Episodes

What does CFP actually mean? In this episode of YSR Shorts, Dennis O’Keefe breaks down the Certified Financial Planner designation and what it requires. From accredited coursework in retirement, taxes, estate planning, and investments to years of experience and a comprehensive exam, Dennis explains what goes into earning and maintaining the CFP mark. He also shares why credentials matter, but why they are only a starting point when choosing a financial professional. Key takeaways: The differenc...

What does comprehensive financial planning actually mean? In this episode, Dennis O’Keefe walks through the real financial planning process. He explains how retirement, investments, taxes, estate planning, and asset protection must work together. Dennis also shares why a plan should be actionable, collaborative, and constantly reviewed, rather than a document that sits on a shelf. Key takeaways: The five core components of financial planning Why planning is a process, not a product The importan...

Tax season is here, and most people approach it tactically rather than strategically. Are you simply gathering documents and hoping for the best, or are you proactively managing your tax situation year-round? In this episode, Dennis O’Keefe shares his approach to strategic tax planning and why understanding your tax situation matters beyond just filing returns. He recounts a frustrating experience with the IRS that taught him valuable lessons about dealing with government agencies. Dennis walks ...

Major companies are restructuring, and voluntary retirement packages are landing on desks across the country. How do you know if taking the offer is the right move for your future? In this episode, Dennis O’Keefe examines the complexities of voluntary retirement offers and involuntary layoffs. He reveals how companies carefully craft these packages to achieve specific workforce reductions and shares insights from HR professionals about the strategy behind these offers. Dennis also discusses the ...

Join us this episode as Dennis O’Keefe outlines the ways AI tools are being used in financial planning and where they currently fall short. He explains how automated systems process information, where they provide efficiency, and the limitations that appear when personal context or situational nuance is required. Dennis also describes the differences between automated platforms, large national firms, and independent fiduciary advisors, focusing on how each model approaches service and decision s...

From “Nigerian princes” to “crypto investments,” scams have evolved, but the playbook hasn’t changed. In this episode, Dennis O’Keefe draws from three decades of experience helping retirees avoid costly traps. Through real stories and a bit of humor, he breaks down how con artists prey on emotion, urgency, and trust and how you can protect yourself and the people you love. What you can expect from this release: Why even intelligent people fall for scams The red flags every retiree should know H...

Planning for long-term care is one of the hardest and most personal financial challenges families face. Let’s cut through the noise to unpack what really works, what doesn’t, and what might cost you dearly down the line. From irrevocable trusts and annuities to asset transfers and Medicaid’s five-year lookback, he explains the real-world tradeoffs every family must understand before taking action. You’ll also hear why many people default to “doing nothing,” and how that can either preserve flexi...

When layoffs or retirement offers appear, whether planned or not, they can stir panic and uncertainty. In this episode of Your Successful Retirement, Dennis O’Keefe, CFP®, draws on more than 30 years of experience helping telecom employees navigate these pivotal transitions. He shares a calm, practical approach to managing the emotional and financial stress that follows a sudden career shift. You’ll learn what to consider before signing a severance agreement, the hidden tax implications many ove...

You’ve seen the Roth conversion hype, the slick Instagram reels, the pushy advisors, the calculators promising massive tax savings. But here’s the real question: Is it actually right for you? We’re breaking the spell of oversimplified Roth conversion advice. The truth? A Roth might not be about you at all; it might be about your children, your legacy, and what happens 20–30 years from now. If you’ve ever wondered whether a Roth conversion is a smart move or a shiny distraction, this episode deli...

It used to be simple: either your family took care of you at home, or you went into a nursing home. But those days are long gone. Dennis O’Keefe walks through the four levels of elder care today: home care, senior living, assisted living, and nursing homes, and explains what each one actually means, how much they cost, and what kind of planning families should be doing now to prepare. He shares stories from his own family, clients, and favorite TV shows (yes, The Sopranos) to help illustrate jus...

In this episode, Dennis O’Keefe takes a candid look at the kinds of investments he personally avoids and why. From gold and crypto to private equity and AI, Dennis shares stories, history, and hard-won lessons about what happens when hype outweighs fundamentals. His goal isn’t to tell you what to buy, but to help you slow down, ask sharper questions, and protect your retirement from unnecessary risk. Key takeaways: Why “hero stories” of big wins can mislead investors The hidden risks behind gol...

When Dennis O’Keefe was growing up, his family called him “Mr. Perfect” and “The Shell Answer Man” because he always had an answer for everything. Decades later, that nickname still fits, especially when it comes to the complicated, frustrating world of healthcare costs in America. In this episode, Dennis dives into one of the most confusing and emotionally charged questions in retirement planning: Why is healthcare so expensive, and where is all that money going? From drug pricing myths to the ...

When it comes to planning for retirement, most of us stop at saving and investing. But what about the years after 80, the stage when care, housing, and advocacy become crucial? In this episode, Dennis O’Keefe, CFP®, shares personal stories of his own family’s journey through late-stage care, housing transitions, and the emotional complexities of supporting loved ones. He explains why thinking conceptually about your future needs before jumping into legal documents or strategies lays the foundati...

What if the greatest financial gift you could give your children isn’t money, but foresight? In this second installment of how to support your adult children, Dennis O’Keefe, CFP®, shifts the focus from today’s challenges to tomorrow’s realities. Drawing on personal stories, national trends, and decades of planning experience, Dennis explores the silent storm ahead: rising living costs, delayed parenthood, demographic shifts, and a changing retirement landscape. You’ll learn how to prepare your ...

What if helping your adult children is holding them back? In this episode, Dennis O’Keefe explores the tough reality many parents face: when does financial support cross the line into enabling? Drawing on personal stories and over 30 years of financial planning experience, Dennis unpacks why today’s 30-somethings are struggling with independence and how parents may be unintentionally making things harder. From soaring housing costs to student loan debt, and from generational shifts to emotional ...

What if the greatest threat to your retirement isn’t your income, savings, or investments, but your debt? In this eye-opening episode, Dennis O’Keefe, CFP®, breaks down why debt is the single most dangerous factor for retirees, often more damaging than people realize. Drawing from over 30 years of financial planning experience, Dennis shares personal stories, historical examples, and common traps that lure people into debt, including 0% offers, home equity loans, credit card traps, and extended ...

How are you planning to fund your child’s college education—cash, loans, or perhaps a towering pile of fortune cookies? Dennis O’Keefe dives into the ever-daunting topic of college expenses. With tuition rates soaring higher than vintage 1980s laptops, Dennis breaks down the different ways to prepare financially and discusses the value of a degree in today’s world. Spoiler alert: It’s not as clear-cut as it once was. Highlights of this episode include: Is a college degree still worth the cost? ...

Why do your investments soar when you’re least expecting them to, only to plummet when you’re not prepared? Join seasoned financial planner Dennis O’Keefe as he highlights the highs and lows of financial planning, focusing this time on mastering the art of managing a thriving portfolio. Drawing on over 30 years of experience, Dennis turns the spotlight on the dangers of greed when everything seems to be going well. Dennis discusses: The powerful emotions driving investment decisions: fear and g...

Curious about why markets crash and how our own brains can trip us up? In this episode, Dennis O’Keefe navigates the complex psychology guiding our financial decisions, specifically when our “reptilian brain” pushes us to act against our best interests during market volatility. Join Dennis, a seasoned financial planner, as he shares eye-opening tales from history, like the notorious 1987 crash and recent 2025 market fluctuations, to showcase why instincts might lead us astray. Discover practical...

Ever wondered how inflation impacts your retirement nest egg? Or how the price shift from eggs to bananas affects your financial plans? Join Dennis O’Keefe, a seasoned financial planner, as he uncovers the complexities of inflation and its profound implications on your future finances. Dennis reflects on the evolving inflation rates through the years and breaks down the Consumer Price Index (CPI), providing you with a solid understanding to navigate your retirement in today’s economic climate De...

Curious about what truly goes into planning a successful retirement? Why is retirement deemed the most challenging life event you’ll ever face? Join Dennis O’Keefe, a seasoned financial planner with over 30 years of experience, as he demystifies the retirement process in this episode. Dennis dives deep into why retirement can be more daunting than it seems and highlights the importance of preparing for this significant life transition. Listen in as he shares a compelling story of a retiree who l...

Is the real estate market heading for another crash, or have we simply hit a plateau? Dennis O’Keefe invites you on a journey through the patterns of past real estate markets that might just give you insight into today’s trends. Dennis breaks down whether we’re on the brink of a real estate bubble, what history tells us about market patterns, and how experiences from past decades can inform current decisions. From reminiscing about infomercials to personal anecdotes about the joys and pitfalls o...

Are you prepared to simplify the complex world of estate planning with trusts? Tune in as Dennis O’Keefe sheds light on the intricacies of living trusts and how they can become a vital component of your retirement planning strategy. Whether you’re considering a trust yourself or just eager to enhance your financial literacy, Dennis breaks it all down in a friendly and digestible way. Dive into the podcast as Dennis shares insights on: The history and purpose of living trusts Differences between...

What exactly do financial planners do? Explore valuable insights into retirement planning with Dennis O’Keefe, a seasoned, certified financial planner with over 30 years of experience. Whether you’ve been retired for years or on the verge of retirement, or are wondering how to plan for your someday retirement, this podcast is your go-to guide. Tune in as Dennis covers: The essence of a true financial planner vs. the common misconceptions [00:02:00] The five pillars of financial planning: retire...