Good evening everyone, and thank you so much for being here tonight.
It is a real privilege to be speaking as one of the first cohort of Lira Winston Fellows, and to have the opportunity to share what this programme has meant to me — not just professionally, but personally.
When I applied for the Fellowship, I remember being asked in the interview:
“Why do you want to join?”
I realised very quickly that I didn’t have a polished or strategic answer ready to give.
I was brutally honest.
I explained that I felt I had reached a real crossroads in my career. I was working in a senior leadership role in a highly successful school — the highest grades in the city — and yet the job felt overwhelming. It was becoming increasingly difficult to balance the everyday demands of school leadership with the needs of students, the expectations of parents, staff wellbeing, and the ever‑changing landscape of educational policy, all against the reality of an ever‑shrinking budget.
And at times, it felt less like leadership and more like sitting permanently around the table on The Traitors — under constant scrutiny, trying to work everyone out, and secretly wishing, just occasionally, to be voted off.
Part of that feeling came from the context in which I work. I am the Deputy Headteacher of Liverpool’s only Jewish school. And while that is something I am immensely proud of, it can also feel deeply isolating.
There is often no one close by with whom to talk through the very particular — and often relentless — realities of Jewish school leadership. From questions of ethics and identity, to financial pressure and the constant, sobering responsibility of security, Jewish education carries layers of responsibility that are both professional and profoundly personal.
And when you are the only Jewish school in a city, there are very few people locally who truly understand those complexities, or with whom you can share the weight of those decisions.
That intensity made itself felt very early on in my role. One of my first responsibilities was attending the retirement function of the outgoing headteacher. When word got out that the new Jewish Deputy Headteacher had arrived, I was mobbed — in the most gloriously Jewish way possible.
People wanted to know where I was from.
Who my mother was.
Which shul I went to.
By the end of the evening, my head was spinning. And on the way home, my husband turned to me and said,
“Wow — that was a bit like being married to Kim Kardashian… just without the glamour, the money, or the TV deal.”
So yes — sometimes being a Jewish school leader in a small Jewish community feels less like a job and more like reality television. Everyone is watching. Everyone has an opinion. Everyone is deeply invested.
It was at exactly that point in my career that I received the email telling me I had been accepted onto the Lira Winston Fellowship.
I was thrilled — and genuinely shocked.
I cannot begin to express what participation in this programme has meant for me.
If I had more time, I could talk about the learning itself — the carefully curated programme, the access to such a wide and impressive range of experts and speakers, and the thoughtful challenge woven throughout. All of that has been exceptional.
But what the Fellowship has ultimately given me goes even deeper than that. It has given me space. Space to step out of constant reaction mode. Space to think rather than simply respond. And crucially, space to address my impostor syndrome head‑on.
Like many leaders, I had become very good at appearing confident while quietly questioning whether I was really good enough, experienced enough, or resilient enough to lead. Through this programme, I have gained the confidence not just to lead — but to own my leadership. To trust my judgement. To recognise my strengths. And to understand that uncertainty is not weakness — it is often a sign of thoughtful, values‑driven leadership.
This programme represents more than professional development. It is an expression of values — a belief that Jewish education matters, that leadership matters, and that the people who carry that responsibility deserve to be invested in.
For me, that belief has been profoundly powerful. In a role that could often feel isolating, the Lira Winston Fellowship has been nothing short of a lifeline — offering connection, perspective and reassurance, and reminding me that I am not navigating these challenges alone, but as part of a community that truly understands the complexity and responsibility of Jewish school leadership.
I never had the privilege of meeting Lira Winston.
And yet all of us who are Fellows have benefited immeasurably from her extraordinary legacy.
This programme stands as a living tribute to her values — an investment not only in individuals, but in the future of Jewish education itself. I know I speak for my fellow Fellows when I say that one of our strongest motivations has been a desire to honour that legacy — to lead with integrity, courage and purpose, and to ensure that the faith placed in us is repaid many times over through the impact we have on our schools and communities.
I would like to offer heartfelt thanks to PaJeS — to the professional team for the care, wisdom and thoughtfulness with which this programme has been delivered; to the trustees for their vision and belief; and to the Winston family, whose generosity has made something genuinely transformative possible.
I also want to say a very personal thank you to Susy and Patrick, and especially to Rachel — who has so often been just at the end of the phone at the exact moment one of those inevitable leadership crises has arisen. That quiet, unwavering support has meant more than I can say.
And finally, thank you to everyone here this evening. By supporting the Lira Winston Fellowship, you are not simply supporting a programme — you are investing in Jewish education, Jewish leadership, and the future of our communities.
Strong Jewish schools need strong leadership. Strong leadership needs investment. And there is no better way to safeguard our future than by investing in the leaders of our Jewish schools.
We need this.
Thank you so much.
October Wright
Deputy Headteacher
King David High School, Liverpool
