Your Successful Retirement

Dennis O'Keefe
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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.

  1. 2D AGO

    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 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 through essential tax considerations, including IRA contributions, 401(k) adjustments, understanding your tax bracket, and avoiding costly withholding mistakes that could result in penalties. Dennis discusses: Why reviewing last year’s return helps you understand your tax bracket and make informed financial decisions How the 2018 Tax Act changed itemization rules and why most Americans no longer need to save receipts Understanding the 1099 composite form and tracking investment income to avoid tax surprises at filing time Why both large refunds and owing money can signal problems with your withholding strategy and how to fix it The difference between tax preparation and tax strategy, and why forward-looking planning saves you money And more! Connect with Dennis O’Keefe:  Successful Money Strategies, Inc dennis@successfulmoney.com  (508) 730-2300  LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

    36 min

  2. JAN 22

    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 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 current employment landscape at major telecommunications companies, the risks of waiting too long to decide, and practical steps to prepare, whether you’re facing a voluntary severance package or potential layoff. Dennis discusses: How companies strategically design voluntary offers to target specific employee groups and achieve precise headcount goals The difference between voluntary severance packages and involuntary layoffs, including benefits and compensation comparisons Key factors to assess when evaluating an offer: retirement readiness, marketable skills, geography, and career trajectory The importance of retraining opportunities and using employer-paid education benefits before a potential departure Why professional guidance from financial advisors and career coaches can help you make informed decisions during transitions And more Connect with Dennis O’Keefe:  Successful Money Strategies, Inc dennis@successfulmoney.com  (508) 730-2300  LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

    34 min

  3. JAN 8

    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 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 support. Key takeaways: AI can help organize data and handle defined tasks, but it does not interpret personal context or long-term considerations. Large firms provide structure, yet personalization may vary depending on how their service models are designed. Independent advisors may identify risks or opportunities that automated systems do not detect. Retirees should consider what level of support they want when evaluating technology-based planning tools. And more! Connect with Dennis O’Keefe:  Successful Money Strategies, Inc dennis@successfulmoney.com  (508) 730-2300  LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

    34 min

  4. 12/23/2025

    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 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 How technology has made old scams new again The one simple tech switch that can reduce fraud risk by 95% And so much more! Connect with Dennis O’Keefe:  Successful Money Strategies, Inc dennis@successfulmoney.com  (508) 730-2300  LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

    41 min

  5. 12/11/2025

    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 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 flexibility or destroy options completely. What you can expect from this episode: The truth about Medicaid and nursing home coverage How irrevocable trusts actually work (and when they don’t) Why “doing nothing” can sometimes be the smartest short-term move The one type of advisor Dennis says to avoid And more! Previous Episodes of Interest: Elderly Planning: What You Need To Know Care Options for Older Americans Connect with Dennis O’Keefe:  Successful Money Strategies, Inc dennis@successfulmoney.com  (508) 730-2300  LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

    39 min

  6. 11/27/2025

    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, 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 overlook, and why COBRA coverage may not be your best option. Dennis also unpacks key strategies around timing your Social Security, managing 401(k) withdrawals, and avoiding the costly pitfalls that can derail your long-term plan. Key takeaways: How to evaluate a severance package and understand its real after-tax value Why preparation matters more than panic when a layoff hits Smarter health insurance choices after employment ends When and why to consider taking Social Security early And more! Connect with Dennis O’Keefe:  Successful Money Strategies, Inc dennis@successfulmoney.com  (508) 730-2300  LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

    37 min

  7. 11/13/2025

    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 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 delivers the clarity you didn’t know you were missing. What you’ll learn: Why tax savings aren’t always the goal (or the outcome) How tax brackets silently kill Roth conversion benefits When a Roth becomes a powerful estate planning tool What you must know before acting on social media advice And more! Connect with Dennis O’Keefe:  Successful Money Strategies, Inc dennis@successfulmoney.com  (508) 730-2300  LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

    33 min

  8. 10/23/2025

    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 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 just how much the landscape of aging has changed and how important it is to drop the outdated myths.  Whether you’re caring for aging parents or thinking about your own future, this episode will give you the clarity and confidence to move forward. What to expect in this episode: What “home care” really includes and why it’s more than just medical help Why food and activities might be the most important factors for long-term independence The truth about Medicaid: what it pays for, and what it doesn’t The emotional and financial trade-offs of preserving money for your kids vs. paying for your own care And more! Previous Episode of Interest:   Elderly Planning: What You Need To Know Connect with Dennis O’Keefe:  Successful Money Strategies, Inc dennis@successfulmoney.com  (508) 730-2300  LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

    29 min
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4.9
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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 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.

Information

  • Creator
    Dennis O'Keefe
  • Years Active
    2022 - 2026
  • Episodes
    135
  • Copyright
    Copyright © 2024 Your Successful Retirement
  • Show Website
    Your Successful Retirement