Most of the people we work with are approaching retirement, and on paper, they’ve done pretty well for themselves. For years, that meant guiding Baby Boomers into their golden years and helping them navigate a fairly predictable set of retirement planning challenges. But lately, we’re working with more Gen X clients, our peers, and the conversation feels different as we prepare for retirement.
Take Matt, for example. He’s 58, built a successful career in pharmaceutical sales before moving into consulting, and earns a high income. He has a hefty amount of home equity and a solid 401(k). So, by most standards, he’s in good shape. Yet he still feels behind.
And that feeling isn’t unique to Matt. Across the board, Gen X clients come to us having done the right things — working hard, building careers, accumulating assets — and still carrying a low-grade anxiety that something has been missed. The math looks fine; the feeling doesn’t match.
That’s the disconnect we see again and again. Having wealth isn’t the same as having a plan.
This is where today’s retirement planning challenges really come into focus. Gen X is navigating a different reality than the generation before us, one shaped by structural shifts in how retirement works and the weight of competing financial responsibilities. But the good news is that once we understand what’s changed, we can build a plan that actually fits.
Gen X: The Generation That Didn’t Get a Retirement Roadmap
If you’ve felt a disconnect around retirement readiness, you’re not imagining it, and you’re not alone.
Gen X, those born between 1965 and 1980, is approaching retirement at a unique moment. The oldest among us turns 60 in 2025. We’re the generation that remembers cheap concert tickets and life before the internet, grew up somewhere between The Breakfast Club and Reality Bites, and now finds itself closer to retirement than it ever expected. But unlike previous generations, Gen X didn’t get a clear roadmap.
The data backs this up. More than half of Gen Xers (54%) say they don’t believe they’ll be financially prepared for retirement when the time comes. And the emotional weight behind that number is significant, as roughly 70% of Gen Xers say they fear running out of money in retirement more than death itself. [1][2]
That tells us this is more of a planning problem than a math problem.
For years, the financial industry trained people to focus on products — what to buy, what to invest in — without ever stepping back to ask: What is this plan actually built to do? That’s where a Functional Retirement Advisor takes a different approach. You can read more about that in our book, but in a nutshell, rather than leading with products, the focus is on building a written, personalized plan that accounts for both the numbers and the person behind them, based on your goals, your timeline, and your life.
These challenges aren’t reasons to panic. Think of them as reasons to plan.
Because when you move from a collection of financial decisions to a clear, written strategy, that anxiety around retirement readiness starts to shift into something more useful: confidence.
The Sandwich Generation Squeeze
One of the biggest realities shaping retirement planning for Gen X is the sandwich generation squeeze, which many of our clients are living through right now.
Gen X isn’t planning for retirement in a nuclear family vacuum. They’re balancing college tuition for their kids, caregiving responsibilities for aging parents, and their own mortgage or lifestyle expenses — often all at the same time. In 2022, Pew Research found that more than half of Americans in their 40s have a living parent age 65 or older while simultaneously raising or financially supporting their own children. That’s not a niche situation. That’s the majority. [3]
And the financial toll is real. Adult children living at home, rising college costs, and elder care are contributing to increased debt burdens and reduced retirement contributions across the generation. Cash flow gets pulled in three directions at once, and that pressure can quietly erode savings potential over time, even in high-earning households. [4]
This is precisely where retirement planning for Gen X has to go deeper than the numbers.
A Functional Retirement Advisor doesn’t just look at account balances and projections. They take time to understand your full life picture — your family obligations, caregiving demands, career stage, and competing financial priorities. That’s what we call the QUALitative side of planning: getting to know you as a person before talking about the money.
Because when you understand why money is being spent, not just where it’s going, you can build a plan that actually reflects how someone lives.
Advisors who only focus on the numbers can miss the story entirely. But when you bring the qualitative and the quantitative together, the plan you build can be both realistic and sustainable.
The Pension Problem
One of the most significant retirement planning challenges most of Gen X faces is something that was decided for them before many of them ever got their first paycheck.
In the 1970s, pensions, also known as defined benefit plans, began phasing out in the private sector in favor of defined contribution plans, shifting the responsibility of saving for retirement from employers to individuals. By the mid-1990s, when the average Gen Xer was entering the workforce, only about 55% of employees were participating in defined contribution plans. Pensions were fading, but a reliable replacement wasn’t fully in place yet. [5]
Gen X became the first generation where the responsibility and the risk shifted entirely to the individual.
That shift has enormous implications for retirement income planning. With a pension, your employer guaranteed income for life. You didn’t have to worry about how long the money would last, whether inflation would erode it, or what would happen if markets dropped the year you retired. The company carried all of that.
When pensions disappeared, individuals inherited every one of those uncertainties — inflation eating away at purchasing power, longer life expectancies stretching savings further, and a Social Security system that may look different by the time many Gen Xers are ready to claim it.
This is exactly the territory a Functional Retirement Advisor is built to navigate.
We’re not picking investments and hoping for the best. Our job is to help you see the full picture — what could happen, what’s likely to happen, and how to construct a plan that accounts for all of it. That means building income strategies that don’t rely on a single source, planning around healthcare costs and longevity, and making decisions with eyes open rather than fingers crossed.
The safety net is gone, which may feel like a reason to panic. But we recommend thinking of it as no more than a reason to plan with more intention than any previous generation has had to.
The Planning Gap
Another retirement planning challenge for Gen X is simply taking action.
Looking back on their 20s and 30s, more than 90% of Gen X respondents in multiple financial industry studies said they regretted having delayed making financial plans for significant life events, and retirement topped that list. That’s not a knowledge problem but a behavioral one, and it’s at the heart of what behavioral investing experts call a self-defeating pattern: the longer a decision gets deferred, the harder it becomes to start. [6]
This pattern is not limited only to those with limited resources. For high-net-worth Gen X clients, the issue often isn’t a lack of money but a lack of a formal, written plan. About 80% of Gen X retirement plan participants say they aren’t confident they’ll maintain their current standard of living in retirement, and many haven’t taken the foundational step of calculating what they actually need. [7]
The antidote to financial paralysis is a concrete first step. We call it finding “your number,” the lump sum of capital needed at retirement to sustain your income and lifestyle for life. You can read about how to calculate it in our free Retirement Success ebook.
Once you define the target, you can build a plan to reach it.
The Emotional Investing Trap
Another one of the more subtle retirement planning challenges for Gen X is emotional decision-making.
This generation has lived through the dot-com crash, the 2008 financial crisis, and COVID-era volatility. Many Gen Xers feel less clear than Boomers about how market swings, inflation, taxes, and healthcare costs could impact their plans.
That uncertainty can lead to emotional investing.
We’ve seen it time and again: selling at the worst possible moment, chasing trends at the top, or reacting to headlines instead of sticking to a strategy. But research from DALBAR consistently shows that investor behavior, not market performance, is one of the biggest drivers of poor outcomes. [8]
And the media doesn’t help. Fear-driven, hyperbolic financial news is designed to grab attention, not guide long-term decisions.
This is where a Functional Retirement Advisor adds real value. The goal is to help you separate logic from emotion and stay committed to your plan rather than trying to predict the market, especially when it’s hardest.
Because in retirement planning, discipline often matters more than timing.
What These Challenges Actually Teach Us
When you step back, all five of these challenges point to one core truth: wealth alone doesn’t equal retirement readiness; a plan does.
The picture isn’t as bleak as it feels. Gen X has wealth in many pockets: retirement accounts, home equity, businesses, and careers still at or near their peak. But assets without structure are just a collection of good intentions waiting to be organized into something that actually works. [9]
That’s where the right advisor makes all the difference. A Functional Retirement Advisor brings more than investment advice. They bring a process that begins with understanding you as a person before a single investment is discussed. They get to know your goals, your obligations, your timeline, and your definition of a good retirement. From there, everything gets integrated: investments, income strategy, tax planning, and the life decisions that don’t show up on a balance sheet.
There’s a cost to that relationship. But it’s important to understand what you’re actually paying for. Recent Vanguard research found that 86% of advised clients reported greater confidence and less stress than when managing their finances alone. And separately, earlier Vanguard research found that behavioral coaching from a skilled advisor can add up to 1.5% to a client’s long-term performance, simply by helping clients avoid reactive decisions and stay the course when markets get uncomfortable. [10]
Today’s retirement planning challenges aren’t barriers but signals that it’s time to move from a collection of financial decisions to a coordinated, written plan built around your life.
And here’s what we want you to take away: no matter how close you are to retirement, it’s not too late to start planning.
If you’re ready to get some clarity around your own situation, we’d like to invite you to schedule a complimentary 20-minute call. No agenda, no pressure, just a real conversation about where you stand and what’s possible from here.
Sources:
1. https://news.northwesternmutual.com/2025-09-09-Reality-Bites-Gen-X-is-Nearing-Retirement-and-More-than-Half-Dont-Believe-Theyll-be-Financially-Ready-When-the-Time-Comes,-According-to-Northwestern-Mutual-Planning-Progress-Study
2. https://www.investopedia.com/gen-x-fears-running-out-of-money-more-than-death-11723770
3. https://www.pewresearch.org/short-reads/2022/04/08/more-than-half-of-americans-in-their-40s-are-sandwiched-between-an-aging-parent-and-their-own-children/
4. https://www.advisorperspectives.com/articles/2025/08/12/gen-x-retirement-gap-challenges-strategies-solutions
5. https://www.newyorklife.com/articles/gen-x-is-facing-a-retirement-crunch
6. https://www.planadviser.com/drawing-lessons-from-gen-xs-financial-missteps/
7. https://www.planadviser.com/drawing-lessons-from-gen-xs-financial-missteps/
8. https://www.dalbar.com/qaib/
9. https://www.asppa-net.org/news/2025/12/gen-x-and-retirement-gloomy-or-resilient/
10. https://corporate.vanguard.com/content/corporatesite/us/en/corp/articles/greatest-value-financial-advice-peace-mind.html
This material has been prepared in collaboration with Crystal Marketing Solutions, LLC, and has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.