#392: Your Core Advantage in the Age of AI Is Knowing What Questions Deserve to Be Asked
Release Date: 03/11/2026
#402: One of the Most Surprising Things I've Learned From 15 Years of Surveying My Audience
High-Income Business Writing
For 15 years, the top answer on every survey I've sent my audience has been the same: I need more clients. Typically, 70 to 80% of respondents pick it without a second thought. This time, only 34% did. I read all 58 responses that came in, then got four people on a Zoom call to dig deeper on their answers. What I found surprised me enough that I want to walk you through it today. A good chunk of the people who picked "clients" weren't describing a clients problem at all. They were describing something else, wearing a "more clients" costume. And the word they kept using, unprompted, in...
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#401: When a Client Is Really Your Boss
High-Income Business Writing
Add up your income from the last six months, then imagine losing your single biggest client tomorrow. For a lot of freelance writers, that one client covers half the income, or more. If that's you, this episode is about the biggest risk you might be carrying right now and what to do about it. I start by reframing what independence actually means for a solo writer. You never stop depending on something. The real question is whether you chose those dependencies on purpose or slowly adopted them without noticing. Then I get specific about the most common one, the single anchor client. I tell the...
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#400: Fragile Independence vs. Resilient Independence
High-Income Business Writing
If you went solo as a writer or marketer, you already made your declaration of independence. You left a paycheck, or a boss, or both. You did the brave thing. Lately, though, you might be wondering whether that independence still holds up. The work feels less predictable. AI keeps changing what clients will pay for. And a familiar thought creeps in: maybe I should go find something more stable. In this episode, I want to talk you out of that trap. I start with a story you think you know, the morning the founders of the U.S. actually signed the Declaration of Independence, which was a lot more...
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#399: When AI Makes Writing Cheap, Judgement Becomes Incredibly Valuable
High-Income Business Writing
Walter Murch, one of the greatest film editors who ever lived, doesn't fix bad footage. He decides what the film actually is, from hundreds of hours of raw material that could tell a dozen different stories. Rick Rubin, one of the most successful and iconic record producers in history, famously describes his role as just listening. He sits on a couch, hears what's true and what isn't, and tells the artist. Artists pay enormous sums for that. Your clients now have the camera. They have the recording equipment. AI is giving them raw material faster and cheaper than ever before. What they...
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#398: The Lucrative AI Training Opportunity for Freelance Writers
High-Income Business Writing
A lot of writers hear the word "training" and picture a conference room full of strangers, a slide deck, and a formal curriculum. That's not what I'm talking about here. The training opportunity most freelancers are sitting on is much smaller, much more personal, and already happening inside your existing client relationships. You're just doing it for free, and you probably haven't recognized it for what it is. In this episode, I break down what AI training actually looks like at the freelancer level: one-on-one coaching with a key contact, a focused small-team engagement, an ongoing...
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#397: How to Pivot on a Client Call Without Sounding Pushy or Salesy
High-Income Business Writing
Knowing you should redirect a client conversation is one thing. Doing it smoothly, without the client feeling like you're steering them somewhere for your own benefit... That’s a different skill entirely. Over the past few weeks we've covered building a small bench of offers, reading the signals in a prospect conversation, and matching what you hear to what you have. Today I want to tackle the part that makes most writers nervous: the actual moment of the pivot. I walk through both versions — the clunky default move most writers make when they're worried about losing the work, and the...
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#396: How to Hear What a Client Isn't Saying on the Discovery Call
High-Income Business Writing
Most prospect calls go sideways before you ever pitch anything. Too often, this is the result of being in “presentation” mode when you should have been in listening mode. In this episode, I walk you through what active listening actually looks like on a live client call. Practical moves you can make in real time, moment to moment, in an actual conversation. A few weeks ago, I recorded an episode on the six signals that tell you what kind of help a prospect actually needs. A few of you wrote in with the same follow-up question: okay, but what does this look like in an actual...
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#395: What Your Prospects Are Really Asking For (And Why You Keep Missing It)
High-Income Business Writing
Most of us get on a call with a prospect, hear the word "content," and immediately start thinking about deliverables. Blog posts, white papers, email sequences. We jump straight to logistics: how long, how many, when's the deadline? That instinct made sense for a long time. But in an AI-shaped market, where the kinds of help clients need are shifting and expanding, it will cost you. It will cost you in deals you didn't win because you pitched the wrong thing. In engagements that started off on the wrong foot. And in relationships where the client never quite felt like you understood their...
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#394: The 4 Ways Clients Will Pay for Your AI Help
High-Income Business Writing
If you've been paying attention to how AI is changing the freelance landscape, you've noticed something: the types of help clients need are shifting. Fast. A year ago, most conversations were about one thing: how do I keep getting hired when AI can produce a first draft (even it it’s low-quality) in seconds? That's a fair question. But it's the wrong place to stop. Because underneath that conversation, something bigger is happening. Clients are recognizing they need different kinds of help. Many don't even know how to articulate what they need yet. They just know they're stuck. And the...
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#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...
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.