A Roth account is a type of individual retirement account (IRA) that is funded with after-tax dollars. This means that the money you contribute to a Roth account has already been taxed and you will not receive a tax deduction for your contributions. However, the money you contribute to a Roth account grows tax-free and you can withdraw your contributions and any earnings on them tax-free in retirement.
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Retiring at 55 is not just retiring ten years earlier. It changes the entire math of your life. From 55 to 65, expenses are often at their highest. You are covering healthcare before Medicare, traveli...
Looking to start a Roth IRA by April 1 so I can get a start on the 5 year rule, I have 401K plans but will need some roth if I have any chance of ever getting under the 400% magi in 4 years, where sho...
Roger Whitney wraps up the four-part series on navigating health care before Medicare by introducing a practical decision-making framework using the OODA Loop—observe, orient, decide, act—to help you ...
Jeremy Keil explains the 5 RMD (Required Minimum Distribution) mistakes in Retirement and how to avoid them. A retiree recently called for help. It was their first year taking Required Minimum Distrib...
The OBBBA's permanent lower tax rates removed the urgency for Roth conversions. Retirees thinking of stopping or blindly continuing them should do this instead.
Learn the pros and cons of different Roth conversion timing strategies and how to choose the right approach for your retirement plan. The post Timing Roth Conversions: Should You Convert at the Start ...
Hana's mom is 92. Mom's husband is 74, and after years of trying to help a family member, nearly a million dollars is gone. How do they stop the bleeding before it's too late, and how much can they sp...
One thing I’ve learned from 30 years of investing and DIY money management is that there is always another way — and often the other way is more “optimized” than the current way. I put optimized in qu...
Retiring after age 65 changes the math and the priorities. You have fewer high-energy years, shorter tax planning windows, and RMDs much closer than most people realize. But you also often have higher...
I manage mine. We had a money manager, but discovered after decades with him that he was collecting a 1% management fee plus there were commissions on some purchases as well as high loads on other fun...
I retired at 62 (now 63) in June 2025,and I have a Roth IRA with 15% and traditional IRA with about 85% of total. My wife is 64 and still working to pad her retirement and for our health insurance. I ...
Did you know you could triple your 401(k) contributions with a mega backdoor Roth tax planning strategy? We share how to maximize your tax free retirement income.
YMYW friends, welcome to 2026. What actually mattered most to you in 2025? It turns out to be tax-free gains on investments, retirement timing, and claiming Social Security. Today on Your Money, Your ...
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...
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...
Roth conversions can save thousands in taxes, but they can also trigger Medicare IRMAA surcharges that quietly add up to more than $5,000 a year. Most retirees never see it coming, because the rules f...
In January, new Roth catch-up rules will prevent workers over 50 who earned more than $150,000 the prior year from making pre-tax catch-up contributions to their 401(k).
Today, I'm thrilled to welcome Fritz Gilbert back for his second appearance on the podcast. Fritz is an award-winning blogger and author of The Retirement Manifesto, one of the most influential retire...
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,...
For most people, taxes feel like a problem for “future-you.” So, the idea of voluntarily paying taxes today can feel counterintuitive. Yet this is exactly the decision behind a Roth conversion, and it...
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...
A year-end personal finance guide covering RMD deadlines, Roth conversions, HSA, contribution strategies, and key tax-saving steps to complete by December 31.
? Show Notes In this Thanksgiving Eve episode, Roger Whitney encourages listeners to carry gratitude into everyday life, emphasizing the value of recognizing specific moments and taking “mental snapsh...
The IRS just announced the official 2026 contribution limits for 401(k)s, 403(b)s, IRAs, Roth IRAs, SIMPLE plans, and catch-up contributions, and there are some meaningful increases you don’t wa...
While time is running out to make Roth conversions before the end of the taxable year, consider taking your time and developing a long-term strategy....
Meera and her husband have $4.5 million in retirement accounts and a $430K income. They want guidance on when to start Roth conversions, how much to convert each year, and whether to continue 401(k) c...
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...
The industry asked for and received a delay in the rule from the IRS in 2023. Now that it's going into effect, here are the key implications for sponsors and savers....
Today, I'm speaking with David McKnight. David is a best-selling author, world-renowned tax strategist, and financial educator who challenges some of the most popular (and misleading) retirement gurus...
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...
Caring for a child or parent can mean a drop in income and a lower tax bracket. Why not take advantage by moving money into a Roth account? Here's how it works....
Government 457(b) plans are about to get more complex as new Roth catch-up requirements come into force. Here's how to prepare for the changes....
Should the new temporary senior tax deduction change your Roth conversion strategy? Joe and Big Al spitball for Chris in Maple Grove, Minnesota, who wonders whether to keep converting to Roth now that...
Are you taking advantage of all your Roth opportunities? We break down the differences between the Roth IRA, Roth 401(k), or the Mego Backdoor Roth 401(k). by comparing your choices with another favor...
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 ...
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 episode, Tammy asks about the pros and cons of doing Roth conversions in retirement to manage Required Minimum Distributions (RMDs) down the road. With $2.9 million in combined IRAs and curren...
In this episode, we tackle Richard's question about why it might make sense to use IRA (non-Roth) accounts first to pay for long-term care expenses. We'll explain the reasoning behind this strategy, i...
In this episode, we tackle Kay's questions about managing her IRA and Roth accounts in retirement. With significant assets, no LTC insurance, and children in differing financial circumstances, Kay wan...
John asks if taking larger IRA withdrawals beyond his RMD to fund his daughter's Roth IRA makes sense as a strategy to reduce future RMDs, lower estate taxes, and pass on tax-free assets. Although thi...
Answering listener questions about the pros and cons of traditional vs. Roth contributions, merging finances when a spouse has no income but owns an IRA, and how to maximize annual contributions to a ...
Joe Anderson, CFP® and Big Al Clopine, CPA tackle one of the trickiest timing questions in retirement planning, today on Your Money, Your Wealth podcast number 553: when should you convert to Roth...
Converting to a backdoor Roth IRA via an IRS "loophole" is an estate planning tool that gives heirs tax-free income in retirement. It can help you, too....
Roth conversions, which transform traditional IRAs into Roth IRAs, are a powerful retirement and tax tool. Here are eight facts to get you started....
Between my wife and I we both have accounts at Fidelity and Charles Schwab. They are a mix of rolled over 401K's, IRA's and Roth. I have been using Empower as a way to view all the accounts and keep a...
John asks if taking larger IRA withdrawals beyond his RMD to fund his daughter’s Roth IRA makes sense as a strategy to reduce future RMDs, lower estate taxes, and pass on tax-free assets. Althou...
I'm probably 3 to 6 years from retirement. Been thinking about doing some Roth conversions at some point and it occurred to me ... I think I have the ability to dictate whether my contributions are pr...
Joe and Big Al spitball on how to avoid screwing up the timing of your Roth conversions, today on Your Money, Your Wealth® podcast number 550. Barrie from New York is 62 and single, and she’...
More employers are offering Roth 401(k)s inside their plans, making these accounts more accessible than ever. But just because your employer gives you the option doesn’t mean it’s automati...