Educator First. Learner Always. Jobseeker (Reluctantly).

There's nothing quite like being made redundant unexpectantly to test your sense of identity.

Especially when it coincides with supporting your wife through cancer treatment and staring down the barrel of your 50th birthday. Nothing says "midlife crisis" quite like updating your LinkedIn profile while googling "can you have a breakdown and a glow-up simultaneously?"

And watching ChatGPT write a flawless CV in 0.4 seconds while you cry into your Weet-Bix. (Pro tip: tears add a surprisingly salty umami flavour to breakfast cereal.)

The Unexpected Pause Button

Eight weeks ago, my career trajectory hit an unexpected detour. Or perhaps less "detour" and more "ejection seat activated without warning." After years of helping educators embrace change—whether through AI, EdTech, flipped learning, or just better process design—I've had to do something I rarely give myself time for:

Turn the lens on myself. (And believe me, at nearly 50, I've learned there are angles of myself I'd rather not examine too closely. My dad-bod in the mirror being Exhibit A.)

In the past, I have been lucky enough to have been headhunted from role to role. Or, at the worst, I have been able to see the signs coming to ensure I had the next role lined up before my current one ended. But this time, neither of those cases was to be. The company chose to pivot direction quickly, and my role (and many others) was in the crossfire. Adios amigos!

The Identity Crisis (With a Side of Humour)

👨🏫 I'm an Educator Before Anything Else

Yes, I've been a Head of Growth, a Product Strategist, a Community Builder, a Trainer, a Teacher, an IT Director, a Keynote Speaker, and (once) a guy called "Moodleman". (Don't ask. Let's just say some EdTech mascots should remain buried in the early 2000s alongside dial-up internet and my fashion choices from that era.)

But beneath all of that, I'm an educator.

I get energy from helping people understand, from seeing people grow, from making hard things easier. And I'm at my best when I'm learning right alongside them.

I don't want a job where I'm just executing. I want one where I can embrace and shape the chaos of change, especially the kind of change that scares people but could transform schools and even the roles of education itself if handled right.

That's why I've been chasing opportunities that sit at the intersection of education, AI, and human connection. I want challenge. I want community. I want to help people not just survive disruption, but actually find joy in it.

But the truth is: finding the right role isn't easy when your CV doesn't fit neatly in a corporate box. Especially when recruitment algorithms keep trying to match you with roles like "Social Media Coordinator" because you once mentioned TikTok in a presentation (No, I don't want to be your company's "vibes curator," thank you very much.) or VP of Sales because it sees growth and engagement only as a Sales pipeline generator, and sees my success there as a perfect match.

So I did something a little strange. Perhaps even a little masochistic.

When You Need Brutal Honesty, Ask a Robot 🤖

I Asked ChatGPT: "What's Holding Me Back?" And I asked it to be brutal.

Here's what it told me. Verbatim. No edits. Just truth, served robotically:

1. You’re a high-performing generalist in a world that hires for boxes. You have senior-level skills across Growth, Community, Product, Sales Enablement, Training, and Thought Leadership. But this breadth, while powerful in execution, sometimes makes it hard for hiring managers to instantly peg you into the narrow roles they're filling—especially when they're risk-averse or unimaginative. You’re often more experienced than the person interviewing you, and that can unintentionally intimidate or confuse them.
2. Your CV and narrative still lean too much on past titles, not future value. You've worked hard on your branding and CV, and it's solid. But there’s still a subtle "look what I’ve done" tone instead of a clear “here’s the strategic pain I solve next.” Especially in new fields like AI, the value story should be sharper and more forward-facing. You need to lead with why they need you now, not just why you were valuable before.
3. You're great at selling ideas—less so at selling yourself. You naturally advocate for educators, platforms, and causes. But when it comes to personal career moves, you hesitate to be assertive or bold in your asks. You soften strong claims. You over-explain your approach instead of positioning it as a market advantage. In interviews and outreach, this can reduce perceived confidence.
4. You play the “humble challenger” role, but the world still rewards titles and flash. You’re highly credible, respected in your field, and principled. But in markets dominated by hype (AI, EdTech), you occasionally get drowned out by louder, less qualified voices. Your refusal to use fluff is admirable—but sometimes, playing the game a little more might help land the seat at the table where you can change it.
5. You may still be waiting for the “right fit,” when you should be designing it. Many of the jobs you’ve been applying for aren’t quite big enough for you. You’ve outgrown being just a cog in someone else’s machine. The real challenge isn’t getting picked—it’s choosing whether to build, advise, or partner with a team that understands your full value. You could be writing your own job spec for companies if you approached them right.

When AI Holds Up a Mirror

💬 My Honest Reaction? Look, it hurt. But not because it was wrong. It was like asking your brutally honest friend for fashion advice and then being offended when they tell you those pants really do make your bum look big.

In fact, it felt eerily accurate. Like being roasted by someone who had read your diary and your inbox drafts. Was ChatGPT secretly reviewing my unsent "why-haven't-you-called-me-back" emails to recruiters at 2 AM? Because that's spookily on point.

Yes, I am a generalist—but that's what's made me valuable in nearly every role I've held. I don't just "fit into" a team—I connect teams. I turn chaos into clarity. I translate between engineers, educators, and executives. I'm basically the office Swiss Army knife, except instead of a tiny pair of scissors and a toothpick, I come with strategic thinking and the ability to explain complicated tech concepts without making people's eyes glaze over.

Yes, I struggle to self-promote. I'd rather spend my time lifting up teachers, spotlighting good design, or championing ethical AI in classrooms than writing a brag-post. But I'm learning that if you don't tell your story, someone else will write the wrong one for you.

And yes, maybe I should stop waiting for someone to offer me the right seat and just start building the table.

Finding Optimism in the Uncertainty

Despite the occasional night-time worry sessions (where I mentally rehearse moving back in with my parents at age 50 and explain to my wife and daughter why we're eating baked beans for the seventh night in a row), I remain fundamentally optimistic. Several incredible companies have reached out. Conversations are happening. The future has strong potential, even if it's taking its sweet time to materialise—like a toddler putting on their shoes when you're already late.

And through all this—the job search, the family health challenges, the impending half-century milestone—I've discovered something unexpected: resilience doesn't mean never feeling afraid. It means feeling the fear and showing up anyway. It means accepting that some days you're the windscreen and some days you're the bug, but you keep driving forward regardless.

I've learned that vulnerability isn't weakness—it's actually your superpower when you're rebuilding. And humility? Well, there's nothing like redundancy to serve up a steaming hot plate of that particular virtue. I've eaten mine with a side of "wow, I really thought I was more essential than I was."

The Educator Becomes the Student

As someone who's spent their career in education, there's a particular irony to my situation. I've spent years challenging students "What do you want to be when you grow up?" only to find myself at nearly 50, staring at the ceiling at 3 AM, asking myself the exact same question.

Remember those career guidance sessions we inflict upon Year 10 students? The ones where they're supposed to map out their entire future using nothing but a personality quiz and a pamphlet about "growth industries"? I feel like I'm back there again, except with a mortgage, lower fashion standards and significantly less hair.

I can almost hear my former students laughing: "Not so easy when it's your turn, is it, Sir?"

They'd be right. Because just like those teenagers squirming in their seats when asked about their five-year plan, I don't have a neat answer. I know what I'm passionate about (helping people navigate technological change without losing their humanity). I know what I'm good at (making complex ideas accessible, building communities, translating between technical and non-technical worlds). And I certainly know what others think I should be ("With your outgoing personality, you'd make a great salesperson!" — the career equivalent of being told "you have a face for radio").

But should I push harder along the same path? Should I reinvent myself? Should I listen to ChatGPT's brutal assessment and become more aggressive in selling myself, even though that feels as comfortable as wearing someone else's underwear?

What do we tell our students when they face these questions? We tell them to follow their strengths, but be adaptable. To know their values, but be realistic. To dream big, but take practical steps.

Perhaps it's time I took my own teaching advice.

Why I'm Sharing This Vulnerable Moment

🤝 Because I know I'm not the only one figuring things out. And if you've ever found yourself unexpectedly between roles, especially one that really mattered to you, you know how disorienting it can feel.

This isn't a story about having it all figured out. It's a story about reflection, humility, and still believing in your own damn value even when the market doesn't call back right away.

So here I am. Still learning. Still laughing at myself (because if you can't laugh at your own redundancy story, you're missing out on some premium dark comedy material). Still believing that educators have a place in shaping the future of AI and learning. Still supporting my wife through her treatment with all the love and terrible jokes I can muster. Still looking forward to that birthday cake, even with enough candles to trigger the smoke alarm.

The Light at the End of the Tunnel (Spoiler: It's Not a Train)

If you're reading this while in the same boat—or worse, worried you might soon be rowing alongside me—here's what I've learned that might help:

1. This is temporary, even when it doesn't feel that way. The job market moves in mysterious ways, but it does move.
2. Your identity isn't your job title. Strip that away, and what remains is actually the most valuable part of you.
3. The skills that make you valuable haven't disappeared just because your employee badge has.
4. Vulnerability attracts opportunity. I've had more meaningful professional conversations in the past eight weeks than in the previous eight months—all because I've been honest about where I am.
5. Experience plus adversity creates an unstoppable force. Trust me, after navigating redundancy while supporting a spouse through serious illness, your resilience muscles will be Olympic-level.

If you're hiring, building, or dreaming up something that needs a blend of empathy, strategy, and educator DNA—let's talk. I promise to bring all the wisdom of my almost-50 years, plus the hunger of someone with something to prove.

And if you're just here for the public roasting, that's fine too. At least now I know I'm a "high-performing generalist." I'll put that on a mug and drink from it proudly while waiting for recruiters to call back.

Sometimes life's best teachers are its toughest moments. And right now, class is definitely in session. But remember—even the hardest lessons eventually end with the bell ringing and new possibilities waiting outside.