Tag: Tax Planning
Is It Worth It To Convert Your IRA To A Roth?

Is It Worth It To Convert Your IRA To A Roth?

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Should you convert your traditional IRA to a Roth IRA? In this YSR FAQ episode, Dennis O’Keefe breaks down the pros and cons of Roth conversions and explains why the answer depends heavily on your tax situation.

Dennis discusses how Roth conversions are taxed, the importance of understanding tax brackets, and why many investors benefit from a multi-year conversion strategy rather than making one large move. He also examines some of the common misconceptions surrounding Roth conversions and why generic online calculators can sometimes produce misleading results.

For those thinking about tax-efficient retirement income or leaving assets to the next generation, this episode provides valuable insight into when a Roth conversion may, or may not, be beneficial.

Key takeaways:

  • How Roth conversions work
  • Why tax brackets are critical to the decision
  • Potential tax pitfalls to avoid
  • Multi-year conversion strategies
  • The estate planning benefits of Roth assets
  • And more!

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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.
Understanding Social Security: Myths, Mechanics, and What Happens Next

Understanding Social Security: Myths, Mechanics, and What Happens Next

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Many people think they understand Social Security, until conflicting answers and uncertainty create confusion.

What’s actually true about how benefits work, and what should you expect in the years ahead?

In this episode, Dennis O’Keefe breaks down how Social Security really works and clears up common misconceptions. He explains how benefits are calculated, why the system is often misunderstood, and what the projected shortfall around 2032 could mean. Dennis also explores how policy changes like tax increases or benefit adjustments may shape the future, helping listeners better understand their options and expectations.

Key takeaways:

  • How spousal and dependent benefits can increase total Social Security income when coordinated properly
  • Why Social Security is structured as an insurance program rather than a personal retirement account
  • How the Social Security Trust Fund works and why funds are being drawn down over time
  • The real reason behind the projected 2032 shortfall and what it means for future benefits
  • Potential changes like higher payroll taxes or income-based benefits that could reshape the system
  • And more!

Connect with Dennis O’Keefe: 

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.
Strategic Tax Planning: What You Need to Know Before Filing

Strategic Tax Planning: What You Need to Know Before Filing

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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: 

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.