From Domains to Entities: Being Findable in 2026

Which version of you is running your business right now? It might be your inner 16-year-old who thinks networking is stupid, or your inner 6-year-old who learned the only way to be seen was to prove how smart she was. Your nervous system doesn’t really care whether you call it mindset or trauma — it’s going to do what it’s going to do. In this episode, we talk with Nicole Lewis-Keeber, MSW, licensed clinical social worker, ICF-credentialed coach, and certified Dare to Lead facilitator, about how childhood trauma and nervous system responses show up in the way we run our businesses. Nicole spent 18 years as a therapist before launching her own business 12 years ago, and she’s been carving out space for this conversation ever since — even when therapists told her she couldn’t talk about trauma outside the therapy room and coaches told her to stop using the word entirely. We get into how our inner children influence everything from sales to visibility to pricing, why urgency is usually a trauma response, and what it looks like to pause and figure out who’s actually making the decisions in your business. This is a practical, honest conversation about what’s underneath the discomfort and what to do about it. * How childhood trauma shows up in business decisions we don’t even realize we’re making * The inner stories impacting Nicole and Jessica’s experiences * The difference between a nervous system response and a strategic business decision * Why urgency in your business is almost always a trauma response worth pausing on * Visibility was hard before digital culture — now it’s a whole different animal * Reframing sales outreach as a kindness when everyone’s nervous system is overwhelmed * The trap of trying to fix an entire broken system through your one small business * Black-and-white thinking about platforms, AI, and marketing as a trauma pattern * Taking pauses away from the dopamine drip of the 2026 information landscape * Getting clear on what you actually want from a platform before you let it into your nervous system “Your nervous system doesn’t give a shit what you call it. It’s just gonna do what it’s gonna do. Many people are walking around with traumatized nervous systems that don’t really realize what they experienced was actually trauma. It doesn’t have to be a big catastrophic thing. It can be smaller — like micro moments that add up. If you want to do something in your life that feels scary, which starting a business feels scary, those adaptations and patterns are probably going to show up. So let’s figure that out.” — Nicole Lewis-Keeber

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

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 2025 Jessica 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 trend Additional Resources Podcast | The Gray Area Why is the Internet bad now? | Evan Armstrong/The Leverage Connect with Us Listen on Spotify Listen on Apple Podcasts Meg Casebolt Jessica Lackey

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

Entrepreneurship is hard. And it’s even harder when your nervous system is stuck in a mode that’s not serving you. In this episode, we sit down with The Entrepreneurs’s Therapist Shulamit Ber Levtov to talk about the nervous system realities of entrepreneurship—especially for those who didn’t become entrepreneurs by opportunity but by necessity. We talk about what it means to choose our nervous system activities, how to understand what’s in (and out of) our control, and the unique paradox of entrepreneurship: you get freedom… and also you’re the one holding the whole thing together. As Shula says, “Entrepreneurship and mental health are inseparable. We write business plans, marketing plans, financial forecasts, but where’s the mental health plan?” Whether you’re burned out or just bracing for what’s next, this episode offers frameworks and honest permission to put real nervous system management at the center of your business. * Why your nervous system is a business asset * How to distinguish between societal pressures, industry pressures, and our own decisions impacting our nervous systems * The paradox of entrepreneurship: control and uncertainty at the same time * Why some of us didn’t “choose” entrepreneurship—and why that matters * The role of locus of control and how it helps you manage business stress * When to phone a friend versus make a business decision in the moment * How to build a personalized nervous system toolkit (without another productivity checklist) “And then there's the very basic individual nervous system reaction to response running your own business. Business success equals survival. Intellectually, I'm not gonna starve and die if my business fails. I mean, it's gonna be stressful, it's gonna be hard. I may have very heightened circumstances. I may lose my house. A lot of really bad sh*t can happen, but it's survivable stuff if your business fails. But this is intellectual knowledge, not nervous system level stuff.” - Shulamit