For Educators

My first private‑school position was as assistant business manager, lacrosse coach, and dorm head at Groton School. At the time, there were no “Chief Financial Officer” titles, only the noble, all‑encompassing title of Business Manager. Chuck Everet, Groton’s recently retired Business Manager, returned for a brief visit during my early years. Groton’s 403(b) plan then offered only two choices: CREF’s flagship stock fund or TIAA’s guaranteed annuity.

A colleague once told me a story about his great-grandfather. He called it The Day My Great-Grandfather Fell. It goes like this.
When my grandfather was 9 years old, his father, my great grandfather, climbed onto the roof to make repairs. He couldn’t afford to hire a professional. He fell. He died.
He left behind my great grandmother, my grandfather, seven other children, and a lifetime of “what ifs.”

For 35 years, I had the privilege of coaching lacrosse after work. From wide-eyed 2nd graders to driven high-school athletes. That meant early mornings, late evenings, and plenty of days when I’d finish coaching a high-school practice...

Like many of the families they serve, private school educators naturally connect their money with their values. They understand that a deeply felt sense of purpose is essential not only for their work... 

Talking openly about money between spouses, between generations, and across branches of a family is one of the most powerful ways to clarify your values and ensure your legacy reflects what matters most...

Many of us first learned about saving from our parents: open a bank account, set money aside, and someday you can buy that toy you really want...

Independent school boards and senior administrators are always looking for effective ways to reward and retain top leadership

Many independent schools have expanded their senior administrator benefit packages to include a non-governmental 457(b) plan

For many Gen X and Gen Y educators, the mantra early in your career was simple: defer taxes now, pay them later. Roth options may not have been available or as widely used when you started...

Why You Still Need a Financial Plan—Even If You’re Investing Solo

Developing Your Legacy of Values

Let’s be honest—living in school housing has its perks. But while the convenience is real, it’s easy to overlook the long-term financial tradeoffs—especially when it comes to homeownership and building equity.

Many educators hesitate to discuss or disclose personal wealth, fearing it might set them apart from colleagues. The reality is that private school educators who are beneficiaries of generational wealth often grapple with how to extend...

For over two decades, I have helped Heads and administrators prepare for life after school with financial confidence. This article outlines what I believe every school leader and teacher should know about a slower, staged retirement...

For over two decades, I have helped Heads and Administrators prepare for life after school with financial confidence. This is a more in-depth article that dives deeper into what I believe every school leader should know about savings...