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Boardrooms


The Siren Call of the Digital Deep
The air in the Ironwood School IT room was thick with the scent of ozone and stale coffee. It was 2:00 AM. A single bead of sweat traced...
larrywpittman
Oct 2, 20253 min read


The Gift of Failure
No one likes to fail. It stings, it bruises the ego, and it makes you question whether you’re on the right path at all. But over time,...
larrywpittman
Sep 29, 20252 min read


The Road Less Traveled: Choosing Your Own Path
Most people prefer the well-worn trail. It feels safer, predictable, and lined with markers of what others call “success.” But I’ve...
larrywpittman
Sep 22, 20252 min read


Strength with a Softer Edge
Servant leadership taught me to put others first. Compassion taught me how to see them. In both the Army and civilian life, you quickly...
larrywpittman
Sep 15, 20252 min read


Leading from the Front, Standing in the Back
Integrity builds trust. Servant leadership honors it. In the Army, leadership wasn’t just about rank on your chest — it was about how you...
larrywpittman
Sep 7, 20252 min read


The Quiet Professional
Humility taught me to look for lessons in the people around me. Gratitude taught me to never forget where those lessons came from. In the...
larrywpittman
Aug 18, 20252 min read


The Lesson I Didn’t See Coming
I was 19, fresh out of a small Florida town and into the Army, carrying the mindset that if I showed up ready to give my best every day,...
larrywpittman
Aug 11, 20252 min read


The Trail Doesn’t End Here
Some friendships and mentors walk with us for only part of the trail. Then, somewhere along the way, they step off, and we’re left to...
larrywpittman
Aug 4, 20251 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


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


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


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
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


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


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


Navigating the Indy School Industry and Outdoor Leadership Insights
When it comes to navigating the independent school industry and leading outdoor adventures, there is a wealth of knowledge to be gained....
larrywpittman
Apr 15, 20252 min read
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