How To Avoid The Pain of Estimated Tax Payments in Retirement #301
In episode 301 of Retire with Ryan, host Ryan Morrissey explains why underpayment penalties for estimated taxes are soaring—$1.3 billion in 2024, triple the 2021 amount—and how retirees can avoid them. He outlines the IRS’s safe‑harbor rules (paying 90% of the current year’s tax or 100‑110% of the prior year’s tax, depending on income) and the quarterly payment deadlines, emphasizing that retirees with investment income, Roth conversions, or large capital gains must treat those earnings like self‑employment income. Morrissey also advises using Form 2210 to detail uneven income timing and highlights that the IRS often assumes income is earned evenly, which can trigger penalties. He urges retirees to coordinate with their accountants and advisors to adjust withholding or make timely estimated payments.
Is The Social Security Lump Sum A Good Deal? #300
In this episode Ryan Morrissey breaks down the Social Security lump‑sum option that some retirees can claim when they delay benefits past full retirement age. Using a client example, he shows that a $14,100 lump sum equates to about an...
How To Manage The Impact From the IRAN War On Your Retirement Portfolio, #299
In episode 299, Ryan Morrissey examines how the Iran war’s surge in oil prices—up roughly 33% since late February—has driven a 6% dip in the S&P 500 and sparked market volatility. He explains why such shocks are often temporary, drawing parallels...
Should You Add a Transfer on Death Beneficiary to Your Assets? #298
In this episode Ryan Morrissey explains how Transfer on Death (TOD) and Payable on Death (POD) beneficiary designations let you bypass probate for bank, brokerage, and other investment accounts. He outlines which assets already have built‑in beneficiary options, the pros...
7 Tax Mistakes to Avoid When Filing Your 2025 Taxes, Ep#296
In this episode Ryan Morrissey outlines seven common tax filing mistakes, from missing the April deadline and failing to report all income to overlooking new 2025 tax breaks and itemization opportunities. He stresses the importance of accurate personal details, double‑checking...
What We Still Don't Know About Trump Accounts, Ep#295
In this episode Ryan Morrissey explains the newly introduced "Trump accounts" (530A accounts) designed to help children build wealth, detailing eligibility, contribution limits, and the $1,000 government seed fund for births between 2025‑2028. He walks through the still‑unclear aspects such...
Is It Wise to Gift My Children Money While I'm Alive? Ep#294
In this episode Ryan Morrissey explores the pros and cons of gifting money or assets to adult children while the parents are still alive. He emphasizes assessing one’s own financial health, long‑term care needs, and the purpose of the gift—whether...
Learn the ABCs of Medicare, Ep293
In this episode Ryan Morrissey breaks down the essentials of Medicare for listeners approaching age 65, covering Parts A, B, C, and D, associated costs, and the critical timing of enrollment to avoid penalties. He explains the differences between original...
