The Overlooked Generation: Why Gen X Feels Stuck (and What to Do About It)

Office Space — Peter Gibbons Leaning Back in His Cubicle

It’s 10:00 pm. The dishes are finally done. Your teenager just yelled at you that you don’t understand anything. You try to shake it off, but you must still send that work email and pick up your mom’s prescriptions. And you still have to go over the talking points for tomorrow’s early meeting. When you are finally in bed, your brain goes haywire, and you ruminate: Is this what I signed up for?

If that hits a nerve, you’re not alone.

This is Generation X's quiet crisis: steady under pressure, invisible in the spotlight, and stretched at every seam.

Born between 1965 and 1980, Gen Xers are rarely front and center in the generational conversation. Boomers marched, took power, and are not relinquishing it. Millennials asked for work-life balance and got it. Gen Z turned content into currency before they had a credit score. But Gen X? We're helping kids navigate identity and screen addiction, managing our parents' care plans, and holding it together on back-to-back Zoom calls. According to a recent Economist article titled "Why Gen X is the real loser generation", our group is caught in a painful middle, facing invisible burdens and underwhelming rewards.

In this post, you’ll find both validation and a way forward. We’ll unpack the cultural and economic headwinds Gen X uniquely faces, explore how our search for freedom came with tradeoffs, and offer a grounded framework, rooted in the Ikigai concept, to move through this chapter with clarity and intention. There is no panacea. Just deep, honest work that honors who you are and what you still want from this life.

The Pressure Gen X Feels

While everyone else is busy debating avocado toast and retirement plans, many of us are quietly living through what economists call the "U-bend of life", a dip in happiness that often hits in your late 40s and early 50s. We’re raising kids, managing aging parents, and questioning whether our careers deliver the meaning we once imagined.

We keep going. Because that’s what we do.

But financially, it’s been a slog. We came of age just as the institutions started cracking. Stable careers turned into constant reorgs. Pensions disappeared. Healthcare got tied to jobs we didn’t love, and jobs got outsourced. We didn’t lose faith in the system; most of us never had the chance to rely on it in the first place. We entered the workforce during economic instability and spent our prime earning years navigating the dot-com bust, the Great Recession, and a volatile housing market. According to The Economist, Gen X saw the smallest real income gains of any modern generation and the first major drop in homeownership rates. Many of us were hit hard by the 2008 crash, losing homes, careers, and years of financial progress.

Reflection: What have I been pushing through that I might need to re-evaluate or release?

The Cost of Choosing Freedom

We grew up letting ourselves in after school and figuring things out independently. Gen X was built on independence, raised on DIY survival, and background noise from MTV. So it’s no surprise we tend to value freedom over structure.

The Economist article highlights how Gen X leans toward autonomy and resists conformity. Many of us opted out of climbing the corporate ladder, and that mindset showed up in films like Fight Club and The Matrix, stories about breaking out and not fitting in.

That same mindset may explain why some of us feel stuck now. When you’ve spent your life avoiding rigid systems, finding footing in them is harder when you need stability. And when the big disruptions hit, a financial crisis, a health scare, those without a safety net are often left scrambling.

Reflection: How can I redefine freedom not as escape, but as intention and alignment?

The Hidden Struggles

And now, just as we begin to imagine some space for ourselves, the ground shifts again, this time with AI. Another disruptive wave. Another system not built with us in mind. For many Gen Xers, AI now threatens the one thing we thought we had left, our experience. First, it was jobs offshored. The offices closed. Now, even our hard-won experience, our wisdom, judgment, and pattern recognition, are being challenged by algorithms. We’re expected to adopt the tools, train others, and stay relevant while still catching up from the last round of disruption.

In my coaching work with Gen Xers navigating midlife transitions, career shifts, caregiving strain, and burnout, I hear the same refrains again and again: “I’ve achieved so much but still feel behind.” “I don’t know what I want, just that this isn’t it.” “I can’t afford to blow everything up, but I also can’t keep going like this.” One client recently joked that we’re the “feral generation” expected to raise kids and lead teams while still figuring ourselves out. There’s truth in that.

• The mortgage was refinanced.

• The college fund that didn’t get built up to what it costs.

• The creative dream that’s still in a box in the attic.

• The ache of feeling behind with no one asking how you’re doing.

Reflection: What story am I telling myself about being “behind,” and what if that story isn’t true?

What You Can Do Now

We weren’t raised with a safety net; we were raised to figure things out as we went. Improvising, adapting, staying afloat, that’s what we’ve always done. And now, that instinct for freedom? It’s not what held us back; it’s what prepares us for what’s next.

If you're at a crossroads, this isn’t about finding your one perfect answer. It’s about building habits that help you evolve again and again. Your next role, project, or pivot is not your final move. It’s a step in a longer, intentional path.

One framework I often turn to with my clients is Ikigai, the Japanese concept of “reason for being.” It helps uncover purpose at the intersection of:

·       What you love

·       What you’re good at

·       What the world needs

·       What you can be paid for

Use it to explore:

·       Redefining success: Aligning with what you value, not what you inherited

·       Auditing your energy: Noticing what fuels you versus what depletes you

·       Reconnecting with meaning: Finding where your strengths meet real needs

·       Designing for sustainability: Creating a life that adapts with you, not around you

Prefer a simpler approach? Ask yourself:

·       What do I want more of in this next chapter?

·       What have I been tolerating for too long?

·       What am I ready to claim that I’ve been avoiding?

Let your answers guide how you define success, not just for this moment, but for the long road ahead.

Try This Today: Ask yourself:

·       What’s one thing I’m doing just because I always have?

·       What’s one small risk I could take in service of something I actually want?

Midlife isn’t a crisis. It’s a recalibration.

As the article notes, the deck may have been stacked against us economically and culturally. But the story isn’t over. This chapter can be one of the most meaningful if we choose to write it with intention.

You already know how to push through, but you may not know how to build something that reflects who you’ve become.

You’ve earned the right to stop proving and start choosing. And the next time it’s 10:00 pm and you’re running on fumes, pause. Not to escape—but to ask yourself what kind of life you still want to build.

It won’t be perfect. But it can be yours.

The challenge now? Trusting that what you want isn’t indulgent. Its direction.