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 and how this might work from both a financial and emotional perspective.
Are You a Head / Senior Administrator or Teacher Facing Burnout?
What’s Next?
Burnout is creeping in. You’re older and wiser but exhausted and contemplating a shift—perhaps working fewer hours, slowing down, or even returning to the classroom. Maybe mentoring a head while stepping away from leadership responsibilities appeals to you. But can you do this both from an emotional and financial perspective? From a financial perspective, most likely, yes! But understanding how to transition effectively is key.
Your Journey So Far
You climbed the educational ladder, starting as an intern, then a teacher, teaching multiple classes while juggling extracurricular responsibilities. You earned an advanced degree, became a department head, then a division head, and eventually rose to Head of School.
Along the way, life happened—you built a family, attended your children’s events while balancing “command performances” at school, and remained ever-present for faculty, parents, and students. Fast-forward 25–30 years: You’ve weathered teacher complaints, parent demands, boardroom debates, disciplinary challenges, and even moments of discord with your Board Chair over major initiatives.
Not everyone burns out—some heads glide smoothly toward retirement. But many find themselves at a crossroads, exhausted and unsure of their next step. You may be 55 or 60, feeling stuck—too old for a career shift, too young to retire. So, what now?
Key Questions to Consider
Before making a decision, assess your situation:
Do you want to remain as Head—either at your current school or by refreshing yourself with a leadership role at a new institution?
Would you consider an interim Headship? Some schools need experienced leaders to step in for a year due to sudden departures. This could be exciting, offering a new environment and a fresh challenge.
Do you still enjoy the “always on-call” work that at times demands 60–80-hour weeks?
Would you prefer more personal time and a break from the relentless administrative treadmill?
Next Steps: Revisit Your Financial Plan
If your answers lean toward change, your financial plan should guide your transition. Assess:
Savings: What have you accumulated over your career?
Essential Needs: What is your fundamental annual spending (this encompasses things like mortgage, food, utilities, etc.)?
Discretionary Aspirations: How much do you want to allocate for travel, gifts, major purchases, living preferences, family, and legacy planning?
Potential Income: How much work—if any—do you and your spouse plan or want to do, and for how long?
Financial plans evolve, and you, your family, and your advisor can explore options that balance lower stress with rewarding work in education or beyond.
Alternative Career Paths in Education
You don’t have to leave academia entirely. Consider:
Returning to Teaching: Enjoy summers and holidays off while guiding students again.
Mentoring a Head or Administrator: Stay engaged in school leadership without carrying the burden yourself.
Consulting for Administrative Placement Firms: Use your expertise to evaluate and recruit top talent for schools.
Understanding what you currently have, your essential expenses, and your additional spending aspirations—while factoring in potential earnings for the next few years—can help you and your financial planner design a strategy that supports a fulfilling life both now and throughout the entirety of your financial plan.
Longevity & Financial Security
One crucial factor in planning: How long do you anticipate living? While unknowable, educators statistically enjoy long, healthy lives. Financial longevity matters—outliving savings is a risk that could result in a financial burden to your loved ones, but leaving even the smallest legacy can help with financial security for future generations.
The Emotional Side of Retirement
Beyond finances, retiring is an emotional transition. The best part? Freedom. No more schedules, obligations, or being “on call.” But many retirees struggle with feeling unnecessary. The camaraderie of school life disappears, and redefining purpose becomes essential.
Phasing out of a school role at a pace that suits you—while remaining engaged with students or peers—can provide both fulfillment and financial stability.
As a wise Board Chair once told me:
“If you handle it just right, everything will work out fine.”
I hope this perspective resonates with you!
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 career. During this 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.