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17 Subtle Signs You’re Headed for Financial Trouble in Retirement

Updated on September 15, 2025 by TMM Staff · Lifestyle

A man holding an empty wallet
©Yunus Tuğ/Unsplash.com

Retirement doesn’t usually fall apart in one big crash–it unravels slowly through small habits, overlooked details, and financial blind spots that creep up over time. Many people imagine financial trouble in retirement as something obvious, like not being able to pay the bills or running out of money completely. But the warning signs show up long before that point. The challenge is that these signs often disguise themselves as “normal” spending patterns, assumptions, or lifestyle choices.

The good news? If you spot the red flags early, you can still course-correct and strengthen your financial foundation before it’s too late. Below are 17 subtle but powerful signals that your retirement security could be at risk–and practical ways to get ahead of them.

Table of Contents

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  • 1. You’re Still Carrying High-Interest Debt
  • 2. You Haven’t Run the Numbers on Your Retirement Needs
  • 3. Your Savings Rate Hasn’t Changed in Years
  • 4. You Depend Heavily on Social Security
  • 5. Your Emergency Fund Is Weak (or Nonexistent)
  • 6. You’re Still Supporting Adult Children Financially
  • 7. Your Investments Are Too Conservative
  • 8. You Haven’t Planned for Healthcare Costs
  • 9. You Don’t Have a Clear Withdrawal Strategy
  • 10. You’re Banking on Downsizing as Your Safety Net
  • 11. You Haven’t Factored Inflation Into Your Plans
  • 12. You Haven’t Updated Your Budget in Years
  • 13. You’re Ignoring Tax Efficiency
  • 14. You’re Counting on Working Forever
  • 15. You Don’t Have Long-Term Care Plans
  • 16. You’re Overestimating Investment Returns
  • 17. You Haven’t Talked About Finances with Your Partner

1. You’re Still Carrying High-Interest Debt

©Towfiqu barbhuiya/Unsplash.com

If credit cards, payday loans, or even car loans are still weighing you down, it’s a sign your retirement savings will be stretched too thin. High-interest debt compounds quickly, and the money you spend servicing it is money that could be building your retirement cushion. Instead of pushing debt into retirement, prioritize aggressive repayment now. Consider strategies like the avalanche method (tackling the highest-interest debt first) or consolidating into lower-interest options. Being debt-free by retirement isn’t just a relief–it’s a necessity.

2. You Haven’t Run the Numbers on Your Retirement Needs

©Getty Images/Unsplash.com

Many people go into retirement with only a rough idea of what they’ll need, often underestimating expenses. Healthcare costs, inflation, and lifestyle expectations tend to push expenses higher than you think. If you haven’t sat down and run realistic projections–using tools, spreadsheets, or a financial planner–you’re essentially flying blind. Knowing your “number” helps you set clear savings goals and make smarter trade-offs today.

3. Your Savings Rate Hasn’t Changed in Years

A piggy bank and some coins
©Andre Taissin/Unsplash.com

If you’ve been contributing the same fixed percentage or dollar amount to your retirement accounts for years, you’re likely behind. Inflation alone makes that strategy unsustainable. As your income grows, your savings rate should too. A good rule of thumb is to gradually increase your contributions–aiming for 15–20% of your income. Even small percentage bumps every year can make a massive difference in your nest egg over time.

4. You Depend Heavily on Social Security

Paper with the words “social security” typewritten on it
©Markus Winkler/Unsplash.com

Relying solely on Social Security is one of the biggest red flags. The average monthly benefit doesn’t come close to covering a comfortable retirement. Treat Social Security as a supplement, not your primary lifeline. Start building multiple income streams–whether through retirement accounts, part-time work, or investments–so you’re not stuck living only on government checks.

5. Your Emergency Fund Is Weak (or Nonexistent)

The word “emergency” surrounded by pills
©A. C./Unsplash.com

Without a strong emergency fund, unexpected expenses–like car repairs, medical bills, or family emergencies–end up draining your retirement savings. Aim for 6–12 months’ worth of expenses in a liquid account. This protects your long-term funds from being tapped prematurely and ensures your investments stay invested, growing instead of being withdrawn at the worst possible time.

6. You’re Still Supporting Adult Children Financially

A father talking to his adult son
©Getty Images/Unsplash.com

Helping your kids might feel natural, but it can quietly erode your retirement security. Many retirees spend thousands each year on their adult children–covering rent, tuition, or bailouts for financial mistakes. While occasional help is fine, making it a long-term commitment can drain your nest egg. Set boundaries early and encourage independence. Your children can always borrow money; you can’t borrow for retirement.

7. Your Investments Are Too Conservative

A 3D rendering illustrating the stock market
©Getty Images/Unsplash.com

Fear of risk often pushes people into overly conservative portfolios, like CDs, bonds, or just keeping money in cash. The problem is, these don’t outpace inflation over decades. Without some exposure to stocks or growth investments, your savings will lose purchasing power. Even in retirement, a balanced mix of growth and stability is key to making your money last.

8. You Haven’t Planned for Healthcare Costs

A graphic illustrating the concept of healthcare
©Galina Nelyubova/Unsplash.com

Medical expenses are one of the biggest retirement budget busters, yet many people leave them out of their planning. Medicare doesn’t cover everything, and long-term care is notoriously expensive. Building in a buffer for healthcare–through HSAs, supplemental insurance, or specific investment accounts–keeps those costs from derailing your financial security.

9. You Don’t Have a Clear Withdrawal Strategy

A woman using an ATM
©Kateryna Hliznitsova/Unsplash.com

It’s not enough to have savings; you need a plan for how to use them. Without a structured withdrawal strategy, retirees often take out too much too soon, leaving themselves vulnerable later in life. Following a sustainable model, like the 4% rule (adjusted for inflation), can keep your funds intact for decades. Working with a planner to customize your strategy is even better.

10. You’re Banking on Downsizing as Your Safety Net

A real estate sign saying “sold”
©Getty Images/Unsplash.com

Many people assume they’ll sell their house and live off the proceeds if money runs low. But housing markets are unpredictable, and downsizing doesn’t always free up as much cash as you think. Plus, moving costs, taxes, and emotional factors make it harder than expected. Treat downsizing as an option, not a guarantee, and build retirement savings independently of your home equity.

11. You Haven’t Factored Inflation Into Your Plans

A graphic illustrating the concept of inflation
©Katelyn Perry/Unsplash.com

Inflation is a silent wealth-killer. What feels like plenty of money today won’t stretch nearly as far in 15 or 20 years. If your retirement plan doesn’t account for rising costs of food, healthcare, and housing, you’ll feel the pinch sooner than you think. Favor investments and strategies that historically outpace inflation, rather than relying on fixed-income streams alone.

12. You Haven’t Updated Your Budget in Years

A person using a calculator and a pencil
©Getty Images/Unsplash.com

Budgets aren’t “set it and forget it.” If you’re using numbers from a decade ago–or not budgeting at all–you’re likely underestimating expenses and overestimating how far your savings will go. Review and adjust your budget annually, factoring in lifestyle changes, rising costs, and retirement goals. A living, flexible budget keeps you grounded in financial reality.

13. You’re Ignoring Tax Efficiency

A person fixing their taxes
©Behnam Norouzi/Unsplash.com

Taxes don’t magically disappear when you retire. In fact, withdrawals from traditional retirement accounts are taxable, and poorly timed distributions can trigger higher brackets. If you’re not planning for taxes–by diversifying account types (Roth, traditional, taxable) or timing withdrawals–you may lose more of your nest egg to the IRS than necessary. A smart tax strategy keeps more of your money working for you.

14. You’re Counting on Working Forever

A senior man working in the office
©Getty Images/Unsplash.com

It’s common to assume you’ll work well into your 70s, whether because you love your job or need the income. But illness, layoffs, or caregiving responsibilities often cut those plans short. Counting on indefinite work is a gamble. Instead, build retirement savings with the assumption you’ll stop working earlier than expected–anything beyond that is a bonus.

15. You Don’t Have Long-Term Care Plans

An older woman at an assisted living facility
©Getty Images/Unsplash.com

Needing long-term care isn’t rare–it’s increasingly the norm. Yet many retirees avoid thinking about it until it’s too late. Without a plan, the costs can wipe out your savings and even force family members into financial strain. Explore options early, whether that’s long-term care insurance, hybrid life policies, or setting aside specific funds for future needs.

16. You’re Overestimating Investment Returns

A photo illustrating the idea of investment growth
©Getty Images/Unsplash.com

Projecting overly rosy returns is a subtle but dangerous mistake. Many people assume their portfolios will keep growing at 8–10% annually, but markets don’t work that way. Planning with conservative return estimates–closer to 4–6%–prevents unpleasant surprises. If you end up with higher returns, great. If not, your plan still holds.

17. You Haven’t Talked About Finances with Your Partner

A couple looking at their bills
©Getty Images/Unsplash.com

Money silence in a relationship can create big problems in retirement. If you and your partner haven’t aligned on spending, saving, or even retirement goals, it’s easy to end up pulling in opposite directions. Schedule open, regular money conversations–covering budgets, healthcare, inheritance, and lifestyle expectations. Alignment now avoids painful surprises later.

Lifestyle

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About TMM Staff

The Modest Man staff writers are experts in men's lifestyle who love teaching guys how to live their best lives.

If an article is published under TMM Staff, that means multiple writers worked on it. For example, sometimes several of us have experience with a certain brand, so we collaborate to publish a more thorough review.

Or, if an article was originally written by one person, but then it was updated by someone else, we'll re-publish it under TMM Staff.

Remember: all of our articles (including those below) are written by real people with decades of combined experience in men's fashion and lifestyle topics.

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