Libsyn Directory

#378: Why AI Change Is Happening Faster Than You Think (and What That Means for Writers)

Release Date: 08/13/2025

#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...

#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...

#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...

#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...

#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...

#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...

#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...

#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...

#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...

#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...

More Episodes

If you're feeling like your freelance business is shifting beneath your feet—but you can’t quite name what’s changed—you’re not alone. Most writers sense something is different… but they don’t know how to respond strategically.

In this solo episode, I dive into what I believe is the real driver behind the changes we’re seeing in the freelance writing space. Yes, the economy has cooled, and that’s still a big factor, since marketing is one of the first areas to get cut when business is slow. But AI is now playing a much bigger role than most writers realize. And the pace of disruption is happening much faster than we’re used to.

I break down the data, the two dominant schools of thought about where AI is taking us, and the five predictions I’m making about the next 18 months. More importantly, I share what I believe you can do right now to adapt and thrive, no matter where you stand on the AI debate.

Whether you’ve been avoiding AI, tinkering with tools randomly, or wondering how to respond to market shifts… this episode will help you make sense of it all and chart a path forward with confidence.

What You’ll Learn

What’s really behind the shrinking pool of freelance writing work, and how AI factors in
The “two schools of thought” on AI’s long-term impact (and which side I lean toward)
Why capability gaps (not talent) are quietly holding writers back
What makes this wave of disruption different from anything we’ve ever faced before
Five bold predictions about AI and the freelance market between now and the end of 2026.

Key Insights and Takeaways

The Economy Isn’t the Whole Story

Yes, budgets are tighter. But the shift we’re seeing in client behavior and referral flow can’t be explained by economics alone. AI is already changing how content is created and reshaping client expectations behind the scenes.

You’re Not Just Competing With Other Writers

You're competing with writers plus AI, and clients don’t always realize that’s what’s happening. But they do notice faster turnaround times, deeper insights, and stronger strategy. That’s the new baseline.

The Problem Isn’t Tools, It’s Random Tool Use

Most writers are reacting to AI passively or using it without a clear strategy. That only leads to frustration and overwhelm. The ones who are thriving are using AI to systematically identify and close capability gaps—areas they previously avoided due to a lack of experience or confidence.

Exponential Change Is Hard to See... Until It Isn’t

We’ve moved from the “gradually” phase to the “suddenly” phase of change. Each new model is doubling the power of the last. If you're still measuring AI by what it could do six months ago, you're behind.

The 18-Month Window

We’re entering a short window where positioning yourself strategically—through capability expansion, not random experimentation—can lead to exponential growth. But that window is closing fast. Writers who miss it may find themselves permanently behind.

Action Steps You Can Take This Week

1. Identify Your Competitive Blind Spot

Is there a type of project, industry, or strategic conversation you avoid because you feel underqualified? That’s your gap. Write it down.

2. Use AI to Explore That Gap

Leverage tools like ChatGPT or Claude to research the format, reverse-engineer a successful project, or role-play a strategic conversation you’d normally avoid.

3. Reframe How You Think About Your Capabilities

Instead of saying “That’s not what I do,” ask, “If I had the right support, could I deliver excellent results here?”

4. Pick One Gap to Work on Systematically

You don’t have to fix everything overnight. But momentum starts with a single capability. Choose one, and take the first step.

Memorable Soundbites

“The disruption is happening faster than most writers can process because our brains aren't wired for exponential change.”
We're not at the beginning of the chessboard anymore. We’re nearly halfway there.”
“You’re competing with writers plus AI, not just with other writers.”
“The tools stay invisible, but the performance gap becomes obvious.”
“This isn’t about learning tools randomly. It’s about using AI systematically to close your biggest capability gaps.”
“Six months from now, you’ll either be expanding your capabilities or watching the gap between you and your competitors widen.”
“You don’t have to become an AI cheerleader to respond strategically. You just have to be honest about what the market is telling you.”
“Hope is not a strategy. Especially when the ground is shifting this fast.”

If this episode struck a chord, I’d be honored if you shared it with a fellow writer or freelancer. Until next time, keep writing, keep adapting, and keep building the business you actually want—not just the one you think you’re stuck with.

Sources Mentioned & Quoted

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