How to Substack like a journalist
Approaching writing with a journalistic rigour
The deadline: Wednesdays at 8AM
The finish line is set in advance. During my finance journalism days, I had a publishing schedule to follow. If my editor had slotted my article about Shariah-compliant investment banks in Southeast Asia for the coming Thursday, I had to have something publish-worthy by then. If not, there simply won’t be a story from my banking news team that day.
I approach my Substack publishing with the same journalistic rigour. My goal: share an essay on my Substack at a consistent time every Wednesday. I show up with an 800-word article that’s contorted itself so many times over the past week. All the other steps in the writing process act in service of this deadline, an arbitrary time that my five years in journalism have trained me to stick to. Collecting interview notes, organizing all the relevant information in one space, and last mile touches all spin the gears towards a well-constructed news article.
Ideation and drafting from conversation
Before I started writing my news article, I needed to first conduct background research and interviews with experts. I’d jot down relevant facts and pinpoint the missing links and try to get the answers from my interviews by asking pointed questions. I’d then ride out the momentum of having everything in recent memory by transcribing the interview recording and plucking out quotes to use in my draft.
For my Substack essays, I emulate the interview calls through a weekly writing group call. I come in with three essay ideas I’ve tagged from my notes app, collected from conversations with friends, highlights on Kindle, and snips from podcasts. (All synced to Roam and tagged [[essay idea]]). During the hour,
, , or help me pick one that excites me the most. When a topic makes me feel “charged”, I can easily elaborate on it and bring out more emotions while selling the idea.I jot down bullet points when chatting about the topic. Often, my idea sparring partner asks questions such as “why is this topic important to you?” and prompt me to dig deeper on certain parts. My surface-level ideas get refined this way. I often walk away with a clear phrase of what the essay will be. In the moments I don’t, I know that transferring thoughts to a blank document will help me get there.
From here, I put together an essay outline, similar to what I’d hand to my news editors when pitching a story. I drag bullet points from my writing calls into an outline and rearrange them until there is some sort of flow.
I then write out my messy first draft, fueled by having the ideas and conversations fresh in my recent memory.
One document to house them all
I have a journalistic instinct to record everything in one place. Back when I was filing my news articles, I had to append all the information I had into one webpage so my editors could see everything I collected such as the weblinks to facts. They often came back with questions about the quotes I put in the article, so I had to keep them handy. My editors also revised my draft on the same page, so I was able to see the article as it evolved.
I similarly house everything that goes into each essay into one Google doc. This page contains all the versions of my drafts, feedback from my friends and research notes that come with it. I create a shareable link and send it out to friends whom I have an essay-feedback dynamic with.
After a day, or after receiving feedback from 1-3 people, I go back into the doc and copy-paste the whole draft to the top. I can preserve the first draft and make liberal changes to the new one without the fear of overworking the piece. I kept a reference copy, after all.
I revise my essay based on the feedback I receive. I first filter the comments. Not every feedback needs to be incorporated if it’s not true to what I want the essay to say. If there’s a comment to restructure the piece, I’ll do that first because it’s easier to shift paragraphs around before rendering them in place with transitions.
explains this via his piece, Alchemy of the Rewrite. Then I’ll go into the nitty gritty. Something I wrote sounds cliché or boring, for example, so I’ll think of a more interesting way to say it.I iterate on my drafts as appropriate, or as comments come in. I tend to spend some time fixing it up each day, making 10%-20% of changes in each version. I revise my drafts during any downtime I can find in the day: lunch breaks, before work, after dinner. If another friend wants to jump in on feedback, they’ll be able to look at the new draft and see if the tweaks I made work. Most of my published essays are between version 3-5.
Approaching the deadline
Similar to how news articles always have a hero image, I try to utilize my photography to represent the essay I’m writing with a unique visual. If I have a specific photo in mind, I’ll set aside an hour to get that shot.
Non-time sensitive news articles are ready in advance, set to publish by the next morning for people just starting their workday to read. Similarly for my Substack, I put in the final edits on Tuesday night. I don’t like scrambling in the morning of the publish day, so I prefer to work into the night about eight hours before and let the piece rest while I sleep. The final touches to the Substack posts include tagging my friends who help shape the essay and adding an update log at the end.
It has been a year of publishing and I haven’t missed a deadline. This weekly ritual has anchored a lot of my ideas into polished, shareable essays. I don’t intend to let this journalistic rigour slip anytime soon.
One of the most effective way to see your drafts from a new perspective is to “melt” them via reverse outlining. This is a weakness of mine, though
has helped me greatly in this regard. Michael explains this reverse outlining process further in the Alchemy of the Rewrite.
Looking back: An American born in 1940 had a 92% chance of doing better than their parents economically. A millennial born in 1984, who would be 40 today, only has a 50% chance. Source: The Equality of Opportunity Project via Scott Galloway.
Update log:
🎨 I spotted two artists from Warrior Painter about two hours after I landed. I noticed them painting and came up to them. Fate worked overtime for this to happen. I joined their plein air session the next morning.
📷 Have already shot eight rolls of film in my four days in Melbourne. I’m so tempted to get them developed here so I can see it straight away. But the analog is an exercise in patience.
☕️ Melbournians deserve to be snobbish about their coffee. They’re so flipping good.
✍🏼
introduced me to her writer and artist friends. They’re a different breed from Hong Kong’s corporate type and show up in colour. They’re all so sweet.🌳 I love trees. Especially when they’re lit against a bright, sunny day.
📖 Started reading The Algebra of Wealth (7% completed) by Scott Galloway. The equation has been on my phone wallpaper for about two years.
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This is very cool. I was trying something similar with my blog lately (although WOP might have disrupted this hah). Even keeping all my links in the same doc with multiple drafts. Good to know actual professionals do this, because I keep it one doc because it's just easiar haha
Open question: are you keeping to the weekly deadline with full-time work as well? I find the process (depending on the piece) can range from absorbing to all-consuming
This is so motivating! Thx for sharing your process.