Expert Interview

    Overcoming Course Fatigue with Charlie Gilkey

    Charlie Gilkey shares strategies for staying motivated and avoiding burnout as a course creator.

    Guest: Charlie GilkeyUpdated February 2026
    Charlie Gilkey

    Interview with Charlie Gilkey

    Founder, Productive Flourishing

    Interview Summary

    Business coach Charlie Gilkey joins Abe Crystal for a deep conversation about creating effective online courses. Charlie—founder of Productive Flourishing, bestselling author, PhD candidate in Philosophy, and former Army Logistics Officer—shares practical wisdom on engaging participants, avoiding scope creep, and getting unstuck when course design feels overwhelming.

    The Transformative Power of Teaching

    Charlie opens with a bold claim that frames the entire conversation: teaching sales is one of the most transformative things you can do for an audience. But here's the catch—it has to be a *really good* learning experience. The online course market is saturated with mediocre offerings, and students are increasingly skeptical.

    The solution isn't to create more content or add more modules. It's to focus relentlessly on transformation. What specific change will your students experience? Can you articulate it clearly in one sentence?

    Few things are more transformative than a really good learning experience. Teaching is one of the most powerful ways to serve your audience.

    Authenticity Grounded in Service

    When Charlie talks about being an "authentic expert," he's not referring to performative vulnerability or manufactured relatability. He's talking about something deeper: a genuine orientation toward service.

    The question isn't "How do I position myself as an expert?" but rather "What's going to best serve my tribe?" This distinction matters because it shifts your focus from self-presentation to student outcomes. Natural expertise—where you actually know what you're talking about—emerges from this service mindset. It's the opposite of "social expertise," which is just convincing people you know things.

    Authenticity comes from asking 'What's best going to serve my tribe?' It's coming from a place of service, not just social expertise where people think you know what you're talking about.

    Know Your Students' Starting Point

    Before designing any course material, Charlie emphasizes the critical importance of understanding where your participants are starting from. He references the Dreyfus model of skill acquisition—novice, advanced beginner, competent, proficient, expert—as a framework for thinking about your audience.

    Most course creators make a fundamental mistake: they design for a vague "everyone" instead of a specific skill level. The content appropriate for a complete beginner is radically different from what serves an advanced practitioner. Think about the difference between a freshman survey course and a graduate seminar. Same broad topic, completely different approaches.

    This has pricing implications too. Advanced students with specific needs are often willing to pay premium prices for targeted, high-level content.

    Think about the difference between a freshman course and a graduate seminar. Many course creators fail to clearly identify where their learners are—and their courses suffer for it.

    The Minimum Question

    Here's where Charlie gets tactical. He introduces what he calls "the minimum question": What's the very minimum students need to learn to get from where they are to where you're trying to take them?

    Anything beyond that minimum is scope creep. And scope creep is the enemy of effective courses. When the course scope is too big, "nobody wins." Students feel overwhelmed and drop out. Creators burn out trying to create too much content. The transformation gets lost in a sea of information.

    This is counterintuitive for experts. We naturally want to share everything we know. We think comprehensive equals valuable. But online learners are distracted. They're checking email, dealing with kids, squeezing in lessons between meetings. You have to simplify your material as much as possible.

    Ask yourself: What's the very minimum students need to learn to get from where they are to where I'm taking them? Anything beyond that is scope creep—and when scope is too big, nobody wins.

    Small Courses Beat Encyclopedias

    Many experts lean toward creating big, comprehensive courses because they intuitively seem more valuable. A 50-module masterclass sounds more impressive than a focused 8-lesson program, right?

    Wrong, according to Charlie. Participants in sprawling courses feel cognitively overloaded and check out. Completion rates plummet. By creating smaller, focused courses, you can get started faster, test your ideas with real students, and develop a library of offerings instead of betting everything on one monolithic program.

    This approach also forces clarity. When you only have 8 lessons to work with, every minute has to count.

    Sometimes experts create big, comprehensive courses because they seem more valuable. But participants will feel cognitively overloaded and check out. Smaller courses let you build a library instead of one giant course that nobody finishes.

    The Courage to Exclude

    One of the hardest skills for course creators is being willing to say "this isn't for you." Charlie is emphatic about this: it takes discipline to say "it's only for these people—if that's not you, don't buy the course."

    Exclusion feels like leaving money on the table. But the opposite is true. When you try to serve everyone, you create a watered-down experience that truly serves no one. Your best students—the ones who would champion your work and provide testimonials—get frustrated alongside the beginners who shouldn't have been there in the first place.

    Get crystal clear about the "future positive state" you're helping students achieve. Then build the entire course around getting specific people to that specific destination. Really clear, really direct.

    It takes discipline to say 'it's only for these people—if that's not you, don't buy the course!' Being willing to exclude is essential to creating a powerful learning experience.

    Find Product-Market Fit First

    Before you spend months creating a course, Charlie suggests a simple step that many creators skip: ask your audience what they want. Survey them. What type of product would they like? How would they prefer to learn this topic—via a workshop, a book, a coaching program, or a course?

    You might discover that your audience doesn't actually want a course at all. Maybe they want a quick workshop. Maybe they want ongoing group coaching. Finding this product-market fit before you create saves enormous time and heartache.

    Charlie's Action Steps

    Charlie recommends these 3 steps to improve your course planning:

    1

    Get crystal clear about who and where

    Know exactly who the course is for and where you're taking them before you start making the course. Write it down in one sentence: 'This course is for [specific person] who wants to achieve [specific outcome].'

    2

    Identify the minimal information needed

    Come up with the very minimal amount of information students need to know to get from where they are to where you're taking them. Cut everything else—ruthlessly.

    3

    Create exercises for quick wins

    Give participants homework, worksheets, and exercises to move from knowing to doing. Make these short, accessible, and achievable. Help them celebrate their progress—that's where true integration happens.

    About Charlie Gilkey

    Founder, Productive Flourishing

    Charlie Gilkey is a champion and catalyst for Creative Giants—the changemakers, thought leaders, and creatives who are trying to do work that matters. He's the bestselling author of 'Start Finishing: How to Go from Idea to Done,' a PhD candidate in Philosophy, and a former Army Logistics Officer. Charlie wakes up every morning figuring out how to help Creative Giants be their best selves in the world.

    Bestselling Author
    PhD Candidate (Philosophy)
    Former Army Logistics Officer
    Productivity Expert
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    Resources & Links

    Topics:
    productivity
    mindset
    burnout

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