HAVE A QUESTION? CALL US AT (872) 266-3015
For the Week of January 23rd, 2026
Shifting Payments, Tax Traps, and the Retirement Crisis No One Talks About
This week’s retirement news hits on every front - your wallet, your calendar, and even your sense of purpose.
From Social Security payment changes and tax-season pitfalls to new pressure from Washington over rising living costs, retirees are facing more moving parts than ever. And beyond the numbers, a deeper crisis is emerging: what happens when retirement feels financially stable but emotionally unmoored? Together, these headlines serve as a reminder that successful retirement takes more than savings - it takes strategy, adaptability, and a clear sense of what comes next.
By RetirementRedFlags.com
Retirement today is a moving target and staying ahead means understanding not just the numbers, but the new rules, risks, and realities.
1. 4 Reasons Baby Boomers Are Rethinking Retirement
Many baby boomers approaching retirement age are finding that traditional retirement isn’t fitting their financial reality. Rising living costs, uncertain healthcare expenses, longevity concerns, and volatility in investment returns are reshaping how boomers plan their later years - making some delay retirement or adjust expectations for income in retirement. These factors highlight that even with savings and Social Security, a full work‑free retirement might not be viable without careful planning.
Action Steps:
✔ Review your projected retirement expenses (housing, healthcare, inflation) and compare them with expected income.
✔ Consider delaying claiming Social Security if you can afford it - later collections typically increase monthly payments.
✔ Work with a financial planner or advisor to stress‑test your long‑term income strategy.
2. Social Security Payment Dates & Changes for 2026
In 2026, Social Security benefits will still mostly be distributed based on your birth date: typically on the second, third, or fourth Wednesday of each month for retirement checks, while Supplemental Security Income (SSI) goes out on the first of each month (with potential adjustments for weekends/holidays). Benefits are also increasing by about 2.8% this year to help offset inflation - roughly ~$56 more per month for the average retiree.
Action Steps:
✔ Mark your specific payment dates on your calendar based on your birth date so you plan bill payments accordingly.
✔ Confirm your direct deposit details with SSA to avoid delays.
✔ Monitor any changes to SSI timing if you or a spouse receive that benefit.
3. Line Items Retirees Should Double‑Check on Their Tax Return
If you’re preparing your 2025 tax return, you should be especially careful about how different income sources are taxed: Social Security income, pension distributions, IRA/401(k) withdrawals, investment gains, and required minimum distributions (RMDs) can all affect your tax bill in unexpected ways. Missing deductions or misunderstanding how these are taxed could cost you money.
Action Steps:
✔ Double‑check how Social Security benefits are taxed in your situation - it depends on your total income.
✔ Ensure you correctly report RMDs and other retirement distributions.
✔ Consider consulting a tax professional before filing to avoid errors and maximize deductions.
4. U.S. Policy Proposals Impacting Living Costs & Retirement Funds
Recent national policy discussions include proposals to make housing more affordable, cap credit card interest rates, and allow retirement funds like 401(k)s to be used for home down payments. While these aren’t finalized policies yet, they signal ongoing debate about how best to ease cost‑of‑living pressures - especially relevant to retirees managing fixed or limited incomes.
Action Steps:
✔ Stay informed about any finalized legislative changes affecting retirement accounts or living costs.
✔ If you’re considering using retirement accounts for non‑retirement goals (i.e. home purchase), assess the tax and long‑term income implications carefully.
5. The Retirement Crisis No One Warns You About: Mattering
Retirement often comes with an unexpected challenge: losing the identity, structure, and social connections tied to one’s career. This article explores how the transition from full-time work to retirement can leave many feeling aimless or disconnected - especially if they haven’t built new sources of meaning. The key takeaway? Retirement isn’t just about freedom from work; it’s about finding new purpose beyond it. That might mean volunteering, mentoring, pursuing creative passions, or simply showing up consistently in community life.
Action Steps:
✔ Reflect on how much of your current identity is tied to your profession and what could replace that sense of purpose.
✔ Try out new activities before retirement to see what brings fulfillment.
✔ Build (or rebuild) social networks that aren’t tied to your career. It’s key to feeling connected and valued in retirement.
If you have any questions about the headlines that hit the news this week, we are answering questions in our free Facebook group The Retirement Red Flags Community. Click below and we will make sure you get added.
The content provided on this website and in any affiliated print or digital materials is intended solely for informational and educational purposes. It does not constitute an offer to sell, or a solicitation of an offer to buy, any securities. Any affiliated or partner entity of RetirementRedFlags.com may offer securities only through formal offering documents and only to verified accredited investors in accordance with Rule 506(c) of Regulation D under the Securities Act of 1933. Any references to retirement income or financial strategies are illustrative and should not be interpreted as guarantees of future performance or income. No material presented herein constitutes legal, tax, or investment advice. All potential investors should consult with their own legal, tax, and financial advisors before making any investment decision.
Copyright 2026 © RetirementRedFlags.com. All Rights Reserved.