The Last Year of a Headship is Weird
Breaking up is hard to do - let's try to embrace the bittersweet
It was about a year ago that I made the decision I wanted to conclude my headship at Westover School June 30, 2023. I had gone from a mental framework of “all in or all out” i.e. to do headship “right” it had to be all consuming, leaving very limited space for the rest of you or your life. After many conversations with wise people in my life, I saw that I could take a middle route, starting to detach, wrapping up a handful of projects and fundraising initiatives as I started to think about the next stage of life and the school moved on to consider its next leader.
Sitting in my study that is not on the Westover campus in October, 2022, clearly that is not how things worked out! (Cue all the cliches about how life happens…) Shortly after my conversation with board leadership about my decision and a cursory conversation about timing for the bigger announcement, my mother had a stroke and in literally a flash went from a elderly person navigating age-related infirmities to being completely unable to manage. It took about a week and a concurrent school kerfuffle that consumed my time and attention, yet again, to put my priorities in stark relief and I altered my timeline to leave in June, 2022.
I am grateful that board leadership was so supportive of me in altering this timeline and I have no regrets at all. It was a wrenchingly hard decision to make at the time and to feel my choice was turning the lives of so many others upside down, in a rush, rather than the gradual, smooth transition I had imagined.
It has been a gift to have this time and I am happy to report that my mother is so much less disoriented and depressed now that my sister (who took a leave from her teaching job) can really dedicate significant, quality time and attention to her and my dad. This is not a tragic situation but it is a difficult one. However his brain is affected by dementia, my dad manages to navigate his altered sensibilities and abilities with placidity. My mother, in her case, is keenly aware and frustrated by the fact she is now so limited and is plagued by a nagging sense of FOMO that she is not joining in making plans for the future the same way we are, even though she easily tires and if pressed, would prefer to stay in her routine, close to home. They are both living in a liminal, temporary space at the end of such vibrant lives and for me, it is hard to watch and hard to cope with in a way where I can consistently keep up the positive energy. (Shoutout to my sister Marie, who is much better at this than me. May you all have such a partner to support declining parents.)
To return to the professional - the last six months of headship was just plain weird. It wasn’t terrible. It wasn’t like parts of 2020 where I felt as if decisions I made could either help or hurt people I was responsible for in a very immediate way. But it was like spending six months wearing pantyhose that didn’t quite fit. Remember that, those of you who have worn pantyhose or tights? Not painful, but uncomfortable and you keep trying to adjust and sometimes you make it worse and it is even more uncomfortable. And what has been so interesting is the number of heads I have talked to since that time that have shared they also found it weird, uncomfortable, unpleasant, in the words of a few, “one of the worst professional experiences of my career” - and this was all from heads who had an amicable parting with their schools.
For me, it was weird that I was going through a process of a major life and career change and largely everyone else in the day to day school was behaving like business as usual. There were some gestures towards transition but even at the trustee level, we had fewer people than usual to get the work done and the trustees had moved on to find an interim and then a permanent head. The development office seemed at a total loss as to what to do with me in this shortened exit timeframe. They were looking at me and I was looking at them and without anyone taking the lead, nothing happened and they went about their business meeting the annual fund goal. As they should!
At every meeting and every conversation around hiring or the year ahead, I would be thinking hey, I’m not going to be here…? But people still wanted me to participate and wanted my input and wanted me to make decisions. It seemed easier than trying to grapple with the reality of the change in front of everyone.
One head who had left a headship and transitioned to another said to me, “You don’t want to check out because that’s the standard criticism from the community - but if you hold on too tight, you break things.” This was very wise insight and also incredibly hard to tell the difference between these things when you’re in the middle of it. And incredibly hard for the trusted people around you to tell the difference because they are going through their own loss process. And there is some necessity to “checking out” - you can’t be Wile E Coyote with knees pumping as you run off the cliff into thin air July 1.
I heard from other heads things like:
After the celebrations were over in the spring, I felt like the community moved on and I still had more than a month to go
I felt like I didn’t belong anymore - I sort of felt like a ghost
The trustees were totally consumed with finding the new head and it felt like it would be a distraction to them to ask for support
There was a strange sense that my departure was somehow disloyal, even though it was for normal professional reasons
“Under the surface” issues with the board bubbled up in ways I was not expecting
And the opposite of what happened to me also happens - people just leave you out of conversations completely.
I think the head’s departure is one of those events where the intersection of personal/family and professional/community gets particularly complicated. I also think many adult school communities struggle with how to deal with authority and a power structure in a frank way. We are “all in this together” but there is a boss. And ironically, many schools truly operate with an absolute monarchy model although there’s plenty of verbiage to the contrary. So it’s hard to surface all the fears about one monarch leaving, one whose ways have become predictable even if people are not always thrilled, and the great unknown coming in.
Even in the case of a long planned retirement, there are feelings of loss, and even of abandonment. It is a moment of grief and we are so bad at grief. It seems we will go to great lengths not to sit with the sadness; it is more comfortable at a day to day level to push it down or be in denial, or even let it surface as anger. At least with anger, it is active and focused outward. I experienced some weird, inchoate anger directed at me from a few people, towards the very end. It did not feel great to be on the receiving end of that anger, even though intellectually I knew it was part of these people’s loss process and wasn’t really about me.
I am very interested in finding new ways to work with departing heads and schools on improving this situation because it will just help a school thrive. A smoother transition will also make for better support for a new head when he or she enters the community. It can be professional - let’s talk about how this is sad and weird and hard but also exciting and how great it is we all are joined together in wanting the best for the institution - and it can be personal with the departing head getting some dedicated coaching as they work through their feelings and the board getting some space to share their feelings and figure out how to emotionally do their best to thank the head and send her on her way. Please feel free to reach out to me at jfaulstich@stonycreekstrategy.com if you’d like to discuss how I can support a transition.
Embracing the bittersweet is hard. We don’t do it well but I also strongly believe it would not take much to do it better. I know I used to be afraid that if I let myself really feel sadness, it would take over; I would stop functioning and all would be lost. What I have learned is that the feelings pass through, you take a deep breath, and keep moving. A dose of sweet is usually just around the corner from the bitter.