Alleyn’s School is a leading co-educational independent day school in Dulwich, London, educating pupils aged 4–18 across its Senior School and two Junior Schools: Alleyn’s Oakfield and Alleyn’s Junior School.

Day of Wicked Problems




Day of Wicked Problems
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Development and Alumni Beyond Alleyns


On Thursday 25 June, Alleyn’s Year 12 students wrestled with six of the most complex and contested challenges of our time — and they didn’t do it alone.

The ‘Day of Wicked Problems’ was designed to move learning beyond the classroom, giving students the opportunity to engage directly with real-world issues and the people working at the heart of them. Through small-group discussions with expert guests, students were encouraged to test their thinking, ask difficult questions and develop informed perspectives - experiences they can draw on in their UCAS personal statements and beyond. Crucially, the day offered insight that goes far beyond textbooks, connecting students with those tackling these challenges in practice.

Five alumni gave their time to support Year 12s, each leading a themed discussion:

  • Becca Windsor de Taboada (2017) on Regulating AI
  • Anna Dighero (Dutton’s 2013), Senior Scientist at the UK Health Security Agency, on the Bundibugyo Outbreak
  • Ted Rosner (Spurgeon’s 2006) of Redemption Roasters on England’s Prison Crisis
  • Noah Eicke (Brown’s 2016), Civil Servant, on The Fracturing World Order
  • Caterina Loriggio (Brown’s 1987), leading the legacy programme for London Borough of Culture, on Who Pays for Public Culture

Each brought something no textbook can offer: the experience of living and working inside an unresolved problem.

Students arrived having researched their topic in advance and took the lead in shaping the discussion, putting their own questions directly to the speakers. Seed questions helped spark debate — for example, in the session on the fracturing world order, students considered whether “the rules-based international order is already dead, or simply on life support - and whether it matters which.”

This approach created a dynamic and intellectually challenging environment, empowering students to think critically, engage confidently and explore the complexity of global issues with those who encounter them every day.

A huge thank you to all of our speakers for giving their time and supporting students.







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Day of Wicked Problems