How I Write

There is a method to the madness (Mostly method. Occasional madness.)

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A few weeks ago, I had two separate conversations with friends about what it’s like to start a newsletter. More specifically, they were interested in understanding my article-writing process from start to finish.

I always love talking about the writing life; I firmly believe that we all have compelling stories that are worth sharing. Writing also helps us find our voice, and in many instances, helps us make sense of life’s difficult moments.

A newsletter (or blog) may seem like a lot of effort, but it gets easier once you establish a process that works for you. What I’d like to do today is share my process for writing articles here on

Hello, Adversity

, from ideation to publication. This process took me a few months to refine, but now that I know it works, it has alleviated a lot of creative anxiety.

I hope that by sharing my routine, you will become more confident in your ability to share your unique perspective with the world. I possess no special talents; I am the quintessential example of “If I can do it, you can too!” (After all, it took me several weeks to figure out how to edit my homepage layout. It’s a low bar.)

Think of the following steps as suggestions rather than hard and fast rules:

Step 1: I consult my content calendar

My content calendar is my security blanket.

I always like to know what topics are in the queue over the next 1-2 months. I like to know that when I hit publish on a post, I know exactly what comes next. My mortal fear is waking up one day and staring at a blank screen for hours on end, with no idea what to write. Just thinking about it gives me palpitations.

I also like to keep a list of adversity-themed topics that I want to write about in the future, but are not yet ready for prime time. For example, I know I want to write about acceptance someday, but it’s a weighty topic that requires further contemplation before I feel ready to put it on my schedule.

I update my content calendar every 2-3 weeks, replacing finished articles with new topics from the aforementioned list. When I do this, I scan the list to see what jumps out at me. If a topic catches my eye, it usually means that I’m ready to write about it.

The key to an effective content calendar is to strike a balance between rigidity and flexibility. Sometimes, the calendar needs to be tweaked, and that’s okay. If I’m not feeling well, or I want to take the week off, I can repost older content or start a discussion thread.

There are also times when I am inspired to write about a topic that isn’t currently on the calendar. When this happens, I move everything on the schedule back a week. For example, today’s topic was on my list of undefined future articles, but it jumped to the front of the line once I spoke with my friends about starting a newsletter.

I have learned the hard way that when my plans get too rigid, they tend to go up in flames. (My friend

Maddie Burton

’s Substack,

Your Five-Year Plan

is about this very topic!) Although it’s important to plan and develop contingencies, leaving room for the unexpected is essential to thriving over the long term.

As entrepreneur and author Derek Sivers likes to say: “The best plan is the one that lets you change your plans.”

Step 2: I identify relevant supporting material

Once I select my topic, the next step is to pull together relevant material to help strengthen the piece. This is where my commonplace book comes into play. I use a program called Notion for all my note-taking. It’s excellent.

In Notion, I have a page titled “Writing and the Creative Process” which is full of quotes and anecdotes about — you guessed it — writing and the creative process. All of the quotes in this article are from there.

I began organizing my notes this way after watching a video by author Ryan Holiday on how he comes up with supporting material for his books. Every book he writes is full of dozens of instructive stories from history. Each story began as a notecard in his commonplace book, which is a bit of a misnomer in that his “book” is actually a giant plastic container filled with thousands of notecards, organized by topic. It hurts my hand just thinking about it.

Although there are benefits to organizing notecards on a table, I prefer to use a computer for my commonplace book. It’s much easier to search for what I need when all my notes are digitally indexed and available at my fingertips. (Not to mention I don’t have the space or dexterity to write out thousands of notecards by hand.)

I have Notion pages on almost every topic that pertains to adversity in some way, from pain and suffering to conquering fear to the pursuit of happiness. Each page contains dozens of quotes and anecdotes from my reading over the years. My commonplace book is a valuable resource for me that gets only more valuable over time.

I can talk about commonplace books all day — if you have any specific questions about how to start your own, don’t hesitate to ask!

Step 3: I adhere to a consistent writing schedule

I have found that a consistent writing schedule is the key to avoiding last-minute meltdowns and panic attacks. Now that I have gone from writing twice a week to once a week, I have settled into the following routine:

Wednesday - Last week’s post is published. Yay! I put the article on social media and take the rest of the day off. I quickly glance at my content calendar and mentally prepare for the next topic.

Thursday - The mental gears begin to turn. I open a new Google doc and put the topic in the title. (For example, this article began as “My writing process.”) I jot down random thoughts about the topic, then consult my commonplace book to paste in any quotes or anecdotes I want to include. This takes around 20-30 minutes. Then, I organize what I have into a rough outline.

The primordial ooze starts to take shape.

Friday and Saturday - I expand the outline into a draft. At this point, what I’ve written is utter garbage. It is incoherent. There are acronyms. There are many, many typos.

As author Ernest Hemingway eloquently put it, “The first draft of anything is s***.”

(Accurate.)

The main goal at this stage is to get a draft written as quickly as possible. Once the first pass is complete, I go back to the beginning and fight, paragraph by paragraph, to turn it into something respectable.

Usually around the two-hour mark, doubt begins to creep in and I argue with myself about whether I should keep going. Who am I to write about this topic? is a familiar mental block.

But I fight back. I have come this far, and I know, deep down, that I wouldn’t have written about the topic if I didn’t feel I was qualified to speak on the subject.

If it’s an article that would benefit from another set of eyes, I send it to my editor Shannon. She is great about challenging me to be more concise and offering suggestions on how to strengthen the narrative.

Sunday - I take Sundays off. I need a break before the final push.

Photo by Kaitlyn Baker on Unsplash

Monday - This is the day the article really starts to take form. When applicable, I look at the edits Shannon sent me over the weekend and weave them into the final draft. My goal is to finish as much of the article today as possible; I don’t like leaving too much for Tuesday. I paste the article into the Substack editor, add images, add section headers, and get it just about ready.

Mondays are when I encounter the most resistance — a combination of writer’s block and procrastination. As author Steven Pressfield writes in The War of Art: “The danger is greatest when the finish line is in sight. At this point, Resistance knows we’re about to beat it. It hits the panic button. It marshals one last assault and slams us with everything it’s got.”

Tuesday - I do any final wordsmithing and get the post ready to go. I always schedule my posts in advance, since it goes out at 7 am Wednesday morning, and….I am never up at 7 am.

I congratulate myself on a job well done. Then I panic.

If I was a normal person, I’d hit the schedule button and be done with it. Alas, I am a perfectionist. An hour later, I manage to convince myself that — just like my first draft — the final product is also garbage.

I check and recheck the links. Even if Grammarly tells me I didn’t make any typos, I reread my article again just to be safe. I re-fight the same sentence construction battles I thought I had won hours before.

Eventually, I realize this is all pointless. Deep down, I know the post is fine, and if there’s a stray typo, it’s not the end of the world.

Wednesday - The newsletter goes out at 7 am. Do I celebrate? Do I pump my fist?

No, let’s be serious. (I think you know where this is going.)

When I wake up, I immediately open the email and check to make sure the links work one last time. Once I see, for the 85th time, that they are indeed okay, then I celebrate. I put the article on social media, breathe a sigh of relief, and take the rest of the day off.

Tomorrow, the process begins anew.

Writing is a process

This is how I write my newsletter every week, but it doesn’t mean it’s the right way. After all, there is no right way. Writing is a subjective process.

I hope, however, that if you are an aspiring writer, you now see that the final product doesn’t come from innate, effortless talent, but rather from a careful process that involves lots of slogging, editing, and rewriting.

As author Sarah Stodola put it in her book, Process: The Writing Lives of Great Authors:

We tend to deify authors, thinking of them as disembodied names who produce the works we crave and admire, failing to realize the long hours, aching fingers, and racked brains that these very human, warts-and-all people suffer in order to complete the books that we take for granted.

Her quote applies to any kind of writing, not just books.

If you don’t think you’re good enough to start writing, don’t get discouraged! You will get better over time. Like anything, it takes practice.

Your voice is important, and the benefits of a consistent writing process can change your life.

I’m living proof of that.

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Audio Extra

12/14/23 update: You can find the recording here.

In this week’s audio post, I share a few of my favorite writing tips, including:

• how I look for quotes and anecdotes for my commonplace book

• how journaling and reading can help you find ideas to write about

• why performance metrics are overrated, and more

Going forward, I am going to send the audio recording out as a separate email to paid subscribers on Thursdays, rather than attach it to the end of the Wednesday post.

You can find these audio recordings in a new section of the homepage called “Audio Extras”. If you aren’t a paid subscriber but want to listen to a specific recording at any point in the future, you can start a 7-day free trial then cancel without being charged. (Although I hope my soothing voice can help change your mind!)