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

Most of us who work for ourselves aren’t one clean thing—we’re cartoonists who also teach, consultants who also write, coaches who also run the whole business. And after a couple decades of that, you can end up with an enormous body of work that almost nobody can actually see, least of all the AI tools now deciding who you are. To talk through what to do with a career’s worth of ideas, we’re bringing on Meg’s friend, colleague, and client, Jessica Abel.
Jessica is a cartoonist and author turned business coach for professional creatives, helping them finish the self-generated work that has no deadline and get paid well enough to actually have time for it. In this episode, she walks us through the very unglamorous process of taking 10-plus years of courses, newsletters, and frameworks, most of it locked behind paywalls or buried in podcast audio, and making it cohesive and legible for both people and AI. She and Meg get honest about why podcasting is great for ideas and terrible for discoverability, what it actually takes to update a Wikipedia page, and why The Guardian counts as proof but a marketing podcast doesn’t.
We talk about the difference between productivity and capacity, why “decide” and “reflect” are the phases everyone skips, and what it means to pay yourself first with your time instead of your leftover minutes. We get into cyclical burnout, idea debt, and the genuinely hard work of deciding what you’re not going to do—and being at peace with it.
* Why “multi-hyphenate” isn’t a bug of entrepreneurial life
* Cyclical burnout: what happens to someone who always has new ideas
* How Jessica consolidated a career-long body of work into something legible using a bottom-up, feedback-driven process (and Claude)
* Capacity as a lens—not just your time, but your neurological and emotional bandwidth—and why it fluctuates by the day and the season
* Grow work vs. build work, and the tension between expanding your audience and cementing a legacy
* What it actually takes to be legible online—AI discoverability, entity confusion, and why Jessica still shows up as a cartoonist first
* The Creative Engine’s four phases—collect, decide, act, reflect—and why decide and reflect get skipped even though they’re the shortest
* The “flexible container”: building a finishing structure with edges that can still absorb a sick kid or a health flare-up
"I actually hate the word productivity and try to not talk about myself as a productivity coach, because—I still have to use it a lot 'cause it's the word people know. But productivity literally means: how do you have the same amount of capacity and jam more stuff into it? How do you get more stuff out of whatever you have available? And of course you can look at it different ways, but that's literally what it means in the economic sphere. Which is just a point of view that doesn't work for humans, and especially creatives and people who have big ideas and are trying to do the self-generated stuff." —Jessica Abel

About our Guest
Jessica Abel
Out on the Wire
In the Weights
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

Aggressively Human went on hiatus for July, and we’re back to talk about what the break actually looked like!
In this episode, we catch up on what our month off actually looked like — Jessica’s West Coast “book tour” meeting Deeper Foundations members across four cities, and Meg’s glaucoma surgery and a quieter, more foundational summer of business work.
We talk about travel, illness, eye surgery, membership relaunches, and the discomfort of resting without immediately filling the space with something new — plus why a genuine pause turned out to be exactly what both the business and the podcast needed.
* Why Jessica took her book on an unofficial “tour” through Seattle, Portland, San Francisco, and LA
* The public transit challenge: one rideshare in twelve days across four major cities
* Meg’s glaucoma surgery, what a week without screen time actually looks like, and why she scheduled it for the slow season
* What it actually looks like to let go of “big, hairy, ferocious projects” for a season without the business falling apart
* Relaunching the Deeper Foundations membership without ever having done a formal launch sequence before
* The “collective pause”: a shared sense that clients, colleagues, and the industry at large all pulled back at the same time this summer
* Why reflection is the step that gets skipped in a weekly podcast cadence — and why that’s a problem worth solving
* The World Cup as a rare moment of monoculture in an increasingly fractured media landscape
* What “resting but not regenerating” feels like when travel and motion replace actual stillness
“I think sometimes when you’re in a production content creation process, you don’t have a chance for reflection. When it comes to podcasting, because of the weekly cadence, you’re always gathering ideas, lining up guests, and thinking about what you want to talk about. Then we have to get together, we have to record, we have to produce, we have to create the show notes — we have to do all these different things. And that fourth step, reflect, is the easiest one to miss, because the cadence has been determined, and we lose sight of what it is we’re trying to do here.” -Meg

Resources
Leaving the Casino
Just for the Summer by Abby Jimenez
Succubus Blues series by Richelle Mead
School of Moxie with Mary Williams
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

Taking the whole month of July off breaks the weekly cadence we’ve held all year—and one of us is famously bad at taking time off. But this isn’t a best-of rerun or a quiet fade; it’s a deliberate choice to downshift, and we wanted to talk openly about why we’re making it and what it actually takes to pull off.
In this episode, we get into what’s behind our summer sabbatical: the planning required to step away (turns out you have to prep in advance), why listenership naturally dips in the summer, and why we decided against reposting old episodes under a “best of” label. Meg talks about her seasonal rhythm—short summers in a cold climate, kids’ camp schedules, less desire to sit at a microphone—and Jessica walks through a stretch of heavy travel, a meaningful family transition, and finally having the room to take a real beat.
We talk about the difference between maintaining and growing, why a body of work keeps earning for you even when you slow down, and the case for “mental composting” as actual business strategy. We also get into relationship marketing that doesn’t look like marketing, and why taking time off doesn’t mean you’re bad at your business. Plus a live tarot pull that may or may not predict another book.
* Why we’re taking all of July off—and why it’s a sabbatical, not just a slowdown
* The prep it actually takes to step away (hint: start two to three months out)
* How summer listenership shifts when everyone’s out living their lives
* Meg’s seasonal rhythm: cold-climate summers, camp schedules, and working less on purpose
* Jessica’s summer of travel, a family transition, and finally taking a beat after years of building
* Why a “body of work” keeps working for you when you stop pushing
* Mental composting and the case for creative downtime (see: Lin-Manuel Miranda in an airport)
* Maintaining vs. growing—and why you don’t always have to be in growth mode
"Taking time off doesn't mean you're bad at your business. But it does mean that if we're going to take time, we need to prepare for that two to three months in advance. Otherwise it's that vacation-y feeling where you cram.
I don't have a whole bunch of curriculum that I'm creating. I'm not writing and launching the book. I'm at a place where I can take a beat, so I'm gonna take it. Past Jessica did a good job, present Jessica is gonna take advantage of that, and future Jessica already knows what she's doing in August and September. There's more launches coming. They're just not happening in July." -Jessica

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

When you need a VA, a podcast producer, or just a new place to get your nails done, what do you actually do? You ask someone. But we don’t recommend someone who just gets the job done — we recommend those providers with outstanding customer experience.
In this episode, we talk with Nikki McKnight—Meg’s romance-podcast co-host, operations expert, and newly minted Certified Customer Experience Professional—about why she niched her business down into customer experience and launched a new business podcast called Would Recommend. Nikki walks us through how she went from “I can do everything” operations work to building a practice around a single belief: that for founder-led businesses, customer experience is the best marketing and retention strategy there is.
We dig into the difference between customer experience and customer journey, why emotions are what actually drive referrals, and how matching your brand promise to your real experience builds (or breaks) trust. There are frameworks—Nikki cannot help herself, and neither can we—but mostly it’s a conversation about the gap between what we say we deliver and what it actually feels like to be on the receiving end of it.
* Why Nikki niched down in belief rather than service or audience—and why that’s easier to sell and refer
* The customer experience pyramid: satisfaction → ease → enjoyment—and why advocacy only lives at the top
* Customer experience vs. customer journey: “the journey is a lane, the experience is the whole highway system”
* Why emotions create memories, memories create perception, and perception is the only thing that drives behavior
* Brand promise as an operational standard (not a mission statement)—and why you can control your promise and experience but never your customer’s perception
* The Mr. Rogers writing rule that changed how Nikki thinks about every email, sales page, and support reply
* Category expectations: how to spot what customers already assume about you—and deliberately disrupt it
* Giving your customers the language to refer you (because “you just need Nikki, go” doesn’t convert)
* When great delivery meets AI-generated marketing—and why a mismatch quietly destroys trust
* Principles vs. methodology, and why lead magnets built on tactics expire the moment the platform changes
* CX train wrecks (yes, QuickBooks and Canva, we’re looking at you) and reporting “from the scar, not the wound”
“Your whole job is to create memories. Because if you can elicit an emotion in someone, emotions are what create memory. When someone creates a memory, then they have a perception of something, and it’s perception that drives behavioral change. You can’t just jump straight to a behavioral change.
And customer experience is not just what starts when someone pays you. It’s not the customer journey. The journey is a lane. The experience is the whole highway system.” - Nikki McKnight

About our Guest
Would Recommend (Nikki's new podcast)
Unreasonable Hospitality by Will Guidara
CCXP – Certified Customer Experience Professional designation
Acceleration Strategy Inc. (12-week customer experience program, Toronto)
Fixable with Frances Frei and Anne Morriss (the Southwest episode)
Derek Thompson's podcast: the NBA / Adam Silver episode
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

SEO in 2026 doesn’t look anything like it did even a year ago, or even a month ago as you’re reading this in June of 2026. If you’re still thinking in terms of domains and backlinks and keyword-driven page views on Google, it’s time to update your worldview.
In this episode, Meg breaks down entity-focused search and discoverability: the shift from optimizing the domain versus optimizing the entity and the person. She explains what an entity actually is (think of it as a star in a constellation, or a suspect on a murder board with red strings connecting everything back to you), and why so many of us have fragmented, disconnected, or missing entity signals without realizing it. This is the same material that opens her Signal mentorship, compressed into one conversation.
We talk about why your full name needs to be on your website, what schema markup does and why it’s suddenly mattering again, and the difference between work you control (your own pages and copy) and the third-party validation you can’t fully control but absolutely need. This is the first step of the slow, compounding, multi-month play—and why the work pays off even if the AI citations take their sweet time to show up.
* Why “it’s not just Google anymore” changes everything about how you get found
* What an entity actually is—person, book, program, company—and how they connect like a constellation
* The three most common problems: missing entities, disconnected entities, and entity fragmentation
* Why Meg’s own podcast and business weren’t connected in the AI knowledge map (and how she fixed it)
* The copywriting habit that’s quietly hurting you: all client-facing language, no expertise or “who I am”
* Schema markup explained in plain English—and the “Same As” code that ties your whole body of work together
* How to narrate a pivot so AI (and humans) know you’re the same person who changed
* Why you can build a perfect entity and still not get recognized without external validation
* The referral guide idea: a “call me when” doc for both the humans and the machines
* How long this really takes—and why Perplexity shows changes before ChatGPT ever will
“We get to signal that we would like things to be entities, but we do not get to decide which are the entities that are recognized. So, Jessica Lackey already exists in the knowledge map. We know that because if you go to ChatGPT or Claude or Google and say, ‘Who is Jessica Lackey?’ there’s an answer there.
But unless you are super clear about this is what I want you to do, AI can pull from anywhere. So if you wanna be more in control of how you’re represented and the language that it’s using about you, then you need to be clearer about how you want to be defined.” -Meg

Resources
Signal Mentorship
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