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Will My Money Last? The One Question That Matters Most

Forget the noise about stocks, bonds, and asset allocation for a moment. Every retirement planning question boils down to one simple concern: will your money last as long as you do?
January 22, 2026
50 min read
retirement planning
retirement savings
financial security
retirement income
Will My Money Last? The One Question That Matters Most

You've probably spent hours scrolling through retirement articles. Should you go 60/40 or 70/30 on your portfolio? What about international exposure? Is 4% still the right withdrawal rate? Before you know it, you're drowning in details, paralyzed by options, and no closer to feeling confident about your future.

Here's the truth: all of those questions are just different ways of asking one thing. Will my money last in retirement?

That's it. That's the question. Everything else is just math we use to answer it.

Once you realize this, retirement planning becomes dramatically simpler. Not easy, but simpler. Instead of juggling a thousand variables, you're solving for one clear outcome. And that changes everything.

Why This Question Gets Buried Under Jargon

The financial services industry has done a spectacular job of making retirement planning feel impossibly complex. You need to understand target-date funds, rebalancing strategies, tax-loss harvesting, required minimum distributions, and about fifty other concepts that sound like they require a graduate degree.

But here's what they don't often tell you: all of those tools exist to serve one purpose. Making sure you don't run out of money before you run out of life.

Think about it. Why do we care about investment returns? Because higher returns mean your money lasts longer. Why do we worry about fees? Because lower fees mean your money lasts longer. Why do we optimize for taxes? You guessed it. So your money lasts longer.

When you strip away the complexity, retirement planning isn't about maximizing wealth or beating the market. It's about ensuring you can pay for groceries, keep the lights on, and maintain your dignity for 20, 30, or even 40 years after you stop working.

That's not just a financial question. It's a human one.

The Three Numbers That Answer the Question

Once you accept that 'will my money last?' is the only question that matters, answering it becomes surprisingly straightforward. You need three numbers:

1. How much money you'll have when you retire

This includes everything: your 401(k), IRA, taxable brokerage accounts, that old savings bond from your grandma, and any other assets you can actually spend. Don't forget to account for what you'll still contribute between now and retirement. If you're 52 and planning to retire at 65, those 13 years of contributions matter enormously.

For most Americans in their 50s and early 60s, this is heavily weighted toward employer-sponsored retirement accounts like 401(k)s. The 2024 contribution limit is $23,000 (or $30,500 if you're 50 or older), which means you can still build significant savings even if you're starting late.

2. How much money you'll spend each year

This is where most people get tripped up. You might think you'll spend less in retirement, but healthcare costs, travel, and helping kids or grandkids can surprise you. A realistic estimate beats an optimistic guess every single time.

Don't forget that your spending will likely change over time. Many retirees find their 60s more expensive (travel, activities, new hobbies) while their 80s tend to be quieter. Healthcare, though, typically increases throughout retirement, especially once you factor in potential long-term care needs.

3. How long you'll need the money to last

Nobody knows exactly how long they'll live, but we can make educated guesses. A 65-year-old man today can expect to live to about 84. A 65-year-old woman? Around 87. But those are averages. There's a decent chance you'll live well into your 90s, and planning for 30+ years of retirement isn't paranoid. It's prudent.

What Complicates the Answer (And How to Handle It)

If retirement planning were just simple division (total savings divided by years of retirement), we'd all be set. Unfortunately, a few factors complicate things:

Inflation slowly erodes your purchasing power

That $4,000 monthly budget might feel comfortable today, but in 20 years, inflation could make it feel like $2,500. Even at a modest 3% annual inflation rate, your money loses about half its purchasing power over 24 years. This is why your investments need to grow during retirement, not just sit in a savings account.

Investment returns are unpredictable

You might average 7% over 30 years, but what if you retire right before a market crash? Withdrawing money during a downturn can devastate a portfolio. This is called sequence of returns risk, and it's why the first five years of retirement are so critical.

Social Security helps, but it's not enough

The average Social Security benefit in 2024 is about $1,907 per month. That's $22,884 a year. It helps, absolutely, but it probably won't cover your full retirement lifestyle. And you need to decide when to claim it. Taking benefits at 62 means smaller checks for life. Waiting until 70 means larger checks, but you need other income to bridge that gap.

Taxes don't stop in retirement

Your 401(k) withdrawals? Taxed as ordinary income. Social Security? Up to 85% can be taxable depending on your total income. Investment gains in taxable accounts? Subject to capital gains taxes. This is why Roth accounts are so valuable. You've already paid taxes on Roth contributions, so qualified withdrawals are completely tax-free.

Healthcare is expensive and unpredictable

Medicare starts at 65, but it doesn't cover everything. Fidelity estimates that the average couple retiring at 65 will need about $315,000 to cover healthcare costs in retirement. That doesn't even include potential long-term care, which can run $100,000+ per year for nursing home care.

The question isn't whether you'll face financial challenges in retirement. The question is whether you'll have a plan flexible enough to handle them.

fidser. Financial Planning Team

How to Actually Know If Your Money Will Last

So how do you get a real answer? You run the numbers. Not once, but repeatedly, testing different scenarios.

Start with the basics

Calculate your expected savings at retirement, estimate your annual spending, and project how long you'll need that money to last. Include Social Security (check your estimated benefits at ssa.gov) and any pensions you might have.

Test different scenarios

What if the market crashes the year you retire? What if you live to 95 instead of 85? What if healthcare costs spike? What if you help your kids with a down payment? Running multiple scenarios gives you a range of outcomes, not just one optimistic projection.

Adjust your plan based on what you learn

If the numbers show you'll run out of money at 82, you have options. You can save more now. You can plan to work a few years longer. You can adjust your expected retirement spending. You can optimize your investment strategy for growth. You can maximize Social Security by delaying benefits.

The power isn't in getting a perfect answer. It's in knowing where you stand so you can make informed decisions.

The Peace That Comes From Knowing

Here's what's interesting: once you get a realistic answer to 'will my money last?', two things happen.

First, if the answer is yes, you stop worrying about every market fluctuation. You stop second-guessing every financial decision. You have a plan, you've tested it, and you can live your life with confidence.

Second, if the answer is no or maybe, you stop feeling helpless. You have specific problems to solve, which is infinitely better than vague anxiety about the future. Maybe you need to increase your 401(k) contributions by 3%. Maybe you need to work until 67 instead of 65. Maybe you need to have an honest conversation about downsizing your home.

None of these are fun realizations, but they're actionable. And actionable beats paralyzing every single time.

The Americans who feel most confident about retirement aren't the ones with the most money. They're the ones who have honestly answered the question: will my money last? And they've built a plan around that answer.

Your Next Steps

Forget about trying to master every aspect of retirement planning. Instead, focus on getting a solid answer to the one question that matters:

  • Calculate your current retirement savings across all accounts
  • Project what those savings will grow to by your target retirement age
  • Estimate your annual retirement expenses realistically
  • Include Social Security and any pension benefits
  • Factor in inflation, taxes, and healthcare costs
  • Run multiple scenarios to test your plan's resilience

If you're married, remember that retirement planning is a joint endeavor. You're planning for two lifetimes, two healthcare journeys, and potentially one person managing alone after the other passes. Those realities need to be part of your plan.

And here's something important: this isn't a one-time calculation. Your answer will change as your life changes. You might get an inheritance. You might face unexpected medical bills. The market might soar or crash. Plan to revisit this question every year or two, adjusting your strategy as needed.

Disclaimer: This article is for informational purposes only and does not constitute financial advice. fidser. is not a certified financial planning firm. Always consult with a qualified financial advisor or planner before making any financial decisions regarding your retirement.

Frequently Asked Questions

How much money do I need to retire so I don't outlive my savings?
There's no universal number because it depends on your expected annual expenses, how long you'll live, and other income sources like Social Security. A common guideline is the 4% rule: if you withdraw 4% of your savings in the first year and adjust for inflation after that, your money should last 30 years. So if you need $40,000 annually beyond Social Security, you'd need about $1 million saved. However, this is just a starting point. Your actual needs depend on your health, lifestyle, location, and family situation. Running personalized projections based on your specific circumstances gives you a much more accurate answer.
What's the biggest risk to my retirement money running out?
For most Americans, it's a combination of three factors: living longer than expected (longevity risk), experiencing poor investment returns early in retirement (sequence of returns risk), and unexpected healthcare costs, especially long-term care. A market crash in your first few years of retirement can be devastating because you're withdrawing money when account values are down, locking in losses. Healthcare costs averaging over $300,000 per couple in retirement can also drain savings faster than planned. The key is building flexibility into your plan, maintaining some growth in your portfolio throughout retirement, and having contingency strategies for these scenarios.
Should I be more conservative with my investments as I approach retirement?
It depends on your timeline and personal situation, but most people do shift toward more conservative allocations as retirement approaches. The traditional approach is to gradually reduce stock exposure and increase bonds as you get older. However, with retirements potentially lasting 30+ years, staying too conservative can be risky too. You need some growth to outpace inflation. A common strategy is to keep enough in safe, liquid investments (bonds, money market funds) to cover 3-5 years of expenses, while maintaining growth investments for the longer term. This gives you stability for near-term needs while still growing wealth for later years. The right balance depends on your specific timeline, risk tolerance, and other income sources.

Ready to Answer Your Biggest Retirement Question?

Use our free retirement calculator to find out if your money will last. Get personalized projections in minutes, no financial degree required.

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fidser.By fidser.
Published January 22, 2026

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