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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How can you give stock worth millions to a loved one without giving them a huge capital gains tax bill? This family's financial adviser provided the answer.
Taxpayers can strategically use these temporary tax opportunities in particular to lock in long-term tax savings. Here's how.
We have some fun news to share at the end of this article, so keep reading to the end find out! Over the holiday break, I was helping a family member do some end-of-year tax planning (I know, we’re TH...
For many people, retirement feels less like a reward and more like a financial cliff. In this episode, we break down seven key factors that lead to a more financially stable retirement. You'll learn h...
Most retirees who make this mistake aren’t reckless. They’re careful. They’re doing what they believe is responsible, and that’s what makes it so painful to see when it backfires. James explains why t...
A $10 million retirement is often imagined as the finish line — complete freedom, unlimited spending, and no financial stress. The reality is more complex. James walks through what an eight-figure ret...
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...
Christian thought he was ready for retirement. He just didn’t realize how heavy the weight had been until he finally set it down. After more than 30 years in a high-stress, always-on role at a global ...
The holiday season inspires generosity, but smart gifting can go far beyond festive moments and gifts under the tree. On the show this week, we're digging into the world of gifting strategies, just in...
2026 brings changes to your 401(k) cathc up contributions. Ignoring these changes could get you in trouble with the IRS or cause a suprise tax bill.
A deep dive into the One Big Beautiful Bill Act (OBBBA) reveals key opportunities in 2026 and beyond.
Not all retirees who live in states that tax Social Security benefits have to pay state income taxes. Will your benefits be taxed?
A business-as-usual approach to taxes in the first year of retirement can lead to silly trip-ups that erode your nest egg. Here are seven common goofs to avoid.
Wealthy retirees often overlook Social Security. But timed properly, it can drive tax efficiency, keep Medicare costs in check and strengthen your legacy.
Under new rules, you may lose an up-front deduction but gain tax-free income once you retire.
Saving a large percentage of your income, minimizing taxes and keeping spending in check can offer a more realistic path to retiring rich.
As 2025 draws to a close, take time to review your finances, maximize tax efficiency and align your goals for 2026 with the changing financial landscape.
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 ...
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...
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...
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.
A one-time billionaire wealth tax won’t trigger an exodus—decades of economic evidence show that exit is rare.
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...
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...
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 ...
Wow, 2025 is almost over. We only have about 2 weeks left to finish tax optimization. Actually, we have less time than that. I want to get everything done before ... Read more The post End of 2025 Tax...
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...
Larry and Barbara Cook thought they were helping government agents. In the end, they found themselves victims of tax and Medicare gotchas, as well as the scammers.
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...
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).
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...
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...
As savers, we are being rewarded with higher risk-free yields. Treasury bills (T-bills), Treasury bonds, and money market funds are still paying over 4% without taking equity or credit risk. Because T...
Year‑end planning is critical for wealthy families, in order to preserve wealth, minimize taxes, and grow wealth. Review these key financial planning ideas before 2026.
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...
With the tax-free money in a health savings account, a person can pay for eyeglasses or medical exams, as well as a $1,700 baby bassinet or a $300 online parenting workshop. Those same dollars can’t b...
? 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...
Explore how Trump accounts compare to baby bonds, why tax policy favors wealthy families, and what economists propose to close the racial wealth gap.
What if the biggest opportunity to grow your retirement savings has nothing to do with chasing the next big investment and everything to do with taxes? In this episode, Ryan…
As 2025 wraps up, now may be the perfect time to tighten up your finances and set yourself up for a stronger year ahead. These 12 year-end money moves may help you save more, lower your tax bill, and ...
What if you could employ gift giving strategies that benefit the receiver and also provide the giver significant strategic financial and tax planning advantages? The post The Unexpected Gifts of Givin...
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...
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...