Aggressively Human: Online Business in the Age of AI, Algorithms & Automations

In this episode, we talk about frameworks — what they actually are, why they matter more than ever for getting found in AI search, how they set your work apart, and how they work as a sales tool without turning your discovery call into a free consulting session.
Search has changed — and with it, that means how we approach our content has changed. Five years ago, a broad range of posts and decent keyword density was enough to get found. Now Google and AI tools are matching intent, not just words… so what do you do when you need to go beyond keywords? We bring in frameworks.
We get into the mechanics: the difference between architectural, transformational, and diagnostic frameworks; how a named framework becomes its own node in an AI knowledge graph; and why a framework does at least 15 times the work of a piece of content that’s just “everywhere.” This isn’t about having the perfect, finished methodology. It’s about why staking your intellectual territory now — even imperfectly — is the move.
* Why AI-mediated search rewards frameworks and how that’s different from the old keyword-matching era
* How the Aggressively Human philosophy would have evolved over time
* What it actually means for a framework to “become an entity” and live independently of you
* How to build a pillar page and content clusters around your named framework
* Using a framework on a sales call to show your approach without doing the work for free
* Why a process framework can give confidence on your skill as a guide — including the hard parts, the identity crisis, the plateau
* The difference between architectural frameworks (here are the pieces) and transformational ones (here’s the journey)
* Frameworks as content engines: how six pillars becomes six newsletters, six webinars, and six entry-point offers
* Why “it’s still jello” is okay — start claiming your semantic territory before the framework is fully formed
* How omnichannel reinforcement (podcasts, guest appearances, newsletters) amplifies a framework’s reach
"Frameworks showcase ‘Here's how I'm different.’ It's not just I have this offer, I have a group coaching program. We meet every two weeks. That's a feature, that's not a methodology. But if you can explain your way of thinking, then AI can parse out what you do that's different. There were two other entities in that recommendation from AI and it differentiated between all of you. Not because you called yourself something different, but because it could parse out your way of thinking and how that client's experience would be different based on who she hired. And that's not something that could have been parsed or understood or recommended five years ago in the old system." -Meg

Resources
The Beacon Framework from Meg Casebolt
Why You Need a Named Framework from Meg Casebolt
Methodology as a Map from Jessica Lackey
The Iron Framework by Mel Deziel (from Creator Kitchen, with Jay Acunzo)
Blair Enns’ Four Conversations Framework
The Former Lawyer Framework by Sarah Cottrell
Curiosity and Why It Matters (book, mentioned by Jessica)
Connect with Us
Listen on Spotify
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Meg Casebolt
Jessica 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

Many conversations about AI in the entrepreneur space default to content generation — blog posts, social captions, first drafts. But that’s only one layer of what AI can do, and for a lot of people, it’s not even the most useful one.
In this episode, we’re joined by Meighan O’Toole of Ops+Bots, a Notion architect and workflow specialist who helps small teams build scalable systems they’ll actually use. Meighan has been using Notion since 2019, is a Notion Ambassador, and brings a perspective shaped by ADHD and navigating long COVID — including nearly a full year where they couldn’t work. That lived experience completely changed how Meighan thinks about what AI is actually for.
We talk about the real difference between LLMs, chatbots, and agents; where Notion AI genuinely shines (and where it doesn’t); and why the tools that reduce administrative burden can be a genuine lifeline for people managing chronic illness, ADHD, or financial constraints.
* The difference between LLMs, chatbots, and agents — and why understanding it changes how you use AI tools
* What Notion AI actually does (and why it’s not about generating content)
* How agents handle meeting notes, statements of work, and client updates — and what that’s worth to a solo operator
* Where agents can support the admin work that many of us (especially with ADHD) don’t have the inclination or capacity to do
* Long COVID, chronic illness, and the part of the AI conversation that’s often missing in entrepreneur spaces
* “Human in the loop” — why AI works best as a co-pilot, not on autopilot
* Privacy, security, and copyright concerns — which are real, which are amplified, and which were already there before AI
* Why class and marginalization belong in the AI conversation
About our Guest
Meighan O’Toole
Resources
Paul Graham’s “Maker’s Schedule, Manager’s Schedule”
Bullshit Jobs by David Graeber
Connect with Us
Listen on Spotify
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Meg Casebolt
Jessica 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

What if the answer to growing your business wasn’t building a funnel or crazy AI workflows, but being human, and building discernment and relationships?
In this episode, we talk with Shannon Mattern, founder of the Web Designer Academy, where she teaches web designers how to package, price, position, and sell their services. She came up through freelance web design herself—undercharging, over-delivering, treating clients like bosses—before closing that side of her business and pivoting to teach others what she had to learn the hard way.
We talk about what’s actually driving undercharging, how AI is a repositioning opportunity when seen strategically, and why the real value of a web designer has never really been the design itself.
* Why web designers undercharge—and why the root cause runs deeper than mindset or confidence
* The codependency cycle: from people-pleasing freelancer to the same patterns showing up in her own business
* Building a business through referrals and word of mouth instead of paid ads and growth hacks
* Why hiring people different from yourself actually improves the business (even when it's uncomfortable)
* Why competing on price is a trap, and what to position on instead
* Why AI tools like Wix and Squarespace aren’t the threat most designers think they are
* Repositioning from “I make websites” to “I’m a business strategist and growth partner”
* How AI is actually a reason to charge more—not less—if you reposition around strategy and business impact
The truth is, designers hear me when I say this or anybody doing anything where like [00:30:00] part of your business relies on a piece of software that your expertise is not knowing how to manipulate that piece of software to. build the thing. It's the fact that you can even translate what a client's needs are something that's going to them the outcomes and results that they want.” - Shannon Mattern

Register for the Simply Profitable Designer Summit, March 16 - 20, 2026.
The way people find and use websites has changed. Learn how to design for conversion in the AI search era.
About our Guest
Shannon Mattern
Free Business Course for Web Designers — raise your prices and stop undercharging
Connect with Us
Listen on Spotify
Listen on Apple Podcasts
Meg Casebolt
Jessica 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

The narrative surrounding self-employment is often binary: you’re either running a full-time business or you’re not. But is that the reality? What would be possible if we treated self-employment as a spectrum? And what do we face as we move across the spectrum in terms of time, money, and momentum? For this discussion, we’re welcoming back Softer Sounds founder, Off the Grid host, and author Amelia Hruby.
In this episode, Amelia shares what led her to a significant decision at the end of 2025: scaling back her podcast studio Softer Sounds dramatically and putting herself on a six-month sabbatical for that side of her business while investing in the creator-style side of Off the Grid. We dive into the idea of self-employment as a spectrum, the many forms it can take across a career, and why moving along that spectrum is a feature, not a flaw.
Hear from all three of us how we cobbled work together to build the income we needed across the years — the bridge jobs, the clients who weren’t the dream but paid the bills, and the years of audience-building that often preceded any real traction. This isn’t a conversation about how to build a six-figure business. It’s about what self-employment actually looks like at different stages, and what we’d do differently if the goal is to simply stay self-employed.
* What Amelia’s six-month sabbatical actually looks like — and why she chose a third option instead of hustling harder or closing the studio
* Self-employment as a spectrum: from side contracts and bridge jobs all the way to full-time business ownership (and back again)
* How Meg, Jessica, and Amelia each cobbled things together to get started — and what cobbling it together still looks like for established businesses
* The role of bridge work in creating the time and mental space to build what you actually want long-term
* Why Amelia chose to focus on Off the Grid and The Interweb instead of doubling down on Softer Sounds
* What publishing books (Amelia’s and Jessica’s came out within a week of each other in October 2025) has to do with long-term business strategy
* Hitting your capacity ceiling — and the different forms it takes at every stage of growth
* Authority building: why showing up consistently before a trend breaks is what actually creates leverage when the trend arrives
* The privilege question: how partner income, healthcare access, and life stage shape what risks you can realistically take
* When and why to go back “in-house”
“The only consistent business models you can count on are being a CPA or owning a funeral home. Otherwise it’s gonna change all the time. If you wanna be self-employed long-term, you have to love the ride of it. You have to love that it changes all the time. Do you enjoy every moment of it? No, I do not relish in the fact that AI perhaps stole half my business. I don’t have to love that. But I have to love dusting myself off and doing something new again.” - Amelia

About our Guest
Your Attention is Sacred Except on Social Media
Off the Grid
Self-Employment is a Spectrum
Connect with Us
Listen on Spotify
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Meg Casebolt
Jessica 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

Every business owner hits that point where the thing that used to light them up now feels like a slog — and it usually happens right when the work matters most. Whether it’s February fatigue, launch number seven, or the creeping suspicion that you’ve said everything you have to say, the impulse to burn it down and start fresh is real. But is it burnout, boredom, or just a season?
In this episode, we talk about the difference between being tired of something in your business and being done with it. We dig into the natural cycles of building — preparing, planting, harvesting, and resting — and why the reinforcement phase (the one that actually creates momentum) is the hardest to stay motivated through. Jessica shares what it’s like to be in the “hardening the cement” stage while wanting to chase something new, and Meg talks about her experience running Social Slowdown for 100 episodes and knowing when it was time to hand off the torch.
This isn’t a pep talk about pushing through or a permission slip to quit. It’s a conversation about learning to read the signals your energy is sending you.
* Why the repetition phase of your business feels boring but is where the real traction happens
* The seasonal cycles of energy and creativity (and why Meg doesn’t launch anything in February)
* Jessica’s harvest-to-reinforcement arc — and the tension between solidifying old work and chasing new ideas
* The green light / yellow light / red light framework for deciding when to push, pause, or stop
* Why your audience hears your message differently every time, even when you’re saying the same thing
* How Meg knew it was time to retire Social Slowdown after 100 episodes and a book
* The difference between reinforcing, repurposing, remixing, and just regurgitating your content
* What to do when you still need to market but have nothing new to say
* Why your best referral partners being in the same slump at the same time is a real business risk
How relationships and referral networks carry your message when you can’t
"Reinforcing is going back in and putting more infrastructure in place to make it stronger. Repurposing is, or rehashing for that example is taking the same information and pushing it out in a different place. Remixing could be finding new ways to explain something." — Meg

Mentioned
Amelia Hruby/Off the Grid
Connect with Us
Listen on Spotify
Listen on Apple Podcasts
Meg Casebolt
Jessica 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