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From the Gridiron to the Battlefield: Life's Journey
MH-47 The roar of the crowd was a distant hum, a muffled echo against the sharp, searing pain in my side. I lay on the damp grass, the...
larrywpittman
Jul 7, 20254 min read


Beyond Tuition: A Blueprint for Financial Resilience
In the idyllic, tree-lined campus of Bushwood Academy, the rhythm of student life hummed a familiar tune. Class bells chimed, laughter...
larrywpittman
Jul 7, 20253 min read


Before First Light – Lessons from a Father
I was six the first time my father handed me a .22 rifle. It wasn’t some grand rite of passage. No ceremony. Just a foggy December...
larrywpittman
Jun 11, 20253 min read


The Rain Barrel
I remember riding in an old Ford pickup with my dad down a dirt road that carved through a field of knee-high ryegrass. It was one of...
larrywpittman
Jun 5, 20252 min read


Shadows in the Sand
Feeling a little nostalgic tonight thinking about my military experiences and want to share. I hope you enjoy, reflect and celebrate...
larrywpittman
Jun 1, 20252 min read
The Voices That Still Guide Me
Some voices never leave you. They echo in your head when you’re standing at a crossroads. They whisper in the quiet moments, show up in...
larrywpittman
May 27, 20252 min read


The Tapestry of Opportunity: A Financial Aid Story
In the heart of the old campus, nestled among the ancient oaks, lived a quiet, powerful force known simply as The Fund. The Fund wasn't a...
larrywpittman
May 16, 20252 min read


Where the Wild Teaches Quietly
There’s something sacred about early mornings in the backcountry—mist rising off a river, the steady hum of a Coleman stove, the soft...
larrywpittman
May 16, 20252 min read


“Finding Your Walden”
My Walden We all have moments where the noise of the world threatens to drown out our inner voice. The demands of work, family, and the...
larrywpittman
May 10, 20252 min read


The Balancing Act: Managing Operational Costs While Investing in Excellence
Being a CFO at an independent school isn't just about crunching numbers; it's a daily, weekly, and quarterly tightrope walk of balancing...
larrywpittman
Apr 28, 20251 min read


The Confluence
At first glance, Henry David Thoreau and Theodore Roosevelt seem like polar opposites. Thoreau, the introspective naturalist, seeking...
larrywpittman
Apr 27, 20252 min read
The Warrior Poet
GREY BULL In the space where shadows fall, Where echoes cry and lost ones call, Between the lines, unseen, unheard, We move with...
larrywpittman
Apr 21, 20251 min read


“The Bond Forged in Blisters and Storms”
Subtitle: Why Shared Adversity Builds Unbreakable Connection There’s a kind of friendship that’s forged only in discomfort—the kind that...
larrywpittman
Apr 21, 20252 min read
Charting the Course: The Importance of Long-Range Financial Planning
Operating an independent school without a multi-year financial forecast is akin to navigating without a map—a significant risk identified...
larrywpittman
Apr 20, 20252 min read


Beyond the Sticker Price: Deconstructing the Tuition Strategy
Setting tuition is one of the most critical strategic decisions for an independent school. It goes far beyond simply covering costs; the...
larrywpittman
Apr 19, 20251 min read


Celebrating a Life Well Lived: A Tribute to My Hero, My Dad
This past weekend, we gathered as family and friends to celebrate the life of an incredible man—our dad. The outpouring of love and...
larrywpittman
Apr 19, 20253 min read


Strategic Communication Themes for Independent School Leadership: An Analysis of Key Industry Topics
Introduction: Setting the Stage for Strategic Communication The independent school sector operates within a dynamic and complex...
larrywpittman
Apr 19, 20251 min read


Mentors on the Mountain
The Unexpected Guides Who Shape Our Path Not every mentor wears the title. Some just show up with a steady stride, a quiet word, or a...
larrywpittman
Apr 19, 20251 min read


The Compass of Authentic Friendship
Subtitle: Why True Friends Are Your North Star There’s something about a trailhead at sunrise that strips away pretense. No signal. No...
larrywpittman
Apr 19, 20251 min read


Lessons from the Boardrooms to the Backroads Subtitle: A Journey Through Mentorship, Friendship, and the Wild Places That Teach Us
Intro Post: “Why Both Worlds Matter” Subtitle: Finding Wisdom Where Strategy Meets Solitude I’ve spent years navigating boardrooms—making...
larrywpittman
Apr 19, 20251 min read
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