High-Income Business Writing Podcast

A few weeks ago I got on a call with someone I coached many years ago. Partway through, I said something almost without thinking. By the time we hung up, I realized it might be the most useful thing I've told anyone in the past month or two. This episode walks through that conversation and the question that triggered it: What would a client create if there were no limits at all? That question used to be dangerous to ask, because the honest answer was almost always bigger than what you could actually deliver. AI changed that math. Now judgment is the whole game. I'll walk you through the real conversation, show you how the same idea plays out for a copywriter and an email marketer, and give you a simple three-step way to test it yourself this week. What You'll Learn Why asking a client what they'd create with no limits used to be a dangerous question, and why that's changed The real story behind the question that reshaped how Ed thinks about client value Why AI made judgment matter more instead of less How the same idea applies whether you're a copywriter, an email marketer, or something else entirely A simple three-step way to test this on one of your own clients this week Key Ideas & Takeaways 1. The Magic Wand Question. Ed asks a coaching client what her client would actually pay for. When she gives the safe answer, he pushes further: if they could wave a magic wand and get exactly what they wanted, what would that be? The honest answer turns out to matter a lot more than the safe one. 2. The Real Constraint Moved. AI removed the ceiling on production. Big answers used to be unrealistic because building them took too long. Now the real constraint is your willingness to experiment and the judgment you bring to what you build. 3. Judgment Over Speed. The tools will happily build almost anything you ask for, whether it's a good idea or not. Deciding what's actually smart to build, and recognizing when what comes back is genuinely good, is squarely your job now. 4. It Works Beyond One Client. The same shift applies to a copywriter whose client casually mentions wanting better onboarding emails, or an email marketer whose client wishes they could predict churn before it happens. In both cases, the real ask is an outcome, not a deliverable. 5. Three Steps To Try This Week. Pick one client, current or past. Ask the magic wand question and write down the honest answer, even if it sounds too big. Then spend 30-60 minutes with AI building a rough version of it, before you ever mention price. Action Steps Pick one client, current or past, ideally a smaller or lower-stakes relationship Ask yourself what that client would create if there were no limits at all, and write down the honest answer Spend 30 to 60 minutes with AI building a rough version of that answer before you ever quote a price Notice where the AI draft falls short. That's your judgment doing its job, so fix that part yourself

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 nearly every conversation was "pivot." In this episode, I share the framework that came out of those conversations. It encompasses three distinct stages people get stuck at when they're trying to make a real change in their business. I also explain why the help you need looks completely different depending on which one you're in. What You'll Learn Why "I need more clients" dropped from the typical 70% I've seen in the past to just 34% this time around The real problem hiding behind that "more clients" answer for a lot of respondents The three stages of a pivot and how to tell which one you're actually in Why almost nobody named AI as their top problem, even though it showed up everywhere The surprising thing the highest spenders want that the DIY crowd doesn't Why it's so hard to think your way through a pivot effectively, even with AI as a sounding board Key Ideas & Takeaways 1. The "Clients" Answer Is Losing Its Grip. For 15 years, "I need more clients" won every survey I've sent, typically with 70 to 80% of the vote. This time it barely cleared a third, and "what I should offer now" jumped into a close second at 24%. 2. A Lot of "Clients" Answers Were Wearing a Costume. When I read the open-ended responses, a quarter to a third of the people who picked "clients" were actually describing something else: niching paralysis, imposter syndrome, or clients pulling work in-house because they're using AI themselves. The real issue sat one step upstream from the answer they checked. 3. The Real Theme Was "Pivot." Nobody was prompted to use that word. Person after person used it anyway, in the survey and in the follow-up calls. 4. AI Is the Wrapper, Not the Problem. Only 3 out of 58 respondents said learning AI was their top concern. But AI showed up in nearly 4 out of 10 open-ended answers, tangled into everything else people are dealing with. Action Steps Figure out which of the three stages you're actually in right now: deciding, validating, or planning If you're deciding, stop looking for a marketing plan. Look for a person or process that can help you build real conviction If you're validating, pick one person you trust and ask them directly whether they'd pay to have this problem solved If you're planning, write down the exact order of steps you think you need, then get a second set of eyes on it.

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 story of how a great, reliable client can grow into 60 percent of your income before you realize it. Then they lose an account, and most of your business is gone in one email. From there, I give you a few practical recommendations: how to run your own concentration number, how to build a second income leg before you need it, where AI genuinely helps, and how to keep a little marketing going even when you're full. What You'll Learn A simple way to measure how much of your business rides on one client, and the number that should worry you Why you never really stop depending on something, even when you're solo, and the dependency most of us drift into The four places concentration hides: one client, one referral source, one channel, one type of work How a great, reliable client can become your biggest risk without you noticing Three practical recommendations for spreading your income so no single client can sink you Where AI genuinely helps you take on more work without burning out Why reducing your reliance on a great client feels disloyal, and why it isn't The one small step to start this week Key Ideas & Takeaways 1. You Never Stop Depending on Something. Going solo doesn't remove dependence. You depend on clients, on referral sources, and on the channels where work comes from. The writers who last choose those dependencies on purpose, instead of slowly adopting them without noticing. 2. The Risk Hiding Inside a Great Client. The better the client, the easier it is to let them grow into most of your income. A reliable agency client becomes 60 percent of your business, you stop marketing, and then they lose an account. In one email, most of your income is gone. 3. A Big Client Can Be a Job in Disguise. When one client is half your income or more, you don't have a business with clients. You have a job with one boss, and none of the protection, perks, or benefits a real job provides. You've taken on all the risk of employment and kept none of the safety. 4. Run Your Concentration Number. Add up what each client paid you over the last year and find the percentage your biggest one represents. If it's over 40 or 50 percent, that's your project for the quarter. You don't have to panic. You just have to know it. 5. Build a Second Leg Before You Need It. The aim is to grow a second and third source of income around your big client, so no single one can sink you. You keep the big client. You just stop letting them be the only thing holding you up. 6. AI Buys You the Bandwidth to Diversify. Most of us let a big client take over because we're already maxed out. When used properly, AI takes a lot of the production load off your plate, the research, the first drafts, the repetitive pieces. Those freed-up hours are what let you take on another client without working nights and weekends. 7. The Hard Part Is Emotional. Reducing your reliance on a great client can feel ungrateful, even disloyal. But diversifying protects you and your family when something goes wrong on their end, and that's usually out of your control. That's just being a responsible owner of your business. Action Steps Run your concentration number this week. Add up last year's income by client and find your biggest client's percentage. Over 40 to 50 percent means it's time to act. Pick one realistic second leg: a new type of client, a new channel, or a new service. Take one small step toward it this week. Hand one production task to AI (research, a first draft, a repetitive piece) so you free up hours for finding that next client. Block one or two hours a week for marketing, even while you're full, so your pipeline never goes cold. Think about where your income is too concentrated, then start building, one small step at a time, over the next few weeks.

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 nervous and human than the painting suggests. Then I get personal about my own decision to go solo 20 years ago. From there, I draw a line between two kinds of independence. The fragile kind that looks like freedom but feels like risky exposure. And the resilient kind that holds up even when a client walks away. Here's the good news. For most of my 20 years, a one-person business had a hard ceiling. You stayed small and exposed, or you grew and got tangled up in payroll and management. The dynamics have changed. There's a third path now, and it changes what's possible for a solo writer. What You'll Learn • Why the morning the Declaration was signed was nothing like the painting, and what that has to do with you • The difference between fragile independence and resilient independence, and how to tell which one you've got • Why the "stable" path (the in-house job, the steady retainer) may be just as shaky right now • The two traps that keep solo businesses fragile: the single anchor client and the one-person ceiling • What changed recently that lets a solo writer take on more without hiring anyone • Why producing more, faster, and cheaper actually makes you easier to replace • The part of your work that stays valuable no matter how good AI gets • Two honest questions to find where your own independence is still exposed Key Ideas & Takeaways 1. The People Who Chose Independence Did It Scared. The signing wasn't the calm, triumphant scene in the painting. Benjamin Rush described a "pensive and awful silence," and men who believed they might hang for what they were doing. They didn't wait for certainty. They committed first, and everything good came after. 2. Feeling Shaky Doesn't Mean You Chose Wrong. When your path feels uncertain, it's tempting to believe a steadier one is waiting somewhere else. But "stable" jobs are being reorganized and automated too. A storm feels the same from inside any boat. Yours is the one you can actually steer. 3. Declaring Independence Is the Easy Part. Going solo is a single moment. Keeping that independence alive is the work that comes after, and it doesn't stop. You re-earn it through the decisions you make for years. 4. The Dynamics Have Changed. For most of the last two decades, a solo writer could only do what one person could physically produce. Growing meant hiring, payroll, and overhead. When used properly, AI now handles a lot of the research, first drafts, and grunt work, so that load can sit inside a one-person business. 5. More Capacity Buys Resilience. This is about resilience. The aim is to serve a wider range of clients, so no single account owns your future, and to turn down bad-fit projects without panic. A resilient business bends when a client leaves. It doesn't break. 6. Producing More Can Make You Easier to Replace. If all you do is produce faster and cheaper, you become a more efficient commodity, and commodities compete on price until there's nothing left. What protects you is the judgment AI can't reproduce. 7. The Gap Between Producing and Producing the Right Thing. Most clients can now generate a competent draft in minutes. What they can't do is decide whether it's the right one or see what it gets wrong for their audience. That judgment, taste, and discernment is what they'll keep paying a real person for. Action Steps Add up what each client paid you over the last year and find the percentage your biggest one represents. If it's over 40 to 50 percent, that's your project for the quarter. Name your single biggest point of fragility this week: one client who's too large a share of your income, or a ceiling set by your own two hands. Pick one production task you still do by hand (deep research, first drafts, cleanup) and hand it to AI this week, so you can spend that time on higher-judgment work. Make a short list of the skills you've undervalued (asking sharp questions, synthesizing, reading the real need) and start treating them as your core offer. Think about the two questions from the close: where is your independence still fragile, and what could you hand off now to free up your judgment?

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 don't have is the ear and the eye. The judgment about what to do with all of it. In this episode, I make the case that this judgment is where your real value lives, and that it lives in two places: before the work starts, and after it's done. Both are underpriced by most writers. Both are in growing demand. What You'll Learn Why the film editor and record producer are the right mental models for where your value sits in an AI-shaped market What "upstream judgment" actually means and why writers have been giving it away for free for years The specific decisions that happen before content is created that AI genuinely cannot make well Why the demand for downstream editorial judgment is growing as AI content floods the market How to identify where your judgment is most needed inside your existing client relationships Key Ideas & Takeaways 1. Your clients have the raw material. They need the judgment. AI is making content production faster and cheaper than ever. What it's not providing is the editorial eye that decides what's worth making and what's worth keeping. That's the gap you can fill. 2. The most important decisions are made upstream. Before a word gets written, someone has to decide what's worth creating, for whom, with what angle, and why. Those decisions require context that doesn't exist in any dataset: the client's internal politics, their buyer psychology, the competitive landscape, what leadership will actually approve. That's where experienced writers have enormous value they rarely charge for. 3. You've been doing advisory work your whole career. Every time you asked a clarifying question that changed a project's direction, pushed back on a brief that didn't make sense, or flagged an angle that wouldn't land with the audience, that was advisory work. It was just embedded invisibly in your writing process. The move is to make it visible and price it separately. 4. Downstream judgment is in growing demand. The more content AI helps produce, the more critical it becomes to have someone with real editorial judgment reviewing it before it ships. Companies that skipped this step are learning the hard way what it costs to publish without a quality filter. That's a real and growing opportunity for writers who position themselves as that filter. 5. You don't have to stop writing. Moving into judgment-focused work doesn't mean giving up the craft. Most writers who've made this shift still write. They do it alongside upstream strategy work and downstream editorial review that puts them closer to the decisions where the real value lives. Action Steps Think of one current client and ask: what decisions are they making before they produce content that my experience gives me an opinion about? Ask the same client: what content are they shipping that nobody with real editorial judgment is reviewing first? Write down one upstream service you could offer this client based on what you know about their strategy, their audience, and their blind spots. Write down one downstream service based on the content quality issues you've noticed in their recent work. Pick one of those two and draft a one-paragraph description of what it would look like as a packaged offer.