“Maybe One More Year”: The Retirement Question Many People Face
Prepared by the Investment & Insurance Planning Services, LLC Team
David J. Blount, CFP® | Rohan Rashid, CFP® | Kat Almonte, CSM
"Maybe one more year."
It's a phrase we've heard from many people approaching retirement.
Often, it isn’t because they want to keep working. They’ve spent decades saving, investing, paying down debt, and preparing for this moment.
Yet when retirement finally becomes real, a different question takes over:
“Do I really have enough to retire and how do I know my money will last?”
For many people, that question can quickly lead to others:
What happens if the market declines shortly after I retire?
How will I replace my paycheck with reliable retirement income?
When should I claim Social Security?
What will healthcare cost?
How should I withdraw money from my accounts?
How will taxes affect my retirement income?
And perhaps the biggest question of all: Would working just one more year make a meaningful difference?
These aren't simply investment questions. They're life questions! Retirement isn't just about leaving a job. It's about feeling confident enough to begin a new chapter.
Can I afford to retire with confidence and am I ready to start living the retirement I’ve worked so hard to achieve?
Why This Decision Feels So Difficult
The Story of Tom and Linda
Consider Tom and Linda, a fictional couple whose story reflects conversations we've had with many families over the years.
Like so many people approaching retirement, they had done what they believed were all the right things. They consistently contributed to retirement accounts, lived within their means, paid down debt, and built a solid financial foundation.
By most measures, they appeared ready to retire.
But every time the subject came up, the conversation ended the same way.
"Maybe one more year."
One year became two. Then two became three.
The issue wasn't necessarily a lack of savings.
It was uncertainty.
After receiving a paycheck for most of their adult lives, the thought of relying on Social Security, retirement savings, and investments instead felt like a major leap. Questions about market volatility, healthcare costs, taxes, and whether their money would last made postponing retirement feel like the safer choice.
If you've ever felt that way, you're certainly not alone.
Working another year can certainly strengthen a retirement plan. It may allow you to save more, delay withdrawals, or increase future Social Security benefits.
Many people describe retirement as unfolding in three stages: the go-go years, the slow-go years, and the no-go years. While everyone's experience is different, the go-go years are often when retirees have the health and energy to travel, spend time with family, pursue hobbies, volunteer, and enjoy the flexibility they've worked so hard to achieve. As time passes, health concerns or mobility limitations may naturally change how retirement looks.
That doesn't mean retiring sooner is always the right answer. For some, continuing to work is financially necessary. Others genuinely enjoy their careers and choose to keep working.
But if uncertainty is the primary reason you're delaying retirement, it may be worth asking a different question.
Instead of asking,
"Would I have more money if I worked another year?"
consider asking,
"Would working another year improve my financial security enough to make postponing retirement worthwhile?"
That's often the conversation that brings greater clarity.
Retirement Changes the Financial Questions
Tom and Linda's experience illustrates something we've seen many times. Delaying retirement isn't always about finances. Often, it's about uncertainty.
During your working years, financial planning is largely about accumulation.
You earn, save, invest, reduce debt, and build wealth.
As retirement approaches, the focus begins to shift.
Instead of asking, "How much have I accumulated?", the question becomes:
"How do I turn what I've accumulated into reliable income that supports the life I want?"
That's where retirement planning becomes more than investment management.
Your investment portfolio remains important, but it now works alongside Social Security, retirement accounts, taxes, healthcare expenses, cash reserves, and a thoughtful withdrawal strategy. Each decision can affect the others, which is why retirement planning is often less about finding one perfect answer and more about coordinating many moving pieces into a strategy that fits your goals.
Turning Questions into Decisions
For Tom and Linda, the breakthrough didn't come from discovering a magical retirement number.
It came from understanding their options.
Imagine sitting down with a financial planner and looking beyond your account balances to the life those savings are meant to support.
What income will you need once your paycheck stops?
How will Social Security, pensions, and retirement savings work together?
How might taxes affect your withdrawals?
What happens if the market experiences a difficult year early in retirement?
Would retiring this year look significantly different from working one more year?
No financial plan can eliminate uncertainty or guarantee future results. Markets change. Tax laws change. Life changes.
But thoughtful planning can help replace uncertainty with perspective, allowing you to make informed decisions based on your own goals, priorities, and circumstances.
Every Retirement Is Different
One of the greatest lessons we've learned after working with families for decades is that no two retirements are exactly alike.
Some people retire earlier than expected. Others continue working because they truly enjoy what they do.
Some dream of traveling the world. Others look forward to spending more time with grandchildren, volunteering, pursuing hobbies, or simply enjoying a slower pace of life.
That's why retirement planning isn't about reaching a single account balance or comparing yourself to someone else's situation.
It's about creating a strategy that connects your financial resources with the life you want to live.
If You're Asking, "Maybe One More Year"...
If you've found yourself saying, "Maybe one more year," you're certainly not alone.
A personalized retirement analysis can help you see what retirement could look like now versus one year from now, including your income needs, Social Security, investments, taxes, and other factors that may influence your decision.
A conversation doesn't mean you're committing to retire tomorrow. It simply gives you an opportunity to understand your options and make a decision with greater confidence.
For many people, retirement isn't delayed because they haven't worked hard enough or saved enough. It's delayed because they want confidence that they're making the right decision.
A thoughtful retirement plan can't predict the future, but it can help you understand your options, evaluate important trade-offs, and determine whether retiring now, or working another year, better aligns with your goals.
After all, you've spent decades preparing for retirement. At some point, the question becomes not just whether you can retire, but whether you're ready to begin enjoying what you've worked so hard to build.
If you're wondering whether now is the right time, we'd be happy to have that conversation with you.
Together, we can review your financial picture, discuss your retirement goals, and help you evaluate what the next chapter could look like so you can move forward with a plan built around your goals, your family, and the future you've worked so hard to create.
Because retirement isn't simply about leaving work. It's about having the confidence to know you're ready for what comes next.
Frequently Asked Questions
How do I know if I have enough money to retire?
There isn't one retirement number that works for everyone. Your retirement readiness depends on factors such as your expected spending, income sources, investments, taxes, healthcare costs, and the lifestyle you hope to enjoy. Looking at these pieces together often provides a clearer picture than focusing on an account balance alone.
Is working one more year always the better financial decision?
Not necessarily. Another year of earnings and savings can strengthen some retirement plans, but the impact varies from person to person. Comparing different retirement scenarios can help you understand whether working longer meaningfully improves your financial outlook.
What should I consider before retiring?
Some of the most important considerations include your retirement income strategy, Social Security timing, healthcare expenses, taxes, investment allocation, and how much you expect to spend in retirement. Evaluating these factors together can help you make more informed decisions.
When should I begin retirement planning?
Ideally, retirement planning should begin several years before your planned retirement date. Starting early gives you more opportunities to evaluate different strategies and make adjustments while you're still working.
This material is provided for general informational and educational purposes only and is not intended as individualized investment, tax, or legal advice. Individual circumstances vary. Consult the appropriate financial, tax, and legal professionals regarding your specific situation.
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