Build Your Freedom Fund Now

In October 2013, I attended the National Association of Independent Schools’s (NAIS) Leadership Through Partnership (LTP) conference for heads of school and board chairs. In the opening session of the three-day conference, the NAIS Board President, himself a head of school, began his remarks with the two lessons we would all remember long after the conference finished:

Lesson #1: When the head screws up, the head gets fired.

Lesson #2: When the board screws up, the head gets fired.

I still remember that moment when I heard those remarks, barely five months into my tenure as head of The Children’s School. I also remembered his warning at the start of my second year, as I warned the board at their fall retreat in 2014, that more changes were coming and I’d need their full support if we were going to fully realize our institutional mission and values. The executive committee was strong and unwavering, but humans are humans and I knew that regardless of whatever support anyone promised me, I needed a backup plan. If I suddenly lost my job, it could take me months to replace this one. I invited a financial planner to our home and his first question to us was, “Why do you want to build your wealth?” I replied, “We value our freedom and flexibility. I want to live and work on our terms, not on someone else’s. Tomorrow, I could lose my job and our livelihood and not because of something I did or deserved. I want the same power to leave tomorrow that the board has over me today.”

Fast forward five years, and in January 2019, I told Neeti that it was time for me to go. Contractually, I needed to give the board at least twelve months’ notice. My first call was to our financial planner: “Kenny, I’m going to tell the school I’m leaving soon. Do we have our Freedom Fund?”1 Once Kenny said yes, Neeti and I began to make our plans for what’d be next for me. In summer 2022, I’d make the same decision; it was time to leave and reclaim our lives and how I’d spend my hours and my days on my terms rather than living up to others’ needs, expectations, and interests.

2019 was not the first time I had made such decisions. The first one was back in 2001 when I graduated from college and turned down prospective jobs on Wall Street for a teaching job in Dallas. For as long as I can remember now, and my mother will back me up on this, I’ve been an independent soul, clear in my values and what matters to me. Instead of going to engineering and business schools then, as my family wished for me, I went into teaching. In 2019 and 2022, my decisions were again motivated by alignment - were those for whom I worked aligned with my values and interests, and ambition for the organization? Were their motivations joined with mine? In some cases, I left behind contractual guarantees for short-term uncertainty.

For several years now, I’ve passed along this advice to new heads of school - build your Freedom Fund. Whatever your reality, it’s not hard to do if you can cultivate the discipline. Focus on your costs, not your income, and you can build it sooner than you think. The Freedom Fund gives you control and control gives you choice… the choice to work on your terms, the choice to stay or leave, the choice to take other risks and experiment a little, the choice to consistently live a life of authenticity and alignment, the choice to reject those short-term compromises, and the choice to build something for the long-term.

I believe simply that I’ll do well if I do good. Doing well, then, is an outcome, not a motivation, of a life spent doing good. Our Freedom Fund enables me that choice.