Overcoming the Illusion of Fear
Last week during the Skeen Stronghold, we explored the power of fierce conversations and how transformative they can be in our personal and professional lives. We discussed how these honest, courageous dialogues can…
Ideas for a more intentional life
InsightsThink deeply.
Live more fully.
A collection of perspectives on purpose, leadership, relationships, and the life you choose to create.
Explore Jack’s original writing and short films. Find a question worth sitting with, a familiar pattern seen differently, or a useful idea for what comes next.
Explore the archive ↓The archive
Follow your curiosity.
The Power of Fierce Conversations
In our everyday interactions, we often find ourselves communicating on a superficial level, often hiding our true feelings beneath a veneer of politeness and people-pleasing. We choose our words so carefully, hoping to…
Pushing the Boundaries of Your Comfort Zone: Achieving a Big Dream
Throughout our lives, we’ve all had dreams, both big and small. But some dreams are especially worthy of pursuit—those that transcend personal achievement and ambition. These are big dreams, ones that make a difference…
What gets you out of bed in the morning?
Each morning we wake up to a brand-new day, each of us with a special reason that gets us moving to start the day. And on a cold, rainy or snowy Monday morning, this often isn’t the easiest of things to do.
Outgrowing Your Shell: The Courage to Become a Bigger You
Imagine you’re a hermit crab, cozy and safe inside your shell. It’s your home, your protection against the harsh world outside. Life is good. But there comes a time when this shell just doesn’t fit anymore. It becomes…
Wear Your Life Scars With Honor
Throughout our lives, every action we take, big or small, is like a ripple. And these actions—whether intentional or accidental—contribute to the constantly shifting currents that shape our life journey.
The Power of “Being Seen” and Embracing Vulnerability
Today, distractions are endless, and our everyday connections can feel superficial. Collectively, there’s a societal preoccupation with “looking good,” especially through the idealized glamour of photo filters and…
Making Real Connections in a Self-Centered World
I have a new friend. He’s 84 years old. And the other day he invited me out to lunch.
Finding Your Path
In the frantic pace of everyday life, it’s often easy to lose sight of what truly matters. We find ourselves caught up in the external stuff; the expectations of others, societal norms, and the pursuit of success. But…
Feeding the Fire Within
Maybe it’s your home. Your retirement nest egg. Or a treasured keepsake. Of course, it’s different for everyone.
Rediscovering Your Inner Greatness
During a recent Skeen Stronghold call, we had an amazing group discussion that uncovered some profound insights about greatness, change, and embracing one’s unique life journey. Here’s a summary of the key takeaways…
The Power of Dreams: Igniting Your Path to Fulfillment
From our earliest memories, we’re captivated by the magic of dreams—the promise of a future filled with purpose, fulfillment and joy. Throughout our lives, dreams can stand as bright beacons, lighting our future path…
What is Your Happiness Strategy?
In our previous blog post, we explored the idea of happiness as a fundamental and universal goal that unites us all.
The Universal Truth of Happiness: A Journey Within
With the holiday season now upon us, I decided to start a blog series about the idea of happiness. I was inspired by a new book that I’m currently reading, “Build the Life You Want: The Art and Science of Getting…
The Art of Mind Management: Being Your Mind vs. Having a Mind
In the realm of leadership, executives and CEOs often find themselves immersed in the ceaseless ebb and flow of thoughts. The dynamic, day-to-day nature of decision-making, strategic planning, and management can create…
Another way into the conversation
Ideas become personal
Inside the Circle.
Hear Roadmap graduates talk with Jack about the questions, choices, and new perspectives that have shaped their lives.
Meet the guests ↗