Boogie Down to Andover

Breaking Barriers and Rewriting Your Life's Impossible Story

When life forces you to rebuild after 40, it's easy to believe the odds are stacked against you. Society tells us that starting over at this age is nearly impossible—that we've missed our window of opportunity. But what if the greatest comeback stories begin precisely when expectations are lowest?

Rise Above The Rim

The most powerful position to rise from is when everyone expects you to fall. That's not a disadvantage—it's your greatest opportunity for transformation.

- Steve Berlack

Growing up in the South Bronx to a working-class family wasn't the typical background for a student at Phillips Academy, Andover—America's top-ranked prep school at the time. My mother worked as a keypunch operator at an electronics company while raising me alone after my father was killed in action in Vietnam when I was just seven months old. My grandparents—a retired seamstress and a former private detective who served in World War II—provided additional support until I was five.

By all statistical measures and societal expectations, attending such a prestigious institution wasn't supposed to be part of my story. Yet not only did I attend Phillips Academy, but I graduated with honors—defying every expectation placed upon me.

This journey taught me something profound that applies directly to where you might find yourself now: when you're rebuilding your life after divorce, your greatest power often comes from the very place others expect you to fail.

The Parallel Journey: Elite Education and Post-Divorce Rebuilding

The transition from the South Bronx to Phillips Academy mirrors the journey many divorced men over 40 face. Both involve:

  1. Entering unfamiliar territory with different rules and expectations

  2. Facing internal and external doubts about your ability to succeed

  3. Leaving behind familiar support systems while building new ones

  4. Developing resilience through daily challenges to your confidence

  5. Redefining your identity in an environment that didn't expect your success

Research by psychologist Martin Seligman demonstrates that resilience isn't an innate trait, but rather a skill developed through overcoming adversity. In his studies on learned optimism, Seligman found that individuals who face significant challenges often develop stronger coping mechanisms than those who face fewer obstacles.

When I first arrived at Phillips Academy, the culture shock was immense. The language, expectations, and unwritten social codes felt like entering a foreign country. Many of my classmates came from generations of wealth and privilege—their families had buildings named after them on campus.

Similarly, navigating post-divorce life can feel like you've been dropped into a world with unfamiliar rules. Dating apps? Co-parenting schedules? Rebuilding finances? It's all new territory.

The Power of Being Underestimated

What I discovered at Phillips Academy—and what you might be discovering now—is that being underestimated carries unexpected advantages. When expectations are low, every achievement becomes meaningful. Every small win builds momentum.

A 2018 study from Northwestern University found that individuals who face significant adversity often develop what researchers call "psychological capital"—a combination of hope, efficacy, resilience, and optimism that serves them well in future challenges.

At Phillips, I didn't have the option of family connections or generational wealth to fall back on. My only path forward was through discipline, determination, and developing new skills. This mirrors your journey now—the old systems and support structures from your married life are gone, forcing you to develop new strengths.

Your Power Moves

  • Embrace the Outsider Advantage (Self-Awareness): Identify one area where being "new" to something gives you a fresh perspective others might lack. Journal about how this perspective could become your strength.

  • Create Your Own Measuring Stick (Mindset Shift): Define success on your own terms instead of comparing yourself to others or your pre-divorce life. Set three goals that matter specifically to YOU.

  • Find Your Bridge Relationships (Leveraging Connections): Identify and cultivate relationships with people who understand both your past and the future you're building—they'll become invaluable navigators.

  • Develop Deliberate Resilience (Trust): When facing challenges, ask yourself: "What skills am I developing through this difficulty that will serve me later?" This transforms setbacks into investments.

  • Document Your Victories (Organization): Keep a weekly record of moments when you succeeded despite doubts—either your own or others'. Review this log whenever your confidence wavers.

The Identity Transformation

The most profound change I experienced at Phillips Academy wasn't academic—it was a fundamental shift in how I viewed myself and my possibilities. Before attending, my identity was largely shaped by my neighborhood and family circumstances. After graduating, I carried a new sense of what was possible.

This identity transformation is precisely what you're navigating now. Divorce changes how you see yourself—sometimes painfully so. But within this challenge lies an opportunity to craft an identity that more authentically reflects who you truly are and what you value.

Sociologist Anthony Giddens describes this as "reflexive identity"—the process through which we actively construct our sense of self through our experiences. Your divorce, like my educational journey, isn't just something that happened to you—it's becoming part of a larger narrative you're actively shaping.

Conclusion: Writing Your Unexpected Chapter

My journey from the South Bronx to Phillips Academy wasn't supposed to happen. Your journey from divorce to a thriving next chapter might seem equally improbable right now.

But the most powerful stories are precisely those that defy expectations. Your current circumstances don't dictate your future any more than my childhood circumstances determined mine. The gap between where you are and where you're headed isn't an obstacle—it's the very space in which your greatest growth will occur.

Your next chapter isn't about returning to who you were before divorce. It's about becoming someone you never imagined possible—someone whose resilience, self-knowledge, and hard-won wisdom create a life more authentic and fulfilling than the one you left behind.