Retirement income can be subject to taxes depending on the specific type of retirement account or benefit you receive and your tax bracket. Here are a few examples of common types of retirement income and how they may be taxed:
1. Social Security benefits: Social Security benefits are generally taxable if you have other substantial income in addition to your benefits. The amount of tax you pay on your benefits depends on your taxable income and tax filing status.
2. Traditional Individual Retirement Account (IRA) and 401(k) withdrawals: Withdrawals from traditional IRAs and 401(k)s are generally taxed as ordinary income at your current tax rate.
3. Roth IRA withdrawals: Withdrawals from Roth IRAs are generally tax-free if you are over the age of 59 1/2 and you have held the account for at least five years.
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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...
It's time to focus on how they can potentially reduce their taxes, align their finances with family goals and build their financial confidence for the new year....
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...
Should your tax preparer also be giving you advice about how to live your tax life? In other words, do you actually need a tax strategist? The post Do You Need a ‘Tax Strategist?’ appeared...
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...
Make the most of year-end by reviewing contributions, taxes, and benefits. Smart planning now can strengthen your finances and set you up for success in 2026....
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...
Most retirees think tax planning ends with knowing their tax bracket, but that's just the beginning. In this episode, we unpack how different income sources interact in retirement, and how seemingly s...
Today we answer a question from Chris about The Good Life Abroad and whether we plan to take a trip with the company. We share our thoughts on the concept, what interests us about their offerings, and...
Today we answer a question from Sandi about how much umbrella insurance coverage you really need — especially as you approach retirement. We discuss why someone might choose a $2 million policy,...
Today we answer a question from Peter about what happens when a parent dies with a fully planned estate that avoids probate — and how the Small Estate Affidavit process works in practice. We dis...
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 the final installment of our 3-part estate planning series, we dive into one of the most overlooked—but critically important—aspects of planning: protecting your heirs' inheritance. It'...
Today we answer Jeff's question about using home equity to pay for end-of-life care — from tapping into equity for in-home support to selling the home to cover nursing home costs. In high-cost s...
In this episode, we shine the light on common estate planning mistakes that can derail even the best intentions. We discuss the risks of failing to update beneficiary designations and why relying sole...
Today we answer a question from Cathy about helping aging parents in California navigate care costs, preserve limited resources, and explore options like pro bono legal support. Although this show doe...
In this episode, we cover key tax considerations around wealth transfer. We cover the differences between federal estate tax and state inheritance tax, and explain why the stepped-up basis is such a p...
In this episode, Brian asks some great questions about using Net Unrealized Appreciation (NUA) for company stock inside a 401(k). We dive into the rules, timing, and strategies that could lead to majo...
In this episode, we explore how to pass on your assets smoothly and efficiently—without dragging your loved ones through probate court. You'll learn why probate can be costly and time-consuming,...
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, ...
In the first part of our series on estate planning, we laid the groundwork for why incapacity planning matters and what documents you need to get started. But there's more to it than just having your ...
Today kicks off a brand-new series on estate planning. Estate planning is one of those things everyone knows they should do—but far too many people put it off, sometimes until it's too late. And...
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...
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...
Planning to travel in retirement? In this episode, I sit down with Andrew Motiwalla from The Good Life Abroad to discuss how retirees can make the most of their travel experiences—without the st...
This week, we're diving into a question about the tax treatment of Special Needs Trusts. There are two types—First-Party and Third-Party trusts—but how does each one affect taxes? We'll br...
For countless retirees, the greatest challenge isn't saving money, but spending it. After years of diligent saving, the transition to drawing down those hard-earned funds can be fraught with anxiety a...
Dan asks: If monthly income from an IRA exceeds $2,908 for a single person, would that result in disqualification for Medicaid? We break down the income limits, potential strategies to navigate Medica...
We've heard this hundreds of time... 'I wish someone had warned me about this when I retired.' More often than not, they're referring to one of five key challenges that catch many retirees by surprise...
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...
Cryptocurrency has changed the financial landscape, and that includes estate planning. Unlike traditional assets, crypto presents unique challenges—there's no customer service line to recover lo...
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...
From President Trump's upcoming tariffs on Canada, Mexico, and China to the historical legacy of the "Chicken Tax," tariffs have shaped economies and industries in ways both expected and unforeseen. 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...
A recent Supreme Court decision in Connelly v. United States has sent shockwaves through closely held businesses employing life-insurance-funded redemption-type buy-sell agreements. In this episode, w...
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...
Sometimes life throws curveballs, and you may end up retiring earlier than planned. In this episode, we dive into JP Morgan's data on why people retire earlier than expected and discuss how to prepare...
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...
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 ...
Today's episode is part rant, part answer to Mike's question about the high cost of prescription drugs under Medicare Part D. We dive into why these costs are so steep, explore alternatives like Canad...
Financial planning often feels like a numbers game—follow the math, and you'll make the best decisions, right? But what happens when the spreadsheet says one thing, and your peace of mind says a...
Today, we tackle a question many retirees face: Can you manage your taxes with DIY software like TurboTax, or is it time to bring in a professional? We'll explore the challenges of navigating tax comp...
Daryl wants a simple explanation of why Health Savings Accounts matter and what makes them such a powerful retirement planning tool. Although this show does not provide specific tax, legal, or financi...
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...
Many retirees think they have a plan when what they really have is an investment pitch dressed up as planning. This episode uncovers why that illusion is dangerous, the costly mistakes it hides, and h...
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...