Category: Financial Planning
The $1 Mistake That Could Cost You Thousands in Retirement (Ep. 18)

The $1 Mistake That Could Cost You Thousands in Retirement (Ep. 18)

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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  • The surprising way Social Security gets taxed and why it’s so outdated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:

Connect with Dan Reese CFP®:

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

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The Danger of Not Knowing What You Don’t Know (Ep. 17)

The Danger of Not Knowing What You Don’t Know (Ep. 17)

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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:

Connect with Dan Reese CFP®:

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You’ve Retired. Now What? The Hardest Financial Shift You’ll Ever Make (Ep. 16)

You’ve Retired. Now What? The Hardest Financial Shift You’ll Ever Make (Ep. 16)

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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:

Connect with Dan Reese CFP®:

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One Big Beautiful Bill: Tax Changes Every Retiree Needs to Know with Brent Oliver (Ep. 15)

One Big Beautiful Bill: Tax Changes Every Retiree Needs to Know with Brent Oliver (Ep. 15)

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Retirement planning doesn’t exist in a vacuum, especially when tax laws are shifting. 

Dan Reese and guest Brent Oliver, Senior Wealth Advisor at Avery Wealth, break down the latest tax legislation and what it means for your future income, charitable giving, and estate plans.

From the extension of lower tax brackets to the expanded standard deduction and SALT cap increase, Dan and Brent cut through the noise to highlight some impactful changes for retirees and pre-retirees. They also explain how to leverage tax-smart strategies, like qualified charitable distributions, to help make the most of your retirement income.

What you’ll learn in this episode:

  • How new tax brackets and deductions affect your retirement strategy
  • The truth about the “senior boost” for deductions
  • Charitable giving incentives and QCD benefits
  • Estate tax updates and planning opportunities
  • And more!

Resources:

Connect with Dan Reese CFP®:

Connect with Brent Oliver: 

About our Guest: 

Brent Oliver is a Senior Wealth Advisor based in Jackson, Michigan, with 11 years of experience in the field. As a CERTIFIED FINANCIAL PLANNER™ professional and Senior Wealth Advisor, Brent helps families identify and work towards achieving their financial goals. His comprehensive approach to wealth management helps families identify where they are today, where they want to be, and what gaps might prevent them from achieving all that is important to them. He has the heart of a teacher and works with clients to ensure they understand why strategies are being employed and how they can help families reach their goals.

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Social Security Myths That May Derail Your Retirement Strategy (Ep. 14)

Social Security Myths That May Derail Your Retirement Strategy (Ep. 14)

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Many people feel confident about Social Security until it’s time to file. That’s when the conflicting advice from neighbors, social media, and self-proclaimed experts can make a complex decision even harder. 

In this episode, Dan Reese, CFP®, breaks down the most common Social Security myths and explains how decisions around claiming, spousal benefits, and timing can affect your broader retirement strategy.

Whether you’re married, divorced, or filing solo, Dan shares key considerations that may help you make a more informed decision and avoid unintended tax and income surprises later on.

What to expect in this episode:

  • Why claiming at 62 may not be the right fit for every situation
  • What to know about spousal benefits and survivor income planning
  • How early filing can affect future tax liabilities
  • Why longevity should factor into your Social Security decision
  • And more!

Resources:

Connect with Dan Reese CFP®:

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Building a Purposeful Retirement Rhythm (Ep. 13)

Building a Purposeful Retirement Rhythm (Ep. 13)

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Retirement isn’t just about stopping work; it’s about starting something new.

What happens after the celebration, the rest, and the first few months off?

In this episode, Dan Reese, CFP®, shares how creating a rhythm, not a rigid routine, can bring meaning, fulfillment, and balance to your retirement years.

He also explains how tools, planning, and a little structure may help retirees feel more confident about how they spend their time.

Dan discusses: 

  • The psychological shift from a structured work schedule to open retirement time, and why having no calendar at all can feel overwhelming
  • The importance of creating a “retirement rhythm” that includes regular fitness, faith-based, social, and mentally stimulating activities
  • How having something on the calendar, whether it’s travel, events, or weekly routines, can add structure and anticipation
  • How ChatGPT can be a creative tool to help retirees plan weekly routines
  • The need to balance structure with flexibility, leaving room for spontaneity while still maintaining core habits that support well-being
  • And more!

Resources:

Connect with Dan Reese, CFP®:

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Early Retirement Right for You? Key Considerations and Strategies (Ep. 12)

Early Retirement Right for You? Key Considerations and Strategies (Ep. 12)

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What are the highs and lows of early retirement? We’re exploring whether it’s everything it’s cracked up to be and the steps needed to make it work for you.

Join Dan Reese from Avery Wealth as he delves into the pros and cons of early retirement. They discuss the allure of having more control over your time and the potential pitfalls that can trip you up. From understanding longevity risks to healthcare gaps and tax implications, this episode aims to provide a balanced perspective on retiring ahead of the traditional timeline. Dan also shares real-life client stories, offering insights into the emotional and financial preparations necessary for this life stage.

Dan discusses:

  • Longevity Risks in Early Retirement (00:09:57)
  • Healthcare Coverage Before Medicare (00:11:47)
  • Sequence of Returns Risk (00:13:01)
  • Social Security Timing and Benefits (00:14:13)
  • Emotional and Purposeful Transition (00:22:06)

Resources:

Connect with Dan Reese CFP®:

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Navigating Market Volatility: How Emotions Impact Your Investments (Ep. 11)

Navigating Market Volatility: How Emotions Impact Your Investments (Ep. 11)

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What drives your investment decisions—logic or emotion? 

In this episode of Ramp Up Your Retirement, Dan Reese of Avery Wealth explores how political emotions can influence investor behavior and market perceptions. From election-year anxiety to partisan-driven reactions, Dan unpacks why it’s essential to stay grounded and stick to a long-term plan, regardless of who’s in office.

Dan discusses: 

  • How emotions play into investment decisions. (00:01:36)
  • The rational behavior of markets in the long term. (00:02:46) 
  • The dangers of reacting to political shifts in investment strategies. (00:03:56) 
  • Real-world examples of market reactions post-elections. (00:07:18) 
  • Strategies to stay the course during market volatility. (00:14:45)
  • And more

Resources:

Connect with Dan Reese CFP®:

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The Importance of Communication in Estate Planning (Ep. 10)

The Importance of Communication in Estate Planning (Ep. 10)

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What does it take to help ensure your wealth supports your family and favorite causes even after you’re gone?

In this episode, Dan Reese CFP® discusses the critical aspects of estate planning, focusing on inheritance and the importance of communication. Discover why talking about money with family isn’t as taboo as you might think and learn ways you can make these conversations more frequent and meaningful. Dan walks through traditional practices and innovative solutions, like family meetings and donor-advised funds, showcasing the power of teamwork in pursuing a legacy that aligns with your values.

Dan covers: 

  • (02:29)The necessity for open and frequent communication about financial plans 
  • (06:41) The strategic incorporation of philanthropy into your estate plans 
  • (08:26) The importance of regular reviews and updates to your estate plans 
  • (10:27, 13:34) Insight into estate planning tools like GRATs and ILITs for managing tax implications 
  • The timing of conversations and financial distributions (18:21)
  • (22:28) Ensuring life insurance policies and beneficiaries are up-to-date
  • And more

Resources:

Connect with Dan Reese CFP®:

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Preparing for Retirement: Key Challenges and Solutions (Ep. 9)

Preparing for Retirement: Key Challenges and Solutions (Ep. 9)

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Are you wondering about the top pitfalls to avoid as you plan for retirement? Why do so many retirees end up facing unexpected financial challenges?

Tune in to this episode, where Dan Reese, host of “Ramp Up To Retirement,” invites Senior Wealth Advisor Brent Oliver to discuss eight critical retirement blunders you should avoid.

Together, they shed light on common mistakes like underestimating the true cost of health care, overlooking future tax liabilities, and relying too heavily on Social Security. Brent emphasizes the importance of flexible planning and proactive tax strategies, sharing insider tips to help ensure a smooth financial journey into retirement. Whether you’re five years away or already retired, there’s something for everyone in this insightful episode.

Dan and Brent discuss:

  • (04:25) Overestimating regular living expenses
  • (07:10) Ignoring skyrocketing healthcare costs
  • (09:56) Misjudging the impact of taxes
  • (14:28) Retiring sooner than anticipated
  • (15:33) Supporting loved ones financially
  • (17:41) Underestimating longevity
  • (20:09) Counting solely on Social Security
  • (22:55) Neglecting required minimum distributions
  • And more

Resources:

Connect with Dan Reese CFP®:

Connect with Brent Oliver: 

About our Guest: 

Brent Oliver is a Senior Wealth Advisor based in Jackson, Michigan, with 11 years of experience in the field. As a CERTIFIED FINANCIAL PLANNER™ professional and Senior Wealth Advisor, Brent helps families identify and work towards achieving their financial goals. His comprehensive approach to wealth management helps families identify where they are today, where they want to be, and what gaps might prevent them from achieving all that is important to them. He has the heart of a teacher and works with clients to ensure they understand why strategies are being employed and how they can help families reach their goals.

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