Your Successful Retirement
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
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 the...
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 takeaway...
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 ret...
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 achi...
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 au...
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 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...
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.
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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 Read more
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 ...
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....
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 char...
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...
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 s...
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 ...
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...
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...
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 spotlig...
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 fin...
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 ...
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