Life is messy. Life is beautiful. So are schools - and that’s ok.

It was a gorgeous mid-July Friday here on the Connecticut shoreline and I hope it is beautiful wherever you are as well. The dogs and I walked a nearby trail that was shady, quiet and ended on a beautiful vista of the Sound recommended by my new neighbor that was a perfect way to start the day.

I want to thank people who have reached out after reading the posts. It has been heartening to hear that so many of the issues I have been contemplating are striking a chord. Please feel free to keep reaching out! I am thinking hard about directions for this newsletter and what will be helpful and additive to our collective aspiration to make great learning environments for kids and fulfilling professional experiences for adults.

One recent comment I wanted to share was someone who expressed an appreciation for the tone and lightness of the approach to these topics. This is from a longtime professional colleague who works not just with schools but with nonprofits and for-profits of all kinds. His observation was that there is often a misapprehension that any conversation about serious things needs to be absolutely serious in tone  - that there can be no playfulness, irony or fun. He thinks this misses an opportunity to help make these topics more accessible and less daunting - and heightens the potential to find new insights, breakthroughs, and connections. 

This made me think about one of the more puzzling aspects of mainstream independent school culture, which is what I call the “best year ever” syndrome. Since I became a head, in particular, it seems that unless you have relatively strong trust with a colleague at another school, any deviation from the party line that it was the “best year ever” at your school was met with discomfort and awkwardness. The vibe was that you were letting the side down if you said anything less - even in relatively private discussions at workshops and conferences. I would wonder - am I the only person thinking things like these tuition prices are insane and who are we really trying to serve? Or wondering how we are going to sustainably and appropriately serve the mental health needs of all our students, even before the pandemic had such an impact?

I would get blank looks when I referenced net tuition revenue and couldn’t parse whether it was that other heads didn’t want to admit they used that model or they were unfamiliar and didn’t want to admit that - and also why NTR seemed to be some kind of source of what I can only describe as shame. And the vague and elliptical discussions among boarding school heads about Chinese student enrollment numbers - kids who are generally excellent students and citizens and whose families really want our experience and see the value proposition.

In DEI conversations with other heads, there was a lot of comfort discussing approaches to financial aid but less in talking about the deeply rooted culture at many of our schools as we were founded by the elite, for the elite. Clearly, this isn’t the school’s or culture’s fault - but it is a fact, a history we carry with us, and a complicated challenge in the 21st century to relevance. And when I ventured to say that I felt as if I had some insight because I didn’t always feel a sense of belonging at my own school - crickets from my peers. And again - I’m not inviting people to join a pity party; I was just trying to share the complications and contradictions I was living with every day.

I am not complaining about the messy reality - what I am positing is a question - why is it so hard for us as school people to have conversations about the messy reality rather than surface conversations? Can’t I really love my schools and value independent schools deeply and acknowledge the many difficult and complicated challenges in front of us? Are people worried if we open up about the messy reality it will all go to hell and, in Humpty-Dumpty fashion, never be put right again? 

The thing is - denial about change will ultimately be more costly than acknowledging the messiness, complications, and contradictions. 

And if we are expected to “put on a good front” in public and not even honestly exchange our hopes and fears with smart colleagues for fear of being disloyal to our institutions, we are losing valuable opportunities to grow stronger both as individual schools and as a group. And keeping these discussions internal-only (“behind closed doors”) just keeps us trapped in the outdated “family” model that is no longer moving us forward.

There are existential problems in front of all of us about meaning and purpose as we sort through both the continuing damage and the aftermath of a global catastrophe. There is none bigger right now than morale - morale for everyone in an organization, whatever organization that might be. And the old transactional approaches won’t cut it - raises, parties, gift cards, notes. These are of course, not bad things and they are direct and transactional gestures of appreciation for work well done. But there is something bigger and deeper here at work that a gift card won’t solve.

And if we can’t live in the honesty, frustration, absurdity and irony of the many contradictions at the heart of our multilayered and most human of endeavors, we won’t be able to get to those deeper explorations we need to have as school communities about the significant meaning and purpose of people’s life work in schools. I used to think it was the administrators’ job to protect teachers from the biggest, most intractable questions so they could do their best work with the kids. But now I think that time is past and to really deal with this ongoing restlessness and discontent, we need to find ways to actively engage our community in working towards new approaches. That is going to take time, trust, creativity and iteration. It’s going to require that communities give everyone, including the leadership, space to recharge and latitude to experiment.  That is much more difficult once you’re back in the day to day. But if we just go back to business as usual, the turnover and churn cycle will just continue.

It can be a really good year in some ways and it can be a really difficult year in others. And that’s OK. Let’s talk about it. You’re not alone. 

Have a great, messy, beautiful weekend everyone!