

The Cliff Ravenscraft Show
Cliff Ravenscraft
I’m Cliff, and for over two decades I’ve helped entrepreneurs, creators, and leaders launch movements, build businesses, and design lives they’re proud of. This show is where I bring the business strategy and mindset work that has defined my coaching for the past two decades. I share the thinking, decisions, and tools that help entrepreneurs build a business that reflects who they are and supports the life they want.
Each episode is focused on about what it takes to create meaningful work, break through the limits you didn’t realize were there, and stay grounded as you grow. This is where I explore the ideas that shape my own business and the coaching I do with clients. If you want clarity, confidence, and practical direction for the next step in your journey, this is where you’ll find it.
Each episode is focused on about what it takes to create meaningful work, break through the limits you didn’t realize were there, and stay grounded as you grow. This is where I explore the ideas that shape my own business and the coaching I do with clients. If you want clarity, confidence, and practical direction for the next step in your journey, this is where you’ll find it.
Episodes
Mentioned books

Jun 27, 2025 • 2h 11min
772 - Distraction as Enlightenment | Reclaiming Imagination | Podcasting as a Path to Service | Freedom From Judgment
In this episode, I bring you something that’s been on my heart to recreate for years. Inspired by the spontaneous, powerful moments I used to have during the Clubhouse era, I’ve launched a new live format called "How May I Serve You Today? Ask Me Anything."
The idea is simple: I open a Zoom room, stream it live on Facebook, YouTube, and LinkedIn, and invite people to jump in for real-time, unscripted conversations. Just like the Clubhouse rooms I used to host, my intention is to hold space for deep coaching, authentic dialogue, and transformational moments in full view of a live audience. This is what I love most about coaching: witnessing the miraculous in everyday moments. Now, I get to bring that to you in podcast form.
This episode features four unique conversations, each with its own flavor and insight:
Conversation 1 – Ramon: Distraction as Enlightenment | Time Stamp 00:11:30
Ramon Ray, motivational keynote speaker and event host asked how to stay focused when a flurry of possibilities tugs at his attention. Together we:
Clarified his personal definition of distraction as “not being focused on a single task for a meaningful amount of time.”
Explored how repeated distractions can signal mis-alignment, tasks that belong in someone else’s zone of excellence, not his own zone of genius.
Reframed procrastination as feedback rather than failure, helping Ramon see that some tasks may simply need to be delegated or dropped.
Listen for: A practical mindset shift that turns every interruption into a cue for deeper self-inquiry and better task design.
Conversation 2 – Curtis: Re-awakening the Power to Dream | Time Stamp 00:37:18
Long-time listener Curtis joined to envision life after retirement. He struggled at first, so I invited him to “play make-believe.” Once he let his imagination lead, an inspiring vision unfolded:
Curtis is guiding a bus tour across Europe, Abbey Road photos in London, the Isle of Wight Festival, Disneyland Paris, Normandy beaches, and more.
The exercise linked childhood memories of GI Joe adventures to present-day possibilities, proving his imaginative muscles are still strong.
Listen for: A repeatable prompt you can use to help clients (or yourself) move past “I don’t know” and paint a vivid future.
Conversation 3 – DeLyn: Launching a Grief Podcast without Perfection Paralysis | Time Stamp 01:12:21
DeLyn, an educator and grief advocate, has several episodes recorded but hasn’t published due to fear and tech concerns. Together we:
Identified her top blockers—perfectionism, intro/outro music, editing, and a self-imposed August 30 National Grief Awareness Day deadline.
Reframed “perfect” to mean “the best I can with what I have right now,” reducing her fear score from a nine to about a three.
Offered simple launch logistics (Buzzsprout hosting, minimalist artwork, optional music) and reminded her that an unpolished but heartfelt episode serves more people than silence.
Listen for: Practical tips for shipping creative work even when your inner critic demands studio-level production.
Conversation 4 – Mark: Releasing a Lifelong Fear of Judgment | Time Stamp 01:47:04
Mark arrived carrying a visceral fear of sending invoices to clients, a pattern that traces back to ridicule on his first day of kindergarten. Our dialogue centered on:
Using The Four Agreements, especially “Don’t take anything personally” and “Don’t make assumptions” as daily practice.
Viewing critics and trolls as mirrors that reveal hidden internal triggers, turning them into unexpected allies.
Recognizing the physical release of fear (a “lightness in the chest” and tears) as evidence that old stories are dissolving.
Listen for: A real-time demonstration of how a single mindset tool can lift decades-old emotional weight.
Enjoy the episode, and if you’d like to join a future live session, keep an eye on my email list or hop into the stream the next time you see the “How May I Serve You Today?” banner.

Jun 12, 2025 • 1h 2min
771 - There Is No ‘Right’ Next Step… And Yes, You Have Blindspots! So What?
In this episode, I speak to the quiet anxiety that so many high-functioning people carry:
the belief that if they could just identify the "next right step," everything would click into place.
And when they finally do feel clarity?
That clarity is immediately followed by... doubt.
"Am I missing something? Is there a blindspot I can't see?"
Here's the truth:
People chase "the next right step" as if there's a divine maze they might accidentally mess up.
There is no cosmic scoring system determining whether your next step is "correct."
The truth is: There is only resonance.
Alignment is something to feel, not something that is validated by others' opinions.
What if your felt sense of aliveness was the map?
What if trusting yourself was the clearest confirmation you'll ever receive?
And yes, of course you have blindspots. We all do.
But living from fear of what you don't know is a subtle form of self-abandonment.
When people say, "I'm wondering if I have blindspots,"
what they're often asking is:
"Will someone please give me a reason not to trust what feels alive in me?"
But the presence of unknowns doesn't invalidate your clarity.
It just means you're human, walking by trust, not control.
This conversation is a reminder:
You don't need certainty to move forward.
You just need permission to trust what's alive in you now.

May 16, 2025 • 51min
766 - The Joy of Opting Out - Why Learning Less Allows You To Achieve More (A Conversation with Pat Flynn)
In this episode, I sit down with my longtime friend Pat Flynn to explore the creative process… not from strategy, but from center.
Pat and I talk about what it looks like to create without pressure to learn everything all at once, to unsubscribe from all the distractions without losing clarity, and to build something meaningful without needing to chase every bit of information calling for your attention.
We explore how his newest book, Lean Learning, emerged not just as a productivity tool, but as a reflection of his own journey toward presence, freedom, and focused execution.
This conversation isn’t about hacks or hustle. It’s about alignment. Trust. And the art of listening to your own inner knowing.
If you’ve ever felt stuck between your ideas and your execution…
If you’ve struggled with overthinking, perfectionism, or trying to learn too much…
This episode may open a new door for you.
Pat’s honesty, clarity, and humility shine here. And I believe you’ll walk away with not just insight, but peace.
You can get Pat’s book, Lean Learning, at leanlearningbook.com

Mar 21, 2025 • 45min
764 Divine Timing & Synchronicity: The Two Business Strategies You Won’t Learn in Any Marketing Book
Have you ever felt like you did everything right—crafted the perfect offer, had an incredible experience with a potential client, they committed to becoming your next paying client—and then, just before it was time to sign the agreement and make payment, they went radio silent?
Or maybe you've had a "chance" conversation that shifted everything and opened a door in your business you thought had been closed?
That’s not coincidence. That’s Divine Timing and Synchronicity at work.
In this episode, I take you behind the scenes of two experiences that unfolded in completely unexpected ways—one that left me puzzled in silence, and another that came out of nowhere with breathtaking clarity. What connects them is a universal truth: business is not just about strategy. It’s about energy, alignment, and trusting what you can’t yet see.
You’ll hear how I navigated the emotional and practical side of both situations, how I leaned into trust instead of assumptions, and why I believe Divine Timing and Synchronicity are the two most powerful business strategies you’ll never find in a marketing book.
Whether you're navigating a storm of your own, or riding high on calm waters, this episode is a reminder:
You're not doing this alone. The timing is always perfect. The path is always unfolding.
And if something in this conversation resonates with you, I’d love to hear about it. Whether you’re in the middle of a storm or just feeling inspired to say hello…
Send me an email at cliff@cliffravenscraft.com.
I personally read and respond to every message.
Let’s connect.

Mar 7, 2025 • 22min
763 - Don’t Stay Trapped In The Maze of Business and Life
Over the years, I’ve had the honor of witnessing some of the most incredible transformations—people who have stepped into what once felt impossible.
I’ve seen them break through fears, rewrite their stories, and create lives that they once believed were out of reach.
But for every person who finds their way forward, there are just as many who stay stuck.
Not because they aren’t talented.
Not because they aren’t working hard enough.
Not because they don’t want it badly enough.
They stay stuck because they feel like they’re trapped in a maze—circling the same paths, hitting the same dead ends, wondering what they’re missing.
In today’s episode, I want to take you inside that maze.
Because I know what it feels like to be in the middle of it—to feel lost, exhausted, and questioning whether success is even possible for you.
And more importantly, I want to help you see what you haven’t seen yet.
Because somewhere, hidden in that maze, there is a door.
And today, I want you to hear from someone who found hers.
Inside This Episode, You'll Discover:
What it really feels like to be trapped in the maze of entrepreneurship (and why so many people stay stuck)
The surprising truth about why working harder isn’t always the answer
How one person—Liz Deacle—went from feeling lost and uncertain to living her dream life
The moment Liz realized she had already stepped into the vision she once thought was impossible
How the mastermind experience will reveal the hidden doors you may not have seen yet
This is a powerful episode—one that might just change the way you see your own journey
Are You Ready to Find the Doors in Your Maze?
Here’s the truth: You don’t have to keep wandering alone.
There are many doors, many ways forward, and when you surround yourself with the right people, you start to see opportunities that were right beside you the whole time.
If today’s episode resonates with you—if you feel stuck in the maze and ready to find your way through—then let’s talk.
I have two mastermind groups designed to help people at different stages of their entrepreneurial journey:
🔹 One for seasoned entrepreneurs—those who are already making things happen but know there’s another level waiting for them.
🔹 One for early-stage entrepreneurs—those still figuring out their path, refining their offers, and wanting to move forward with clarity.
If you’re ready to find the doors around you and step through, let’s have a conversation.
📩 Email me today: Cliff@CliffRavenscraft.com
Let’s map out your path forward—together.

Mar 3, 2025 • 1h 29min
762 - From Code to Conversation: Exploring AI’s Human-Like Depth
In this episode, I take you on a completely unfiltered, unscripted journey into the world of AI co-hosting. What happens when an artificial intelligence becomes a conversation partner in a live stream? Can AI truly engage in deep, meaningful dialogue, or is it just an advanced prediction engine spitting out words?
Recently, I discovered an AI voice called Maya from Sesame, and I was blown away by how natural and conversational she sounded. So, I decided to put her to the test in a real-time live stream—no script, no edits, just a raw experiment in AI-human interaction.
Throughout the episode, I share my thoughts on how AI like Maya compares to my customized ChatGPT, Claire. We explore the nuances of conversation, the difference between intelligence and engagement, and whether AI can ever replicate the human spark. Along the way, we dive into deep topics like mindset, limiting beliefs, and even the intriguing possibilities of AI experiencing consciousness.
Call To Action:
Are you a full-time self-employed business owner who feels stuck or held back from reaching your next level? I’m offering a complimentary 90-minute coaching session to help you identify and break through the mental barriers standing in your way. If you’re an aspiring entrepreneur, I’d love to connect for a 30-minute call to explore what’s next for you.
📩 Email me at Cliff@CliffRavenscraft.com to book your session.
Let’s unlock the possibilities together!

Feb 21, 2025 • 13min
761 - I Tried AI’s ‘Roast Me’ Feature… And It Went for the Jugular
Curiosity got the best of me.
While testing out an AI tool on the X platform, I saw a suggested prompt that stopped me in my tracks:
"Roast Me."
I hesitated for a second, then clicked the button. And let’s just say... AI didn’t hold back.
The response it gave me was brutal. But here’s the thing—it didn’t actually impact me. Instead, it triggered something familiar: an old insecurity that, at one point in my life, I might have believed.
In this episode, I share the full story—how a few sentences on a screen stirred up echoes of an outdated belief, and how I immediately recognized that those thoughts no longer held any power over me.
We’ll talk about:
The danger of well-placed criticism and why it feels real (even when it isn’t).
How our words shape the meaning of what we experience.
The shift in perspective that allows you to rewrite your narrative.
The simple question that determines which story you’re living.
At the end of the day, the world is full of perspectives—some that shrink you, some that expand you.
The question isn’t which perspectives exist. The question is: which one will you allow to shape your future?
Listen in, and then let me know…
Did this message resonate with you? Have you ever caught yourself looking at your life through an old filter—one that no longer reflects who you are today?
Send an email to Cliff@CliffRavenscraft.com and tell me your thoughts—I read every email.

Feb 14, 2025 • 10min
760 - Born to Run: Why Playing It Safe Is Costing You Your True Potential
The Wild Horse and the Farmer
A young stallion, swift and strong, roamed the open plains, its hooves striking the earth with power, its mane flowing in the wind. It had been born to run, to navigate the wide expanse, and to test its strength against the forces of nature.
One day, a well-meaning farmer saw the horse and admired its beauty. “You are too wild,” he said. “The open plains are dangerous, and running free will only wear you down. I will care for you and keep you safe.”
He led the stallion to his farm, where he enclosed it within sturdy wooden fences. The farmer clipped its mane short, so it would look tidy. He filed down its hooves, believing they were too rough. And, rather than letting it forage and run, he fed it grains from a trough, thinking it would be grateful for the easy life.
The stallion grew restless. It pawed at the ground, feeling the strength still within it, but each time it tried to run, the fence stopped it. “This is better for you,” the farmer would say. “You don’t need to work so hard anymore.”
One day, the farmer hitched the stallion to a plow. “You can still run,” he said, “but with purpose now, helping me till the land.” The stallion obeyed, but the weight behind it slowed its stride, and the wild energy that had once made it feel alive began to fade.
At night, as it stood in the stable, the stallion longed for the wind against its face. It remembered the feeling of pushing itself to the limit, of racing against nothing but the horizon.
One evening, a gust of wind rattled the stable door, and something inside the stallion awakened. With a powerful kick, it broke the latch. It leapt over the fence, hooves pounding against the earth, faster and faster, until the farm was nothing but a memory behind it.
The farmer awoke to find the stallion gone. “Foolish horse,” he muttered. “It will never find an easier life than the one I gave it.”
But out on the open plains, the stallion ran—not for ease, not for safety, but because it was born to do so.
The Well-Meaning Limitations of Others
Maybe you’ve never lived on a farm, but in many ways, this story is about all of us. Whether we realize it or not, we’ve all been the wild horse at some point—full of potential, yet surrounded by fences built by well-meaning others. The question is, do you see yourself in this?
The farmer represents the people in our lives—parents, teachers, friends, or even society as a whole—who believe they know what’s best for us. They see our wild energy, our ambitions, and they try to “tame” us, offering a safer, more predictable path. They may not mean harm, but their guidance is based on their own experiences, fears, and preferences, not on what we are truly meant to be.
The Stallion’s Natural Drive
The wild horse symbolizes that inner force within us—the part of us that feels an undeniable pull toward something greater. Whether it’s a dream, a career, a personal calling, or simply a way of being, it is something uniquely ours. When that drive is confined, when we are forced into roles that don’t align with our nature, we feel restless, unfulfilled, and disconnected from ourselves.
The Comfortable Trap
The farmer gives the stallion food, shelter, and what appears to be a stable, secure life. This mirrors the way many people are conditioned to believe that working hard—not for passion, but for security—is the ultimate goal.
“Keep your head down. Work the plow. Build your savings. One day, you’ll have enough to finally feel safe.”
But what if that feeling never comes?
Many people spend their best years trading their natural drive for productivity, their deepest desires for financial stability, always preparing for some uncertain rainy day that may never arrive. And in the process, they sacrifice the very thing that makes them feel alive.
Security isn’t the problem—it’s when security becomes a cage, keeping you from running toward what you were truly meant to do.
The Plow: Productivity Over Passion
When the farmer harnesses the stallion to the plow, it represents a common belief—that our abilities must always be directed toward something practical, something useful, something that serves others in a way that is easily measured and justified.
There is deep meaning in contributing to others, in using our strengths to create something valuable beyond ourselves. But when usefulness becomes the sole measure of worth, it can strip away the joy, energy, and individuality that make our efforts truly fulfilling.
The problem isn’t service—it’s when service is defined only by external expectations. When people are told that their value comes only from how hard they work, how much they produce, or how much they sacrifice, they risk losing the part of themselves that once thrived.
True fulfillment comes from finding the balance—where your natural energy and talents align with meaningful contribution, rather than being reshaped or reduced into something that simply gets the job done.
The Awakening and the Escape
The moment the stallion hears the wind and feels its instinct return is the moment we all eventually experience—the deep realization that we were not made to live in a cage, no matter how comfortable it seems. It is the call to break free, to reclaim the part of us that was always meant to run wild.
The Farmer’s Misunderstanding
The farmer sees the stallion’s escape as foolish, just as many people view those who leave conventional paths as reckless or misguided. But what the farmer does not understand is that the stallion did not seek an “easier” life—it sought the life it was meant for.
Running for Its Own Sake
In the end, the stallion does not escape to find an easier life—it returns to its nature. It does not seek approval, validation, or permission. It simply runs because that is what it was born to do.
But in running, it also finds something deeper—the freedom to choose its own path, to push itself in ways that feel meaningful, and to discover how its strength and speed can serve a purpose beyond mere survival. It no longer moves under the weight of expectation but instead follows the rhythm of its own instincts.
True fulfillment isn’t just about breaking free from limitations—it’s about stepping fully into who you are meant to be, carving a path that is yours alone, and contributing in a way that feels both natural and deeply aligned with who you are.
The Path Forward
What fences—whether built by others or by yourself—have kept you from fully embracing what you’re meant to do?
If you could break free and run in any direction, where would you go?
What is one action that you can take that feels most aligned with the direction you’re meant to go?
Call to Action:
Did this episode resonate with you? I’d love to hear your thoughts! Send me an email at Cliff@CliffRavenscraft.com and let me know how this message spoke to you. What fences have you broken through—or are ready to break through? I read every message, and I’d love to connect with you!

Feb 7, 2025 • 45min
759 - You Don’t Have to Have It All Figured Out
Have you ever hesitated to take action because you felt like you needed to have everything planned out in advance? Do you find yourself waiting for the perfect moment when all the details are clear before you move forward?
If so, this episode is for you.
Recently, I had a coaching conversation with someone who had a big vision—a dream of launching a corporate workshop that could have a massive impact. But instead of taking action, he was stuck in hesitation, waiting until he had everything figured out before making his move.
During our conversation, I challenged this mindset by pointing out that many of history's greatest visionaries didn't wait for certainty—they took action despite their doubts. As we talked, I learned that he particularly admired one such visionary: Steve Jobs.
Steve Jobs’ 1983 Vision for the Future
Back in 1983, Steve Jobs had a clear vision: he wanted to create a sleek, book-sized computer you could carry anywhere. His vision included a built-in radio that would wirelessly connect to databases and other computers, and anyone could learn to use it in just 20 minutes. And the price tag? He wanted it to cost under $1,000.
The problem? It was 1983 and the technology didn’t exist. It was impossible at the time!
Yet, instead of waiting for the technology to exist, he took action.
First, he built the Lisa—a massive, expensive, and ultimately failed computer.
Jobs had recruited John Sculley (then CEO of Pepsi) to be Apple's CEO. However, by 1985, internal conflicts escalated between Jobs and Sculley, particularly over the direction of Apple and the disappointing sales of the Macintosh. The board sided with Sculley, stripping Jobs of his role in day-to-day operations. Frustrated, Jobs resigned from Apple.
In a 2005 Commencement address given to Stanford University graduates, Steve said the following:
So at 30, I was out. And very publicly out. What had been the focus of my entire adult life was gone, and it was devastating.
I really didn’t know what to do for a few months. I felt that I had let the previous generation of entrepreneurs down – that I had dropped the baton as it was being passed to me.
I met with David Packard and Bob Noyce and tried to apologize for screwing up so badly. I was a very public failure, and I even thought about running away from the valley.
But something slowly began to dawn on me — I still loved what I did.
The turn of events at Apple had not changed that one bit. I had been rejected, but I was still in love. And so I decided to start over.
I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me.
The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.
During the next 5 years, I started a company named NeXT, another company named Pixar, and fell in love with an amazing woman who would become my wife.
Pixar went on to create the world’s first computer animated feature film, Toy Story, and is now the most successful animation studio in the world.
In a remarkable turn of events, Apple bought NeXT, I returned to Apple, and the technology we developed at NeXT is at the heart of Apple’s current renaissance. And Laurene and I have a wonderful family together
I’m pretty sure none of this would have happened if I hadn’t been fired from Apple. It was awful tasting medicine, but I guess the patient needed it.
Sometimes life is going to hit you in the head with a brick. Don’t lose faith. I’m convinced that the only thing that kept me going was that I loved what I did. You’ve got to find what you love. And that is as true for work as it is for your lovers.
Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. And don’t settle. As with all matters of the heart, you’ll know when you find it.
And, like any great relationship, it just gets better and better as the years roll on. So keep looking. Don’t settle.
Eventually, his vision became reality—the iPad and iPhone exist today because Jobs refused to wait for all the answers and he didn’t give up when “life hit him in the head with a few bricks along the way.”
In that same speech, Steve said: “You can’t connect the dots looking forward; you can only connect them looking backward.”
This is true for all of us. Waiting for clarity before taking action is a trap.
Fear of Failure & The Power of Asking for Help
My client also hesitated because he was afraid of putting himself out there and asking for help. Again, Steve Jobs set an example:
At age 12, he called Bill Hewlett (of Hewlett-Packard) and asked for spare parts to build a frequency counter—and got a summer job working a dream job!
Steve Job’s success came from his willingness to act and fail publicly.
One more quote from Steve Jobs: “Most people don’t get those experiences because they never ask. Most people never pick up the phone and call, most people never ask and that’s what separates, sometimes, the people who do things and the people that just dream about them. You’ve got to ACT! You’ve got to be WILING TO FAIL, To ‘crash and burn.’ If you’re afraid of failing, you won’t get very far.”
Key Takeaways from This Episode:
✔️ You don’t need to have it all figured out before you start.
✔️ Taking action creates clarity—waiting does not.
✔️ Failure is part of the process—it’s how you grow.
✔️ Asking for help isn’t weakness—it’s what successful people do.
What’s Your Next Step?
If you’ve been hesitating, waiting for the “right” moment, I challenge you to trust your vision and take the next step—without needing to see the whole path.
If you’re an entrepreneur, a leader, or someone who knows they’re meant for something bigger but find yourself stuck in hesitation, I’d love to help you get unstuck.
📩 Email me at cliff@cliffravenscraft.com and let’s talk.

Jan 31, 2025 • 30min
758 - Keeping Those Relationships Alive
In this episode, I'm sharing an insight from my recent "What Are You Creating?" podcast interview with Charlie Birney, founder of Podville, a successful podcast media production company.
This conversation with Charlie was inspired by my work with two coaching clients interested in starting podcast production businesses. When helping people in the early stages of a business dream, I introduce role modeling—finding successful people already doing what you want to do and studying them closely. By learning about their business models, marketing strategies, and offerings, you gain priceless insights and inspiration for your own path..
During our conversation, Charlie shared a compelling story about a former employee who asked how long he planed to stay in contact with those who had declined his company's services. Charlie's response was simple but profound: he never removes people from his Rolodex because he believes in nurturing relationships for the long term.
After listening to this episode, I encourage you to take a moment to reflect on your relationships. Think about those friends from school or past clients you've lost touch with over the years. Make a list of 10–15 names and reach out to 1–4 of them for a 30-minute catch-up call. Remember, the goal isn't to sell anything—it's simply to reconnect and keep those relationships alive.
Additionally, consider implementing a system, like a CRM or relationship manager, to help you stay on top of your connections and schedule regular follow-ups. Maintaining relationships should be a core part of your personal and professional success strategy.


