The Squeeze: Why Your Midlife Career Might Be Quietly Losing Value
How to Avoid the Midlife Career Squeeze (Before It Hits Your Confidence)
Are your job applications falling flat—even when you’re asking for less money? You may be stuck in The Squeeze, a hidden midlife career trap. Here’s how to escape it.
You’ve still got the skills, the experience, and the track record. So why are your job applications falling flat—even when you’re asking for less money?
Let me introduce a concept I’ve observed in hundreds of career stories: The Squeeze. It’s not a buzzword. It’s a slow, confidence-eroding phenomenon that many midlife professionals experience without realising it.
It begins quietly—maybe your proposals start getting ignored, or job applications that once led to interviews now go unanswered. Maybe you’ve even lowered your salary expectations, but still, no one bites.
The real kicker? It's not just your bank balance being affected—it’s your self-worth.
What is The Squeeze?
The Squeeze happens when your skills or career story begin to blend into the background. You’re no longer seen as a valuable individual offering something distinct. Instead, your experience becomes commoditised—seen as interchangeable, generic, or even outdated.
You might notice:
You’re using vague language like "strategy" or "leadership" instead of naming your actual brilliance.
Your CV or pitch doesn’t spark curiosity—just polite silence.
You’re applying for lower-paid roles and still getting passed over.
And over time? That invisibility creeps inward. Confidence dips. Shame sets in. Joy at work feels... out of reach.
Who’s Most at Risk?
From my research and client work, The Squeeze tends to hit three groups hardest:
1. Small Business Owners
Especially those who can’t clearly articulate the problem they solve or who they solve it for. They get lost in the crowd and end up undercharging—or overlooked entirely.
2. Generalists
If your offer is “I do a bit of everything,” you’ll blend into a beige sea of sameness. The market now craves specialists who solve specific, valuable problems.
3. Leaders with Blunted Edges
You may have climbed the ladder but left your specialist skills behind. Now, when it’s time to reposition, your pitch lacks sharpness and specificity.
Real Humans. Real Stories.
Let me bring this to life with a few examples:
Rory, a seasoned strategy consultant, was losing roles to younger, cheaper candidates. Once we uncovered and clarified what he uniquely offered, he landed a role where his grey hairs were seen as wisdom—and worth paying a premium for.
Kieran was told his demographic wasn’t being prioritised. Brutal, but true. He didn’t shrink. Instead, he refined his offer, sharpened his value proposition, and has enjoyed four years of well-paid, meaningful work since.
Jolene, a small business owner bored out of her skull, repositioned her brand and now earns more in half the time—with more fun, satisfaction, and a global business born from it.
You can read more about Jolene’s journey here.
So… How Do You Avoid The Squeeze?
No fluff here. Career redesign after 40 isn’t a “3 easy steps” journey. But there are three proven strategies that can make a meaningful difference:
1. Discover Your Superpowers
Get crystal clear on what you do uniquely well. And no, I don’t mean “leadership” or “communication.” I mean the gritty, tangible skills that set you apart—spoken in your own words, not CV speak.
📥 Download the Superpower Starter Kit to start naming your brilliance.
2. Get Obsessed With a Specific Problem
Choose your lane. What problem do you genuinely care about solving? Who specifically faces it? Specialisation doesn’t limit your future—it opens more doors.
3. Refine Your Messaging
You must communicate your value until it lands. If your pitch doesn’t make someone say, “Ooh, do you do that?”—it needs work. No matter how brilliant you are, if people don’t get it, they won’t buy it.
What Now?
You’re not too old. You’re not too expensive. You’re not done.
You’re just not being seen—yet.
The antidote to The Squeeze is visibility, specificity, and brave clarity about what makes you different. And if you need help with that, I’ve built two powerful ways to support you:
💬 The Fierce Emporium – A one-year programme designed to help you refine your pitch, design small experiments, and get real-time feedback.
🚀 The Fierce Accelerator – More hands-on. More tailored. More momentum.
Final thought:
You deserve to work less and earn more—doing work that lights you up. But first, you have to stop blending in.
That, my friend, is where joy at work begins.
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makes people lean in and ask, hi, do you do that?
If not, it's time to work on your messaging, because no matter how brilliant you are, if people don't get it, they just won't buy it. No matter how much you charge.
[00:10:48] Inside The Fierce Emporium & Fierce Accelerator
We work through all of these and more in the Fierce Emporium with one full year of support to ask questions, to compare how others do it, to get loads of feedback, to design experiments, to get your messaging reviewed and to refine your positioning so that you can earn what you want or need to earn for the rest of your working life.
And if you want more personalized help, consider the Fierce Accelerator Program. I'll include links in the show notes.
[00:11:20] Final Message: You’re not too expensive—you’re just blending in
Here's what I want for our listener who is finding themselves applying for jobs that pay less than they're worth and still not getting chosen. I want you not just to keep earning, but to earn your value to work less. And earn more to do meaningful work that lights you up and pays you properly. To stand out like Madonna's La Isla Bonita, in a world of noise.
You're not done. It's not too late, and you are not too expensive. You just need a clearer, sharper, and more specific pitch about your potential value, more specific than you've ever needed in your career to date. You need to stop blending in and start standing out as the unique superpower and truly fierce human that you are.
And that sounds like joy at work to me.
