Your Successful Retirement
Your Successful Retirement

Your Successful Retirement

Dennis O'Keefe

Overview
Episodes

Details

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.

Recent Episodes

What Does “Fiduciary” Really Mean?
MAR 26, 2026
What Does “Fiduciary” Really Mean?
<p><span style="font-weight: 400;">What does it mean to be a fiduciary? In this episode of YSR Shorts, Dennis O’Keefe explains the fiduciary standard and why it matters in financial services. He discusses disclosure, compensation structures, and why fiduciary status should be part of your evaluation, not the only factor. Dennis also shares real-world examples that highlight the importance of asking deeper questions.</span></p> <p><b>Key takeaways:</b></p> <ul> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Definition of fiduciary in financial services</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Why disclosure matters</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Limits of fiduciary protection</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">The importance of evaluating competence and trust</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">And more!</span></li> </ul> <p><b>Connect with Dennis O&#8217;Keefe: </b></p> <ul> <li><a href="https://www.successfulmoney.com/"><span style="font-weight: 400;">Successful Money Strategies, Inc</span></a></li> <li><a href="mailto:[email protected]"><span style="font-weight: 400;">[email protected]</span></a><span style="font-weight: 400;"> </span></li> <li><span style="font-weight: 400;">(508) 730-2300 </span></li> <li><a href="https://www.linkedin.com/in/dennisokeefe-/"><span style="font-weight: 400;">LinkedIn: Dennis O&#8217;Keefe</span></a></li> <li><a href="https://www.linkedin.com/company/successful-money-strategies-inc./"><span style="font-weight: 400;">LinkedIn: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.facebook.com/successfulmoneystrategies"><span style="font-weight: 400;">Facebook: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.instagram.com/successfulmoneystrategies/"><span style="font-weight: 400;">Instagram: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.youtube.com/@SuccessfulRetirementPodcast"><span style="font-weight: 400;">YouTube: Your Successful Retirement Podcast</span></a></li> </ul> <p><span style="font-weight: 400;">All content presented is for educational purposes only and </span><span style="font-weight: 400;">should not be construed as </span><span style="font-weight: 400;">an endorsement of any third party, or as</span><span style="font-weight: 400;"> 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 </span><span style="font-weight: 400;">reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. </span><span style="font-weight: 400;">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.</span></p>
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7 MIN
Should You Pay Someone to Manage Your Money?
MAR 26, 2026
Should You Pay Someone to Manage Your Money?
<p><span style="font-weight: 400;">Should you pay someone to manage your money? In this episode, Dennis O’Keefe explains the behavioral side of investing. He shares why emotional reactions during market volatility can hurt long-term results and how professional management can help create separation and discipline. Dennis also compares corporate management firms and boutique advisory relationships, outlining the pros and cons of each.</span></p> <p><b>Key takeaways:</b></p> <ul> <li><span style="font-weight: 400;">Why investor behavior matters during market swings</span></li> <li><span style="font-weight: 400;">The value of emotional separation in decision-making</span></li> <li><span style="font-weight: 400;">Differences between large firms and boutique advisors</span></li> <li><span style="font-weight: 400;">The importance of proactive guidance</span></li> <li><span style="font-weight: 400;">And more!</span></li> </ul> <p><b>Connect with Dennis O&#8217;Keefe: </b></p> <ul> <li><a href="https://www.successfulmoney.com/"><span style="font-weight: 400;">Successful Money Strategies, Inc</span></a></li> <li><a href="mailto:[email protected]"><span style="font-weight: 400;">[email protected]</span></a><span style="font-weight: 400;"> </span></li> <li><span style="font-weight: 400;">(508) 730-2300 </span></li> <li><a href="https://www.linkedin.com/in/dennisokeefe-/"><span style="font-weight: 400;">LinkedIn: Dennis O&#8217;Keefe</span></a></li> <li><a href="https://www.linkedin.com/company/successful-money-strategies-inc./"><span style="font-weight: 400;">LinkedIn: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.facebook.com/successfulmoneystrategies"><span style="font-weight: 400;">Facebook: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.instagram.com/successfulmoneystrategies/"><span style="font-weight: 400;">Instagram: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.youtube.com/@SuccessfulRetirementPodcast"><span style="font-weight: 400;">YouTube: Your Successful Retirement Podcast</span></a></li> </ul> <p>&nbsp;</p> <p><span style="font-weight: 400;">All content presented is for educational purposes only and </span><span style="font-weight: 400;">should not be construed as </span><span style="font-weight: 400;">an endorsement of any third party, or as</span><span style="font-weight: 400;"> 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 </span><span style="font-weight: 400;">reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. </span><span style="font-weight: 400;">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.</span></p>
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7 MIN
How to Protect Yourself From Scams and Identity Theft in Retirement
MAR 12, 2026
How to Protect Yourself From Scams and Identity Theft in Retirement
<p><span style="font-weight: 400;">You may not realize how much of your personal information is visible every single day. From store apps to credit reports, small exposures can quietly add up over time.</span></p> <p><span style="font-weight: 400;">In this episode of Your Successful Retirement, Dennis O’Keefe explores a topic that affects every retiree and pre-retiree, even if they don’t realize it: how visible you are online. From data tracking at your local grocery store to unsolicited credit card offers, Dennis walks through practical ways to reduce your digital footprint and lower your risk of scams and identity theft.</span></p> <p><span style="font-weight: 400;">He shares a personal story about tracking down a retired firefighter who intentionally made himself nearly invisible online, and why that level of caution may not be extreme after all. Dennis also explains how small steps, like protecting your Social Security number, reviewing your credit report annually, and using call-blocking services, may help reduce exposure to fraud.</span></p> <p><strong>Key takeaways:</strong></p> <ul> <li><span style="font-weight: 400;">Protect your Social Security number like your financial life depends on it</span></li> <li><span style="font-weight: 400;">Why reviewing your credit report annually matters</span></li> <li><span style="font-weight: 400;">How retail apps track consumer behavior inside stores</span></li> <li><span style="font-weight: 400;">Ways to reduce junk mail and credit card offers</span></li> <li><span style="font-weight: 400;">Why unsecured email can put sensitive data at risk</span></li> <li><span style="font-weight: 400;">And more!</span></li> </ul> <p><b>Connect with Dennis O&#8217;Keefe: </b></p> <ul> <li><a href="https://www.successfulmoney.com/"><span style="font-weight: 400;">Successful Money Strategies, Inc</span></a></li> <li><a href="mailto:[email protected]"><span style="font-weight: 400;">[email protected]</span></a><span style="font-weight: 400;"> </span></li> <li><span style="font-weight: 400;">(508) 730-2300 </span></li> <li><a href="https://www.linkedin.com/in/dennisokeefe-/"><span style="font-weight: 400;">LinkedIn: Dennis O&#8217;Keefe</span></a></li> <li><a href="https://www.linkedin.com/company/successful-money-strategies-inc./"><span style="font-weight: 400;">LinkedIn: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.facebook.com/successfulmoneystrategies"><span style="font-weight: 400;">Facebook: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.instagram.com/successfulmoneystrategies/"><span style="font-weight: 400;">Instagram: Successful Money Strategies, Inc</span></a></li> <li><a href="https://www.youtube.com/@SuccessfulRetirementPodcast"><span style="font-weight: 400;">YouTube: Your Successful Retirement Podcast</span></a></li> </ul> <p>&nbsp;</p> <p><span style="font-weight: 400;">All content presented is for educational purposes only and </span><span style="font-weight: 400;">should not be construed as </span><span style="font-weight: 400;">an endorsement of any third party, or as</span><span style="font-weight: 400;"> 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 </span><span style="font-weight: 400;">reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. </span><span style="font-weight: 400;">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.</span></p>
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27 MIN
What Does CFP® Really Mean? (And Why It Matters)
FEB 26, 2026
What Does CFP® Really Mean? (And Why It Matters)
<p><span style="font-weight: 400;">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 they are only a starting point when choosing a financial professional.</span></p> <p><b>Key takeaways:</b></p> <ul> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">The difference between “financial planner” and CFP</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Education, experience, and exam requirements</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Ongoing continuing education standards</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Why credentials should be part of your evaluation, not the only factor</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">And more!</span></li> </ul> <p><b>Connect with Dennis O&#8217;Keefe: </b></p> <ul> <li style="font-weight: 400;" aria-level="1"><a href="https://www.successfulmoney.com/"><span style="font-weight: 400;">Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="mailto:[email protected]"><span style="font-weight: 400;">[email protected]</span></a><span style="font-weight: 400;"> </span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">(508) 730-2300 </span></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/in/dennisokeefe-/"><span style="font-weight: 400;">LinkedIn: Dennis O&#8217;Keefe</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/company/successful-money-strategies-inc./"><span style="font-weight: 400;">LinkedIn: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.facebook.com/successfulmoneystrategies"><span style="font-weight: 400;">Facebook: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.instagram.com/successfulmoneystrategies/"><span style="font-weight: 400;">Instagram: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.youtube.com/@SuccessfulRetirementPodcast"><span style="font-weight: 400;">YouTube: Your Successful Retirement Podcast</span></a></li> </ul> <p><span style="font-weight: 400;">All content presented is for educational purposes only and </span><span style="font-weight: 400;">should not be construed as </span><span style="font-weight: 400;">an endorsement of any third party, or as</span><span style="font-weight: 400;"> 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 </span><span style="font-weight: 400;">reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. </span><span style="font-weight: 400;">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.</span></p>
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8 MIN
What Is Comprehensive Financial Planning? (It’s Not a Binder)
FEB 26, 2026
What Is Comprehensive Financial Planning? (It’s Not a Binder)
<p><span style="font-weight: 400;">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.</span></p> <p><b>Key takeaways:</b></p> <ul> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">The five core components of financial planning</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Why planning is a process, not a product</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">The importance of implementation and follow-through</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Why ongoing evaluation keeps a plan relevant</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">And more!</span></li> </ul> <p><b>Connect with Dennis O&#8217;Keefe: </b></p> <ul> <li style="font-weight: 400;" aria-level="1"><a href="https://www.successfulmoney.com/"><span style="font-weight: 400;">Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="mailto:[email protected]"><span style="font-weight: 400;">[email protected]</span></a><span style="font-weight: 400;"> </span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">(508) 730-2300 </span></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/in/dennisokeefe-/"><span style="font-weight: 400;">LinkedIn: Dennis O&#8217;Keefe</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/company/successful-money-strategies-inc./"><span style="font-weight: 400;">LinkedIn: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.facebook.com/successfulmoneystrategies"><span style="font-weight: 400;">Facebook: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.instagram.com/successfulmoneystrategies/"><span style="font-weight: 400;">Instagram: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.youtube.com/@SuccessfulRetirementPodcast"><span style="font-weight: 400;">YouTube: Your Successful Retirement Podcast</span></a></li> </ul> <p><span style="font-weight: 400;">All content presented is for educational purposes only and </span><span style="font-weight: 400;">should not be construed as </span><span style="font-weight: 400;">an endorsement of any third party, or as</span><span style="font-weight: 400;"> 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 </span><span style="font-weight: 400;">reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. </span><span style="font-weight: 400;">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.</span></p>
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7 MIN