prep first, write second

Day 5: Writing Makes You a Better Speaker


  • Writing helps you hone ideas before having to speak them
  • Writing publicly lets others criticize your work, which prepares you for future writing
    • You develop the ability to predict counter-arguments and counter those
  • Writing over time will improve your verbal style. It also allows you to frequently refine what you write, meaning you can make your idea as clear and concise as possible.

Day 6: Note-Taking is Time Travel


  • Kendrick Lamar takes notes constantly
  • The notes you take will jog other memories
  • Capture just enough to help with the recall
  • Notes have no shelf life. They last forever. My wiki is a great place to store these notes.

From the video:

  • Ideas can be reused in multiple articles
  • The ideas generated from one piece can seed ideas for other articles
  • Notes should be captured for at least one of the following reasons:
    • Inspiring: anything that excites you when you see it
    • Useful: anything that could be used as a future building block
    • Easily Lost: anything you don’t think you’ll be able to find in the future
    • Personal: unique or hard-won knowledge
  • Don’t save everything you read. Maybe 5%.

Next video talked about writer’s block.

Day 7: Learn to Write Fast


  • If you already have a library of notes to pull information from, it’s easier to write
    • This could likely also be applied to most forms of creation
  • Collect relevant ideas from other sources
    • Books, conversations, evergreen notes
  • An alternative is to talk about your idea and record it using
    • Talking forces you to structure your ideas
    • Repeat to refine the idea
  • Don’t start writing until a plan exists

Day 8: Writing Can Save You Time


  • Not taking the time to write things down saves time in the short term, but has a compounding cost over the long term
  • Written notes make ideas permanent
  • Once written down, an idea can be remixed and reused

Day 9: Learn Like an Athlete


  • Implementing a strict learning plan helps knowledge workers accelerate
  • Learning Plan Goals
    • Build skills
    • Complete projects
    • Increase productive power
  • Implementing a learning plan:
    • Operate on 3-month sprints
    • Commit to a new learning project every quarter
    • Focus on the end goal, not the skill
  • Find something not too easy or too hard. Just enough to be challenging without demotivating you if you hit a wall.
  • Publish your learning process online (this ties into the same concepts as Show Your Work!)

Day 10: The Three B’s of Creativity


  • Our best thinking and creativity comes from when we are relaxed. We leverage the three B’s to provide that.
  • Bed (Sleep)
    • Allows your body to rest
    • Subconscious mind gets to be in control
  • Bath (Leisure)
    • The goal is to disconnect from the stresses of life
      • Notifications on the phone
      • Drama
    • Context switching for 30 minutes can help relax the body (no citation was given for this statement. Is this true?)
  • Bus (Movement)
    • Exercise gives you an opportunity to clear the mind a bit
    • Walking gives you an opportunity to think

Day 11: You Already Have a Voice


  • “Voice” = “personality on the page”
  • You will find your voice by actually writing
  • Your writing will improve the more you write
  • You can still write about ideas that others have written about
    • Your voice will present it in a unique way

Day 12: Look for Things that Don’t Make Sense


  • Something not making sense means that we don’t understand something, not that it’s wrong
    • Our model is wrong
  • If it doesn’t make sense, there’s an opportunity to learn from it
  • If something surprises you, then there’s a good chance it’ll surprise your readers
    • See: Phil Edwards

Day 13: Lateral Thinking with Withered Ideas


  • The Game Boy was specifically designed around old, cheaper technology
  • Old and undervalued ideas can be used for new content
  • What Intellectual Phase Transitions occurred?

Day 14: The Go For It Window


  • Paths that look risky can actually be safe and vise versa
    • If a path looks safe, it may be because others have already walked it
    • This means that there’s less opportunity because the market is saturated, and that means your idea is less likely to take off
    • If a path looks risky, it may be because few have already walked it
  • Airbnb managed to make crashing at a stranger’s place acceptable
  • In short, it is the right opportunity at the right time
  • The trick is to find those hidden opportunities

Day 15: Find Your Shiny Dime


  • The Shiny Dime is the smallest viable idea you can write about
  • Should be capable of being summarized in a single sentence
  • When writing about a specific topic, reject all ideas that don’t fit within that one-liner
    • Save them for later, though! There may still be value in them!
  • Writing helps bring ideas for the forefront, which provides the content once you have established what your shiny dime is
    • Every topic is bigger than it seems

Day 16: POP Writing


  • POP is a three-variable framework for evaluating your writing
    • Personal
      • Use stories and emotions — what you’ve seen yourself
      • Shared feelings establish a connection between you and your reader
      • Too much makes the reader question why they should care
    • Observational
      • Noticing patterns that others may miss — provides the Eureka moment
      • See: Day 10 and Day 12
      • Too much makes the work hard to digest and painful to read
    • Playful
      • Makes the reading fun and enjoyable
      • Too much and you won’t be taken seriously
      • See: Tim Urban

Day 17: Write While You Read


  • Do what it says on the tin
  • Taking notes while writing means your ideas are still fresh in your mind
    • Taking notes later means you’ll forget things
  • Notes should be lightweight and evergreen
  • Avoid taking Kindle highlights without writing a note along with them, otherwise the highlight won’t stick.
    • Write why the highlight stuck with you

Day 18: Write While You Walk


  • Mary Oliver wrote while walking
  • Creativity and ideas can flow while you’re moving
  • When you’re walking, capture ideas on a notepad or on your phone with

Day 19: Create a Physical Structure


  • Jotting down ideas and have them represented physically helps you refer back to those notes easily without taking up your own memory.
  • David recommends using Post-It Notes when writing anything longform, and putting those Post-It Notes on a wall
    • They can be rearranged or played with, but at any one time you only need to focus on one of them.
    • See: using scratch paper in math

Day 20: Talking Can Cure Writer’s Block


  • For those that have lots of thoughts but struggle to write when at the computer, then dictating ideas to your phone can alleviate this.
  • Record conversations, for ideas in the future.

See: Day 18, Writer’s Block

Day 21: Assume You’re Not Original


  • Just as Derek Sivers says that you should assume you’re below average, you should also assume you’re not original.
    • Assuming you’re below average puts you into a learning mindset
    • Assuming you’re not original encourages you to seek out people who are original so you can learn from them
  • Look for those that don’t imitate and build upon their ideas

Day 22: Write About Earned Secrets


  • Earned Secrets are a good source of content
  • Access-based ones are great because only you or a small subset of people have that knowledge, which means that your content will be unique.
  • Revelation-based ones come from looking at already-public information from a new perspective.
    • The catch here is that unique perspective usually requires expertise in the subject, so as a learner this may be difficult to get

Day 23: Create a Story Box


  • Create a place that you can easily dump writing ideas into
  • When you need inspiration for what to write, look through this story box for ideas
  • The stories won’t be the main focus of what you’re writing, but can serve two purposes:
    1. If you are frequently writing stories about the same general theme, then that theme can be written about
    2. If you need a story to lead into a point you want to make, then the story box can provide that
  • This approach is used by designers using sites like Pinterest.

Day 24: Leave a Summary for Yourself


  • Whenever you are working on the same piece for multiple sessions, write a summary at the end so you can resume working as fast as possible.
  • The summary should include:
    • The next task to accomplish
    • Where you’re stuck
    • What you’re thinking about
  • This doesn’t need to apply to just writing, but any multi-session task
  • The goal is to reduce friction next time you work on this piece
  • ~100 words should be fine. Just a short summary.

Day 25: The Islands and Bridges Strategy


  • Precursor:
    • There’s two forms of writing: articles where you know what you’re trying to say (Clear Thesis), and articles where the writing of said article helps discover what you’re thinking (Foggy Intuition)
    • This day discusses writing for Foggy Intuition
  • Islands = individual, distinct thoughts
  • Bridges = connections between those thoughts
  • When writing a Foggy Intuition article, write your islands first
  • Aim to reduce the interdependencies between the islands
    • The goal here is to be able to reorder and reorganize those islands as required to make the article flow
    • Too many interdependencies forces your hand for how the article should be structured
  • Once the structure of the article is complete, write your short transitions between the islands
  • In general, don’t feel like you have to have the whole concept of an article before starting to write it.

Day 26: Hide Your Work


  • The title of this reads like you should keep your writing for yourself, but David is suggesting that you should release what you have edited and trimmed down
  • Something that is easy to read is hard to write, so you need to spend lots of time editing and trimming the unnecessary fat.
  • Something to think about: how does this compare to Show Your Work!? These two concepts seem to contradict each other. David is targeting writers; perhaps it depends on the medium in which you’re working? Both are for creatives, based on how Seth Godin defines a creative in The Practice.

Day 27: Imitate, Then Innovate


  • To improve your writing, find a style of writing that jives with you, then imitate it.
  • Whenever you feel resistance to that imitation, note that and then embrace it, because that’s your personal style coming through.
  • Learn to identify writing styles.

Day 28: Bring a Unique Dessert


  • Your writing won’t gain any traction unless it has something unique to offer.
  • That uniqueness can be one of two approaches:
    • A completely uncharted topic that nobody has talked about before
    • A topic looked at from a different perspective
  • Aside: I don’t have anything that differentiates me, except for that Traefik article.

Day 29: The Raymond Chandler Rule


  • Aim for some sort of mini-epiphany every 250 words or so.
  • This stems from the novelist Raymond Chandler, who used to use index cards in his typewriter, and every index card had to have something happen on it (and not be just filler words).
  • Long concepts can still be valuable, but there needs to be something useful frequently.
  • The goal is to keep the reader’s attention.

Day 30: The Right Kind of Original


  • We have an expectation that everything has to be original, but most things have been written about already. That’s okay.
  • Innovation comes from rehashing what others before us have done.

Study hard what interests you the most in the most undisciplined, irreverent and original manner possible. — Richard Feynman

Day 31: Intellectual Phase Transitions


  • Creativity comes from combining multiple ideas from multiple sources and creating new ideas from those.
  • Look to find connections between ideas by comparing and contrasting. See if you can figure out how to combine ideas together.

And that is the idea that creativity is combinatorial, that nothing is entirely original, that everything builds on what came before, and that we create by taking existing pieces of inspiration, knowledge, skill and insight that we gather over the course of our lives and [recombine] them into incredible new creations. — Maria Popova

Day 32: Summarize the Canon


  • Each discipline has books that are considered de facto; summarizing this content is a good place to start generating content.
  • These books have stood the test of time and are considered de facto for a reason.
  • Take the ideas and provide context. Make the theory relevant.

Day 33: Avoid Cliché Ideas


  • A cliché is too general to draw attention. You’re not contributing anything new by being general.
  • In order to contribute something new — and for people to want to continue to read what you produce — you need to be specific, to talk to the details of your topic.
  • Alternative topics:
    • Approach topics from a different angle
    • Talk about under-explored topics

Day 34: Write a Summary Box


  • When you know what you’re going to say, ensure you stay focused and on-topic. Writing a short abstract or summary in advance and referring back to it will help.
  • Without this, your writing can meander and you end up not focusing on the smallest point you’re trying to make.

Day 35: The But & Therefore Rule


  • The “But & Therefore Rule” comes from Trey Parker and Matt Stone, creators of South Park.
  • While some stories are told with “and then” to tie concepts together, Trey and Matt instead use “but [situation] therefore” to introduce unpredictability, entertainment, and conflict.
  • Consider this when doing creative writing to deviate from conventional styles.

Day 36: Diversify Your Vernacular


  • The advice “write like you speak” is good up until a point. Once you hit that point, this advice is limiting.

  • When we speak, we have the benefit of tone to help convey information. We lose this ability when writing.

  • Perell suggests that there are three types of words for writers to consider:

    1. Words that people know and use
    2. Words that people know but don’t use
    3. Words that people don’t know nor use

    Look to bring in words that people know but don’t use to help provide the missing “spice” to your written words.

Day 37: FAST Writing


  • FAST is an acronym that stands for Find, Assemble, Speak, and Teach. Perell recommends this approach for those that can’t dedicate their entire lives to writing (i.e. almost all of us).
  • Find: passively research and collect information. You need to do this before you even know what you’re going to write about. Consider a second brain to store this info.
  • Assemble: write down a list of scattered ideas about the topic. If you’re starting to write, you should already know what you’re talking about, not learning about it while you write. Collect your notes together before actually writing.
  • Speak: talk with other people about the idea. Talking is faster than writing, and will help crystallize ideas, and others asking questions will help you cover all of the required talking points.
  • Teach: by writing (and sharing your work online), you’re demonstrating what you’ve learned and helping teach others. Others can then learn from what you’ve written and provide feedback, which in turn improves your writing.

Day 38: The Three Deadly Sins


  • Avoid weak, wasted, and redundant words:
    • Weak: words that lack potency. There’s no spice.
    • Wasted: filler words that don’t contribute to your point. For example, replace “due to the fact that” with “because”.
    • Redundant: saying the same thing more than once. For example, in “baby puppies”, “baby” is redundant.
  • Avoid this by compressing your sentences.

Day 39: Expression is Compression


See: sentence compression

  • You’ll have nothing to write about if you don’t experience life. Writers don’t spend their entire lives sitting down and writing; they get out and experience the world.
  • To captivate an audience, your writing needs to be tight and focused, keeping the reader engaged.

Day 40: Write CLEAR Sentences


  • CLEAR is an acronym that stands for: Create a rhythm, Link your sentences, Eliminate anything that adds confusion, Add colourful details, Remove unnecessary details
  • Create a Rhythm: vary sentence length to keep the reader captivated.

    “Don’t just write words. Write music.”

    — Gary Provost

  • Link Your Sentences: Each sentence should logically flow from one to the next sentence. Across the whole piece, each paragraph should flow from one to the next.
  • Eliminate Anything That Adds Confusion: exactly what it sounds like. To figure out what causes confusion, read your writing out to yourself. If you catch yourself stumbling, revise that area.
  • Add Colourful Details: Creative writing should not just convey facts or statements, but should make the reader feel something. The detail you add about your experience provides that.
  • Remove Unnecessary Details: Remove anything that isn’t required.

    “If you can communicate the same idea with fewer words, it’s more likely to be read and understood. A sentence that’s easier to translate is also easier to understand.”

    — Derek Sivers

Day 41: CRIBS: My Writing Feedback Formula


  • CRIBS is an acronym for providing writing feedback, which stands for: Confusing, Repeated, Interested, Boring, Surprising. Note that this is not something you’d use on your own writing, but on someone else’s.
  • Confusing: is the author trying to sound smart? They should use clearer, simpler language. Does the point meander? The author may not know enough about your current topic.
  • Repeated: do you say the same thing over and over? Simplify your writing. Don’t be redundant.
  • Interesting: identify the areas you find interesting. The writer should double down on these.
  • Boring: identify areas you don’t find interesting. These will drive other readers away. Boring areas should be removed or rewritten to be made interesting.
  • Surprising: point out areas that you didn’t know and didn’t expect. The author should lean into these, creating as many as possible.

Day 42: The Public to Private Badge


  • In order to grow your audience, you need to convince people to be willing to be contacted by some sort of private means, such as by an email newsletter.
  • Publish content on public sites such as Twitter or YouTube to be discovered. Make the content good enough to get people to subscribe to you off of the platform.
  • Your public presence can vanish at any point. Your private presence is around for as long as you want it to be.

Day 43: The Soulja Boy Strategy


  • You can grow as a writer and creator by curating content for others
  • Note that curation is not aggregation; anybody can collect a bunch of links together, but the point is to find things that you think are worthwhile, provide commentary, and to get others to discover you because of what you curate.
  • Quality matters more than quantity. By curating content, you are also endorsing it. Believe in the content you curate.

Day 44: Don’t Find a Niche. Create One.