Failing: Totally. Utterly. Absolutely.

What does it feel like?

Leadership is celebrated in success, but what happens when you achieve everything asked of you, yet, somehow, you are branded a failure?

These reflections are for leaders who checked every box, fulfilled every expectation, and still watched their reputation shatter.

When Everything Unravels

Early progress was overshadowed when I uncovered deep-rooted, previously unknown financial issues, and union tensions escalated into one of the longest continuous local strikes in the sector’s history. After over 50 days without teaching, I had no choice but to self-assess the college as Grade 4 (Inadequate), later confirmed by Ofsted.

This is not an account of the events themselves, but a personal reflection on the emotional and leadership journey through collapse, and back towards hope.

The Shame. The Silence

For me, it felt like drowning while everyone expected you to wave cheerfully from the surface. Like screaming in a crowded room, being unseen and unheard. It meant dragging myself into meetings with a smile, knowing I’d face ridicule, resistance and resentment.

There were days I genuinely considered leaving the sector, not because I’d given up, but because the emotional weight had become too much to carry.

There’s a lot of talk about failure: Fail fast, Fail forward, Every failure is a learning opportunity. And maybe that’s true, eventually. But when you’re in the thick of it, just trying to get through the day, that kind of language feels hollow. I wasn’t failing fast; I was failing in slow motion: months of conflict, fatigue, and resistance.

And yet, I never stopped. I kept showing up, kept making decisions I believed were right for students and for the organisation’s future. But nothing seemed to land. Nothing seemed enough.

Then came the shame.

I felt I was letting students down, especially those I’d always championed. I felt I was letting down staff who did support what I was trying to do but were too afraid to say so publicly. Some offered quiet solidarity through messages or private words. But in public? Silence.

That silence stung.

I wasn’t upset by disagreement; I’ve always welcomed debate. But I was hurt by how quickly some allies, once vocal in their praise, seemed to vanish. Not all, but many.

And then there was the media: publications that mocked, tore into me, personalised their attacks without context or fact. I wasn’t being examined; I was being ridiculed. And beneath it all was a familiar pattern of scrutiny and stereotyping that leaders who look like me recognise too well but are often told not to speak of.

I really felt it physically. The crushing exhaustion. The tightness in my chest. That sick, twisting ache deep in my gut. I knew my health was suffering, but I didn’t feel I had the right to stop. I was the leader. I had to be strong. Even as I was breaking.

But surviving isn’t the same as leading.

The shift came at my first conference in nearly two years. I’d avoided public gatherings, terrified they might confirm my deepest fears. I was speaking with a colleague I truly admire for their resilience, and I found myself saying, “I am ashamed. I am a failure.”

They looked at me and simply said, “You’re not. I’ve been there. Most of us have. We just don’t talk about it.”

Somehow, those quiet words cut through the shame.

Since then, I’ve had many conversations with other leaders who’ve admitted they’ve felt the same: gutted by the job, disoriented by silence, exhausted by the pressure of carrying everything while being made to feel like a villain. In those moments of shared honesty, one line keeps surfacing, not just between us, but echoed across the sector like an accepted mantra:

“You’re only as good as your last gig.”

That’s a brutal sentiment. Not just because it erases everything that came before, but because it reduces years of service, tens of thousands of students, thousands of principled decisions, to a single moment. That work doesn’t vanish because of one merciless ordeal. And yet, I’ve felt the weight of that phrase, how casually it is said, and how deeply it can wound. It can leave you questioning whether any of it mattered.

Failure is Human, Not Final

That questioning cuts deep, especially for someone who built a career on believing in giving others second, third, and fourth chances. That’s what drew me to this sector. And this is the cruel irony: I’ve spent over two decades telling students they’re more than their worst day, only to face a system that reduces leaders to theirs.

And in that space, I also wrestle with the feeling that people are talking about me, even though I know I’m not so important that they are. But in my mind, I can’t help imagining they’re saying one of two things: either “We told you so, he was never that good,” or “We thought he was a strong leader, how wrong we were.” This sense of judgment follows me, and it’s hard not to carry it into every encounter. Even with friends and family who love me and know what I endured, there’s a part of me that feels I’ve let them down, too.

Logically, I know they aren’t judging me. But emotionally, it’s hard to silence that voice.

I’m not writing this to wallow. I’m writing because if you’re in that space, I want you to know: you are not the only one.

Feeling ashamed doesn’t mean you are shameful.
Feeling broken doesn’t mean you are broken.
Feeling like a failure doesn’t mean you’ve failed.

Back then, I couldn’t see the lessons. I was just trying to breathe.

What that failure taught me about power, resilience, and the real cost of standing firm, I’ll share in the next piece.

For now, sit with this truth: failure isn’t academic. It’s the embarrassment you feel when you look at those you love, and the tear you wipe before it maps shame down your cheek. And somewhere, amidst all that, the first long breath of what now could be.

By Mandeep Gill