How to Build a Retirement Plan That Works No Matter What the Economy Does

August 14, 2025

We’re all feeling it these days: the underlying feeling of uncertainty about what lies ahead. Each day, we see headlines about inflation, Social Security’s future, or market swings. Unsurprisingly, Gallup tells us that the top three American fears have to do with money: the economy, availability/affordability of healthcare, and inflation. 


If you’re in your 50s and 60s, these concerns probably hit even closer to home. You’re not just thinking about the economy in general terms. You’re wondering how it will affect your specific retirement plans. Your mind likely turns to: 


  • Increasing healthcare costs – can you absorb unexpected costs on a fixed income?
  • Inflation and market volatility – will the value of the dollar diminish your retirement savings?
  • Social Security uncertainty – will it exist when you retire?
  • Having enough saved – will your retirement budget hold up when the time comes?


About 1 in 4 Americans over 50 are delaying retirement, and it’s not hard to understand why. 


With thoughtful planning and the right strategies, you can build confidence in your ability to maintain your lifestyle on a fixed income, regardless of what economic curveballs come your way.


5 Key Strategies to Prepare for Living on a Fixed Income


Uncertainty doesn’t have to derail your retirement plans. By addressing these five critical areas, you can build a foundation that allows you to enjoy the retirement you’ve worked toward. 


1. Review (And Potentially Adjust) Your Retirement Timeline


One of the most powerful tools you have is flexibility with your retirement timeline. While certain ages qualify you for benefits or withdrawals from certain accounts, there’s no concrete age you have to retire at.


Traditional retirement at 62 or 65 might not make sense for your unique situation; you should feel free to alter your timeline to make sense for you and your family.


Consider Your Social Security Strategy 


Your Social Security benefits increase each year you delay claiming them beyond your full retirement age, up until age 70. For many people, this creates a meaningful boost to their guaranteed monthly income. If you can afford to wait, this strategy alone can significantly strengthen your fixed-income foundation.


Explore Phased Retirement Options


Rather than going from full-time work to complete retirement overnight, consider a gradual or phased transition. Many of our clients find success with:


  • Part-time consulting in their field of expertise
  • Freelance work that leverages their skills
  • Small business ventures they've always wanted to try
  • Investment properties that generate passive income


This approach not only eases the financial transition but often provides a sense of purpose and engagement during early retirement. 


2. Fine-Tune Your Investment Mix and Retirement Income Strategy 


Adjusting your portfolio is an ongoing responsibility, not a one-time task before retirement. Continue to revisit and rebalance as a proactive part of your retirement plan. Equally important is creating multiple income streams to reduce your reliance on any single source.


Diversify Your Retirement Income Sources


Think of building several income bridges instead of relying on one massive one. Your retirement income might come from Social Security, traditional retirement accounts (401(k), IRA), Roth accounts for tax-free withdrawals, and taxable investment accounts for flexibility. Each serves a different purpose in your overall strategy.


Is Your Portfolio Inflation-Resistant?


Cash can feel safe, but inflation quietly erodes its purchasing power over time. If you want an honest look at the hard numbers of inflation, see the Bureau of Labor Statistics CPI Inflation Calculator.


For example, we see that $1,000,000 in 2015 has the buying power of $1,380,194 in 2025. You would need an extra (almost) $380,000 to make up for inflation.


Inflation is a reality of the economy that everyone deals with, but your investment strategies can mitigate its impact on your net worth. Consider allocating a portion of your portfolio to assets that historically perform well during inflationary periods. 


Don’t Abandon Growth Too Soon


If you're retiring in your early 60s, you could have 20-30 years ahead of you. Being overly conservative with your investments might feel safer in the short term, but it could leave you struggling to maintain your lifestyle later.


A balanced approach that includes growth-oriented investments can help ensure your money lasts as long as you do.


3. Reduce Outstanding Debts


The Federal Reserve’s most recent Survey of Consumer Finances reports that the average older adult (ages 65 and up) carries between $95,000 and $172,000 in debt. The bulk of those debts is from outstanding mortgage balances, but credit card and medical debts contribute significantly. 


Prioritize Your Debt Payoff Strategy 


High-interest debts from credit cards and personal loans can take up a lot of room on a fixed income. Consider whether it makes sense to use some of your current higher income to aggressively pay down these balances before you retire. 


There are two primary ways of tackling multiple debts:


  • Avalanche: Pay off your balances starting with the highest interest rates.
  • Snowball: Pay off your balances from smallest to largest.


Entering retirement debt-free can be a very freeing experience. 


Consider Your Mortgage


Your mortgage situation is more nuanced. Some retirees find comfort in owning their home outright, while others benefit from maintaining their mortgage if it's at a low interest rate, and money can be invested for higher returns. The right choice depends on your specific situation and comfort level.


4. Plan for Healthcare Costs and Insurance Transitions


Healthcare expenses are frequently retirees' most underestimated cost. Add in Medicare's maze of coverage options, and it's no wonder many retirees feel unprepared. Planning for these expenses and understanding your options before you need them can prevent costly surprises that strain your fixed income. 


Understand Your Medicare Options


If you're 65 or older:

  • Enroll in Medicare during your Initial Enrollment Period (IEP), which begins 3 months before your 65th birthday and extends 3 months after


  • Consider supplemental coverage options:
  • Medigap (if you choose Original Medicare Parts A and B)
  • Medicare Advantage (Part C) as an alternative to Original Medicare
  • Prescription Drug Coverage (Part D), if not included in your plan


If you’re under 65 and retiring, consider: 


  • COBRA coverage from your employer allows you to keep your current plan for up to 18 months, but you'll pay the full premium plus administrative fees (typically $400-$700 per person monthly)
  • Your spouse's employer plan (if available and you're eligible)
  • An Affordable Care Act (ACA) marketplace plan


Prepare for the end of employer-sponsored insurance coverage about a year in advance to avoid lapses in coverage.


Build a Healthcare Reserve


According to the 2025 Fidelity Retiree Health Care Cost Estimate, a 65-year-old individual may require approximately $172,500 in after-tax savings to cover health care expenses in retirement.


Consider establishing a separate savings account specifically for medical expenses. Health Savings Accounts (HSAs), if you're eligible, offer triple tax advantages and can be particularly valuable for retirement healthcare planning.


5. Create a Flexible Retirement Budget


It’s wise to reevaluate where your money is going every month so you can enjoy once-in-a-lifetime retirement opportunities fully. This, combined with an emergency fund, helps avoid lifestyle creep and the stress of unexpected expenses.


Plan for the “Retirement Smile”


Retirement spending tends to move in a “U” shape: higher spending in early retirement, less in the middle, and back up again towards the end. 


While your bucket list trips and experiences are significant expenses, they’re often one-and-done. Most people do these things early on in retirement and slow down into a more predictable financial rhythm. Towards the end of retirement, costs often increase again to cover long-term care needs.


Organize Your Budget Into Categories


Consider dividing your retirement expenses into essential costs (housing, utilities, healthcare), lifestyle expenses (travel, dining, hobbies), and discretionary spending (gifts, major purchases). 


Cover your essentials with your most reliable income sources like Social Security, while funding lifestyle expenses through portfolio withdrawals that can adjust during market downturns.


How Can You Reduce Your Future Cost-of-Living?


Consider ways you can capitalize on your existing assets to better position yourself for the future. If you’ve built significant home equity, downsizing or moving to a more affordable city may be a great option, as you’ll benefit from liquidity and reduced costs. 


Rely on A Trusted Fiduciary Financial Planner


If you’re feeling anxious about the future, know this: you’re not stuck doing it on your own. 


With the help of a fiduciary financial planner, you can not only see if your plan holds up against inflation and economic uncertainties, but they will: 



  • Prioritize tax-efficient retirement withdrawal strategies
  • Strategize Required Minimum Distributions (RMDs)
  • Create a sustainable withdrawal strategy


The best thing you can do for a healthy retirement is to leverage the experts. At Five Pine Wealth Management, we create comprehensive financial plans that align with your financial goals and personal values. 


If you'd like to discuss how these strategies might apply to your specific situation, we're here to help. Email us at info@fivepinewealth.com or call 877.333.1015 to schedule a conversation about your retirement planning needs. 



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Is Paying Off Your Mortgage in Your Late 50s the Right Move?

February 19, 2026
Key Takeaways Paying off your mortgage before retirement reduces monthly expenses, lowers your income needs, and provides psychological peace of mind, but ties up money in an illiquid asset. Keeping your mortgage and investing instead may provide higher long-term returns, better liquidity, and tax advantages, but requires comfort with debt and market volatility. Your mortgage interest rate, risk tolerance, retirement timeline, and other income sources should all factor into your decision. A hybrid approach — paying down part of the mortgage while keeping some money invested — can provide a balance between security and growth potential. At 58, let's say your mortgage balance is $180,000. Your retirement accounts have grown to $850,000. So now you’re wondering: should I just pay off this mortgage and be done with it? We have this conversation regularly with clients in their late 50s and early 60s. Some choose to go ahead and pay off their mortgage. Others keep it and invest the difference. There’s nothing wrong with either choice, but what’s right for you depends on your specific situation. We’re here to walk you through how to think about this decision: The Case for Paying Off Your Mortgage Before Retirement There’s something undeniably satisfying about owning your home outright. Beyond the emotional relief, there are practical reasons that make sense: Reduced monthly expenses in retirement. Housing is typically your highest fixed cost. Eliminating that payment frees up cash flow for other priorities, like travel, healthcare, and helping the grandkids with college tuition. Lower income needs mean lower taxes. When you don’t have a mortgage payment, you don’t need to withdraw as much from retirement accounts. Smaller withdrawals often mean staying in lower tax brackets and (potentially) reducing Medicare premiums. Peace of mind during market downturns. If we hit a recession early in your retirement, having no mortgage means you won’t feel pressured to sell investments at depressed prices to cover housing costs. Guaranteed return on your money. Paying off a 4% mortgage is like earning a guaranteed 4% return (tax implications aside). We had a client who paid off her $220,000 mortgage at 59. Mathematically, she probably could have earned more by investing that money. But her reasoning made sense for her, “My parents stressed about money their whole retirement. I don’t want that. I want to know that my house is paid for, no matter what happens.” For her, the psychological benefit outweighed the potential investment returns. The Case for Keeping Your Mortgage and Investing Instead For others in their late 50s, keeping the mortgage and investing that money elsewhere makes more financial sense: Higher potential investment returns. If your mortgage rate is 3-4% and you can reasonably expect 6-8% average returns from your diversified investment portfolio over time, the math favors investing. Maintain liquidity and flexibility. Money tied up in home equity isn’t easily accessible. You’ll have more options if that money is in investment accounts rather than in illiquid home equity. Tax advantages of mortgage interest. If you itemize deductions, you might still benefit from the mortgage interest deduction, which reduces the effective cost of your mortgage. Inflation works in your favor. Your mortgage payment stays the same while everything else gets more expensive. In 10 years, your $2,000 payment will feel smaller relative to other expenses. We worked with a couple who were considering paying off their $300k mortgage at age 57. Their mortgage rate was 3.25%, they were in a high tax bracket, and they had at least twenty years of retirement ahead. They decided to keep the mortgage and invest instead. Five years later, their investment account had grown enough that they could pay off the mortgage if they chose to, while still having substantial assets left over. The Middle Ground: A Hybrid Approach You don't have to choose all-or-nothing. Some clients find that a combination works best: Pay down part of the mortgage . Reduce your balance and shave a few years off your repayment timeline while maintaining some liquidity. Recasting and refinancing options can also lower your monthly payment. Plan for a future payoff . Keep the mortgage while you're still working and in higher tax brackets. Then plan to pay it off in a few years when you retire and your income drops. Use bonus income strategically . Consider using windfalls, bonuses, inheritance, business sale proceeds, to pay down the mortgage while keeping your regular savings and investments intact. How to Think Through Your Decision Here's how to evaluate the mortgage payoff vs investing decision for your situation: What's your mortgage interest rate? Below 4%, the mathematical case for keeping it gets stronger. Above 5%, paying it off starts looking more attractive. How much liquid savings do you have? If paying off your mortgage would drain your emergency fund or leave you with little accessible cash, that's a red flag. What's your risk tolerance? Be honest. If having a mortgage payment keeps you up at night, no investment return will make up for that stress. What are your other retirement income sources? Social Security, pension, rental income — these reliable sources might make carrying a mortgage more manageable than you think. When Paying Off Makes Sense Based on our experience, paying off your mortgage before retirement tends to work best when: Your mortgage interest rate is relatively high (5%+) You'd still have 6-12 months of expenses in emergency savings after payoff You're naturally debt-averse, and the monthly payment creates genuine anxiety You have other sources of retirement income You plan to stay in this home for the foreseeable future When Keeping Your Mortgage Makes Sense Keeping your mortgage and investing instead usually works better when: Your interest rate is low (below 4%) You're in a high tax bracket where the mortgage interest deduction provides value You have a long time horizon (20+ years of retirement ahead) You're comfortable with investment volatility You want flexibility and liquidity in your financial plan Getting Help With Your Decision At Five Pine Wealth Management , we help clients work through these decisions regularly. We review your complete financial situation, run the numbers, and help you understand the trade-offs so you can make a confident decision. A good financial advisor can run projections showing both scenarios, factor in your complete financial picture, help you stress-test different economic scenarios, and integrate this decision with your broader retirement, tax, and estate planning strategies. Whether you decide to pay off your mortgage or keep it and invest, what matters most is that the choice aligns with your goals, risk tolerance, and peace of mind. If you're wrestling with the mortgage payoff vs. investing question and want to talk through your specific situation, we're here to help. Call us at 877.333.1015 or email info@fivepinewealth.com . Frequently Asked Questions (FAQs) Q: Should I use my 401(k) to pay off my mortgage? A: Generally, no. Withdrawing from retirement accounts before 59½ triggers penalties. Later, large withdrawals can push you into higher tax brackets. If you want to pay off your mortgage, it's usually better to use funds from taxable investment accounts or savings rather than tapping tax-advantaged retirement accounts. Q: What if I want to downsize in a few years anyway? A: If you plan to sell and move to a smaller home within 3-5 years, keeping your mortgage makes more sense. You'd be paying it off only to sell shortly after, and that money could work harder for you in investments until you make your move. Q: Can I change my mind later if I keep the mortgage?  A: Yes, you can always pay it off later if your circumstances or feelings change. Once you pay it off, however, accessing that equity again (without selling) typically requires a new loan or a home equity line of credit, which isn't always simple or cheap.

What High Earners Overlook After Maxing Out Their 401(k)

January 26, 2026
Key Takeaways High earners maxing out 401(k)s at $24,500 are only saving about 8% of a $300,000 income in their primary retirement account. The mega backdoor Roth strategy can increase total 401(k) contributions to $72,000 annually with tax-free growth. A comprehensive approach can create nearly $3 million in additional retirement wealth over 20 years. It's 2026. You're checking all the boxes. You're earning upwards of $300,000 annually, and you're maxing out your 401(k) every year. You've reached the $24,500 contribution limit and feel confident about securing your financial future. Then you realize $24,500 represents less than 8% of your income. Over 20 years, this gap adds up to millions in lost opportunity. Thankfully, you're not stuck with the basic 401(k) playbook. There are sophisticated strategies beyond your contribution limit. 5 Strategic Moves for High Earners with Maxed-Out 401(k)s Here are five sophisticated strategies that can help you build wealth beyond your basic 401(k) contributions. All projections assume a 7% average annual return and are estimates for illustrative purposes. 1. Mega Backdoor Roth Contributions If your employer's 401(k) plan allows after-tax contributions, this could be your biggest opportunity. With employee contributions, employer match, and after-tax contributions, the combined 401(k) limit for 2026 is $72,000 ($80,000 if you're 50 or older). The mega backdoor Roth works because you immediately convert those after-tax contributions into a Roth account, where they grow tax-free forever. The catch: Not all employers offer this option. You need a plan that permits after-tax contributions and in-service Roth conversions. The impact: The available space for after-tax contributions depends on your employer match. With a typical employer match of 3-6% (roughly $10,000-$21,000 on a $350,000 salary), you could contribute approximately $26,500-$37,000 annually. At 7% average returns over 20 years, this creates approximately $1.1-$1.5 million in additional tax-free retirement savings. 2. Donor-Advised Funds for Charitable Giving If you're charitably inclined, donor-advised funds (DAFs) offer a way to bunch several years of charitable contributions into one tax year, maximizing your itemized deductions while still spreading your giving over time. You get an immediate tax deduction for the full contribution, but you can recommend grants to charities over many years. The funds grow tax-free in the meantime. The catch: Once you contribute to a DAF, the money is irrevocably committed to charity. You can't get it back for personal use. The impact: Contributing $50,000 to a DAF in a high-income year (versus giving $10,000 annually) can create immediate federal tax savings of $15,000-$18,500 while still allowing you to support the same charities over five years. 3. Taxable Brokerage Accounts with Tax-Loss Harvesting Once you've maximized tax-advantaged accounts, strategic taxable investing becomes your next move. The key is working with a financial advisor who implements systematic tax-loss harvesting throughout the year. Tax-loss harvesting involves selling investments at a loss to offset capital gains elsewhere. Done strategically, this can save thousands in taxes annually. The catch: Long-term capital gain rates (0%, 15%, or 20%) are lower than ordinary income tax rates, but you're still paying taxes on gains. It's less tax-efficient than retirement accounts, but far better than ignoring tax optimization. The impact: For high earners in the 35-37% ordinary income brackets, the difference between long-term capital gains (20%) and ordinary rates is significant. Effective tax-loss harvesting on $50,000 in annual gains over 20 years could save $150,000+ in taxes. 4. Health Savings Account (HSA) Triple Tax Advantage HSAs offer a unique triple tax benefit: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. With 2026 contribution limits of $4,400 for individuals and $8,750 for families, this adds another powerful layer to your strategy. You can invest HSA funds just like an IRA and let them grow for decades. After age 65, you can withdraw the funds for any purpose, medical or otherwise. The catch: You must have a high-deductible health plan to qualify for an HSA. After age 65, non-medical withdrawals are taxed as ordinary income (like traditional IRA distributions), but you still benefit from the upfront deduction and decades of tax-free growth. The impact: Contributing the family maximum ($8,750) annually for 20 years at a 7% average annual return creates approximately $355,000-$360,000 in tax-advantaged savings. 5. Backdoor Roth IRA Contributions Not to be confused with mega backdoor Roth contributions! Even if your income exceeds the Roth IRA contribution limits, you can still fund a Roth through the backdoor method: make a non-deductible contribution to a traditional IRA, then immediately convert it to a Roth IRA. The catch: If you have existing traditional IRA balances, the pro-rata rule complicates things. You may want to consider rolling those funds into your 401(k) first if your plan allows. The impact: Contributing $7,000 annually through the backdoor Roth for 20 years at 7% average annual return creates approximately $285,000-$290,000 in tax-free retirement savings. What Compounding These Strategies Looks Like Over 20 Years Let’s look at approximate outcomes based on a 7% average annual return. 401(k) Only: Annual contribution: $24,500 Total after 20 years: ~$1M 401(k) + Mega Backdoor Roth: Annual contribution: $72,000 Total after 20 years: ~$3M Note: Mega backdoor Roth space varies based on your employer's match. These calculations assume you're maximizing the total annual limit. Comprehensive Approach (under age 50): Mega Backdoor Roth: ~$3.0M HSA: ~$350K-$360K Backdoor Roth IRA: ~$285K-$290K Strategic taxable investing with tax-loss harvesting Total retirement savings: ~$3.6M+, plus taxable investments Comprehensive Approach (ages 50-59): With higher contribution limits and catch-up contributions, total retirement savings can reach ~$4M+ over 20 years. Comprehensive Approach (ages 60–63 with enhanced catch-up contributions) Higher contribution limits during peak earning years allow for meaningful acceleration of retirement savings. The exact impact depends on timing, contribution duration, and existing balances. The Bottom Line The difference between stopping at your basic 401(k) and implementing a comprehensive strategy can approach $3 million or more in additional retirement wealth over time. Why Strategic Coordination Matters These aren't either/or decisions. The most effective approach coordinates multiple strategies while ensuring everything works together. At Five Pine Wealth Management , we help high-earning clients build comprehensive plans that go beyond the 401(k). We coordinate your employer benefits, tax strategies, and investment accounts to create a cohesive approach that maximizes your wealth-building potential. This requires working across several areas: Analyzing your employer's 401(k) plan for mega backdoor Roth opportunities Implementing systematic tax-loss harvesting in taxable accounts Coordinating Roth conversions and backdoor contributions Optimizing your HSA as a long-term retirement vehicle Ensuring charitable giving strategies align with your tax situation Maximizing catch-up contributions when you reach milestone ages As fiduciary advisors, we're legally obligated to act in your best interest. That means we're focused on strategies that serve your goals, not products that generate commissions. Ready to see what's possible beyond your 401(k)? Email us at info@fivepinewealth.com or call 877.333.1015 to schedule a conversation about your specific situation. Frequently Asked Questions (FAQs) Q: Does my employer's 401(k) plan automatically allow mega backdoor Roth contributions? A: No. You need a plan that permits after-tax contributions and in-service conversions to Roth. Check with your HR department. Q: How do I prioritize which investment strategies to use? A: Generally, maximize employer match first (it's free money), then fully fund your 401(k), explore Mega Backdoor Roth if available, max out your HSA, consider backdoor Roth IRA contributions, and then move to taxable accounts with tax-loss harvesting. We can help determine the right sequence for your circumstances.