Your Successful Retirement

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 IRA considerations...

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 cal...

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 habits you can buil...

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 from a multi-year conversion strategy rather than making...

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...

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 more confident car-buying decisions. He...

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 withdrawals in retirement, and why age can play...

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 of two workers with dramatically different retirement account balances and r...

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 explains how he...

What is a trust, and why do so many families use them in estate planning? In this YSR FAQ episode, Dennis explains the basics of revocable living trusts and how they help simplify estate settlement while avoiding probate. This conversation covers how trusts are structured, how assets are transferred into a trust, and why many people use trusts to help manage property, investment accounts, and inhe...

Should you place your house into an irrevocable trust? In this YSR FAQ episode, Dennis explains why irrevocable trusts can become far more complicated than many people expect. This conversation covers why families consider irrevocable trusts for nursing home or Medicaid planning, along with the long-term tradeoffs that come with giving up control of property. Dennis also explains the tax implicati...

Estate planning is easy to delay until the people you love are left sorting through the fallout. What happens when missing documents, wrong beneficiaries, or an unfunded trust create delays, costs, and family stress? In this episode, Dennis O’Keefe shares hard-earned lessons about estate planning mistakes that can burden children and other loved ones. He covers why wills matter, how powers of atto...

What exactly is probate, and why do so many families want to avoid it? In this YSR FAQ episode, Dennis explains how the probate process works, where it originated, and why having a will does not automatically keep your estate out of probate court. Using stories from English history to modern-day estate settlement examples, this episode breaks down why probate can become slow, public, and expensive...

Do you actually need a will? In this YSR FAQ episode, we break down one of the most common estate planning questions and explain why a will still matters, even if some of your assets already have built-in protections. Dennis walks through how jointly owned property, beneficiary designations, and transfer-on-death accounts work, and what happens when someone passes away without a will. This episode...

It’s easy to believe something just because it sounds confident or is widely accepted. But what if the stories we trust most, from history to headlines to financial advice, are often simplified, distorted, or just plain wrong? In this episode, Dennis O’Keefe discusses how human nature pushes us toward easy answers and how those shortcuts can lead to poor financial decisions. Whether it’s vir...

Should you consider an annuity, or avoid it altogether?  This week, Dennis O’Keefe breaks down how annuities work, why they are often sold rather than bought, and when they may or may not make sense. Using a real client scenario, Dennis explains how annuity proposals can be positioned in ways that don’t always benefit the investor. He also walks through the structure of annuities, including insura...

What should investors actually do during a recession? In this release of YSR Shorts, Dennis O’Keefe challenges the common reactions people have when markets decline and explains why those instincts often lead to poor outcomes. Using historical examples and a real-world perspective, Dennis explains why market downturns are part of the economic cycle and how disciplined investors approach them diffe...

College planning rarely works the way most parents remember it. In this episode, Dennis O’Keefe shares a personal and eye-opening look at today’s college financial aid system after recently guiding his son through the process. What’s changed over the years may surprise you. How applications are submitted, and how aggressively colleges are offering aid… More importantly, he talks about what familie...

Everyone talks about index funds.  Do they actually know what they are? Dennis O’Keefe cuts through the jargon and explains what an index really is, why the S&P 500 represents 85% of all US market wealth, and how an index fund lets you own a piece of it without the guesswork. He also covers the key advantages: low cost, simplicity, and flexibility, along with one important disadvantage w...

Most people confuse asset allocation with diversification, but they are two very different things. In this episode of YSR Shorts, Dennis O’Keefe explains how asset allocation works, where it came from, and why it is one of the most powerful tools in long-term investing. Dennis traces the concept back to Roger Gibson’s groundbreaking 1989 research, breaks down the pie chart model he use...

Many people think they understand Social Security, until conflicting answers and uncertainty create confusion. What’s actually true about how benefits work, and what should you expect in the years ahead? In this episode, Dennis O’Keefe breaks down how Social Security really works and clears up common misconceptions. He explains how benefits are calculated, why the system is often misunderstood, an...

What does it mean to be a fiduciary? In this episode of YSR Shorts, Dennis O’Keefe explains the fiduciary standard and why it matters in financial services. He discusses disclosure, compensation structures, and why fiduciary status should be part of your evaluation, not the only factor. Dennis also shares real-world examples that highlight the importance of asking deeper questions. Key takeaways:...

Should you pay someone to manage your money? In this episode, Dennis O’Keefe explains the behavioral side of investing. He shares why emotional reactions during market volatility can hurt long-term results and how professional management can help create separation and discipline. Dennis also compares corporate management firms and boutique advisory relationships, outlining the pros and cons of eac...

You may not realize how much of your personal information is visible every single day. From store apps to credit reports, small exposures can quietly add up over time. In this episode of Your Successful Retirement, Dennis O’Keefe explores a topic that affects every retiree and pre-retiree, even if they don’t realize it: how visible you are online. From data tracking at your local grocery store to...