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• How insurance reviews and year-end planning help protect against gaps and outdated coverage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

Resources:

• Carson Wealth Retirement Readiness Quiz
• 2026 Calendar: Key Tasks & Financial Dates

Connect with Dan Reese CFP®:

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

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