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:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

Most business owners say they feel prepared to step away, but available data suggests gaps in readiness.

In this episode, Dan Reese breaks down insights from the National State of Owner Readiness Report and explains common areas where small and mid-sized business owners may lack preparation for a significant financial transition. With a large portion of many owners’ net worth tied up in their business, exit planning often involves business, personal, and financial considerations.

Dan walks through common elements often associated with readiness, including understanding business value, identifying wealth gaps, and planning considerations for life after the business following a transaction.

Dan discusses:

• The role small and mid-sized businesses play in the U.S. economy
• The commonly referenced three legs of exit planning: business, personal, and financial considerations
• The role formal business valuations can play in exit planning
• The wealth gap and how lifestyle expectations may affect a transition
• And more

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

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:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

Gold is in the headlines again.

Prices are higher this year, we see gold ads on TV, and fear-based marketing may be convincing more retirees to convert their savings into precious metals. But is gold truly as safe as it’s perceived to be, or are investors falling for glitter over substance?

Dan Reese delivers a calm, factual look at the emotional and financial realities of gold investing. From physical bars to ETFs, Dan explains the pros, cons, and costly surprises many people overlook, especially when they’re acting out of fear.

Here’s what to expect:

• The emotional appeal of gold and how it’s used in marketing
• Why physical gold may cost more than you think to buy, sell, and store
• How gold ETFs could offer a simpler, lower-cost option
• Why timing, taxes, and diversification matter more than hype
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

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:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

Connect with Brent Oliver:

• Avery Wealth
• LinkedIn: Brent Oliver, CFP®

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.

Did you know that even one extra dollar of income in retirement may trigger higher taxes, Medicare premiums, or health insurance costs?

This week, Dan Reese explains common retirement planning situations where a single extra dollar in income can unexpectedly spike your taxes, Medicare premiums, and insurance costs. From IRMAA surcharges to Social Security taxation rules to ACA subsidy limits, Dan explains how understanding these often overlooked thresholds can help retirees make more informed financial decisions.

He also walks through smart strategies to avoid them, like Roth conversions, withdrawal sequencing, and charitable giving tactics that can help protect your nest egg and optimize your income.

What you’ll learn:

• How IRMAA charges can balloon Medicare costs overnight
• The surprising way Social Security gets taxed and why it’s so outdated
• The ACA income cliff that could cost you thousands in health subsidies
• Proactive planning tools to keep your retirement tax-efficient
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz
• The Danger of Not Knowing What You Don’t Know (Ep. 17)

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

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

One of the biggest risks to your retirement may not be the market. It could be overconfidence.

Dan Reese examines the genuine risks of DIY financial planning, particularly in a world inundated with AI tools and financial influencers who oversimplify complex decisions. From emotional investing to overlooked tax landmines and Medicare surprises, Dan breaks down why retirement planning involves more than simply choosing investments.

You’ll learn how behavioral biases, sequence-of-return risk, and misunderstood withdrawal strategies may impact your financial future if overlooked.

What to expect:

• Why investment planning is the “easy” part, but is rarely done well
• The psychological traps of self-managing your money
• Medicare costs, IRMAA, and the illusion of “free” healthcare
• How a CFP helps you see what you don’t know and plan for what comes next
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese

Most people think the hard part is saving for retirement, but the real challenge begins when the paychecks stop.

Dan Reese walks through the crucial mental and financial shift from accumulation to decumulation and why so many retirees get it wrong. From tax surprises and market volatility to emotional roadblocks and overlooked estate planning, Dan breaks down the common pitfalls and shares what it takes to create a truly sustainable income plan.

You’ll learn how to map out long-term tax liabilities, balance guaranteed vs. variable income, and build financial confidence in retirement.

What to expect in this episode:

• The #1 mistake retirees make when “flipping the switch”
• How market downturns affect withdrawals differently from contributions
• Why tax surprises can be more common (and dangerous) in retirement
• How to align spending, legacy goals, and income with confidence
• And more!

Resources:

• Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

• Avery Wealth
• LinkedIn: Avery Wealth
• LinkedIn: Dan Reese