Tag: Financial Planning
What Your Parents’ Retirement Can Teach You About Planning Your Own (Ep. 38)

What Your Parents’ Retirement Can Teach You About Planning Your Own (Ep. 38)

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Your parents’ retirement experience can reveal lessons that are difficult to see while you’re still working. What has changed between their generation and yours, and which financial habits still hold up?

In this episode, Dan Reese, CFP®, explains how retirement planning has changed across generations and what you can learn by asking your parents thoughtful questions. He covers the shift from pensions to personal savings, the healthcare gap before Medicare, longer life expectancies, lifestyle creep, and the possibility of retiring earlier than planned. Dan also shares ways families can talk about money without making the discussion feel intrusive.

Key points:

  • Why testing your retirement plan against leaving work at 62 can help you prepare for an earlier-than-expected retirement
  • How the shift from pensions to 401(k)s places more responsibility on your personal retirement savings
  • Why Medicare premiums, supplemental coverage, and long-term care need separate consideration in retirement
  • How lifestyle creep can raise the amount of income you’ll eventually need to replace after leaving work
  • Questions you can ask your parents about retirement without starting with account balances or net worth
  • And more!

Resources:

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Roth vs. Pre-Tax 401(k): Choosing When to Pay Taxes for Retirement (Ep. 37)

Roth vs. Pre-Tax 401(k): Choosing When to Pay Taxes for Retirement (Ep. 37)

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Choosing between Roth and pre-tax retirement savings can feel simple until taxes, healthcare costs, income changes, and future withdrawals enter the picture.

In this episode, Dan Reese, CFP®, explains how Roth and pre-tax 401(k) contributions affect when you pay taxes and why the more appropriate choice may change throughout your career. He covers why lower-income years may favor Roth contributions, when pre-tax savings may become useful, and how Roth assets can provide added flexibility in retirement. 

Dan also explores employer matches, Roth IRAs, contribution limits, healthcare subsidies, Medicare premiums, inherited accounts, and the value of reviewing your savings strategy as your income and circumstances change.

Key points:

  • How Roth and pre-tax 401(k) contributions determine when taxes are paid on your retirement savings
  • Why lower tax rates early in a career can make Roth contributions worth considering for younger savers
  • How promotions, career changes, business income and changing household income can affect your savings choice
  • How Roth savings may provide flexibility when managing taxable income, healthcare-related costs and tax brackets during retirement
  • How Roth IRAs and Roth 401(k)s differ, and what to know about employer matching contributions
  • And more!

Resources:

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When Should You Claim Social Security? (Ep. 36)

When Should You Claim Social Security? (Ep. 36)

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When should you claim Social Security, at 62, full retirement age, or 70?

The answer can affect more than your first monthly payment, including your future income, taxes, portfolio withdrawals, and the benefit available to a surviving spouse.

In this episode, Dan Reese, CFP®, explains how Social Security benefits differ when claimed at age 62, full retirement age, or age 70. He examines break-even calculations, annual cost-of-living adjustments, life expectancy, earnings limits, and household claiming decisions. Dan also explains how delaying benefits may create room for Roth conversions, change portfolio withdrawals, and support a surviving spouse. 

Key points:

  • How claiming at 62, 67, or 70 can produce significantly different monthly Social Security payments
  • Why cost-of-living increases compound differently when your starting Social Security benefit is higher
  • When health, longevity, income needs, and other retirement resources may influence your claiming age
  • How delaying Social Security may create additional time for Roth conversions and lower taxable income
  • Why couples should consider survivor income before either spouse begins receiving Social Security
  • And more!

This 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:

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

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

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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®:

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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)

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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:

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

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

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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:

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Choosing the Right Exit Path for Your Business (Ep. 31 | Pt. 7)

Choosing the Right Exit Path for Your Business (Ep. 31 | Pt. 7)

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Selling a business involves both financial and personal considerations, and the transition path you choose may influence your long-term business, employee, and personal goals.

In this episode, the seventh in the business exit planning series, Dan Reese walks through the most common exit paths available to business owners, including strategic sales, private equity, ESOPs, management buyouts, and family transitions. He breaks down the pros and cons of each, explains how payment structures like earnouts and lump sums work, and addresses what buyers are actually looking for. 

Dan also highlights the biggest mistakes owners make, from waiting too long to ignoring tax planning and cultural fit.

Dan discusses:

  • How a strategic sale may result in higher valuations when a buyer sees immediate synergies with your existing business and processes
  • Why private equity may involve a larger upfront payment structure, and how earnouts and equity shares factor into the deal structure
  • How ESOPs may provide tax-related considerations, employee ownership opportunities, and continuity planning benefits for some companies for owners who want a gradual exit
  • Why the highest purchase price may not align with an owner’s broader priorities when legacy, culture, and employee impact matter to you
  • How procrastinating on exit planning and value acceleration may limit flexibility and preparation during a future transition
  • And more!

Resources:

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Building Business Value Beyond the Numbers (Ep. 30 | Pt. 6)

Building Business Value Beyond the Numbers (Ep. 30 | Pt. 6)

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What contributes to a business’s value when it’s time to step away?

Is it just the numbers, or is there something deeper that drives what buyers may be willing to pay?

In this episode, Dan Reese breaks down part 6 of the business exit series, focusing on ways to potentially enhance business value before a sale. He explains why financials alone do not tell the full story and introduces four key drivers, human, customer, structural, and social capital, that can influence valuation. 

Dan walks through how leadership, customer structure, internal processes, and reputation can shape buyer perception and future potential. 

Dan discusses:

  • Why two businesses with identical financials can sell for very different prices based on structure and team strength
  • How recurring revenue and customer diversification may support stability and buyer confidence
  • The importance of human capital and building a team that can support long-term business continuity
  • How structural capital, including processes and systems, may improve scalability and transferability
  • Why social capital and reputation can play a role in how buyers evaluate long-term potential
  • And more!

Resources:

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Managing Business Risk Before an Exit (Ep. 29 | Pt. 5)

Managing Business Risk Before an Exit (Ep. 29 | Pt. 5)

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Growth gets most of the attention, but what happens when hidden risks start to impact what an outside buyer may consider when evaluating your business?

What would an outside buyer see that you might be overlooking today?

In this episode, Dan Reese breaks down the fifth part of the business exit series, focusing on how business owners can help address risks that may affect value before a sale. He explains how risks like key person dependency, customer concentration, and weak systems may influence what buyers are willing to pay. 

The conversation highlights practical ways help to identify and manage these risks, including building leadership depth and improving processes. Dan also shares why viewing your business through a buyer’s lens can change how you prepare for an exit.

Key takeaways:

  • How reliance on one person can limit business value and create challenges when transitioning ownership
  • Why customer concentration and inconsistent revenue streams raise concerns for potential buyers
  • The impact of undocumented processes on hiring, training, and overall operational stability
  • How regulatory and legal exposure can influence valuation and ongoing profitability considerations
  • Practical steps to help reduce risk, including leadership depth, audits, and working with specialists
  • And more!

Resources:

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What Is Your Business Really Worth and How to Increase It Before You Exit (Ep. 28 | Pt. 4)

What Is Your Business Really Worth and How to Increase It Before You Exit (Ep. 28 | Pt. 4)

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Most business owners assume they know what their company is worth, but that number is often far from reality.

What factors actually influence value, and how can small changes today impact what you walk away with later?

In this episode, Dan Reese continues the business exit series, breaking down how business owners can better understand valuation and prepare for a future exit. He explains the role of EBITDA, the risks buyers evaluate, and how leadership depth and systems impact value.

The conversation also highlights emotional bias in pricing and practical ways to strengthen a company over time. Listeners will learn how consistent improvements and proper planning can help support stronger outcomes when it matters most.

Key takeaways:

  • Why many owners misjudge their business value and how a proper valuation helps establish a clearer baseline
  • How emotional attachment can distort pricing expectations and may negatively impact decision-making
  • Why building leadership depth can help reduce perceived risk and increase appeal to potential buyers
  • How EBITDA adjustments provide a clearer view of profitability beyond tax-driven accounting choices
  • Why buyers scrutinize systems, customers, and financials, and what that means for preparation
  • And more!

Resources:

Connect with Dan Reese CFP®:

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