#392: Your Core Advantage in the Age of AI Is Knowing What Questions Deserve to Be Asked
Release Date: 03/11/2026
#393: The Capability Gap Is Closing Fast (and What That Means for Your Business)
High-Income Business Writing
Freelancing used to reward the people who could do the work. Now it’s starting to reward the people who can direct the work—clearly, strategically, and with the right tools. If you’ve felt that shift lately (more demands, broader scopes, faster timelines), you’re not imagining it. In this episode, we’re breaking down what happens when the old limitation—“I can’t do that (yet)”—starts to disappear. You’ll learn a simple mental model for thinking about capability gaps (the classic learn the “how” vs. hire the “who”) and why AI is quickly becoming a third option: a...
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#392: Your Core Advantage in the Age of AI Is Knowing What Questions Deserve to Be Asked
High-Income Business Writing
If you’ve been telling yourself, “AI can’t replace what I do because I bring the human touch,” I want you to hear this: that belief might be costing you work. In today’s episode, I’m sharing a deceptively simple (and very practical) way to future-proof your value as a freelance writer in an age where “good enough words” are getting cheaper by the day. The premium isn’t in your ability to produce powerful sentences anymore. Rather, it's your ability to produce meaning. And meaning comes from judgment: knowing what to chase, what’s true, and how to shape it so it actually...
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#391: Your Dreams Just Got Closer — A Different Take on the Matt Shumer + Ann Handley AI Debate
High-Income Business Writing
In the past couple of weeks, two smart people looked at the same moment in AI and came away with opposite advice. says wake up, this is urgent, denial is dangerous. says slow down, stop panicking, protect your judgment. I agree with both of them. And yet I think their arguments are incomplete. In this episode, I offer a third stance: value doesn't just vanish during disruption. It gets rebundled. Reorganized. Repackaged into new bundles of tasks, trust, judgment, and responsibility. And whoever understands that process early gets to position themselves on the right side of it. I...
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#390: When Clients Ask: “Shouldn’t This Cost Less Now That You Use AI?”
High-Income Business Writing
Here’s a question you may have heard already from a client or prospect when you submit a quote or proposal: “Wait… you use AI now. Shouldn’t this cost less?” On the surface, it sounds like a pricing question. But underneath, there’s something much more important going on. It’s a sign that the client is still thinking in terms of time, keystrokes, and effort—while you’re trying to sell judgment, standards, and outcomes. In this short episode, I walk through how to handle that objection without getting defensive, without negotiating against yourself, and without pretending AI...
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#389: She Shut Down a Profitable Agency (Here’s Why Writers Should Pay Attention)
High-Income Business Writing
Today’s episode is a little different. Over the past year, I’ve been talking more openly about the shifts happening in our industry. And a few weeks ago, I made a clear decision, which I announced in my first newsletter of 2026: the focus of this podcast and my newsletter going forward will center on AI… and the disruption, changes, and opportunities it’s creating for writers. AI is reshaping business models, demand, pricing, and even the types of roles writers are being hired for. And I know this conversation can make a lot of people uncomfortable. It forces us to look at signals...
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#388: How to Quickly Go from Messy Transcript to Clear Outline with AI
High-Income Business Writing
Working with transcripts can feel overwhelming. Client calls. Workshop recordings. Interview transcripts. Pages and pages of raw material—good ideas buried under tangents, half-finished thoughts, and off-the-cuff remarks. The problem usually isn’t lack of content. It’s too much of it! In this episode, I walk you through a simple, repeatable workflow I use to turn messy transcripts or rough notes into a clear, usable outline—without losing the nuance that actually matters. If you’ve ever dropped a transcript into AI, asked it to “summarize this,” and felt underwhelmed by the...
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#387: The Freelancer Health Reset—5 Micro-Habits That Actually Stick, Including Key Midlife Insights for Women
High-Income Business Writing
Freelancers are great at pushing through. We hit deadlines, juggle clients, and squeeze productivity out of thin air. But here’s the truth many of us avoid: Our physical health often pays the price. In today’s episode, we’re talking about the side of freelancing that rarely gets airtime — the slow erosion of our health when the business becomes the only priority. And we’re doing it with someone who brings deep experience, grounded wisdom, and a refreshingly simple approach: my friend Lucie Robazza, a certified health coach, personal trainer, kinesiologist, and founder of . ...
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#386: The Packaging Problem—Why Your AI Help Isn't Making You Money (Yet)
High-Income Business Writing
Freelancers are giving away their most valuable AI insights, and not getting paid for it. In today’s episode, we’re taking a hard look at one of the biggest blind spots for freelance writers and content pros right now: the failure to package your AI knowledge into a paid offer. Your clients want to use AI. They’re trying. But they’re confused, overwhelmed, and scared of doing it wrong. And guess what? You already have the skills and experience to guide them. But unless you turn that informal help into a structured service, it’s just free advice that goes nowhere. In this...
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#385: What to Do When Clients Break Their Promises
High-Income Business Writing
Ever had a client drop the ball? They miss a key deadline, shift direction mid-project, or conveniently “forget” what you both agreed on? It’s maddening, right? Those moments can make even the most seasoned freelancer question everything about their business. But here’s the twist: those “broken promises” might actually be pointing to your biggest opportunities for growth. In this short episode, we’re diving into what really lies beneath client chaos — and how to turn frustration into a roadmap for stronger systems, better communication, and a more resilient business. ...
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#384: The Value Shift—Where the Money Goes When AI Makes Content Creation Effortless
High-Income Business Writing
Freelancers everywhere are feeling it. The ground beneath our feet is shifting, because AI isn't just changing how we write. It's also changing where value lives in our industry. In this episode, I break down what few people are talking about: your writing skills might still be world-class, but they're now solving the wrong problem. Much of what I discuss was inspired by the brilliant new book Reshuffle: Who Wins When AI Restacks the Knowledge Economy by . The constraint that once made your writing indispensable has moved. And if you don't move with it, you risk becoming the business...
info_outlineIf you’ve been telling yourself, “AI can’t replace what I do because I bring the human touch,” I want you to hear this: that belief might be costing you work.
In today’s episode, I’m sharing a deceptively simple (and very practical) way to future-proof your value as a freelance writer in an age where “good enough words” are getting cheaper by the day.
The premium isn’t in your ability to produce powerful sentences anymore. Rather, it's your ability to produce meaning. And meaning comes from judgment: knowing what to chase, what’s true, and how to shape it so it actually strikes a chord with the reader.
I start with a real email from memoir ghostwriter Michele Roldan-Shaw. From there, I present the five types of questions that deserve to be asked. These are the questions that uncover stakes, tension, specificity, transformation—and ultimately the story your client can’t see on their own (and AI can’t reliably pull out without your guidance).
I’ll show you what that looks like in real projects too, from interviews that completely change the direction of a case study to memoir work that goes far beyond a simple chronology.
If you’ve been struggling to answer, “Why should a client pay me when AI can generate drafts?”... this episode will help you build a clearer, stronger, more confident answer.