PODCAST · business
Your Successful Retirement
by Dennis O'Keefe
Discover the secrets to a successful retirement with Dennis O’Keefe, a seasoned CERTIFIED FINANCIAL PLANNER™ with over 30 years of expertise. Whether you’ve been retired for years, are on the verge of retirement, or are wondering how to plan for your “some-day” retirement – this podcast is your go-to guide. Gain exclusive strategies tailored to optimizing your retirement benefits, hear real-life stories from retirees, and absorb invaluable wisdom from our guest leaders.
Episodes
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How Healthcare, Taxes, and Government Policies Could Affect Your Retirement (Ep. 144)
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...
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Is It Worth It To Convert Your IRA To A Roth?
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...
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How Often Should I Check My 401(k)?
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...
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How to Buy Your Next Car Without Overpaying (Ep. 143)
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...
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Should You Contribute To Your 401(k) On a Roth Basis?
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…
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How Much Money Do I Need For Retirement?
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…
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How to Filter Market Noise and Focus on What Really Matters
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...
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What Is a Trust?
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...
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Should I Put My House in an Irrevocable Trust?
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...
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Estate Planning Mistakes That Can Burden Your Family (Ep. 141)
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...
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What Is Probate?
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...
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Do You Need a Will?
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...
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Don’t Trust the Easy Answer: How Bad Information Can Hurt Your Financial Decisions
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...
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Should I Be Doing This Annuity?
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...
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What Happens If We Have Another Recession?
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…
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What Families Need to Know About College Planning Today
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...
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What Is An Index Fund?
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 …...
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What Are Asset Allocations?
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...
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Understanding Social Security: Myths, Mechanics, and What Happens Next
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...
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What Does “Fiduciary” Really Mean?
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…
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Should You Pay Someone to Manage Your Money?
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...
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How to Protect Yourself From Scams and Identity Theft in Retirement
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…
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What Does CFP® Really Mean? (And Why It Matters)
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…
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What Is Comprehensive Financial Planning? (It’s Not a Binder)
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…
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Strategic Tax Planning: What You Need to Know Before Filing
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...
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Voluntary Retirement Offers: What You Need to Know Before Deciding
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...
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Can AI Really Replace Human Financial Guidance?
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...
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Protecting Your Money from Modern Scams
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…
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Long-Term Care: The Most Overlooked (and Misunderstood) Part of Financial Planning
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...
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Your Guide to Layoffs, Severance, and Retirement Decisions
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,...
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Are Roth IRAs Worth It?
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…
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Care Options for Older Americans
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...
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Investments You May Want To Avoid
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...
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Why is Healthcare So Expensive?
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…
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Elderly Planning: What You Need To Know
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,...
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How To Financially Support Your Adult Children, Without Enabling Them (Part 2)
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...
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How To Financially Support Your Adult Children, Without Enabling Them (Part 1)
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...
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How Debt Can Derail Your Retirement
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…
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Funding College Without Breaking the Bank
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...
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Greed vs. Fear: Managing Emotions in Your Investment Portfolio
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…
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Outsmarting Instincts in Market Chaos
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...
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How Inflation Shapes Your Financial Strategy
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...
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Overcome Financial Anxiety and Retirement Fears
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…
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Are We Headed for Another Real Estate Crash?
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…
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Unlock the Secrets of Living Trusts
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...
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Financial Planning Unveiled: What You Need to Know for a Secure Future
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…
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Financial Wellness: Your First Meeting with an Advisor
When it comes to financial planning, the first meeting is about more than just crunching numbers—it’s about understanding your full financial picture, addressing your concerns, and setting a foundation for informed decision-making. Join CERTIFIED FINANCIAL PLANNER™, Dennis O’Keefe walks you…
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The Pros and Cons of Automated Investment Services
Are you overwhelmed by investment management ads promising to handle your money easily? What’s the deal, and are they worth it? Dennis O’Keefe dives into the world of automated investment management and the critical differences between computer and personal touch in retirement planning. With over...
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Estate Planning Mistakes That Could Cost You Everything
Estate planning is one of those things we all know we should do, yet most of us keep pushing it off—just like changing the furnace filter (which, by the way, can have disastrous consequences if ignored). But failing to plan your estate properly can leave your loved ones with unexpected legal and...
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Managing Healthcare Costs During Retirement
What’s the real cost of retirement health insurance? Dennis O’Keefe explores the often-overlooked costs of health insurance in retirement, a critical expense many fail to account for when planning their financial future. With over 30 years of experience as a CERTIFIED FINANCIAL PLANNER™, he...
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ABOUT THIS SHOW
Discover the secrets to a successful retirement with Dennis O’Keefe, a seasoned CERTIFIED FINANCIAL PLANNER™ with over 30 years of expertise. Whether you’ve been retired for years, are on the verge of retirement, or are wondering how to plan for your “some-day” retirement – this podcast is your go-to guide. Gain exclusive strategies tailored to optimizing your retirement benefits, hear real-life stories from retirees, and absorb invaluable wisdom from our guest leaders.
HOSTED BY
Dennis O'Keefe
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Frequently Asked Questions
How many episodes does Your Successful Retirement have?
Your Successful Retirement currently has 159 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Your Successful Retirement about?
Discover the secrets to a successful retirement with Dennis O’Keefe, a seasoned CERTIFIED FINANCIAL PLANNER™ with over 30 years of expertise. Whether you’ve been retired for years, are on the verge of retirement, or are wondering how to plan for your “some-day” retirement – this podcast is your...
How often does Your Successful Retirement release new episodes?
Your Successful Retirement publishes regularly with 159 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Your Successful Retirement?
You can listen to Your Successful Retirement on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Your Successful Retirement?
Your Successful Retirement is created and hosted by Dennis O'Keefe.
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