The Retirement Brief: October 4-5 (2025)
- Mark Fonville, CFP®
- Oct 4
- 7 min read
EXECUTIVE SUMMARY
This week's Retirement Brief offers critical insights for high-net-worth investors navigating an evolving retirement landscape.
From the revolutionary "90+ rule of retirement" that challenges conventional planning wisdom to Medicare's surprisingly stable 2026 outlook, we're seeing significant shifts in how affluent retirees should approach their golden years.
As October tax deadlines approach and cyber threats against seniors escalate—with $4.8 billion lost to fraud in 2024 alone—proactive planning has never been more essential.
Meanwhile, savvy retirees are discovering that strategic travel hacking can transform bucket-list adventures from prohibitively expensive to surprisingly affordable. These articles provide the actionable intelligence you need to optimize your financial security, protect your assets, and maximize the quality of your retirement years.
Wishing you a thoughtful and rewarding read this weekend.
This Week's Essential Reading for High-Net-Worth Individuals Age 50+
(Kiplinger)
The traditional retirement planning playbook is being rewritten as advances in medicine and longevity research suggest many of today's retirees could easily live into their 90s or beyond. This fundamental shift demands a complete rethinking of every major retirement decision—from investment allocation to Social Security timing.
The article introduces the "90+ rule," which advocates planning every financial move with the assumption you'll live past 90. This isn't pessimism; it's prudent preparation. The implications are profound: working even three to six months longer can boost retirement income as much as increasing contributions by 1% annually over 30 years. Financial advisors emphasize maintaining equity exposure for inflation protection, as many retirees actually increase spending post-retirement rather than scaling back as once assumed.
Perhaps most critically, the piece highlights the importance of delaying Social Security until age 70 when possible. For someone with a $2,000 monthly benefit at age 67, waiting until 70 could increase it to $2,480—an extra $480 per month that, compounded over a 25-year retirement with cost-of-living adjustments, represents hundreds of thousands in additional lifetime income. The message is clear: if you're planning to live long, plan accordingly.
(Newsweek)
In a rare piece of positive news for the 65 million Americans relying on Medicare, the Centers for Medicare and Medicaid Services announced that premiums for Medicare Advantage and Part D prescription drug plans will actually decrease in 2026. This stability stands in stark contrast to the premium spikes affecting commercial health insurance.
Average monthly Medicare Advantage premiums are projected to drop from $16.40 in 2025 to $14 in 2026, while standalone Part D premiums will fall from $38.31 to $34.50. The annual out-of-pocket maximum for Part D will rise modestly to $2,100 from $2,000, but overall the news is encouraging for retirees on fixed incomes. Access remains robust, with over 99% of beneficiaries having access to at least one MA plan and 97% having access to ten or more options.
The Medicare Open Enrollment period runs from October 15 through December 7, 2025, providing a critical window for beneficiaries to review and potentially switch plans. Healthcare experts emphasize the importance of comparison shopping during this period, as many beneficiaries stay in suboptimal plans despite better options being available. High-net-worth individuals should be particularly mindful of the "Medicare Advantage trap"—switching back to traditional Medicare can become prohibitively expensive for those with chronic conditions due to risk-rated Medigap premiums.
(Wedbush Securities)
October represents a critical inflection point for tax planning, with the October 15th extension deadline looming for 2024 returns and year-end 2025 tax optimization opportunities still within reach. This timely advisory from Wedbush Securities highlights both immediate action items and strategic planning moves that can significantly impact your tax liability.
For those who filed extensions, October 15, 2025 is the absolute deadline to submit 2024 federal returns—missing it triggers failure-to-file penalties and interest charges that compound quickly. Beyond this immediate concern, the piece emphasizes leveraging the One Big Beautiful Bill tax legislation passed in mid-2025, which introduced increased standard deductions and new provisions including qualified overtime deductions and auto loan interest limits.
The strategic opportunity lies in year-end planning: maximizing retirement account contributions before December 31st, particularly for those over 50 who can take advantage of catch-up contributions. For high-net-worth investors, this is the time to review portfolio allocations in light of recent inflationary pressures and interest rate shifts, harvest tax losses to offset gains, and ensure optimal positioning for 2026. The message is clear: October's deadlines are just the beginning—proactive planning now prevents costly surprises later.
(Cybersecurity Ventures)
The statistics are sobering: seniors aged 60 and over collectively lost $4.8 billion to internet fraud in 2024, according to the FBI's Internet Crime Complaint Center. As cybercriminals increasingly target older adults—who statistically have substantial savings, may be less tech-savvy, and tend to be more trusting—cybersecurity has become an essential component of retirement planning.
This newly released guide, "Senior Cyber: Best Security Practices for Your Golden Years," along with its companion 40-minute video, addresses the alarming reality that seniors face disproportionate targeting by online criminals. The resource covers everything from basic internet security to the critical issue of healthcare privacy protection—particularly important for the aging population managing sensitive medical information online.
The timing couldn't be more critical as October is National Cybersecurity Awareness Month. From phishing scams and tech support fraud to sophisticated social engineering attacks, the threats are evolving rapidly. For affluent retirees, the stakes are even higher—protecting substantial assets requires constant vigilance, strong password practices, two-factor authentication, and a healthy skepticism toward unsolicited communications. The fundamental message: in the digital age, cybersecurity isn't optional—it's an essential wealth preservation strategy.
(Kiplinger)
While 70% of seniors plan to travel in retirement, 45% cite cost as their biggest barrier, according to a 2025 AARP national poll. This comprehensive guide shatters that barrier with ten proven strategies that can slash travel costs by 20-50% without sacrificing quality or experiences.
The tactics range from maximizing senior discounts—including the $80 lifetime National Parks pass for those 62+—to strategic timing like traveling off-season for 20-40% savings on airfare and accommodations. One particularly compelling strategy for retirees: extended stays. Monthly apartment rentals through Airbnb or Vrbo often come with 20-50% discounts compared to weekly rates, and when you're retired, why rush?
You can cook your own meals, truly immerse yourself in a destination, and dramatically reduce per-day costs.
Technology becomes a powerful ally through apps like Kayak and Momondo for price comparisons, while group tours from operators like Road Scholar offer bulk discounts plus the social benefits of traveling with like-minded peers. The piece also covers often-overlooked savings opportunities like credit card rewards programs specifically designed for retirees, travel insurance that can prevent financial disasters, and even creative options like home swapping or volunteering for conservation projects that provide free accommodations. The bottom line: with smart planning, the world remains accessible even on a retirement budget.
Final Thoughts
This week's readings underscore a fundamental truth about modern retirement: longevity is both a blessing and a planning imperative. The convergence of extended lifespans, evolving healthcare costs, sophisticated cyber threats, and the desire for enriching experiences demands a more comprehensive and proactive approach to retirement planning than previous generations required.
Whether you're recalibrating your portfolio for a potential 30+ year retirement, navigating Medicare's complexities, safeguarding your digital assets, or optimizing your travel budget, the common thread is clear—informed, strategic decision-making today creates security and opportunity tomorrow. The retirees who thrive in their 90s won't be those who simply hoped for the best, but those who planned for it.
We hope you enjoyed this week's reading.
Have thoughts on these articles or suggestions for future topics? We'd love to hear from you.
Maintaining financial security up to and through retirement can be hard. Would you like to just have our team do your retirement planning for you? Request a free retirement assessment today!
Wishing you a wonderful weekend,
About the author:
CEO and Senior Financial Advisor
Mark is the CEO of Covenant Wealth Advisors and a Senior Financial Advisor helping individuals age 50+ plan, invest, and enjoy retirement comfortably. Forbes nominated Mark as a Best-In-State Wealth Advisor* and he has been featured in the New York Times, Barron's, Forbes, and Kiplinger Magazine.
Disclosures: Covenant Wealth Advisors is a registered investment advisor with offices in Richmond, Reston, and Williamsburg, VA. Registration of an investment advisor does not imply a certain level of skill or training. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. The views and opinions expressed in this content are as of the date of the posting, are subject to change based on market and other conditions. This content contains certain statements that may be deemed forward-looking statements. Please note that any such statements are not guarantees of any future performance and actual results or developments may differ materially from those projected. Please note that nothing in this content should be construed as an offer to sell or the solicitation of an offer to purchase an interest in any security or separate account. Nothing is intended to be, and you should not consider anything to be, investment, accounting, tax, or legal advice. If you would like accounting, tax, or legal advice, you should consult with your own accountants or attorneys regarding your individual circumstances and needs. This article was written and edited by a CERTIFIED FINANCIAL PLANNER™ professional with the assistance of AI. No advice may be rendered by Covenant Wealth Advisors unless a client service agreement is in place. Hypothetical examples are fictitious and are only used to illustrate a specific point of view. Diversification does not guarantee against risk of loss. While this guide attempts to be as comprehensive as possible but no article can cover all aspects of retirement planning. Be sure to consult an advisor for comprehensive advice.
