
Rule Breaker Investing November 2025 Mailbag: Be a FOR Person
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Nov 26, 2025 Robert Brokamp, a Senior Motley Fool retirement expert, and Andy Cross, Chief Investment Officer, join to discuss the intricacies of retirement planning. They share strategies for managing concentrated portfolio positions, guidance on selling stocks for life goals, and tips for creating future children's portfolios. The conversation also touches on the importance of gratitude and community, insights on withdrawing retirement income, and the benefits of leaving long-term stocks to heirs. It's a heartwarming blend of practical advice and personal anecdotes.
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Listener Offers To Join The Fool
- Sean M. offered to work at The Motley Fool after crediting the company for inspiring his investing journey.
- David pointed him to careers.fool and highlighted open roles like senior manager revenue optimization.
Build An Income Cushion Before Retirement
- If you have oversized winners near retirement, build an 'income cushion' of several years of portfolio-provided income.
- Consider trimming concentrated holdings as you near retirement and rebalance into diversification.
Use Your Sleep Number To Guide Trims
- Assess your "sleep number"—the volatility you can tolerate—and judge large positions by whether you can live through big drawdowns.
- Aim for at least a 3–5 year time horizon for any sizable position and adjust allocations accordingly.








