Mailbag: Out Of the Market Too Long & Taxes in Retirement

Two listener questions spark a conversation about the emotional and practical sides of retirement planning. David talks about strategies for easing back into the market after sitting on the sidelines and how retirees can think about taxes when withdrawing from IRAs, brokerage accounts, and Roth accounts. These are the kinds of questions many investors face as they transition into retirement, and without the right guidance, the wrong answers may negatively affect your plan.

Here’s some of what we discuss in this episode:

😱Market Re-Entry: Fear of missing gains vs. fear of crashes

 📉 Market History: Declines happen but recoveries follow*

📆 Dollar-Cost Averaging: Gradual investing can help reduce** timing risk

🧠 Risk Tolerance: Your emotional response matters in downturns

🧾 Retirement Taxes: Withdrawal strategy could affect tax outcomes



*Past market performance may not be used to predict or project future results

**Diversification does not ensure a profit or guarantee against market loss