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

Elderly Planning: What You Need To Know

September 11, 2025 • 29 mins

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 …

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How To Financially Support Your Adult Children, Without Enabling Them (Part 2)

August 28, 2025 • 31 mins

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: …

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How To Financially Support Your Adult Children, Without Enabling Them (Part 1)

August 14, 2025 • 32 mins

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 …

How Debt Can Derail Your Retirement

July 24, 2025 • 28 mins

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, …

Funding College Without Breaking the Bank

July 10, 2025 • 34 mins

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 …

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Greed vs. Fear: Managing Emotions in Your Investment Portfolio

June 26, 2025 • 29 mins

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 …

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Outsmarting Instincts in Market Chaos

June 12, 2025 • 26 mins

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 …

How Inflation Shapes Your Financial Strategy

May 22, 2025 • 32 mins

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 …

Overcome Financial Anxiety and Retirement Fears

May 8, 2025 • 28 mins

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 …

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Are We Headed for Another Real Estate Crash?

April 24, 2025 • 29 mins

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 …

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Unlock the Secrets of Living Trusts

April 10, 2025 • 31 mins

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 …

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Financial Planning Unveiled: What You Need to Know for a Secure Future

March 27, 2025 • 33 mins

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 …

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Financial Wellness: Your First Meeting with an Advisor

March 13, 2025 • 25 mins

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 through what happens in that initial conversation and how he and his team have designed …

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The Pros and Cons of Automated Investment Services

February 27, 2025 • 27 mins

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 30 years of financial planning experience, Dennis shares invaluable insights …

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Estate Planning Mistakes That Could Cost You Everything

February 13, 2025 • 28 mins

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 financial nightmares. Join …

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Managing Healthcare Costs During Retirement

January 23, 2025 • 29 mins

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 provides invaluable guidance tailored to telecom industry employees preparing for retirement. …

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How to Keep Your New Year’s Financial Resolutions

January 9, 2025 • 28 mins

Are you ready to make small changes that could impact your financial future? Dennis O’Keefe explores the power of simple adjustments in retirement savings tailored for telecom employees facing retirement or career changes. We all know how fleeting resolutions can be, but what if a few small shifts could enhance your financial well-being? Join Dennis …

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Supercharge Your Retirement Savings!

December 12, 2024 • 23 mins

With over 30 years of expertise as a CERTIFIED FINANCIAL PLANNER™ for telecom employees, Dennis offers insights into maximizing your 401k contributions and why starting early is crucial. He explores the power of compound interest, sharing an example of three hypothetical savers, demonstrating that starting contributions early—even with lower amounts—leads to significantly higher retirement savings. …

How To Empower Your Children With Money Skills

November 28, 2024 • 27 mins

Teaching financial responsibility to children helps set the stage for financial independence as young adults. Join host Dennis O’Keefe as he explores the impact of teaching financial lessons to children. Using personal anecdotes and insightful stories, Dennis highlights how you can help shape your child’s understanding of finances. Top takeaways include: The importance of letting …

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7 Tax Myths

November 14, 2024 • 32 mins

With over 30 years as a CERTIFIED FINANCIAL PLANNER™ specializing in telecom retirement, Dennis combines humor and clarity to debunk common tax myths. Through engaging stories, he offers fresh perspectives on complex topics like billionaire taxes, corporate levies, and home capital gains, making it easier for listeners to grasp the realities behind these often misunderstood …

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Your Successful Retirement

Episodes

.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Elderly Planning: What You Need To Know

.css-r6mb8g{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:1;overflow:hidden;}How To Financially Support Your Adult Children, Without Enabling Them (Part 2)

How To Financially Support Your Adult Children, Without Enabling Them (Part 1)

How Debt Can Derail Your Retirement

Funding College Without Breaking the Bank

Greed vs. Fear: Managing Emotions in Your Investment Portfolio

Outsmarting Instincts in Market Chaos

How Inflation Shapes Your Financial Strategy

Overcome Financial Anxiety and Retirement Fears

Are We Headed for Another Real Estate Crash?

Unlock the Secrets of Living Trusts

Financial Planning Unveiled: What You Need to Know for a Secure Future

Financial Wellness: Your First Meeting with an Advisor

The Pros and Cons of Automated Investment Services

Estate Planning Mistakes That Could Cost You Everything

Managing Healthcare Costs During Retirement

How to Keep Your New Year’s Financial Resolutions

Supercharge Your Retirement Savings!

How To Empower Your Children With Money Skills

7 Tax Myths

Popular Podcasts

Elderly Planning: What You Need To Know

How To Financially Support Your Adult Children, Without Enabling Them (Part 2)