And Why a Financial Planner Can Help Evan An Educator
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.
Chuck had spent 22 years in Groton’s business office, watching markets rise and fall. With the calm confidence of someone who had seen it all. He offered a simple piece of wisdom: “If you can go to sleep from your 20s to your early 60s and ignore the market and everything else going on in the world, just put all of your retirement savings in stocks and you’ll be fine.”
Chuck was a Jack Bogle believer before Jack was a household name. But following that philosophy is incredibly difficult because humans are imperfect when it comes to money.
Our Brains Weren’t Built for Modern Finance
As educators in the room know, the human brain is not wired to make smart financial decisions. It was built for survival, not long‑term planning. Our primal wiring pushes us toward instant gratification, emotional reactions, and social behaviors that once kept us alive, but today this wiring often works against our financial wellbeing.
All of our devices seem to get constant software updates. Yet our brains have not meaningfully changed in tens of thousands of years. We still carry the instincts of our tribal ancestors. In prehistoric times, you couldn’t save buffalo meat for later. The tribe had to consume it before it spoiled. Refusing to share meant banishment, and banishment meant death. That instinct to consume quickly, share broadly, and live in the moment still echoes in our modern financial behavior.
Layer onto that our personal and family histories, beliefs, and experiences around money and you get a deeply individualized financial psychology. This psychology shapes how each of us thinks, feels, and acts with money, often in ways that contradict what we know we should do.
“Telling Isn’t Teaching” And Advice Alone Isn’t Enough
Educators know the old adage: telling isn’t teaching. Students for the most part learn through experience, engagement, and guidance, not through a teacher reciting facts.
The same is true in financial planning.
Our simply telling our clients to “buy low and sell high,” “save more than you spend,” or “avoid debt” does not create meaningful change. The internet is full of simplistic advice (think robo advisors and now Claude), yet millions of people still struggle with saving, investing, and long‑term planning. Why? Because financial behavior for the most part is driven by psychology, not information.
You know better. But you can’t always do better.
Common Examples of Human Money Imperfection
· Overspending and under saving
· Buying into markets when prices are high and selling when they’re low
· Chasing “get rich quick” opportunities
· Lack of diversification
· Saying you want one thing but acting differently
· Money‑related trust issues with advisors, spouses, or family
· Blowing a bonus, inheritance, or windfall
· Avoiding estate planning
· Giving away money out of guilt
· Supporting adult children at your own financial expense
· Difficulty saying “no” to financial requests
· Chronic money conflict within relationships
· Hiding or lying about financial actions
· Anxiety around spending even when you can afford it
· Sacrificing health or relationships in pursuit of “more”
· Avoiding money issues altogether
· Lack of motivation or direction in career or financial life
These are not failures. They are human.
The Value of a Financial Planner
Given all these imperfections, a good financial planner does far more than provide technical knowledge. A skilled planner must understand your personal, family, and cultural background, and how these shape your financial decisions. They must also understand their own worldview and biases so they can recognize your biases without imposing theirs. Think of the great sports coach who didn’t just tell you where to stand on the field or how to stroke the ball, but explained it in a way that finally clicked. That’s the kind of guidance a thoughtful financial planner provides: insight delivered in a way that resonates, empowers, and helps you act with clarity.
A financial planner and investment advisor’s technical knowledge alone is not enough. Compassion, curiosity, and the right tools to guide, coach, and support meaningful change are essential.
A skilled financial planner and advisor helps you overcome your mental obstacles, align your behavior with your goals, and make decisions that support long‑term wellbeing, not just short‑term emotion.
Our Approach at Clear Skies Planning & Wealth
At Clear Skies Planning & Wealth, our mission is to bring relevant research, thoughtful guidance, and genuine compassion to every client relationship.
To do this well, we must see your worldview through your lens, not ours. After all, who are we to tell you how to spend your money?
Our role is to help you feel, think, and behave in a financially healthy and responsible way, grounded in your values, your experiences, and your goals. If we are going to be truly client‑centered, the work must be about you.
Clear Skies Planning & Wealth is honored to champion the financial wellbeing of independent school educators and our wider community of clients.
David Brown was the Chief Financial Officer/Business Administrator at Blanchard Memorial School, Groton School, Alexander Dawson School, Rippowam Cisqua School, and Portsmouth Abbey & School over a 23-year school career. During that time, he advised and/or helped heads and administrators assemble and negotiate benefit packages that would ensure a comfortable life through “end of plan”. For over 10-years Dave has helped his clients effectively plan, save, and invest to and spend appropriately through retirement.
For personalized financial planning and/or investment guidance, contact Clear Skies Planning & Wealth Strategies at www.clearskieswealthplanning.com or directly at 720-833-8611.
Clear Skies Planning & Wealth Strategies, Inc provides advisory services through XY Investment Solutions, LLC, an SEC registered investment advisor. All views included in this communication are subject to change. Please contact Clear Skies Planning & Wealth Strategies to receive a copy of our Form ADV and other disclosure information.
