“Winning the award meant the world and gave me many opportunities that previously I may not have had.”

Stephen Cabrera
Winner, Teaching Award for Enterprise, 2006
Currently Director of development at St Joseph’s College, Beulah Hill, London


Winning the award meant the world and gave me many opportunities that previously I may not have had, talking at universities, conferences and sharing my ideas and what we as a school had achieved. It was humbling to see things we created being used in other schools as examples of best practice.

It definitely gave me more pride in my job and has looked useful on my CV!  My next role was as deputy headteacher, the headteacher knew of me through my work in Surrey and wanted me to apply.

I started working at Epsom and Ewell High School as a Business Studies teacher in 1995.  I moved to Rydens School as head of department in 1999 and grew a dept from 1.5 (equivalent) teachers to four. When specialist schools came in the headteacher felt Business and Enterprise would be suitable owing to the success of the department and also as having worked previously in industry I always tried to network and get external partners in to work with students. We were one of the first Business and Enterprise schools in Surrey and it was an industry partner who nominated me for my award.

One of the nicest and best things to come out of winning was the opportunity to be a judge for the awards. Getting to visit and see others who are so brilliant at what they do was a privilege and inspiring.


Did I always know I wanted to a teacher? My mum did! I had a number of false starts working in the City but once I walked into my first class as a PGCE I felt I belonged and not regretted it since. 

Over the years I’ve evolved to cope with the changing nature of pupils and the increasing use of social media which had made things a lot more open and difficult to monitor. It has made it harder from a pastoral point of view. And as a deputy headteacher pastoral work has always had an important role in my day to day life.


There have been a few memorable moments in my career – winning a teaching award; seeing other schools when I have visited using my ideas and making them better than I envisaged; seeing students grow and come back to thank me for giving them aspirations.

And one of my first students ran the England World Cup Rugby campaign when they grew as giants, thanked me for his marketing passion from my A -level lesson.


Always be consistent and never underestimate the potential that students have. In my experience they have always gone beyond my expectations and constantly surprised me. 


It has certainly become more results focused, an exam culture that is not student focused.  At Key Stage 4 in particular we are forcing students through a very narrow door, I worry it is ruined for a generation. Underfunding and staffing shortages is affecting students.

I’ve stayed because I love my job, but I do think we need to give teaching its respect back. Teachers should be valued, paid what they are worth and have more work/life balance.