8 May 2026
As May edges closer to its final days, many teachers find themselves staring at the same date every year: 31 May. The deadline. The moment of truth.
Are you handing your notice in?
Are you staying put — again — for another year?
That question is what sparked a deeply personal conversation between Craig and Dave. What followed wasn’t a discussion about pedagogy, resources or the latest initiative. It was something rarer: an honest look back at a teaching career — the good, the bad, the naïve, the brilliant — and the uncomfortable question that sits underneath it all:
If we could go back, would we still choose teaching?
The answer, perhaps surprisingly, was yes.
“If I could go back 30 years…”
Dave began teaching in 1997. That’s nearly three decades at the chalkface — long enough to have seen initiatives come and go, exam reforms cycle endlessly, and staffrooms transform beyond recognition.
So, if given the option to rewind the clock?
“I’d absolutely do it again.”
Craig’s answer mirrored that sentiment. Teaching, for all its frustrations, was clearly the profession he was meant for. He misses the classroom. He misses the connection, and like many teachers, he didn’t start there, industry came first.
Should graduates go straight into teaching?
Both Craig and Dave took a non-linear route into teaching, spending time in industry before stepping into the classroom. For computer science, and many subjects that experience proved invaluable.
Industry meant real deadlines.
Real consequences.
Real stories.
It meant being able to say to a class, “This isn’t just theory — this is how it actually works.”
There’s no disrespect intended towards teachers who go straight from school, to university, to the classroom. Many are outstanding but lived experience grounds the curriculum in something authentic. It helps students see relevance, not just content.
It also helps teachers themselves because here’s the uncomfortable truth many of us only discover once the door closes behind us and we face our first class alone:
We don’t know the subject as well as we think we do.
Imposter syndrome wears a lanyard
Dave remembers his first lesson vividly: teaching stacks to a Year 12 class. It didn’t go as well as he expected. Students asked innocent, naïve questions, the kind that only learners ask, and those questions exposed gaps in his understanding almost instantly. Not because he wasn’t capable, but because he’d never been on the receiving end of that kind of scrutiny.
It was imposter syndrome, dressed up as professionalism, and if you’re nodding along right now, you’re not alone. Almost every teacher has felt that moment of “I hope nobody realises I’m making this up as I go along.” Don’t despair, here’s the thing teaching quietly teaches us:
You don’t need to know everything.
You need to know how to find out.
Research backs this up. Teacher subject knowledge matters, but it’s nowhere near the top of what drives pupil attainment. Clear explanation. Relationships. Communication. Clarity. These matter more.
Some of the most knowledgeable teachers struggle to teach. Others, with less encyclopaedic recall, thrive because they know how to translate complexity into understanding.
Teaching isn’t about knowing everything.
It’s about learning relentlessly — and modelling how.
Promotion, rejection, and learning the hard way
Career progression in schools tends to split into two paths: pastoral or academic. Craig always knew which route he wanted and one of his defining moments came early, losing a Head of Department role to a colleague with less subject knowledge but vastly more life and leadership experience. At the time, it felt unjust. Years later, Craig saw the truth. Leadership isn’t about being the best at the subject. It’s about managing your team. Filtering pressure. Standing between people and the storm. That colleague taught him what no training course ever would — and shaped the leader Craig would eventually become.
Failure, it turns out, was necessary.
The tutor group moments that define a career
Ask any teacher what they miss most if they leave, and chances are it won’t be the schemes of work. It’ll be the kids.
Dave’s story about a Year 7 detention might seem minor, a homework diary unsigned, but it revealed everything about his values. Where a colleague saw rules and punishment, Dave saw fear, relationships, and trust being broken. That moment motivated him to step into pastoral leadership, not because he wanted power, but because he believed children don’t need to be punished for every mistake. School is a safe place to fail.
Craig’s story, a quiet confession many tutors will recognise, echoes the same idea. Two chronically late boys. Endless detentions. Escalation towards exclusion. Instead of punishment, Craig made a compromise. Not an official one. Just a human one.
They stopped being late.
It wasn’t a policy.
It wasn’t written down.
It worked.
They respected him. They trusted him, and in return, they met him halfway.
Was it perfect? No.
Was it the right approach? Debatable.
Was it teaching? Absolutely.
So… would we do it again?
Yes.
Not because teaching is easy.
Not because it’s how it used to be.
Not because the system always works.
But because when it works, when you reach the unreachable, protect the vulnerable, translate confusion into clarity, or quietly change a student’s trajectory, there’s nothing else quite like it.
If you’re staring at 31 May wondering whether to stay or go, maybe the real question isn’t:
“Am I tired?”
But:
“Do I still care?”
And if the answer is yes, even a worn, bruised, complicated yes, then you already know what to do.
Check out the ‘At the chalk face’ podcast for more!
