📕 Issue #78 - How I Wrote 200 Articles in 200 Days

I don’t write full time.

I have a day job as a product manager.

I sit in meetings all day and sometimes have to work through nights.

Yet, I managed to write 200 articles in 200 days. Let me tell you how I did this. 

Why did I write 200 articles?

When my bridesmaid, Evelyn, ended her long-distance relationships, I wanted to share my experience with her. I didn’t feel ready, but I knew Evelyn would benefit from hearing my story. I had something to say and someone to read my work, so I leaped to publish my first article on how to make long-distance relationships work. Sometimes the world needs to hear my voice before I am ready. 

I used to read a book a week and pamper my day with podcasts and blogs. In fact, I have collected so much stuff that my first 80 essays are purely from my notes. I waited four years to see if this body of knowledge will magically turn into wisdom. Nothing happened. This begs the question:

How did I make time to publish 200 articles in 200 days? 

Well, it typically starts after dinner. Dinner might have been chicken legs and jasmine rice. As I took the final sip of my oolong tea, sitting in the family room with the last bit of light coming in, I would ask my fiancé, Chris, “What should I write about tonight?” I like to bounce ideas off of Chris and he always responds with the same question, “What’s on your mind?” Talking my ideas out loud helps clarify my focus. “200 days (this letter), team management, and Model Breakers (my book),” my intuition declared. 

After Chris walked away, I opened my laptop to check out my recent drafts on Substack. I ensured that there were at least 30 working drafts at all times. My intuition chimed in as I went through them. That intuition would beget my energy for the next two to three hours. 

“But I just don’t have enough time.” 

Maybe you do. Maybe you haven’t realized that the time you spend living is content creation in progress. The key to turning your experience into words is prioritization. 

The reality is that you are prioritizing, consciously or subconsciously, all the time. Working on your day job, investing in your passion projects, and spending time with your loved ones are all one life. Remember that you are not paid to work from 9 to 5. You are paid to deliver impact. It is more productive to work on things that bring the most joy to each moment.

Meetings end early? Get some words down. Don’t stress about finishing the whole piece on the go. Start by sending these small deliverables to your future self. There is no such thing as work-life balance. Working, resting, and writing are all the same thing—your life. 

Writing SOP

The way I live is the way I write.

If LivingOS is a product of my daily writing, the newsletter is my manifestation of life. Contrary to professional writers, I spend most of my time outside of my writing desk. Exploring new experiences, coaching a team, and tackling organizational challenges are all part of my writing process. My ideas come from wanting to get better. Therefore, my writing ranges from writing the first 50k words for my book to identifying my self-sabotage.

How to define what to write about next?

Part of my content creation is done through conversations with friends. I spend 20% of my time testing ideas for new topics. Before writing this letter, I asked my LivingOS, On Deck, and newsletter community to share what they are most interested in. I also interviewed my earliest readers to get their perspectives. 

Think of these surveys as MVP (minimum viable product) for writing. Before I write out the actual essay, I would ask friends to vote for titles they are most interested in. This way, I can invest my energy in building out MVP that will get the most return.

How to maintain 30+ drafts at all times?  

The best way to create content is through intentional living. I have trained my mind to see the world through the lens of “How can I make a story out of this?” I use the following standard operating procedure to capture new thoughts: 

  1. Every night, I write down 2-3 sentences to capture the most memorable moment of the day. 

  2. Every week, I curate the best stories and turn them into a draft in my Content Hub and link them to related topics in my Topic Forests. The Content Hub serves as a playground where new posts emerge. 

  1. I stop writing before I am finished so that I can keep my interest and momentum going. This early stopping process also made me spin off five drafts on average for every article I write.  

    “The best way is always to stop when you are going good and when you know what will happen next. If you do that every day when you are writing a novel you will never be stuck.” —Hemingway

How to turn drafts into daily production?

Sometimes I finish the writing in one (long) sitting. Sometimes I switch drafts if I don’t find the current one sparking joy any longer. While every day looks different, I follow this standard procedure (with steps 1-7 for writing and steps 8-9 for editing):  

  1. Flesh out the notes from the most recent draft until I get stuck. 

  2. Make some oolong tea, clarify my thoughts by talking out loud, and transcribe them with Otter.ai.

  3. Edit the transcription into a story until I get stuck. 

  4. Find a new environment, alternating between my desk and couch. 

  5. Sprint with the new environment until I get stuck. 

  6. Wander around my second brain to get new inspirations. 

  7. Keep writing, alternating between 2), 4), and 6) until I have a rough draft. 

  8. Share the rough draft with Chris and prepare my shift towards my editing brain. 

  9. Read the piece out loud. Optimize the hook. Review everything with Grammarly one last time.

Once the essay is out of me, I shut the laptop and storm out.  

Writing Principles

Write in your authentic voice. 

My writing went from general advice to specific life musings. Instead of branching to more topics, I began to share my fears, dreams, and hesitations. People came for the content and stayed for the character. Aim to share your intimate and unfiltered thoughts, and you will intrigue your readers. 

Optimize for long-term value, instead of market value. 

I only abide by one criterion: “Will I find value in reading this piece of content five years from now?” For example, I would rather walk you through how I let my early hire go than help you nail a product management interview. While writing about product management gave me thousands of subscribers, I realized that these catchy subjects dishonored my true self and passion. 

On Day 99, I made a conscious choice to prioritize founder-market fit over product-market fit. Instead of writing about career hacks, I decided to focus on helping you create your own game of life. By ruthlessly delivering long-term value, I have built a community where people from all around the world come to learn and grow together. 

Writing is a muscle, a marathon, and a legacy. I want to bring inspiration and empower people to start something impactful in their lives. 

As I write this newsletter to you, I am also writing to my current and future family. I want my future kids and grandchildren to read this newsletter and know everything about Charlene. That's my legacy. That's living life. 

So here we are, the conclusion of my 224th essay published. Building the LivingOS community. Intentional with my time. 224 cups of oolong tea, countless edits and brainstorming with my fiancé, and living to create content.

I am Charlene, and I’m changing the world one letter at a time.  

If you got something out of reading this letter, your friends might like it too. ❤️

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I will guide you, step by step, to rewrite your stories, get into the right actions, and create a calendar you love by the end of the fellowship. ❤️

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See you next week,


Thanks to Chris L, Charlie R, Juhan T, Kevin L, Reza S, Carolina P, and Joey D, Rishi D, Tom W, Lisa T, Mohammed M, Nicholas S, Federico A, Matt K, Justin N, Benjamin S, Nick S, Patrick T, and Will Q for reading drafts of this. 

And one more thing…

In case you are still wondering how I pull all this together or need some extra inspiration, check out the first-ever vlog we made for you… ❤️