The experience paradox
When Expertise Becomes a Liability
There comes a point in your career when you start questioning whether your experience is still seen as an asset or if it’s quietly being viewed as a liability. It often hits you during a job search, but it can creep in long before that—when someone refers to you as “the old guy” in the office or when younger colleagues start getting tapped for projects you once led effortlessly.
It’s a strange and humbling moment, especially for those of us who’ve built our careers on a foundation of hard-won expertise, strategic wins, and leadership that delivered results. You spend years mastering your craft, earning your place at the table, and one day, you’re left wondering: Is my depth of experience now working against me?
When Did Experience Become a Liability?
Let’s talk about the job search process for a moment. For decades, your experience was your golden ticket. Every line on your résumé, every leadership role, every strategic success—those were your calling cards. You didn’t have to jump through hoops to land a role. Your work spoke for itself.
But somewhere along the way, the rules changed.
Now, we’re navigating a system that thrives on checkboxes and keyword filters. Applicant Tracking Systems (ATS) reduce decades of experience to a set of buzzwords, and recruiters often make snap judgments based on whether you seem like a “fit”—and let’s face it, fit can sometimes be code for “younger and cheaper.” Suddenly, that extensive experience can feel like too much.
Overqualified. Outdated. Not agile enough. The labels come fast, and often without a fair chance to challenge them.
The Unspoken Questions We Ask Ourselves
When this shift happens, it’s easy to start doubting yourself. You’ll stare at a job application form and think:
Should I tone down my leadership roles?
Do I really need to mention that 15 years ago I spearheaded a major turnaround?
Is this the moment I sand down my edges, trim my experience, and just try to fit in?
It’s a demoralizing place to be, and I’ll admit—I’ve been there. I’ve stared at job descriptions wondering if the very things that make me great at what I do are now holding me back.
But here’s the thing: we shouldn’t have to make ourselves smaller to get through the door. Our experience—the long nights, the big wins, the failures we learned from—is what makes us valuable. If a system can’t recognize that, then maybe the system is what needs to change.
The Corporate Blind Spot
The irony is that organizations often face crises that only experienced leaders can solve. They’re looking for steady hands, strategic thinkers, and people who have weathered storms before. And yet, when the time comes to hire, the process often screens out the very candidates who fit the bill.
The same leadership and expertise companies claim to want—and desperately need—are dismissed as being “stuck in their ways” or “not a culture fit.” It’s a blind spot that’s costing companies dearly.
Breaking the Cycle
So what do we do? How do we shift the narrative, both for ourselves and for the organizations that seem to undervalue what we bring to the table?
First, we need to remind ourselves of our worth. That may sound obvious, but it’s easy to forget when you’re staring at yet another rejection or feeling sidelined at work. Our experience—our decades of navigating challenges, leading teams, and driving results—is a superpower, not a weakness.
Second, we need to push back against the systems that diminish our value. Whether that’s rethinking how we present ourselves on résumés and in interviews or challenging outdated hiring practices, we have a role to play in reshaping perceptions of what seasoned professionals bring to the table.
Finally, we need to remember that this isn’t just about us. The next generation is watching. By standing firm and valuing our experience, we’re setting the stage for a workplace that values depth and diversity—not just in backgrounds, but in life stages.
It’s Not You. It’s Them.
To anyone else feeling the weight of these questions, let me say this: It’s not you. It’s them. The system is flawed, and it’s overlooking some of its most valuable players.
Keep showing up. Keep owning your experience. Because your time will come—and when it does, you’ll be ready to lead with the confidence and wisdom that only comes from years of showing up, learning, and delivering results.
Let’s stop questioning whether our experience is a liability and start embracing it for what it is: a game-changing advantage.