#359: How to Enjoy a Better Freelance Lifestyle by Unlocking the Secrets of Luxury ‘Points Travel’
Release Date: 11/20/2024
#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...
info_outline
#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...
info_outline
#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 . ...
info_outline
#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...
info_outline
#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. ...
info_outline
#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_outline
#383: The Art of ‘Conversing’ with AI
High-Income Business Writing
Imagine walking into a friend’s house and rattling off a 20-minute monologue with every single detail of a challenge you’re facing. No pause. No space for questions. Just a nonstop, 20-minute word vomit. That’s how most of us are using AI. We dump a giant wall of text into a prompt, cross our fingers, and hope for magic. Instead of working with AI, we’re treating it like a command line. No wonder the results often fall flat! In this short episode, I share a better way—one that mirrors the way we’d talk with a trusted colleague. When you approach AI as a conversation...
info_outline
#382: The Truth About AI and Freelance Writers — What 157 Writers Just Revealed
High-Income Business Writing
The AI adoption picture is nuanced In this episode, I share some fascinating insights about AI usage among writers and the impact it’s having on their business. Last month, I sent out a simple 10-question survey to my community about AI usage, fears, and business impact. I received 157 complete responses from writers across every experience level, from brand-new freelancers to 15+ year veterans. What they shared was, in some ways, congruent with what I’ve been saying for the past few months on the topic of AI integration in our businesses as freelancers. But in other ways, the...
info_outline
#381: How to Have Better, More Productive Conversations with AI
High-Income Business Writing
AI is changing how we work. But many freelancers are falling into the trap of using it in the least effective way possible: by relying on massive, fully pre-written prompts that remove you from the creative process. In this episode, I share a better, more natural approach that treats AI like a trusted collaborator rather than a black box you dump instructions into. You’ll learn my simple 3R Prompting framework and see how an iterative, conversational workflow can help you get sharper insights, stronger ideas, and better final results. What You’ll Learn in This Episode Why...
info_outline
#380: The AI Writing Debate — Moving From False Dichotomies to Creative Synthesis
High-Income Business Writing
The conversation around AI and writing is heating up. But too often, it’s framed as a false choice: AI is either “bad” and deceptive, or it’s the ultimate shortcut to productivity. In this solo episode, I challenge that binary thinking and unpack the real issues at stake for freelance writers. Sparked by a provocative LinkedIn post from Mariya Delano, CEO of Kalyna Marketing, this discussion dives into the myths and misconceptions that keep us stuck in unproductive debates. I lay out 10 false assumptions fueling the AI writing controversy. And I explain why the future belongs to...
info_outlineAs freelancers, many of us crave the freedom to explore new places without the financial burden that travel can bring.
But what if you could fly in luxury without spending a fortune? That's where points travel comes in, and today's guest is a true expert in this game.
Spencer Howard, the mastermind behind Straight to the Points, has helped countless people book premium travel with points instead of cash—making dreams of business and first-class travel a reality.
In this episode, Spencer shares his journey from a political career to building a freelance writing business to becoming a full-time freelancer in the world of points and miles. He dives deep into the strategies freelancers can use to leverage credit card rewards and optimize points for travel, breaking down complex topics like transferable points and airline-specific credit cards.
And he explains how to do this without getting into debt or paying credit card fees that don’t make sense.
I learned a lot from this conversation. I realized that many of my hang ups about points travel were unfounded. And I discovered that I’m actually making some pretty big mistakes with a strategy I assumed was getting me huge travel perks (but it’s really not a great value!).
If you love to travel, you’re going to find several actionable tips on how to maximize your points, avoid common pitfalls and plan your next dream trip—all without breaking the bank or getting into debt.
Enjoy!