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Introducing The Five Regrets to Avoid in Life, a compelling new podcast series from PathNorth, hosted by Jamie Haith and featuring candid conversations with PathNorth Founder and CEO, Doug Holladay....
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Introducing The Five Regrets to Avoid in Life, a compelling new podcast series from PathNorth, hosted by Jamie Haith and featuring candid conversations with PathNorth Founder and CEO, Doug Holladay. This five-episode season invites listeners into a reflective journey, exploring the pivotal regrets that often surface at life's end—and how to live intentionally to avoid them.
Doug Holladay, a former White House advisor, Goldman Sachs executive, Georgetown University professor, and author of Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life, brings decades of insight into what truly matters. His work with PathNorth—a community dedicated to helping leaders broaden their definition of success—centers on creating spaces for meaningful conversations about purpose, relationships, and legacy.
In this series, Doug and Jamie delve into five core regrets that many face later in life:
Tune in to The Five Regrets to Avoid in Life and embark on a transformative exploration of purpose, connection, and intentional living.
show less
Doug Holladay, a former White House advisor, Goldman Sachs executive, Georgetown University professor, and author of Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life, brings decades of insight into what truly matters. His work with PathNorth—a community dedicated to helping leaders broaden their definition of success—centers on creating spaces for meaningful conversations about purpose, relationships, and legacy.
In this series, Doug and Jamie delve into five core regrets that many face later in life:
- Failing to pursue one's true purpose
- Neglecting to nurture deep relationships
- Prioritizing success over significance
- Withholding forgiveness—from oneself and others
- Ignoring one's spiritual core
Tune in to The Five Regrets to Avoid in Life and embark on a transformative exploration of purpose, connection, and intentional living.
Episodes & Posts
Episodes
Posts
6 JUN 2025 · In this final episode of The Five Regrets to Avoid in Life, Doug Holladay and Jamie Haith take on one of the most difficult—and transformative—truths of the human experience: the cost of withholding forgiveness. Whether directed toward others or ourselves, the inability to forgive can quietly shape our relationships, decisions, and inner peace.
Doug shares how forgiveness is often misunderstood as forgetting or minimizing what happened. But true forgiveness, he explains, isn’t about erasing the past—it’s about choosing freedom over bitterness, and healing over self-protection. Drawing on stories from his own life and those of leaders he's walked alongside, Doug offers a path forward through the pain.
This episode is a profound reminder that forgiveness is not weakness—it’s strength. And choosing it just might release us from one of life’s deepest regrets.
30 MAY 2025 · In this episode of The Five Regrets to Avoid in Life, Doug Holladay and Jamie Haith delve into the quiet fear that keeps many of us stuck: the fear of change, of stepping into the unknown, and of losing the identity we've worked so hard to build. Doug shares powerful stories of leaders who, despite their success, hesitated to pivot—to leave, to begin again, or to grow in a new direction—because they feared what might be lost.
Together, they explore the internal tension between stability and transformation, and why clinging to comfort can become its own kind of trap. Doug offers a reframing: What if the greatest risks in life aren’t about failure, but about the risk of never becoming who you were meant to be?
This episode is an invitation to embrace evolution, welcome reinvention, and move toward change that may not always make sense on paper, but speaks deeply to the soul.
23 MAY 2025 · In this episode of The Five Regrets to Avoid in Life, Doug Holladay and Jamie Haith explore a regret that often surfaces too late: the cost of avoiding authentic connection. As Doug shares from his work with CEOs, diplomats, and entrepreneurs, a common theme emerges—many people struggle to let their guard down, even with those closest to them.
Together, they examine why we so often settle for surface-level relationships—out of fear, busyness, or the illusion of independence—and what’s lost when we do. Doug offers honest reflections and practical insights into the power of vulnerability, trust, and presence in cultivating deeper human connection.
This episode invites listeners to take inventory of their relationships and ask: Where am I hiding behind performance or perfection? And what could open up if I led with authenticity?
16 MAY 2025 · In this episode of The Five Regrets to Avoid in Life, Doug Holladay and host Jamie Haith take on one of the most pervasive traps in modern life: a narrow definition of success. Together, they unpack how chasing status, wealth, or achievement—while culturally celebrated—can leave us feeling empty or off-course.
Doug shares stories from decades of working with high-performing leaders who, despite their accomplishments, often feel a quiet sense of disillusionment. What happens when you reach the top of the ladder only to realize it was leaning against the wrong wall?
This episode challenges listeners to redefine success on their own terms—anchored in meaning, relationships, and personal values—rather than external benchmarks. With wisdom and humility, Doug offers a vision of success that is expansive, human, and deeply fulfilling.
9 MAY 2025 · In the opening episode of The Five Regrets to Avoid in Life, PathNorth Founder and CEO Doug Holladay sits down with host Jamie Haith to confront a fear many of us carry but rarely name: the fear of facing our own story. In this candid conversation, Doug shares how our unwillingness to examine the full arc of our life—our past wounds, unfinished chapters, and unspoken longings—can quietly shape the way we lead, love, and live.
Rooted in decades of experience working with leaders around the world, Doug offers a compassionate invitation to engage your story with honesty and curiosity. He and Jamie explore how embracing your full narrative—rather than hiding from it—can become the gateway to healing, deeper purpose, and meaningful connection.
This episode challenges listeners to pause, reflect, and consider: What parts of your story are you avoiding? And what might change if you faced them?
Introducing The Five Regrets to Avoid in Life, a compelling new podcast series from PathNorth, hosted by Jamie Haith and featuring candid conversations with PathNorth Founder and CEO, Doug Holladay....
show more
Introducing The Five Regrets to Avoid in Life, a compelling new podcast series from PathNorth, hosted by Jamie Haith and featuring candid conversations with PathNorth Founder and CEO, Doug Holladay. This five-episode season invites listeners into a reflective journey, exploring the pivotal regrets that often surface at life's end—and how to live intentionally to avoid them.
Doug Holladay, a former White House advisor, Goldman Sachs executive, Georgetown University professor, and author of Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life, brings decades of insight into what truly matters. His work with PathNorth—a community dedicated to helping leaders broaden their definition of success—centers on creating spaces for meaningful conversations about purpose, relationships, and legacy.
In this series, Doug and Jamie delve into five core regrets that many face later in life:
Tune in to The Five Regrets to Avoid in Life and embark on a transformative exploration of purpose, connection, and intentional living.
show less
Doug Holladay, a former White House advisor, Goldman Sachs executive, Georgetown University professor, and author of Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life, brings decades of insight into what truly matters. His work with PathNorth—a community dedicated to helping leaders broaden their definition of success—centers on creating spaces for meaningful conversations about purpose, relationships, and legacy.
In this series, Doug and Jamie delve into five core regrets that many face later in life:
- Failing to pursue one's true purpose
- Neglecting to nurture deep relationships
- Prioritizing success over significance
- Withholding forgiveness—from oneself and others
- Ignoring one's spiritual core
Tune in to The Five Regrets to Avoid in Life and embark on a transformative exploration of purpose, connection, and intentional living.
Information
| Author | PathNorth |
| Organization | PathNorth |
| Categories | Non-Profit |
| Website | - |
| skwiecien@pathnorth.com |
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