Tag: Roth Conversions
Do Roth Conversions Still Make Sense After Tax Law Changes? (Ep. 35)

Do Roth Conversions Still Make Sense After Tax Law Changes? (Ep. 35)

By |

If you’re approaching retirement with a large traditional IRA, deciding whether to convert to a Roth account can affect your future taxes, Medicare costs, and what your heirs receive.

How do taxes, Medicare costs, retirement income, and estate planning all connect when making this decision? The right decision depends on your situation, not just what tax rates are doing.

In this episode, Dan Reese, CFP®, explains how recent tax law changes have shifted the reasons people may evaluate Roth conversions as part of their retirement planning. He shares how Roth conversions can affect retirement taxes, future required distributions, and the assets passed to heirs. Dan also explains how reviewing your current financial picture, evaluating different tax-bracket scenarios, and coordinating with financial and tax professionals can help clarify the potential trade-offs.

Key points:

  • How Roth conversions can affect retirement taxes, Medicare premiums, and future financial decisions
  • Why recent tax law changes changed the reasons many people consider Roth conversions
  • How inherited retirement accounts can create tax concerns for the next generation
  • Why spreading conversions across multiple years may help manage tax brackets
  • How financial planning connects taxes, income, investments, and estate decisions
  • And more!

This information is not intended to provide specific legal, tax, or other professional advice. For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Converting from a traditional IRA to a Roth IRA is a taxable event.

Resources:

Connect with Dan Reese CFP®:

Podcast: Play in new window | Download | Embed

Subscribe: Apple Podcasts | RSS | More
How to Know If Your Financial Advisor Is Really Helping You Plan for Retirement (Ep. 34)

How to Know If Your Financial Advisor Is Really Helping You Plan for Retirement (Ep. 34)

By |

Are you getting financial advice, or are you simply getting investment updates?

Many people build strong relationships with their financial advisor, but that doesn’t always mean every part of their retirement plan is being addressed. Knowing what questions to ask can make a meaningful difference before small planning gaps become bigger problems.

In this episode, Dan Reese, CFP®, explains how to evaluate whether your financial plan is covering the areas that matter most. He shares the 3-lane planning framework, covering investments, retirement income, and tax planning, and discusses how Social Security, Medicare, estate planning, and long-term tax decisions work together. Dan also explains why planning performance often matters just as much as investment performance when preparing for retirement.

Key takeaways:

  • How fiduciary advice differs from investment-focused conversations and why that distinction matters
  • Why retirement income, tax planning, and investments should work together instead of separately
  • Questions to ask when evaluating whether your advisor is addressing your complete financial plan
  • How Social Security and Roth conversion decisions can influence lifetime retirement taxes
  • Why planning performance may have a greater financial impact than investment returns alone
  • And more!

Converting from a traditional IRA to a Roth IRA is a taxable event.

Resources:

Connect with Dan Reese CFP®:

Podcast: Play in new window | Download | Embed

Subscribe: Apple Podcasts | RSS | More
Tax-Focused Estate Planning Before Retirement (Ep. 33)

Tax-Focused Estate Planning Before Retirement (Ep. 33)

By |

Estate planning is often treated as a task to complete later, but many of the biggest financial decisions begin long before legal documents are signed.

How can tax planning, retirement income planning, and investment decisions work together to support your long-term goals while potentially improving how assets are transferred?

In this episode, Dan Reese explains why estate planning is much more than wills and legal paperwork. He shares how investment planning, retirement income planning, and tax planning all influence one another through what he calls the three lanes of the financial highway. Dan also explores how Roth conversions, beneficiary designations, charitable giving, and account positioning can affect taxes during retirement and for future generations. 

Throughout the conversation, he emphasizes creating a coordinated strategy while there may still be more planning flexibility.

Key takeaways:

  • How investment, retirement income, and tax planning work together instead of as separate decisions
  • Why estate planning begins with strategy before legal documents are created and updated
  • How Roth conversions may influence taxes paid by both retirees and future beneficiaries
  • Why beneficiary designations and asset location can change long term tax outcomes
  • How coordinated planning may uncover opportunities across multiple financial decisions
  • And more!

Resources:

Connect with Dan Reese CFP®:

Podcast: Play in new window | Download | Embed

Subscribe: Apple Podcasts | RSS | More
What Really Happens Behind the Scenes in a Financial Planning Firm (Ep. 24)

What Really Happens Behind the Scenes in a Financial Planning Firm (Ep. 24)

By |

Most people see one or two meetings a year and assume that’s the whole picture. But real planning is happening year-round, often when no one is sitting across the table.

In this episode, Dan Reese, CFP, pulls back the curtain on how an annual service calendar guides financial planning throughout the year. He walks through how winter tax planning sets the foundation, how spring portfolio reviews and tax strategies are handled, and why summer and fall are critical for scenario planning, insurance reviews, and year-end decisions. Dan explains how systems help avoid missed opportunities, reduce costly mistakes, and keep everything aligned across taxes, investments, and planning.

Key takeaways:

  • Why organizing planning work by seasons helps prevent last-minute decisions and overlooked deadlines
  • How early year tax planning supports smarter moves during market downturns
  • What happens during spring investment reviews and ongoing portfolio alignment
  • Why summer is used for deeper tax analysis and real-life scenario testing
  • How insurance reviews and year-end planning help protect against gaps and outdated coverage
  • And more!

Converting from a traditional IRA to a Roth IRA is a taxable event.

Resources:

Connect with Dan Reese CFP®:

Podcast: Play in new window | Download | Embed

Subscribe: Apple Podcasts | RSS | More
Roth Conversions for High Earners: Timing, Taxes, and Long-Term Control (Ep. 23)

Roth Conversions for High Earners: Timing, Taxes, and Long-Term Control (Ep. 23)

By |

Retirement tax decisions often feel simple on the surface, but the ripple effects can last decades. The real question is not whether taxes will be paid, but when, how, and by whom.

In this episode, Dan Reese, CFP®, walks through how Roth conversions, a taxable event, can fit into a broader retirement and estate plan for high-income earners. He explains when conversions may help manage future tax exposure, Medicare premiums, and inherited IRA issues. The conversation also covers market downturns, early retirement gap years, state tax differences, and why scenario planning is essential before acting.

Key takeaways:

  • How Roth conversions can affect heirs, estate plans, and long-term family tax outcomes over multiple generations
  • Why higher income does not automatically rule out conversions, and how added income can trigger hidden taxes
  • How market downturns may lower the taxable cost of converting retirement assets
  • Why early retirement gap years can create valuable planning windows before Social Security begins
  • How moving between low-tax and high-tax states can change the timing and value of conversions
  • And more!

Resources:

Connect with Dan Reese CFP®:

Podcast: Play in new window | Download | Embed

Subscribe: Apple Podcasts | RSS | More
The Risk of Following TikTok Finance (Ep. 21)

The Risk of Following TikTok Finance (Ep. 21)

By |

Online platforms surface a steady stream of financial content, often from influencers whose guidance is not tailored to individual situations.

In this episode of Ramp Up to Retirement, Dan Reese discusses the difference between broad online commentary and fiduciary planning, and how that gap can affect real retirement decisions. He walks through examples involving Roth conversions, Social Security timing, and investment choices that are sometimes framed too broadly in short-form content.

What to expect:

  • How social algorithms can pull you into financial advice content
  • Possible motivations behind influencer content
  • What fiduciary standards require (and what they do not)
  • How personalized planning can help you assess decisions and potential tradeoffs
  • And more!

Converting from a traditional IRA to a Roth IRA is a taxable event.

Resources:

Connect with Dan Reese CFP®:

Podcast: Play in new window | Download | Embed

Subscribe: Apple Podcasts | RSS | More
The $150,000 Gift That Derailed Their Retirement with Brent Oliver (Ep. 19)

The $150,000 Gift That Derailed Their Retirement with Brent Oliver (Ep. 19)

By |

Mark and Susan thought they did everything right: no debt, over a million saved, markets trending up. But one well-intentioned gift to their kids set off a chain of financial consequences they didn’t anticipate.

In this episode, Dan Reese is joined by Brent Oliver for a hypothetical case study exploring how using the concept of a financial “postmortem”, an exercise in looking back to uncover what went wrong and why. You’ll hear how early retirement optimism, overconfidence, and lack of a coordinated plan may result in unexpected taxes, reduced income, and potential long-term challenges.

Here’s what to expect:

  • Why starting strong doesn’t always mean finishing strong in retirement
  • How a single decision can derail your entire income plan
  • The hidden dangers of IRMAA and tax bracket creep
  • How to rebuild confidence with structure, buckets, and stress testing
  • And more!

Resources:

Connect with Dan Reese CFP®:

Connect with Brent Oliver: 

About our Guest: 

Brent Oliver is a Wealth Manager at Avery Wealth, Inc. He focuses on providing wealth management solutions to retirees and pre-retirees in the Mid-Michigan Area. Brent helps affluent clients address their five biggest concerns: preserving their wealth, mitigating taxes, taking care of their heirs, ensuring their assets are not unjustly taken and charitable giving.

Brent has been with Avery Wealth, Inc. since 2013 where he uses a consultative process to gain a detailed understanding of his clients’ deepest values and goals. He then employs customized recommendations designed to address each client’s unique needs and goals beyond simply investments.

Successful individuals and families work with Brent to:

  • Develop and implement a comprehensive wealth management plan to help them reach their financial dreams.
  • Make smarter decision in today’s uncertain political, economic and social environment.
  • Obtain an independent second opinion from a top financial advisor in their community.

Previously, Brent owned and operated Midwest Wireless Communications, LLC, a successful business, in the Jackson Area. He hosts a weekly radio show/podcast, The Retirement Café, which focuses on educating listeners on a wide variety of financial planning and investing topics. He is currently a Trustee on the Western School Districts Board of Education.

Disclosure:

The scenarios discussed are hypothetical and for educational purposes only. They do not represent actual clients or guarantee future results. Investment involves risk, including possible loss of principal.

Podcast: Play in new window | Download | Embed

Subscribe: Apple Podcasts | RSS | More