Year-end tax planning can affect decisions you’ve already made about retirement accounts, investments, major purchases, and charitable giving. What should you review before December closes the door on another tax year? In this episode, Dennis O’Keefe explains five tax planning areas worth reviewing before 2027. He covers 401(k) contributions and employer matches, IRA and spousal …
Required minimum distributions often sound straightforward until timing, taxes, and deadlines begin affecting the decisions you make. Many retirees discover there is more flexibility than they expected, but there are also situations where delaying a distribution can create unintended tax consequences. In this YSR FAQ episode, Dennis O’Keefe explains how required minimum distributions are calculated, …
Many financial decisions feel unrelated until taxes quietly change the outcome. Knowing where your income falls can influence everything from retirement withdrawals to Roth conversions, yet many people don’t realize how much flexibility they actually have. In this YSR FAQ episode, Dennis O’Keefe explains why understanding your tax bracket is one of the most valuable …
How could decisions about healthcare, taxes, housing, and government spending affect your retirement and financial future? Many ideas sound appealing at first, but the details behind implementation, cost, and long-term effects can shape the outcome in unexpected ways. In this episode, Dennis O’Keefe examines how political discussions around healthcare, taxes, housing, and government spending could …
Should you convert your traditional IRA to a Roth IRA? In this YSR FAQ episode, Dennis O’Keefe breaks down the pros and cons of Roth conversions and explains why the answer depends heavily on your tax situation. Dennis discusses how Roth conversions are taxed, the importance of understanding tax brackets, and why many investors benefit …
How closely should you monitor your retirement accounts? In this YSR FAQ episode, Dennis O’Keefe explains why both neglecting your 401(k) and obsessively checking it can create problems. Using examples from his own experience and lessons from past market cycles, Dennis discusses the importance of reviewing account allocations, maintaining proper diversification, and periodically rebalancing your …
Thinking about buying a car? It can feel overwhelming, especially when prices, financing, trade-offs, and dealership tactics all compete for your attention. How do you know you’re paying a fair price, and what steps can help you avoid expensive mistakes before you sign? In this episode, Dennis O’Keefe shares practical strategies to help you make …
A Roth 401(k) can be a powerful retirement savings tool, but is it the right choice for everyone? In this YSR FAQ episode, Dennis O’Keefe discusses how Roth 401(k) contributions work and the factors that determine whether they make sense for your situation. The conversation explores current versus future tax brackets, the benefits of tax-free …
One of the most common retirement questions is also one of the hardest to answer: How much money is enough? In this YSR FAQ episode, Dennis O’Keefe explains why there is no universal retirement savings target and why your spending habits matter far more than a simple rule of thumb. Dennis shares a real-life example …
Trying to predict the market can feel overwhelming when headlines, opinions, and daily volatility are everywhere. How do you separate meaningful economic signals from distractions? What information actually helps you make better financial decisions over the long term? In this episode, Dennis O’Keefe shares why market predictions are often little more than educated guesses and …