Year-End Planning: Estimated Tax Payments
As the year comes to a close, Roger Whitney reflects on the power of words, walks through an important year-end tax planning reminder for retirees, shares listener stories and perspectives, and invite...
Social Security is a government-run program in the United States that provides a source of income for retirees, as well as for people who are disabled or the survivors of deceased workers. The program is funded through payroll taxes, and it is designed to provide a basic level of financial security for those who are no longer able to work.
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As the year comes to a close, Roger Whitney reflects on the power of words, walks through an important year-end tax planning reminder for retirees, shares listener stories and perspectives, and invite...
Jeremy Keil explains the 5 steps you can take if you are planning to retire in 2026 or 2027. If you’ve been planning to retire in 2026 or 2027, it might feel like you still have plenty of time. But in...
I am planning on retiring next year. Between Social Security, a small pension, and rolling my 401K over into and IRA with a 5% return on CDs, I would make $40,000 more per year than I make working now...
A 23% benefit cut, retroactive payments, and new tax rules may impact when you should claim Social Security. These five factors can help you rethink your timing.
Could a counterintuitive tax move today potentially lead to thousands in savings — or an unexpected tax trap tomorrow? In this episode, we discuss: Why some retirees intentionally harvest capital gain...
Choosing the right Social Security strategies can be a $100,000 (or more) question. Find out how to make the most of this benefit with 15 easy tips. The post Social Security Strategies: 15 Tips for Ma...
Medicare premiums and taxes can shrink Social Security benefits. Plan ahead to protect retirement income.
Jeremy Keil explains the top 3 tax efficient strategies for charitable giving in 2025. Most people give to charity because it’s meaningful to them — not because of the tax break. And that’s the right ...
This post is follow-up to our post of December 22, 2024 and will again highlight the benefits of using the Actuaries Longevity Illustrator (ALI) to help you develop reasonable lifetime planning period...
After enactment of the Social Security Reform Act of 1983, Social Security actuaries determined OASDI’s (Social Security’s or the system’s) long-range actuarial balance (LRAB) to be .02%, meaning that...
Jeremy Keil explores 7 money moves you can consider before the new year to lower your taxes and keep more of your money in retirement. Every December, people scramble to finish holiday shopping, trave...
Most retirement advice quietly assumes you have a partner: two incomes, two Social Security checks, someone to split expenses with, someone to catch the slack if something goes wrong. But for singles,...
Most retirees unknowingly leave thousands of dollars on the table just by filing for Social Security the wrong way. In this episode, Ryan and Tyson Thacker reveal how the right…
Learn how Social Security benefits may apply to spouses, ex-spouses, and surviving partners. Find out if you’re eligible for extra payments and how to claim what you’re owed.
Think waiting until 70 is the gold standard for Social Security? We dig into the real math behind delayed retirement credits and the hidden trade-offs that rarely make it into the headlines. Drawing o...
About 10 years ago, I tried logging onto SSA.gov to check my Social Security benefits. You would think after decades of paying FICA taxes (6.2% for SS, 1.45% for Medicare), the government might make i...
Seniors and people with disabilities calling the Social Security Administration (SSA) face endless looping music, long wait times, useless robot messages, and extended periods between a request and an...
Retiring with a pension changes everything about your retirement math. Most people think about retirement in terms of net worth—how close they are to a million, two million, or more. But if you have a...
You’ve worked and paid into Social Security for decades. Deciding when to claim those benefits is one of the few choices that can truly move the needle on your retirement income. For most retire...
? Show Notes In this episode, Roger Whitney dives into the essentials of required minimum distributions, explaining the age thresholds, how the amounts are calculated using IRS life expectancy tables,...
As you approach retirement, understanding spousal benefits can empower both you and your partner to make well-informed decisions. The post Spousal Benefits: Learn How to Make the Most of Social Securi...
Learn key factors to consider before filing for Social Security. Understand timing, earnings limits, and how to maximize lifelong benefits for you and your spouse....
I expect to retire in the next 12-24 months, and I’m looking for advice on how to handle multiple income streams. Like a lot of people, for almost 40 years, nearly all our household income has c...
If you’re hoping the 2026 Social Security COLA will help ease the pressure of rising costs, don’t get your hopes up. The 2026 increase is only 2.8%.¹ With inflation, Medicare premiums...
Joe Anderson, CFP® and Big Al Clopine, CPA spitball withdrawal strategies, Roth conversion timing, and saving priorities for every stage of life, today on Your Money, Your Wealth® podcast numb...
To read this story on KSL.com, click here. For most Americans, Social Security is more than a paycheck — it’s the foundation of their retirement. But the timing of when…...
The playbook for filing for Social Security has been turned on its head. What worked for previous generations could end up costing you a small fortune. One reason is the…...
Bills don't stop once you retire — and you can't expect your Social Security checks to cover them all. Don't risk running out of money. Instead, make a plan....
A single misunderstanding about Social Security spousal benefits can cost couples thousands over retirement. This episode unpacks the real math behind how Social Security treats spouses, ex-spouses, a...
FROM THE ARTICLE. AARP-backed bill aims to tweak SSA wording to help older adults decide when to start benefits. By Deirdre Shesgreen, AARP. Published November 06, 2025. Could a little wordsmithing by...
My wife and I have always been savers. Now in retirement I'm struggling to spend any money beyond the required bills, food, and payments. With our pensions and social security, the basics are way more...
Planning for Retirement: Social Security and Beyond!Tuesday, Dec 2, 2025. 2:00 p.m. ET • 1:00 p.m. CT • 12:00 p.m. MT • 11:00 a.m. PT. Duration: 60 Minutes. Zoom - Free Online Event. FR...
? SHOW NOTES In this episode, Roger Whitney explores the art of retirement goal setting with his signature blend of practical advice and thoughtful reflection. He sits down with Cesar Aguirre, who sha...
Those “3x by 40, 6x by 50, 10x by 67” charts feel official—until your life doesn’t match the average. In this episode, James shows why age-based savings benchmarks miss the mar...
You've heard it a thousand times: "Wait until 70 to file for Social Security." But if that's such obvious advice, why do most retirees file earlier? In this episode, we uncover the hidden cost of wait...
I am planning to retire (hopefully) soon, and I keep reading things that say I'll need 70% of my pre-retirement income, or 80%, or 90%. The idea being that you will lose some of the expenses related t...
FROM THE ARTICLE. Social Security Weighs Major Changes to Disability Rules. Advocates say regulations could affect hundreds of thousands of older adults sidelined from work by illness or injury. By Sh...
Interesting Social Security Scenario - What’s your take on this? ? or ? A (breadwinner) parent divorced a real deadbeat parent after 14 years of marriage -and (2) kids. Neither ever remarried. T...
In this episode, we break down the newly signed One Big Beautiful Bill Act (OBBBA) and what it means for retirees. From the extension of the 2017 tax cuts to new rules around Roth conversions, Social ...
Today we answer a question from Ken, a recent retiree at 63, about how his Social Security claiming decision impacts his wife's future spousal benefit. We break down how spousal benefits are calculate...
In this special episode, we catch up on a backlog of insightful listener questions—covering everything from estate planning and Social Security taxation to Roth conversions and Medicare rules. I...
In this inbox episode, we break down how the Social Security earnings limit works—especially for C corp owners who split income between salary and dividends. Learn what counts toward the limit, ...
Rosemary's husband is scaling back to 32 hours a week as part of his transition plan before switching careers. With Social Security in mind, she asks: Will this reduced income impact their future bene...
In this episode, we address Joe's question about how claiming Social Security benefits early can reduce withdrawals from retirement accounts and potentially lead to greater long-term growth. Joe share...
In this episode, we answer Lori's question about whether the repeal of the Government Pension Offset (GPO) will increase her survivor benefits and how it could impact benefits for those with similar c...
So far in 2025, early Social Security filings have jumped dramatically compared to last year. Nearly half of those filing early say they're doing so because they're worried about cuts. But will filing...
When should you claim Social Security? For high-net-worth retirees, this is not a simple decision. In this episode, we explain why Social Security is not just a monthly check but a strategic part of a...
Policy experts across the political spectrum share similar goals: To restore long-term solvency while improving its ability to support lower-income workers in old age....
My wife and I plan to retire at the end of 2028. While we both have good paying jobs now, for most of our adult lives, we've been barely making it - raising children and living paycheck to paycheck. O...
When you work and collect Social Security benefits before your FRA, you are subject to the Retirement Earning Test that could result in a temporary reduction of your benefits....