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Your Successful Retirement

Your Successful Retirement

Di: 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.Copyright © 2024 Your Successful Retirement Economia
  • How Do Required Minimum Distributions (RMDs) Work?
    Oct 22 2026

    Required minimum distributions often sound straightforward until timing, taxes, and deadlines begin affecting the decisions you make.

    Many retirees discover there is more flexibility than they expected, but there are also situations where delaying a distribution can create unintended tax consequences.

    In this YSR FAQ episode, Dennis O’Keefe explains how required minimum distributions are calculated, when they begin, and why understanding the rules before your first distribution matters. He discusses the option to delay your initial RMD, why that choice doesn’t always produce a better outcome, how taking two distributions in one year can increase taxable income, and what retirees should consider before deciding when to withdraw their money.

    Key takeaways:

    • How required minimum distributions are calculated using your prior year account balance
    • Why your first RMD may be delayed, but rarely produces the best tax outcome
    • How taking two distributions in one year can increase taxable income
    • When brokerage firms notify retirees about annual distribution requirements
    • Why planning ahead reduces unnecessary tax surprises during retirement
    • 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.

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    8 min
  • How Do You Know Your Tax Bracket and Why Does It Matter?
    Oct 22 2026

    Many financial decisions feel unrelated until taxes quietly change the outcome.

    Knowing where your income falls can influence everything from retirement withdrawals to Roth conversions, yet many people don’t realize how much flexibility they actually have.

    In this YSR FAQ episode, Dennis O’Keefe explains why understanding your tax bracket is one of the most valuable habits you can build before making financial decisions. He walks through the largest jumps in the current tax code, explains how those changes affect Roth conversions, capital gains, and retirement withdrawals, and shares a simple way to find reliable tax information without memorizing complicated IRS tables. He also explains why keeping a current tax reference guide nearby can make planning easier throughout the year.

    Key takeaways:

    • How larger jumps between tax brackets can affect retirement withdrawals and investment decisions
    • Why Roth conversion amounts often depend on the available room before the next bracket
    • How capital gains taxes change based on your taxable income
    • Where to find a reliable annual tax reference guide in just a few minutes
    • Why understanding your tax bracket helps you make more informed financial choices
    • 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.

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    7 min
  • How Healthcare, Taxes, and Government Policies Could Affect Your Retirement (Ep. 144)
    Oct 8 2026

    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 O’Keefe examines how political discussions around healthcare, taxes, housing, and government spending could affect retirees and people preparing for retirement. He explores universal healthcare, rent control, education costs, taxes, and the importance of looking beyond simple solutions to understand potential consequences.

    Dennis explains why healthcare systems require careful consideration of costs, access, and personal choice, while also discussing how government decisions can create ripple effects that affect affordability and availability. He also shares his perspective on evaluating economic claims with a focus on facts rather than headlines.

    Dennis discusses:

    • How universal healthcare costs are paid through taxes, insurance, and other systems
    • Why policy decisions can create unintended effects for consumers and communities
    • How rent control and education loans changed incentives and affordability over time
    • Why tax discussions require considering deficits, spending, and long-term impacts
    • The importance of examining economic claims beyond simple political messages
    • 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.

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    29 min
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