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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.
If your house is too cluttered, it's probably time to do something about it. Decluttering will save you time; space; and, yes, money. The post Decluttering as a Financial Strategy appeared first on Th...
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...
Jeremy Keil weighs the opportunities and risks associated with giving your money away to your kids and charity. Most retirees I talk with don’t worry about whether they can give money away. They worry...
In this Christmas Eve episode, Roger Whitney explores the basics of charitable giving as part of an intentional retirement plan, with a timely focus on year-end decisions. He explains how charitable d...
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 ...
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...
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...
In this episode, Roger Whitney, a retirement planner with 30 years of experience, breaks down annual gifting limits and year-end planning. He shares practical strategies for giving that make a real im...
Steve spent more than two decades building video games, working with a team that felt more like family than coworkers. By all measures, he loved his work. But a heart attack in 2021 changed everything...
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,...
Retiring at 50 sounds bold, almost unthinkable for most people, but for Kent, it was the only decision that made sense once life, loss, and perspective pushed everything into focus. In this conversati...
? Show Notes In this episode, Roger Whitney kicks off a month-long series on year-end planning for retirement. He shares insights on tax loss harvesting, a technique that can help you minimize capital...
I have just returned from another enjoyable but exhausting trip to London to see our granddaughters. On this occasion, rather than driving, Mister E and I took the train and the journey proved to be t...
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...
Get insights for the best way to use your money. What are the pros and cons of paying off mortgage vs. investing? The post Should You Pay Off Mortgage or Invest? appeared first on Boldin.
When you think about retirement, it’s easy to picture it as one long chapter, but financially, it’s really a series of different seasons. Your needs, lifestyle, and spending change over time, and your...
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...
Spend safely in retirement? It sounds promising. Discover how to implement this retirement income strategy developed at Stanford. Read more… The post Want Reliable Retirement Income? Use the Sp...
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....
Is your financial plan fit for purpose — or is your adviser peddling an outdated strategy? When you see these red flags, it's time for a second opinion.Evan...
How do I turn my savings into a steady paycheck that lasts the rest of my life?There are a few ways to approach this challenge, but one of the most popular, and surprisingly flexible, is called the sy...
In this episode of Retirement Reality, Darren shares what it’s really like to walk away from work at 54 and why it still feels surreal. After decades of saving, hitting his number, and paying of...
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...
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...
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...
When you're job hunting, AI may undermine your best efforts. Here's how older women can throw a wrench in the algorithm....
It’s not too early to start planning your spending for 2026 even though you haven’t yet determined your January 1, 2026 Funded Status. You or your spouse may be considering spending in 202...
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...
What if the “smart” money choice isn’t the choice that builds your best life? This Root Talks episode starts with a bucket-list moment for James—throwing the first pitch at a P...
Meeting your goals is more likely if you stick to your strategy despite market volatility and scary headlines. Consistency makes a difference....
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...
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...
When people think of what could haunt their retirement, they often imagine running out of money, facing unexpected expenses, or living too long. But as we discuss in this episode, there's a more insid...
Tax planning often slips to the bottom of our financial to-do lists—until a surprise bill or missed opportunity crops up. But behind the scenes, the right process for an ongoing tax strategy can...
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 of Retirement Reality, meet Donovan, a 55-year-old retiree who turned an unexpected career exit into an opportunity for freedom, reflection, and new purpose. Donovan shares how one def...
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 ...
John asks about buying the individual sectors of the S&P 500 and rebalancing based on performance instead of simply buying an index fund. Devin shares the pros and cons that he can see with this s...
In this episode, we dive into Stephen's fascinating question about estate planning for the far future—trusts designed to preserve wealth for individuals who undergo cryonic preservation. Is this...
Your mindset can make or break your retirement. Are you a Pollyanna, Delegator, Controller, or Realist? In this episode, we dive into the four common mindsets retirees bring to the table and how each ...
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 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...
Retirement can be stressful, especially when the markets are unpredictable. In this episode, we'll talk about a simple strategy to give you peace of mind and financial stability in retirement. You'll ...
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...
Winning the lottery may be rare, but estate tax mistakes aren't. In this episode, we use the recent $1.8 billion Powerball jackpot to highlight how generational wealth can be eroded by estate taxes an...
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...
For many affluent retirees, the biggest financial fear isn't market volatility or rising taxes. It's this simple question: What happens if I'm not the one here to manage the plan? In this episode, we ...