

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

Sep 2, 2025 • 1h 11min
791 - When the Noise Clears: Lessons from August’s Free The Dream Workshop
When I recorded Episode 787 back on August 11th, I was filled with anticipation. The Free The Dream Workshop was just around the corner, and I wanted to give you a sense of what was coming.
Now, just a few weeks later, the event has taken place… and it’s hard to put into words just how powerful it was. In this episode, I want to take you behind the scenes and share not only my reflections but also Stephanie’s insights and the real, unfiltered experiences of the people who were in the room.
Here’s what you’ll hear in this episode:
The Power of Clearing the Noise
You’ll hear why getting out of your normal environment, even for two days, can shake up the patterns that keep you stuck and open the door to new possibilities.
Customized Breakthroughs, Not Cookie-Cutter Content
Rather than following a strict agenda, we began by asking each attendee:
“If you could walk away with one miraculous change this weekend, what would it be?”
What happened next was nothing short of transformational. We watched each person’s intentions get met, and in some cases, completely surpassed, over the two days.
Scott Blair’s Testimony
Scott shared that within just a few hours, he experienced a breakthrough so profound he would have felt his entire investment was worth it even if the workshop had ended right then and there. And yet, the breakthroughs kept coming.
Stephanie’s Reflections
You’ll hear Stephanie talk about the moments that stood out most to her, the conversations over lunch and dinner, and even the hilarious moments with the whiteboard drawings that made perfect sense to those in the room… and absolutely none to anyone else.
What We’re Changing Moving Forward
This workshop confirmed several things for us:
Future sessions will be capped at 10 participants to keep the experience intimate.
Meals will continue to be included when group size allows, because the conversations over food were as transformative as the sessions themselves.
The “state your miracle” opening exercise is here to stay. It set the tone for everything that followed.
Why This Work Matters
At its core, Free The Dream isn’t just about goals or business or mindset. It’s about remembering the part of you that’s still waiting to be lived… and giving it space to breathe again.
My hope is that this episode stirs something in you. Maybe it’s clarity. Maybe it’s courage. Maybe it’s the reminder that your dream isn’t dead. It’s simply waiting for you to make space for it.
The next Free The Dream Workshop is already on the calendar. Maybe this is your time.
Register today at FreeTheDreamWorkshop.com

Aug 26, 2025 • 39min
790 - Trusting the Journey in the Midst of Life’s Greatest Trials
I want to share two stories with you today. One from my mentor, Dan Miller, and one from my friend Freya Casey.
Both have confirmed the way I see life, faith, and even death itself.
Dan was told in December of 2023 that he had advanced pancreatic cancer. No treatment. No cure. Six months to live at most.
His very first words to me after receiving that diagnosis?
“So I have this gift…”
He wrote about the conversations he was having with his wife Joanne, their kids, and grandkids. About celebrating now rather than later. About reflecting on legacy, gratitude, and even anticipating “an incredible spiritual transformation” with excitement.
He wasn’t bitter. He wasn’t fearful. He wasn’t even anxious.
He was fully alive.
That message, and the peace behind it, lined up with what I already knew to be true at a deeper level… that real faith isn’t proven by what we say we believe, but by the peace and presence we carry when life gives us every reason to fall apart.
For much of my life, I met many people, and at times, I was one of them, who claimed faith in God yet carried fear, anxiety, and worry about the smallest things. But by the time I received Dan’s text, that was no longer my reality.
Dan embodied what I’ve come to know as true. He had encountered something far deeper than doctrine or dogma. He knew what it meant to live in alignment with love itself, to experience the presence of God as a living reality rather than a religious concept.
And then there’s Freya.
Freya has been a client and friend for over a decade. She’s a single mother of three, pregnant with her fourth, a business owner, a creator and recently diagnosed with advanced stomach cancer while pregnant.
Yet when she reached out to me, she wasn’t falling apart.
She was calm. Peaceful. Clear.
Not because she knew the outcome.
But because she wasn’t resisting reality.
She was fully present, creating her reality moment by moment, choosing to trust rather than fear, to open rather than control, to soften rather than fight.
Freya and I have been having many private conversations over the past few months about what she’s been walking through. One day, she decided to join me on one of my open live streams.
She felt her story might encourage someone else who needed to hear it. What unfolded became yet another living example of what it looks like to trust the journey in the midst of life’s greatest trials.
If you want to hear her story in her own voice, and feel the peace that carries through every word, listen to this episode.
My hope is that what you hear will do more than inspire you.
I hope it awakens something within you. A quiet knowing that peace really is possible, even in the middle of life’s greatest storms.
With gratitude,
Cliff
An Invitation: If what you hear in this episode resonates with you and you’d like to go deeper, I want to personally invite you to join us at the Free The Dream Workshop. This two-day experience is designed to help you clear the noise, uncover what’s next, and remember the part of you that’s still waiting to be lived.
The next session is happening August 29–30, right here in my hometown, and for this limited time, it’s a pay-what-you-want event. That means you can even attend for free if that’s what works for you right now. (Note: The next session will be hosted in October 2025. Dates have now been confirmed!!!! The dates are Friday and Saturday, October 17th and 18th)
You can learn more and reserve your spot at FreeTheDreamWorkshop.com

Aug 22, 2025 • 1h 2min
789 - The Truth Behind Stress And Fear
When Jordan showed up for my How May I Serve You? livestream, he came with a familiar question:
"Cliff, you’ve been through big events and big stress. What have you learned about managing it?"
He wasn’t asking about marketing, business models, or strategy. He was looking for relief from the kind of stress that nearly wrecked him two years ago when the weight of his first live event landed him in the hospital.
And as we started talking, I realized something powerful:
Jordan didn’t need a few tips on “stress management.” He was longing for something deeper, a way to live without the constant undercurrent of fear and pressure.
So instead of giving him a list of strategies, I asked:
“What if the goal wasn’t to manage stress… but to eliminate it altogether?”
That one question changed everything.
Meeting Him Where He Was
Now, here’s what made this conversation unique:
Jordan comes from a faith background shaped by Christianity.
Jordan shared that prayer, Scripture reading, and faith in Christ bring him real peace, but it rarely lasted through the rest of his workday.
I invited him, from within his own framework of faith, to carry that same experience of peace into every part of his day, not just the quiet moments of prayer and meditation.
I shared how I’ve learned to live from a place of peace so steady that stress no longer drives my life.
We talked about what it means to actually trust rather than control, to be present rather than endlessly managing outcomes.
And I could feel the shift happening in real time.
The Turning Points
Here are just a few moments that landed powerfully for Jordan and that will likely land for you too:
From “manage” to “eliminate”: Jordan came in seeking tips on managing stress. I asked him, "What if the goal wasn't to manage stress, but to eliminate it entirely?" That single question transformed his perspective, shifting him from seeing stress-free living as a 50/50 possibility to a 7 out of 10 on his belief scale. By the end of our conversation, he was fully convinced it was possible.
Peace that doesn’t last: He admitted that prayer, Scripture, and meditation bring him real peace, but as soon as the workday starts, the peace fades. That gap between the quiet moments and the rest of life became a key focus.
A faith-based model for peace: I reminded him of Jesus’ words about being anxious for nothing and the invitation to “take my yoke upon you.” He realized he had already been trying to apply this and said it helped, yet about 30% of the stress was still there.
Naming the real source: When we dug deeper, Jordan saw that 90% of his stress wasn’t uncertainty about the event itself, it was self-doubt. The event would likely be fine. It was his inner critic running the show.
Generating his own practices: As we talked, Jordan began suggesting his own solutions: setting reminders, scheduling check-ins, being more intentional with how he carries peace into his day.
Bringing Presence into the workday: I pointed out how he feels God’s presence in the morning but then tackles the workday alone. He laughed and admitted that’s exactly what happens. and began to imagine what it would look like to stay connected throughout the day.
Releasing rumination and perfectionism: We reframed mistakes as simple notes for next time rather than problems to obsess over now. He saw clearly that stressing about them wouldn’t change this event’s outcome.
People-pleasing comes into view: Jordan realized a huge part of his stress came from trying to prevent negative comments and manage how others see him, something he ultimately has zero control over.
The “desire” pivot: When I asked if he truly desired a stress-free life, he paused. Part of him wondered if he’d grown comfortable with chaos. That question unlocked a deeper layer of self-awareness.
Ending with possibility: By the end, Jordan said he fully believed a stress-free life was possible and he was willing to explore what it would take to live that way.
Why This Conversation Matters
For the past five and a half years, I’ve had soul-level conversations like this behind closed doors with one-on-one clients.
But when I started these How May I Serve You? livestreams, I hoped that someday, one of them might open into the same depth, so the world could see the kind of transformation that unfolds when we move beyond strategies and into the heart of what’s really going on.
This conversation with Jordan became that moment.

Aug 14, 2025 • 54min
788 - How to Reach the People You're Meant to Serve
In this episode, I had the privilege of speaking with David, a naturopathic doctor with a thriving local practice and a powerful desire to serve people on a much larger scale.
He came to our conversation with a question that so many purpose-driven creators wrestle with:
“How do I reach the people I’m meant to serve… especially when I doubt whether I’m charismatic or creative enough to stand out?”
What followed was a deeply generative exploration. I invited David to step into a future where his vision was already fulfilled, where he was leading transformational group coaching programs, impacting thousands through his content, and receiving glowing testimonials from clients who had completely changed their lives.
Together, we reverse-engineered that dream, uncovering the practical, soulful, and surprisingly simple path that could take him there.
In this conversation, we explore:
What makes someone resonant vs. merely visible
Why charisma is optional, but courage is essential
The freedom that comes when your message becomes more important than your ego
My own messy beginnings in podcasting (complete with one-star reviews)
The power of starting with what you have—even if it’s just 13 subscribers
How to make peace with “bad content” on the road to transformation
Why the people who need your message aren’t looking for polish—they’re looking for truth
If you’ve been waiting for permission to speak, to create, to be seen…
Let this be the moment you stop waiting.
You already have everything you need to begin.
Ready for your own breakthrough?
Join me for a future “How May I Serve You?” live session at https://www.cliffravenscraft.com/join
You bring the question. I’ll hold the space.
Free The Dream Workshop
If this episode resonates with you, I’d love for you to join me at the next Free The Dream Workshop. It’s a two-day experience designed to clear the noise, uncover what’s next, and remember the part of you that’s still waiting to be lived. Learn more and register at FreeTheDreamWorkshop.com.

Aug 11, 2025 • 1h 7min
787 - Free The Dream Workshop Explained: Stories, Insights, and How to Know If It’s Right for You
What we envision as “bigger” often turns out to be less effective than the intimate alternative. Sometimes, a smaller gathering proves more beneficial for everyone involved.
In this episode, I share the story of the original Free The Dream message and how it has evolved over time. You’ll hear why we shifted our vision from hosting annual conferences with hundreds or thousands of attendees to creating more frequent workshops with much smaller groups.
I also explain why I’ve stopped measuring the value of an event by how many seats are filled and why the deepest breakthroughs often happen when the room is small enough for everyone to be fully seen and heard.
In this episode, you’ll discover answers to the following questions:
What is the Free The Dream Workshop?
Who is it for?
What benefit would you get from attending?
What content is covered in the sessions?
Should you attend a Free The Dream Workshop?
The second half of this episode features an audio segment from three attendees of the first-ever Free The Dream Workshop. You'll hear their powerful stories of transformation: how they walked in with uncertainty or limitation and left with newfound courage, peace, and a fresh vision for their personal lives and businesses.
Register For Free The Dream Workshop
If this episode resonates with you, whether it's igniting a desire for clarity, suggesting a new direction, or simply creating space for self-reflection, I invite you to join us for the next Free The Dream Workshop on Friday and Saturday, August 29th and 30th, 2025.
This is a two-day experience designed to clear the noise, uncover what’s next, and help you remember the part of you that’s still waiting to be lived.
Whether you come with a clear goal or just a sense that something needs to change, you’ll leave with fresh insight, practical tools, and the courage to take your next step.
You can learn more and secure your spot at FreeTheDreamWorkshop.com.

Aug 1, 2025 • 40min
782 - Not Sunshine and Rainbows: The Truth Behind Dream Jobs
In this deeply personal episode of The Cliff Ravenscraft Show, I reconnect with longtime listener and creative soul Boone Langston, whose journey from uncertainty to alignment took him all the way to Denmark—where he now designs official LEGO sets.
What begins as a moment of appreciation quickly unfolds into a rich, multi-layered conversation about purpose, provision, creative calling, and the nonlinear path that leads us home.
Boone vulnerably shares the ups and downs of his journey: the years of not knowing, the pressure of finding “the thing,” the courage to pivot, and even a moment when he and his wife nearly lost their home. You’ll hear how saying yes to resonance—whether through LEGO, video, or teaching—eventually led to a wild ride of opportunities, including a spot on LEGO Masters and a full-circle moment working with the LEGO Group itself.
We explore:
The difference between faith and knowing
What it means to live in alignment with your values
Why the path often requires letting go of old success stories
How love, family, and creativity can guide your decisions more than certainty ever could
This is more than a conversation about career. It’s a conversation about remembering who you are and choosing to take that next step, even when you can’t see the whole map.
At the end, I share more about the upcoming Free The Dream Workshop happening August 29–30, a two-day experience to clear the noise, uncover what’s next, and remember the part of you that’s still waiting to be lived. Reserve Your Seat Today at FreeTheDreamWorkshop.com

Jul 29, 2025 • 33min
779 - Am I Self-Employed or a Business Owner? Releasing the False Dichotomy
In this episode, I reconnect with my longtime friend Colin Yearwood for a deep, soul-level conversation about identity, control, and redefining success.
Colin vulnerably shares the tension he’s been holding around the question, “Am I a business owner or just self-employed?” After nearly a decade of serving powerfully inside other people’s coaching programs, he finds himself wrestling with whether he’s built what he once dreamed of—or something even better.
Together, we unpack the illusion of control, the inherited beliefs we carry from entrepreneurial culture, and the freedom that comes from choosing fulfillment over formulas. I share some of my own journey of walking away from scalable income streams, and we explore the truth that alignment, not outside approval, is the highest form of success.
If you’ve ever wondered whether your business “counts” because it doesn’t match someone else’s blueprint, this conversation is for you. There is deep peace waiting on the other side of self-acceptance.
At the end, I share more about the upcoming Free The Dream Workshop happening August 29–30, a two-day experience to clear the noise, uncover what’s next, and remember the part of you that’s still waiting to be lived. Reserve Your Seat Today at FreeTheDreamWorkshop.com

Jul 23, 2025 • 1h 13min
778 - Loving What Is: Releasing the Belief That You Should Be Further Along
In this deeply reflective conversation, Michael Jones joins me for a powerful exploration of risk, money, drive, and perception. It began as a question about entrepreneurial risk tolerance, but quickly evolved into something much more profound.
We explored the illusion of certainty, the myth of control, and how even the belief “I should have more money” can quietly sabotage focus, creativity, and peace. I guided Michael through Byron Katie’s framework called The Work, using his relationship with money as a powerful real-time example. What emerged was a radical reframing: the realization that we always have exactly the amount we should have, because it is what is.
We unpacked how clinging to expectations about income, progress, or the “right” business strategy can trap us in stress loops, leading to action that’s busy but unfocused. And we talked about how true sustainability and impact come not from reacting to fear or lack, but from moving with clarity and internal alignment.
This episode is for anyone who has ever second-guessed themselves, clung to a thought that brought suffering, or wondered whether they were “falling behind.” If you've wrestled with the illusion that there’s only one “right” path, or that your current state isn’t good enough, this is your reminder to love what is… and create from there.

11 snips
Jul 19, 2025 • 1h 3min
774 - Real Business Growth, One Conversation at a Time
In this discussion, Lauren Kretzmer, a licensed therapist transitioning to coaching, shares her journey of integrating EMDR and hypnosis into her work. She explores authentic ways to connect with clients, emphasizing that personal conversations can lead to business growth. The conversation highlights the power of podcasting as a medium for sharing one's message and overcoming fears of imperfection. Listeners will find practical tips on launching a podcast quickly, focusing on genuine communication over technical finesse to foster meaningful connections.

Jul 17, 2025 • 43min
773 - You're Never Stuck: How to Evaluate, Realign, and Begin Again
In this episode, I had the joy of connecting with Josh, a long-time listener who first discovered my work at the age of 15. Now 24, he's running his own business, working for a startup, and navigating what it means to live with purpose and alignment.
Josh came into the live stream with a deep and powerful question: How do I stay focused on long-term goals without getting stuck in the wrong short-term commitments? His honesty sparked a rich conversation about clarity, discernment, and the rhythm of fresh starts.
Together, we explored how “being stuck” is often the result of asking ourselves the wrong questions. Questions rooted in guilt, fear, or the illusion that there’s only one right path. I offered a framework that invites continual reflection and conscious recommitment. Whether once a year, once a month, or every single day, we always have the freedom to pause, evaluate, and begin again.
This conversation reminded me just how powerful a clear vision can be, not as a rigid plan, but as a North Star we realign with through every season, project, and decision. Josh’s story is a beautiful example of growth, faith, and intentional living.
If you’ve ever questioned whether your current commitments are still aligned with your values, or wondered how to avoid feeling “stuck,” I believe this episode will offer something valuable for your journey.


