Your Successful Retirement

Your Successful Retirement


Latest Episodes

Protecting Your Money from Modern Scams
December 23, 2025

From Nigerian princes to crypto investments, scams have evolved, but the playbook hasnt changed.In this episode, Dennis OKeefe draws from three decades of experience helping retirees avoid costly traps.Through real stories and a bit of humor, he

Long-Term Care: The Most Overlooked (and Misunderstood) Part of Financial Planning
December 11, 2025

Planning for long-term care is one of the hardest and most personal financial challenges families face.Lets cut through the noise to unpack what really works, what doesnt, and what might cost you dearly down the line.From irrevocable trusts and annui

Your Guide to Layoffs, Severance, and Retirement Decisions
November 27, 2025

When layoffs or retirement offers appear, whether planned or not, they can stir panic and uncertainty. In this episode of Your Successful Retirement, Dennis OKeefe, CFP, draws on more than 30 years of experience helping telecom employees navigate these

Are Roth IRAs Worth It?
November 13, 2025

Youve seen the Roth conversion hype, the slick Instagram reels, the pushy advisors, the calculators promising massive tax savings. But heres the real question: Is it actually right for you?Were breaking the spell of oversimplified Roth conversion advi

Care Options for Older Americans
October 23, 2025

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 OKeefe walks through the four levels of elder care today: home care, senior living, assisted living, and nursing hom

Investments You May Want To Avoid
October 09, 2025

In this episode, Dennis OKeefe 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 fundam

Why is Healthcare So Expensive?
September 25, 2025

When Dennis OKeefe 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 h

Elderly Planning: What You Need To Know
September 11, 2025

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 OKeefe, CFP, shares personal stories of his own fami

How To Financially Support Your Adult Children, Without Enabling Them (Part 2)
August 28, 2025

What if the greatest financial gift you could give your children isnt money, but foresight?In this second installment of how to support your adult children, Dennis O’Keefe, CFP, shifts the focus from todays challenges to tomorrows realities. D

How To Financially Support Your Adult Children, Without Enabling Them (Part 1)
August 14, 2025

What if helping your adult children is holding them back?In this episode, Dennis OKeefe 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 pl