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.

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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.

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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. 

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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.

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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.

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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.

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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.

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

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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.

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Selling your business may feel like the finish line, but for many owners, it can mark the start of a completely new chapter. One surprising statistic discussed in this episode: nearly 70% of business owners report regretting the sale within a year. In many cases, owners may feel unprepared for what comes next.

In this episode, Dan Reese wraps up the business exit-planning series by exploring the emotional, financial, and personal realities that follow a business sale. From the shift in identity that happens after stepping away from daily operations to the challenge of transitioning from entrepreneur to investor, Dan explains why many business owners find that a successful transition involves more than just the valuation.

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If you’re a business owner thinking about an exit, or already navigating life after one, this episode offers perspective on navigating the transition after a business sale. 

Whether you’re years away from selling your business or already thinking about life after work, this episode offers insight into building a retirement plan designed to align with your financial goals, personal priorities, and long-term legacy.

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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.

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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. 

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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.

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