Most professionals I meet in their 50s and 60s have done the hard part. They’ve earned, saved, and invested for 30-plus years. Somewhere around 55 or 60, they look up and realize that the retirement they’ve been saving for is right around the corner.
That’s when they start wondering: Am I actually ready? Am I doing all the right things?
I’d love for people to come to me sooner, but the truth is, a lot of my first meetings happen right at this point. The good news is, this stage of life is still prime time for retirement planning.
Saving Isn’t the Same as Planning
One thing that still surprises me after decades in this industry is how often I talk to people who assume saving and planning are the same thing. But in fairness, it’s an easy mistake to make.
Take Matt and Molly—not their real names, but their story is real. At 59, they had good incomes, a paid-off home, and a healthy 401(k). By most measures, they looked ready for retirement.
But in our first conversation, one thing became clear: they had saved diligently for decades without ever building an actual plan. That’s a distinction I see all the time with high earners. You contribute consistently, avoid big mistakes, build real wealth, and then one day you realize no one has ever connected the dots between your accounts and how you’ll use them in your actual life.
If you’ve spent years contributing to your 401(k), investing consistently, and avoiding major financial mistakes, it’s natural to feel like you’ve been “planning” for retirement all along. But many people have missed a step, not because they were irresponsible, but because no one ever explained the difference clearly.
Saving is putting money away. Planning is understanding things like whether it’s enough, when you can realistically retire, how your retirement income will work once paychecks stop, how taxes may affect withdrawals, and how to make your assets last through a retirement that could span decades.
A recent study from the Employee Benefit Research Institute found that 46% of retirees in 2025 left the workforce earlier than planned, often due to health issues, caregiving responsibilities, or corporate restructuring. Involuntary factors accounted for more than three-quarters of early retirements. The old “I’ll just work a few more years if I need to” approach is far less reliable than people assume. [1]
This matters especially for Gen X. The oldest Gen Xers are now in their 60s; the youngest are in their mid-40s. According to the National Institute on Retirement Security, a large percentage of Gen X households have very little saved for retirement at all. If you’ve consistently saved and built assets, you are already more prepared than many of your peers. [2]
In my book, Retirement Success, I draw an important distinction between a product and a plan. Most people own financial products: 401(k)s, IRAs, brokerage accounts, and insurance policies. But those products aren’t a retirement strategy on their own. A Functional Retirement Advisor starts with your life first (your goals, your family, your concerns, your vision for what’s next) and builds a coordinated plan around it. Even at 55, 58, or 62, getting serious about that process now can make a significant difference.
Why Smart People Put Off Retirement Planning
For most people in this stage of life, waiting has nothing to do with laziness. It’s usually some combination of being busy, assuming things are probably fine, and not knowing exactly where to start. You build a career, raise a family, manage a household, and contribute to your accounts along the way. Then retirement gets close, and the decisions ahead start to feel complicated.
That’s because they are. Social Security timing, healthcare costs, tax strategy, withdrawal sequencing, income planning. These are real questions, and they interact with each other in ways that aren’t obvious.
Ironically, the stress this creates often becomes the very thing preventing people from seeking help. A recent Northwestern Mutual study found that 35% of Gen Xers say financial uncertainty keeps them up at night at least once a month, yet only about one-third currently work with a financial advisor. [3]
The problem is that procrastination is a self-defeating pattern. Avoiding the issue may create short-term comfort, but it often leads to long-term costs.
And the solution isn’t trying to solve your entire retirement overnight. It’s taking one concrete step at a time. A Functional Retirement Advisor helps simplify the process so the planning starts feeling manageable instead of overwhelming. You don’t need every answer before you begin. You just need to begin.
What Happens Without a Plan
Without a formal retirement plan, some of the biggest financial decisions of your life get made by default instead of by design.
Questions like when to take Social Security, which accounts to draw from first, how much you can safely spend in the first few years of retirement, and how to manage taxes may get answered reactively, one decision at a time, without anyone looking at how each choice affects the others.
That matters because the margin for error narrows once you stop earning a paycheck. And for high earners, the stakes are higher. More assets often mean more complexity, greater tax exposure, and more places where uncoordinated decisions can cost you over time.
Look at Matt and Molly again. On paper, they were in great shape. But once we started planning, they realized they’d never actually talked about how retirement income would work. Matt assumed they’d delay Social Security until 70. Molly planned to claim earlier. Most of their savings sat in tax-deferred accounts, which set up a larger future tax bill than either of them realized. And neither had accounted for how healthcare costs and inflation would affect spending over a retirement that could last 30 years or longer.
A Functional Retirement Advisor provides more than investment management. We provide clarity, insight, behavioral guidance, and an ongoing partnership designed to help you avoid costly emotional and strategic mistakes over time. Research from Vanguard and others, which I cover in detail in the book, has shown that disciplined planning and behavioral coaching can considerably improve long-term outcomes.
Your 50s and Early 60s Are Still Prime Time
Here’s the part most people overlook: this stage of life isn’t just about catching up. In a lot of ways, your 50s and early 60s are when retirement planning has the most leverage.
For most professionals, these are peak earning years. Mortgages are further along. Children are more independent. Income has grown after decades of career growth. Used intentionally, this window can accelerate retirement readiness in ways that earlier years simply couldn’t.
That’s exactly what happened with Matt and Molly. Once they stopped looking backward at what they “should have done sooner” and started focusing on what was still possible, the whole conversation changed. They had time to make strategic decisions that could improve the quality and flexibility of their retirement for decades.
Today’s IRS rules also create opportunities for late-stage savers. Workers age 50 and older can make significant catch-up contributions to retirement accounts, and SECURE 2.0 expanded those limits even further for many people in their early 60s. But contributions alone are not the strategy. The real impact comes from decisions around Social Security timing, Roth conversions, tax planning, investment behavior, and withdrawal sequencing over the next 5–10 years. [4]
My first job as a Functional Retirement Advisor isn’t to judge the past. It’s to calculate where you actually stand today. In my book, I call this “Your Number,” the lump sum needed to sustainably generate the retirement income your lifestyle requires.
Once you know your number, you can identify the gap, if there is one, and build a realistic plan forward. That kind of clarity changes everything, because retirement planning stops being abstract and starts being actionable.
What Working With a Professional Actually Looks Like
A lot of people put off working with an advisor because they don’t know what the process looks like. They assume the conversation will feel like a sales pitch. Or they worry about being judged for not having everything perfectly organized. None of that should be true. A good retirement planning relationship feels very different.
A Functional Retirement Advisor starts by getting to know you as a person before discussing products, investments, or strategies. The first conversation is usually centered around questions like: What does retirement look like to you? What concerns you most? What kind of lifestyle do you want to protect? What are you trying to accomplish for your family?
Only after those answers come into focus should the technical planning begin.
That’s important because the questions keeping most pre-retirees awake at night aren’t product questions. They’re questions like: Do we actually have enough? When can we retire? What happens if the market drops right after we stop working? How do we turn savings into income without making costly mistakes?
Trust and empathy are non-negotiable in this kind of relationship. A good advisor listens more than they talk, explains things clearly, and starts with a plan rather than a product pitch. Red flags include advisors who immediately tout performance, promise unrealistic returns, drown you in jargon, or spend the entire meeting talking about themselves.
Finding the right fit is less intimidating than most people expect. You want clarity, partnership, and someone who genuinely understands both your financial situation and your life.
The Best Time to Start Is Now
You don’t need to have every answer, or even know what questions to ask, before starting the conversation. A complimentary 20-minute call can help you understand where you stand today, what opportunities still exist, and what retirement could realistically look like from here.
Sources:
1. https://www.thestreet.com/retirement/retirement-planning-cant-protect-you-from-the-most-common-exit
2. https://www.nirsonline.org/articles/new-report-finds-alarming-retirement-outlook-for-generation-x-3/
3. 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
https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-catch-up-contributions
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