Libsyn Directory

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

Release Date: 08/13/2025

#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...

#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...

#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...

#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...

#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...

#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...

#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 . ...

#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...

#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. ...

#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...

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

TOPICS