Stop reprompting. Start building skill-powered workflows

Three Questions Before You Say Yes (in the AI Era)

I’ve been reading The Way of Excellence [https://www.bradstulberg.com/] by Brad Stulberg [https://www.bradstulberg.com/] — subtitle, a guide to true greatness and deep satisfaction in a chaotic world. The timing feels right. AI is reshaping jobs, companies, and the skills that matter. Every week I talk to leaders asking some version of the same question: where do I put my time now? One section in Chapter 2 really resonated with me. Stulberg calls it selecting worthwhile pursuits — and it gave me a diagnostic I am starting to use on every new project, every inbound opportunity, every commitment I’m weighing. TL;DR: * Decades of research on motivation point to three core needs: autonomy, competence, and belonging * Before saying yes to a project, job, or commitment, ask: will this increase or decrease autonomy, competence, or belonging in my life? * In an AI-disrupted career, this filter matters more — because the wrong yes compounds faster * For existing commitments, ask what conversations or moves would restore any of the three * Bonus: turn the filter into a prompt and riff with Claude or ChatGPT on the decisions you’re stuck on Graymatter is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. The Three Needs Stulberg pulls from decades of self-determination research. We thrive over the long haul when three needs are met: Autonomy — some control over how we spend our time and energy. Not total freedom. Just a real say in the how. Competence — a path toward concrete improvement in our chosen pursuits. The thing we’re doing needs to grow our craft, not just consume our hours. Belonging — connection to something beyond ourselves. A person, a community, a lineage, a tradition. An emotional stake in why this work exists. His line that stopped me: “The more time and energy we spend on pursuits that afford us autonomy, competence, and belonging, the better.” Simple. But almost nobody applies it when evaluating the next thing on their plate. Why This Filter Matters Right Now A year ago, a lot of work was good enough. The pay was fine, the scope was clear, the path was predictable. You could stay on autopilot and be okay. That’s over. AI is redrawing the edges of what humans should do. Tasks that felt worth doing in 2024 are now commodity output. Roles that felt stable are getting reassembled. The leaders I coach are making harder choices — about what to say yes to, what to drop, and what to rebuild. In that environment, the wrong yes doesn’t just waste time. It compounds. Every month spent on a pursuit that drains autonomy, stalls competence, or isolates you is a month your peers are getting sharper on the things that will actually matter in 2027. Which is why Stulberg’s question has become my default diagnostic: Will this increase or decrease autonomy, competence, or belonging in my life? How I’m Using It Three ways I’ve been running this filter in the last few weeks: On new opportunities. When something lands in my inbox — a speaking gig, a consulting ask, a collaboration — I don’t jump to the calendar. I ask the three. Does it give me more control over my time, or chain me to someone else’s schedule? Does it push my craft forward, or just repeat what I already know? Does it connect me to people and ideas I care about, or is it a transaction? If two of the three are a no, I pass. No agonizing. On existing commitments. Stulberg adds a second move most people skip. For work you’re already in, ask what actions would enrich the three. How can I protect more autonomy here? What conversation with my team would rebuild competence momentum? What would reconnect me to why this work matters? A good commitment doesn’t need to be abandoned — it often just needs a small intervention. As a prompt, when I’m stuck. This is where the AI angle gets practical. When I’m genuinely torn, I paste the situation into Claude and run it through the filter: I'm deciding whether to [take on / continue / walk away from] this project: [brief description — scope, time commitment, stakeholders, outcome] Use Brad Stulberg's framework from The Way of Excellence. Evaluate this on three dimensions: 1. Autonomy — will it increase or decrease my control over my time and energy? 2. Competence — will it grow my craft, or just consume hours? 3. Belonging — does it connect me to something beyond myself, or is it purely transactional? Give me a direct read on each, then the trade-offs I should weigh before saying yes or no. Claude doesn’t decide for me. But it surfaces the angles I’d missed — especially the ones I was quietly avoiding. The Harder Version of the Question The sharpest line in the chapter is this: “What would it look like to shape our lives for more mastery and mattering?” That’s the harder question. Not should I say yes to this one thing, but: Am I designing my life around pursuits that grow me and connect me — or am I letting it happen to me? In an AI era where almost everything about work is in motion, the leaders I watch thriving are the ones asking this out loud. They’re not waiting for the dust to settle. They’re picking the pursuits that compound autonomy, competence, and belonging — and pruning the ones that don’t. That’s the real work. AI is the accelerant. But what you’re accelerating — that’s still the decision only you can make. Your Turn Pick one commitment on your plate right now. Run it through the three. → Is it giving you more or less autonomy than it did six months ago?→ Is it building real competence, or just repeating what you already do well?→ Do you feel connected to the people and the purpose behind it? If the answer is honest and uncomfortable, that’s the signal. The next move isn’t always quit — sometimes it’s a conversation, a scope change, a recommitment. But the filter cuts through the noise. Reply and tell me what came up. I read every response. Stay curious. Stay hands-on. James The book is The Way of Excellence by Brad Stulberg [https://www.bradstulberg.com/]. Worth reading the whole chapter on the psychology of excellence — chapter two is where this framework lives. If this was useful, forward it to one person weighing a hard yes right now. They can subscribe at graymatter.jamesgray.ai [https://graymatter.jamesgray.ai]. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit graymatter.jamesgray.ai/subscribe [https://graymatter.jamesgray.ai/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

AI Didn't Create This Question. It Just Made It Impossible to Ignore.

In the final session of my last AI cohort, something unexpected happened. We’d spent weeks learning tools, building workflows, writing prompts. And then, one by one, people started sharing — not what they’d built, but who they were becoming. Someone said AI had made them more creative than they’d felt in years. Another said they could see a broader version of who they could be. A third said: for the first time in a long time, I know what I want to do next. That wasn’t a conversation about AI. That was a conversation about the Life’s Task. Robert Greene writes about this in Mastery — the idea that each of us has a primal inclination, a thread that runs through everything, and that the work of a lifetime is to find it and follow it fully. I’ve been reading Greene for years. But I didn’t expect AI to be the thing that brought his theory to life in real time — accelerating the moment when people finally see what’s possible for them. AI isn’t just changing how we work. It’s forcing a deeper question: what are you actually pointing this at? Five Strategies for Finding Your Life’s Task Greene offers five strategies. I walked through all of them in this episode — here’s the map. 1. Return to Your Origins — The Primal Inclination StrategyGo back before the job titles, before the expectations, before the world told you what to be good at. What drew you in as a child? What did you lose yourself in? I ask this in every cohort, and what strikes me is how quickly people remember — and how long they’ve been ignoring it. That pull was never random. It was always pointing somewhere. 2. Occupy the Perfect Niche — The Darwinian StrategyDon’t compete in a crowded lane. Find the intersection that is uniquely yours — where your combination of skills, experience, and inclination has no direct competition. That’s where you thrive. 3. Avoid the False Path — The Rebellion StrategySome paths are chosen for the wrong reasons — money, approval, inertia. Greene calls this the false path. Recognizing it takes courage. Leaving it takes more. 4. Let Go of the Past — The Adaptation StrategyWhat got you here won’t necessarily get you there. If AI has reshaped your industry or your role, the task isn’t to hold on — it’s to find what carries forward and build from there. 5. Find Your Way Back — The Life-or-Death StrategySome people only find their Life’s Task after a crisis forces the question. A job loss. A health scare. An industry upended. The disruption isn’t the end — it’s the redirection. The Inner Quest The Inner Quest is a series within the Graymatter podcast — dedicated to one of its three pillars: mastering yourself. Alongside mastering AI and building what matters, this is the thread I believe matters most. Not tools. Not frameworks. The deeper journey — to find ourselves, evolve ourselves, and adapt ourselves. The quest that runs beneath everything else. The one that doesn’t end. Every episode, one idea worth sitting with. This is that series. Your Reflection Prompt Somewhere inside you, you already know. There is something — in your heart, in your bones — that is your Life’s Task. Something that would bring out your uniqueness in a way nothing else can. You’ve caught glimpses of it. You may have pushed it away. It’s likely that you haven’t had the courage to fully touch it, to say it out loud, to pursue it. That’s not weakness. That’s human. The Life’s Task asks everything of you, and that’s terrifying. But here’s what I want you to sit with: we don’t know how many days we have. None of us do. And when you hold that truth — really hold it — the question changes. Not “what should I do with my career?” But: what would I honor? What is the one thing you can see, right here, right now — your Life’s Task, your opportunity, the thing that is uniquely yours to bring into the world? Write it down. Even one sentence. That’s where it begins. I’d love to know what comes up for you. Drop it in the comments — even one sentence. You might be surprised what you write. -James This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit graymatter.jamesgray.ai/subscribe [https://graymatter.jamesgray.ai/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

You Can't Automate What You Don't Understand: Deconstructing Workflows for AI

Here’s something I see all the time: A leader wants to automate prospect research. Or customer outreach. Or content creation. They’ve done the process hundreds of times. They know it works. But when they try to apply AI? They get stuck. Not because the AI isn’t capable. But because they’ve never had to explain their process with the kind of precision an AI needs. The workflow lives in their head as intuition—not as clear, repeatable steps. On Friday, I hosted a Lightning Lesson where we tackled this together. Over 340 leaders and professionals joined me to walk through how to take something you know intimately and break it down so AI can actually execute it. No theory. Just a real workflow, deconstructed step by step. Graymatter is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. The Challenge: Getting What’s in Your Head Into Structure Think about something you do regularly in your business. Maybe it’s qualifying leads. Analyzing feedback. Preparing reports. Now imagine explaining every single step to someone who’s smart but has never done it before. Not just the what—the how, the why, the decision points, the nuances. Suddenly it’s not so simple, right? That’s the gap. You have expertise that’s second nature. AI needs explicit instructions. Deconstruction is how you bridge that gap. And honestly? The process of breaking it down often reveals things you didn’t even realize you were doing—which makes your process better, with or without AI. What We Built Together In this session, I walked through a workflow I use for LinkedIn prospect research. Nothing fancy—just a practical business process: * Start with a buyer persona (the kind of prospect you want to find) * Search LinkedIn for people who match that profile * Evaluate each prospect against specific criteria * Generate personalized engagement recommendations * Output everything in a structured format The interesting part isn’t the workflow itself. It’s how we approach building it. Key Concepts You Can Apply Immediately 1. The “What/Why vs. How” Principle You shouldn’t be writing detailed AI instructions from scratch. That’s the old way. Instead, you define the business outcome and sketch high-level steps. Then let AI generate the detailed execution instructions. You bring domain expertise. AI brings execution precision. Stay in your lane. 2. Meta-Prompting: Let AI Write AI Instructions Here’s the actual technique: “You are an expert workflow designer and prompt engineer. Please write a prompt for this scenario. The outcome is [your goal]. Here are the high-level steps: [your steps]. Now write the detailed instructions.” Let the model craft the “how” while you focus on the strategic “what and why.” I demonstrate this live in the session—you’ll see how much better the AI-generated instructions are than what most people write manually. 3. Skills vs. MCPs: Understanding the Difference This came up multiple times in Q&A because it’s genuinely confusing. Skills teach Claude how to do something. Procedural knowledge. “Here’s how to write a LinkedIn post in my style.” MCPs (Model Context Protocol) give Claude access to something. Tool connectivity. “Here’s how to read from and write to my Notion database.” They work together. Skills provide the methodology. MCPs provide the capability. 4. Build a Workflow Registry Don’t just build workflows ad hoc. Create a system. I show my Notion setup where every workflow is documented with: * Name and business process assignment * Description and expected outcome * Trigger conditions * The actual steps * Links to AI assets (prompts, personas, templates) * Status tracking This becomes your institutional knowledge. Your competitive moat. 5. The Clarity Test Here’s how you know if a workflow is ready to automate: Can you explain it clearly enough that a smart person who’s never done it could execute it successfully? If not, you’re not ready for AI yet. The work is in the deconstruction, not the automation. 6. Create Reusable AI Assets In the demo, I use a buyer persona stored as a markdown file. It’s an AI asset I can plug into multiple workflows—prospect research, email outreach, and content creation. Think in building blocks. What pieces of knowledge or context can you document once and reuse everywhere? Questions That Came Up The Q&A was where things got practical. People asked questions like: “Should I design my Notion database first, or let Claude do it?” (Start simple with what makes sense to you, then let Claude optimize based on your actual workflow) “When do I need a Skill versus just a good prompt?” (Skills when you’re doing the same thing across multiple workflows and want consistent execution) “How detailed should my workflow steps be?” (Detailed enough that the AI knows what to do, but not so prescriptive that you lose flexibility) These weren’t hypothetical. These were people actively working through this in their businesses, hitting real obstacles, finding real solutions. Why This Matters Right Now We’re past the “playing around with ChatGPT” phase. The tools are ready. The question isn’t whether AI can help your business—it’s whether you can articulate your processes clearly enough to take advantage of it. The leaders who figure this out aren’t necessarily the most technical. They’re the ones who can think operationally, break down their expertise, and build systems that scale. That’s what this Lightning Lesson is about. Not the technical wizardry (though we cover that too). The mindset shift from “What can AI do?” to “What do I need done, and how do I break it down?” Want to Go Deeper? This Lightning Lesson gives you the approach. If you want to actually build these systems with hands-on guidance and expert feedback, I’m running two cohort courses: Claude and Claude Code for Builders – Starts Tomorrow (January 26) This course is primarily for “builders” - business people who want to go deep on Claude’s capabilities, Claude Code for agentic workflows, and building a prototype application (e.g., website) 25% founder discount for this inaugural cohort. View syllabus and enroll → [https://maven.com/james-gray/claude] Hands-on Agentic AI for Leaders – Next cohort starts February 2 This is for business leaders and non-technical builders who want to move from experimentation to actually deploying AI in their operations. We build real workflows, deploy them, and develop the literacy to lead AI transformation. Rated 4.8/5. Over 250 students trained. View syllabus and enroll → [https://maven.com/james-gray/hands-on-ai-for-leaders] The best AI implementation starts with clear thinking about your business, not with fancy prompts. Watch the session. Pick one workflow. Break it down. That’s where real progress starts. — James This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit graymatter.jamesgray.ai/subscribe [https://graymatter.jamesgray.ai/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

The Easiest Path to Happiness (That We All Ignore)

This is a self-mastery post—part of my commitment to help you master AI, master yourself, and build what matters. Because here's the truth: the best AI tools in the world won't save you if you're stuck on the satisfaction treadmill, chasing the next feature instead of loving what you already have. Let's talk about that. Daily Nugget “The easiest way for us to gain happiness is to learn how to want the things we already have.” - A Guide to the Good Life by William B. Irvine [https://amzn.to/4quCzix] Hey, everybody. It’s Monday, January 19th, and I want to share something with you. I love books. Every day, I read from The Daily Stoic by Ryan Holiday and The Daily Laws by Robert Greene. A lot of times, we need reminders of really important things—basic things, even—but we need to hear them again. When I find nuggets, I want to share them with you. One book that helped me through a difficult period years ago is The Guide to the Good Life. It’s based on Stoic philosophy, and there’s a chapter in here that I keep coming back to. It’s about hedonic adaptation—this very human tendency to be insatiable. The Satisfaction Treadmill Here’s what the author says: “We humans are unhappy in large part because we are insatiable.” You know this treadmill. We achieve something we’ve worked hard for, and almost immediately, we want more. There’s nothing wrong with being successful or wanting to grow. But it’s when that pursuit starts controlling our lives and making us unhappy that we need to pause. The author explains it this way: “We are unhappy when we detect an unfulfilled desire in ourselves. We work hard to fulfill this desire in the belief that on fulfilling it, we will gain happiness. The problem, though, is that once we fulfill a desire for something, we adapt to its presence in our life, and as a result, we stop desiring it—or at any rate, we don’t find it as desirable as we once did. We end up just as dissatisfied as they were before fulfilling the desire.” Your job. Your relationship. Your home. The things we once dreamed of having, we now take for granted. The Solution So what’s the answer? The author writes: “One key to happiness is to forestall this adaptation process. We need to take steps to prevent ourselves from taking for granted, once we get them, the things we worked so hard to get.” And here’s the nugget—I have this highlighted because it’s so true: “The easiest way for us to gain happiness is to learn to want the things we already have.” This advice is easy to state. The trick is putting it into practice. How do we convince ourselves to want the things we already have? Your Assignment Today I talk to a lot of people who are b******g and complaining about things that, frankly, are irrelevant. I think if we really embrace this idea of loving the things we already have, we’ll not only be happier—we’ll probably be less stressed as we go throughout our days. So here’s my challenge: Take a pause and think about all the amazing things you have in your life. Your health. Your family. Your friends. Really embrace those and love them. And ask yourself: Is there something you’re pursuing that’s driving you astray because you feel unsatisfied? Because you’re insatiable for that thing? This was the nugget I reminded myself of today. I’m hoping this short reflection can give you a dose of happiness, too. What’s one thing you already have that you could appreciate more today? Hit reply—I’d love to hear from you. Graymatter is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit graymatter.jamesgray.ai/subscribe [https://graymatter.jamesgray.ai/subscribe?utm_medium=podcast&utm_campaign=CTA_2]

Stop reprompting. Start building skill-powered workflows

TL;DR: → Your workflow instructions are probably too vague or too long (300-line mega-prompts don’t work)→ Claude Skills package your expertise into reusable how-to manuals that activate automatically→ The process: Map workflow → Break down steps → Build skills → Test and reuse→ Live demo: Building a meeting notes organizer skill in real-time→ One simple prompt can trigger multiple skills that execute complex workflows flawlessly I just wrapped my Lightning Lesson on “Design Your First Skill-Powered Workflow” and wanted to share the recording with you. Most people get workflow instructions wrong in one of two ways: Too high-level: “Research our competitor and write a brief.” Claude guesses. You get mediocre results. Too detailed: A 300-line mega-prompt that hits context limits and still doesn’t perform. The real issue? Tasks that require precise procedural control—the kind you execute manually with rigor—need a different approach. That’s where Claude Skills come in. What You’ll Learn in This Session The mental model: Think of Skills as instruction manuals. When you ask Claude to “organize meeting notes,” it automatically reads the how-to manual you’ve created, complete with edge cases, examples, and resources. The activation pattern: Claude reads all your skill metadata when you boot up. When keywords in your prompt match a skill, it pulls the full instructions and executes. No more explaining the same process 50 times. The build process: * Map your workflow (business process → workflows → steps) * Identify skill-worthy tasks (repeatable + need rigor) * Collaborate with Claude to build the skill * Test it and add to your toolbox Live demonstration: I built a meeting notes organizer skill from scratch in the session—you’ll see the exact questions Claude asks, how to answer them, and what the final skill looks like. Real workflow example: I showed my Lightning Lesson creation workflow that went from this 300-line manual process to a single prompt: “Create a new Lightning Lesson on [topic]” → Claude designs the lesson, creates a Word doc, and saves it to the Notion database. Three skills activated automatically. Why This Changes Everything Here’s what clicked for attendees: Skills aren’t just about saving keystrokes. They’re about packaging your domain expertise so Claude doesn’t have to read your mind. When you build a skill, you’re creating IP. Reusable assets you own. A war chest of procedures that compound over time. I’ve built 50+ skills for my one-person business. Each one unlocks work I used to find too cumbersome to do consistently. Watch the Full Session The recording walks through: * The decomposition framework (Process → Workflow → Skill) * Live skill creation with real-time Q&A * How skills activate based on keywords * My actual Notion database showing skill-powered workflows * Common mistakes and how to avoid them Go Deeper: Claude for Builders Course If you want to get hands-on and go deeper with Claude, Claude Code, and Cowork, join me for a cohort adventure to learn with other builders who want to operationalize high-value use cases. In 5 weeks, you’ll build: ✅ Foundation: Configure your builder stack and design systematic workflows✅ Reusable Assets: Build Claude Skills that execute your expertise on demand✅ Collaborative AI: Deploy workflows where Claude works WITH you✅ Autonomous Workflows: Build multi-agent systems and browser automations that run independently✅ Applications: Ship web app prototypes using agentic coding—no engineering required You get intimate cohorts, 1:1 coaching, and lifetime access. We build together—not lectures. First cohort launches Jan 26 — limited to 20 builders. Use promo code FOUNDER to save 25%, shape the course, and attend again free in 2026. See the full syllabus → [https://maven.com/james-gray/claude] Your Turn Drop a comment and tell me: What’s the first workflow you’re going to supercharge with Claude skills? I read and respond to every comment—and the best ideas might become future Lightning Lessons. Stay curious,James P.S. Two more Lightning Lessons coming up if you want to keep building: → Deconstruct Your Workflows for Agentic AI — Friday, Jan 24 (sign up for free [https://maven.com/p/f0f660/deconstruct-your-workflows-for-agentic-ai] ) - Learn a framework to break workflows into AI-executable steps → Build Your Agentic Workflow Registry — Friday, Jan 31 (sign up for free [https://maven.com/p/b5a3c0/build-your-agentic-workflow-registry])Map all your processes, workflows, and AI assets in a registry This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit graymatter.jamesgray.ai/subscribe [https://graymatter.jamesgray.ai/subscribe?utm_medium=podcast&utm_campaign=CTA_2]