What are you putting off because it feels too uncomfortable, uncertain, or far away?

We often tell ourselves we are waiting for the right time, a clearer plan, or enough courage to finally begin. But sometimes the familiar weight of avoidance simply feels safer than taking a step into the unknown.

In this episode of Permission Slip-Ups, Kate and David talk with entrepreneur and serial founder Jermaine Ee about intentional living, meaningful work, and what happens when we stop delaying the conversations and experiences that matter most.

Jermaine shares how his understanding of success and legacy has changed over time. In his twenties, he wanted to be admired for what he built. Today, after years of introspection and the unexpected loss of his mother, his definition of a meaningful life has become much simpler: he wants the people he loves to remember that when he was with them, he was fully present.

He also shares the moving story of taking his mother to Salzburg to experience the world of The Sound of Music—a dream she had never considered possible. Neither of them knew it would become her final trip.

Together, they explore:

• Why avoidance is often an understandable response to uncertainty, not a character flaw
• How emotionally uncomfortable or abstract decisions keep us stuck
• Why we wait for permission, courage, or the "right time"
• What our calendars and spending habits reveal about what energizes us
• How meaningful work connects purpose with what genuinely matters to us
• Why the first step does not need to solve everything—it only needs to begin
• How presence, relationships, and impact can become a more meaningful definition of legacy

This is a conversation about personal growth, purpose, loss, authenticity, and the courage to stop waiting for life to become urgent.

What is one meaningful thing you keep telling yourself you will do someday?

Contact us:

Jermaine Ee

Kate Turner

David Cooke

Who are you when the role that helped define you no longer fits?

For years, Oscar Chacon's identity was shaped by structure, service, teamwork, and the uniform he wore as an officer in the United States Air Force and Space Force. But when he transitioned into civilian life, he found himself confronting a much more personal question:

Who am I beneath the role?

In this episode of Permission Slip-Ups, Oscar joins Kate and David for an honest conversation about identity, masculinity, leadership, vulnerability, and the uncertainty that often accompanies major life transitions.

Together, they explore:

• Why our careers, responsibilities, and accomplishments can quietly become our identity
• What happens when the "why" that once guided us begins to change
• Why so many men feel pressure to become the lone wolf and figure everything out alone
• How vulnerability creates trust, connection, and more authentic leadership
• What it means to become whole rather than perform an image of perfection
• How community, curiosity, and personal agency can help us move through uncertainty
• Why fear asks, "What if?" while faith responds, "Even if"

Oscar reminds us that we do not need to have a grand philosophical answer for where our lives are going. Sometimes the next honest answer is enough:

"I just want to wake up happier."

This conversation is for anyone moving through change, questioning who they have become, or searching for a life that feels more authentic, meaningful, and aligned.

Does your calendar reflect what matters most to you—or the person you believe you are supposed to be?

When life gets busy, most of us assume we need to manage our time better. We rearrange our schedules, squeeze more into the day, and promise ourselves that we will make time for what matters when things finally slow down.

But what if the real problem isn't time?

In this episode of Permission Slip-Ups, Kate and David explore what our priorities reveal about our identity, values, capacity, and the expectations we carry.

Sometimes the roles we have worked so hard to fulfill—the responsible parent, successful professional, reliable friend, committed partner, or person who always says yes—quietly begin determining how we spend our lives.

Together, they discuss:

• Why we may not have a priority problem, but an identity problem
• How busy seasons can reveal what truly matters
• Why the structure that once served us may no longer fit who we are today
• How obligation and guilt keep us committed to things we no longer want
• A practical three-question framework for evaluating new commitments
• Why being at your best is not about performance—it is about how aligned and whole you feel
• How clarity can give us permission to pause, trust ourselves, and say no

If you have built a successful life but feel pulled in too many directions, this conversation offers an opportunity to slow things down, reconnect with what matters, and create more room for a life that feels authentic, meaningful, and aligned.

What might change if you stopped asking, "How do I fit everything in?" and started asking, "What actually deserves my best?"