Required Distributions – Ramp Up to Retirement

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

By Ramp Up to Retirement | February 11, 2026

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How insurance reviews and year-end planning help protect against gaps and outdated coverage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.

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

By Ramp Up to Retirement | January 28, 2026

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!