9 Substack articles you should read this weekend
Learn something new and fascinating this weekend.
I know your reading list is probably already drowning. Mine too. But I stumbled into nine pieces this week that actually earned their spot in my brain, and I figured you might want to know about them before they disappear into the Substack void.
Some of these will piss you off. Some will make you question choices you made five years ago. One is in French, and I’m recommending it anyway because the ideas are brilliant. And at least two of them reveal patterns about how we’re all sleepwalking through major shifts we haven’t fully processed yet.
So here’s what’s worth your time this weekend.
1. The Art of Reinvention: When Less Became More
Did you know English became the global language basically because it got lazy?
The article opens with a hilarious fictional conversation between an Anglo-Saxon and a Viking trying to buy sheep from each other, both butchering each other’s complicated word endings until they just... give up and strip everything down to the basics. “Ok... sheep!!”
That’s essentially what happened to English. While German speakers are still wrestling with der, das, die, and French learners are memorizing seventeen forms of “to go”, English just dropped all its endings. The writer, Ash Stuart, makes this fascinating argument about why we can verb anything, why “Google it” just works, and how we’ve somehow come full circle back to Proto-Indo-European’s four-letter word roots. History is weird.
2. The American Dream Is Dying
Maryam Mehrtash, an Iranian woman who fled war as a child, finally became an American citizen this year. She thought she’d be celebrating. Instead, she felt like she’d arrived at a funeral.
That opening carries the weight of the entire piece. It’s this profound cognitive dissonance—achieving your childhood dream in a country where the dream itself is visibly crumbling. She doesn’t do political blame or nostalgia. She just lays out the math: the cost of homeownership, the weight of medical debt, the percentage of adults who no longer believe hard work leads anywhere. Even the people who “made it” are quietly leaving.
But what makes this good is that it’s not doom. It’s an invitation. She’s saying maybe the death of the old dream is a chance to build something real instead of resuscitating an illusion.
3. I Lost $50k+ Pretending My Strategic Genius Was Just “Freelance Work”
For 6 years, Mara, a premium digital business manager, would walk into someone else’s chaos—scattered tools, broken workflows—and fix it. Build systems. Create clarity. But her own business was a disaster. She started passion projects and abandoned them, had brilliant ideas and never launched them, made plans she didn’t follow.
The problem wasn’t her strategy. The problem was that she saw herself as “just a freelancer” instead of a business owner. She’s unpacking the three specific mistakes that cost her over $50k: confusing planning with progress, not tracking wins, and thinking systems kill creativity. If you’ve ever blamed “not having enough time” while secretly knowing the problem is you, this one’s going to sting in the right way.
4. The $2,000 Book About the Richest Man You’ve Never Heard Of
Daniel Ludwig was richer than Rockefeller. He controlled more oil tankers than Onassis. He was number one on Forbes’ first-ever richest Americans list in 1982. And I guarantee you’ve never heard of him.
Why? Because he made sure of that. Today, if you want to read this book, you’re paying two grand on Amazon.
He scolded employees for using paperclips in airmail, flew economy while commanding a global shipping empire, invented a financing hack that built tankers with zero capital, then sunk over a billion dollars trying to tame the Amazon. Then gave away everything away to cure cancer. In this article Charlie Garcia captures something true about wealth: the people with the most money often want the least attention. There’s a strange wisdom in that silence.
5. Rien ne va plus
This one’s in French, but hear me out.
LinkedIn’s organic reach just collapsed by 50%. About 61% of posts are now AI-generated. And yet Marie Gaymard’s metrics keep climbing. Her thesis is that you can’t AI your way out of becoming replaceable.
She argues that when algorithms shift and automation floods every feed, your only defense is what she calls “internal forces”—the ability to think clearly, say things people want to read, position yourself with conviction. There’s an Australian study she cites: 55% of professionals using AI at work experienced decreased self-compassion. When you delegate everything that once required effort, you start losing your sense of what you’re capable of. Performance and accomplishment aren’t the same thing. Even if you don’t speak French, the ideas translate perfectly.
6. I Made Perplexity Comet My Substack Assistant for a Week
AI browsers want to replace Chrome, and these guys actually tested whether they can.
For a full week, Ashwin Francis and Raghav Mehra made Perplexity Comet their only AI tool for everything—research, content analysis, market intel, draft reviews. Then they documented what worked and what absolutely didn’t. Comet crushed it at daily market intelligence (30 seconds instead of hours). Struggled hard with data extraction (kept stopping like a lazy intern). But gave surprisingly sharp writing critique that caught things he’d missed.
What I appreciate is the honesty. No sponsored hype. Just working writers admitting when the old way is still faster. Their deeper point: we’re measuring AI tools with outdated productivity metrics, when the real value might be spotting patterns you’d never see manually.
7. I Used Machine Learning to Make Sense of 39,000 Substack Articles
Most people wonder what’s trending on Substack. This writer built a database and let the algorithms tell her.
Using clustering and semantic search across 39,000 articles from 2,500 newsletters, Karen Spinner mapped the platform’s entire content landscape. What she found: AI ethics has the most articles, but politics generates 10-20x more engagement per piece. About 59% of articles get fewer than ten reactions. The “sweet spot” for length is 1,500-2,000 words—unless you’re already famous, in which case you can write three words and get thousands of likes.
What’s valuable here is seeing the weather system when you’ve been walking in the rain. It’s data journalism about writing itself, showing patterns that are invisible when you’re just one person publishing into the void.
8. Look Down. You’re Wearing the Wrong Shoes
You’re optimizing your profile instead of your life, and Francisco wants you to stop.
The shoes metaphor is his central point: if the path you’re on requires constant stress and repeated failure, maybe you’re wearing the wrong shoes entirely. Not the wrong strategy. The wrong shoes. He’s arguing that people would rather DM potential partners than approach someone in real life. Complain about politics online than take action. Perform tolerance for the algorithm instead of being honest with the people who actually love them.
His three solutions are almost offensively simple: stop calling people who won’t call back, listen more than you talk, choose friends by values not circumstances. It sounds obvious until you realize how few people actually do it. If you’ve felt like you’re performing for everyone’s approval but your own, this will land.
9. Barbara Osiro on Cultivating Inclusion and Leadership in AI
Most AI ethics conversations happen in boardrooms with reliable WiFi. Barbara Osiro runs them in Kenyan communities where power blackouts last for hours.
This interview by Rebecca Mbaya is about what inclusion actually requires when you can’t assume electricity, internet, or literacy. When the threats women face through technology get completely skipped in standard curricula. When African voices are absent from conversations about AI being built for them.
Osiro’s framework is different: inclusion isn’t just about access but also about authorship. Women shouldn’t just learn AI ethics, they should define what safety means. The wins she tracks are teachers localizing AI into Swahili, rural educators becoming trainers, mentees starting their own initiatives. When her team showed up to a training and hit a power blackout that lasted the entire session, they didn’t cancel… they redesigned everything for offline learning. That’s the difference between theory and practice.
Bonus: The 4 Coaching Competencies That Future-Proof Your Leadership
This article by Elina translates coaching competencies from corporate jargon into actual human behavior. What do you do when your direct report misses another deadline and your instinct is to just do it yourself? How do you build the kind of safety where problems surface before they become fires? If you’ve ever thought “my team needs more ownership” while simultaneously micromanaging every detail, this will make you squirm. In a good way.
So that’s what I’ve got for you. Nine pieces that actually earned their space in my brain this week. Some will challenge you. Some will just make you think differently about something you thought you understood.
Pick one. Read it with your coffee tomorrow morning. Let me know which one hits.
And if you make it through all nine this weekend, you’re either extremely disciplined or avoiding something important. Either way, respect.
Thank you so much for reading. Feel free to share your thoughts in the comment section.
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OMG thank you for sharing 🙏🏼 It means a lot. And you also gave me new people to check out 🤭 Thank yoouu 🫶🏻
The coffee is brewed...I'm going in.
Solid idea, this post, and wonderful summaries. I'm pleased you bannered Karen Spinner's work here as well.