Ensh*ttification is by design (and what to do about it)
The platforms we built our businesses on are breaking down—and not by accident. In this episode, Jessica and Meg take on ensh*ttification, the term coined by Cory Doctorow to describe how digital platforms inevitably decay over time. From Facebook and LinkedIn to Substack and AI, they discuss the predictable four-phase cycle that turns once-useful tools into algorithmic wastelands.Book released October 2025Jessica walks through what that cycle looks like for LinkedIn and Substack, while Meg connects it to the decay of creative platforms like Medium and Kindle publishing. Together, they explore what creators and experts can do when every channel feels rigged—and what it means to build on digital “rented land.”It’s part diagnosis, part “what now”: a conversation about recognizing when the rules have changed, when to adjust your strategy, and how to build resilient foundations that outlast the next platform crash.* The origin of the term “enshittification” and how Cory Doctorow describes the four-stage cycle* What Facebook, LinkedIn, Twitter, and Substack teach us about platform decay* How AI tools are repeating the same subsidized-growth pattern as social media* The false nostalgia for “when it worked” and how fast cycles now move* What to do when the strategy you learned in phase one stops working in phase three* How to spot market arbitrage opportunities before they close* Why foundations, relationships, and your body of work are the only real insurance* How to keep your business discoverable without chasing every new trendAdditional ResourcesPodcast | The Gray AreaWhy is the Internet bad now? | Evan Armstrong/The LeverageConnect with UsListen on SpotifyListen on Apple PodcastsMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com
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Beyond Copywriting: AI Bots in your business with Mary Williams
While AI still can’t fold your laundry, it can help you build a business that runs smarter—and a life that runs smoother. In this episode, Jessica and Meg talk with Mary Williams, the librarian-turned-tech director behind Sensible Woo and the new Sasquatch Media Grounds studio in Portland. From haunted recording spaces and tarot cards to spreadsheets and AI bots, Mary shows what it looks like to blend intuition with technology.She shares how she built her “AI team”—including Remy, the snarky Gen Z assistant who filters her inbox and protects her calendar—and why she treats her chatbots like departments inside her business. They talk about how AI can help reduce emotional labor, from grocery budgets to health tracking, and what it means to build systems that keep the human at the center.This conversation is filled with practical ways to make AI feel less robotic (and maybe a little more like a helpful intern who swears), while lightening your load with technology that actually serves you.* Mary’s path from librarian and tarot reader to tech director and business coach* How she organizes AI “staff” into departments—finance, operations, marketing, and more* The surprising power of giving your bots names and personalities* Why AI reveals more about your delegation habits than you think* How to build an AI “board of advisors” with personas like Mark Cuban or Reese Witherspoon* Emotional patterns people bring to technology (and what that says about leadership)* Creative personal uses for AI—from meal-planning and purchasing decisions to health tracking“I would argue if you had an intern, if you had a Gen Z Remy with you, you’d still fact check them because they’re young, they’re learning. I need to make sure that everything’s right. And in that sense, you’re still doing the same functions, you’re not doing less, you’re really not doing more. It’s just moving along faster.” - MaryAbout our GuestMary Williams: Sensible Woo | Sasquatch Media GroundsYou, Me ChatGPT WorkshopListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com
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Leaving the Casino: The Origin Story
What happens when every business book tells you what to think—but never explains what or how to do it?In this episode, Meg interviews Jessica about her new book, Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works. The conversation traces how the book came to life—from frustration with hollow business advice to the creation of a grounded, systems-based framework for experts who want to stay small, sustainable, and sovereign.Jessica shares how she read her way through the entire business section—books that were motivational but hollow, all premise and no practice. Some were thinly veiled sales funnels; others were memoirs pretending to be manuals. None answered the questions solo business owners actually ask: How do I make better decisions? What kind of business am I running? What’s enough? And how do I make this sustainable?They explore what’s missing from most business books, the trap of “CEO-energy” culture, and the myth that scaling is the only path forward. Jessica shares how years of client work, research, and teaching evolved into a practical field guide for soloists who want to build differently—without gambling their time or integrity.Get the details behind Leaving the Casino!* Why Jessica wrote Leaving the Casino after realizing most advice ignores context* How the online business world sells tactics that don’t fit most experts* Why many books are either memoirs or funnels to a paid program* How Jessica went from consulting to creating and publishing the book* The limits of frameworks like Profit First, Traction, and Essentialism* The risks of outsourcing sales, marketing, and finance too early* Responsibility, enoughness, and right-sized growth as operating principles* How privilege and life circumstances affect what “success” looks like* Why the book blends manifesto and textbook—both call-to-arms and manual* Jessica’s hope that it becomes a long-term reference for expert entrepreneursResourcesLeaving the Casino: Stop Betting on Tactics and Start Building a Business That WorksConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com
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Moving towards conflict with Shivani Mehta Bhatia
What happens when our usual ways of dealing with conflict stop working (if they ever worked)?In this episode, Shivani Mehta Bhatia joins Aggressively Human to talk about the changing nature of conflict—especially in a world shaped by grief, uncertainty, and fraying trust.We explore how conflict has shifted post-2020, how our nervous systems are adapting (or not), and why repair feels harder than ever. We talk about Shivani’s approach of “conflict midwifery,” destructive versus generative conflict, and what it means to build and lead with more care in increasingly reactive times.Whether you’re navigating tension in your team, your audience, or your closest relationships, this conversation offers a more humane way through.* What conflict looks like now—and why it feels more brittle* The 5 parts of Shivani’s “prism of conflict”* What “conflict midwifery” means and how it changes the repair process* What ChatGPT says are the fixes of our current polycrisis* What it takes to repair when there’s no shared script* What’s the smallest possible actions we can take in conflict* Leading and relating in a time of collective dysregulation* How we can prepare—not avoid—hard conversationsAbout our GuestShivani Mehta BhatiaMonthly Conflict ClinicConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com
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How to navigate the cycles of creativity without blowing up your business with Megan Dowd
What happens when your content calendar makes you want to set your business on fire?In this episode, Megan Dowd joins Aggressively Human to talk about what it actually looks like to build a business that respects your creative cycles—and what happens when you don’t. From the pressure to always be visible to the collapse that can follow, we explore what it’s like to build a business while also being a human with a nervous system.We talk about the performance trap of “consistent content,” what to do when you’re no longer interested in your own work, and when and how to use data and systems to support you.This is a conversation about honoring your capacity without disappearing, how to say no to content you resent, and why creative rest is not a threat to your business—but often the reason you stay in it at all.* What it really means to have a “human-first” business (hint: it’s not about the right font)* The burnout that comes from forcing content for the algorithm* Navigating visibility after a performance hangover* When to blow up your content calendar for the thing you’re excited about — and when not to* Choosing the work that feels good, even when it doesn’t scale* The myth of “consistency” and what your audience actually needs from you* The identity whiplash of letting go of “known” offers to create something new* How Megan is reshaping what success looks like in her next chapterAbout our GuestMegan DowdConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com
About Aggressively Human: Online Business in the Age of AI, Algorithms & Automations
In a world focused on more: more content, more followers, more marketing, more scale, more noise… we’re facing less trust, less contact, less reach.
We’re drowning in AI-generated slop, being pitch-slapped by “personalized” email funnels that couldn’t be farther from authentic, and struggling to be seen by a pay-to-play algorithm.
It’s never been easier to create and connect more cheaply and at more scale, with less trust and more skepticism.
But for experts and service-based businesses? We’re seeing the pendulum swing back.
The answer isn’t to play by these trends. It’s to be **aggressively human.** aggressivelyhuman.substack.com
Listen to Aggressively Human: Online Business in the Age of AI, Algorithms & Automations, The Diary Of A CEO with Steven Bartlett and many other podcasts from around the world with the radio.net app
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