Chris’s Summary:Jim and I are joined once again by Jacob for the third and final part of our series on transition period strategy. This time, we focus on the practical side of asset positioning: how near-retirees can begin structuring spending reserves without overreacting to short-term volatility. We use an example case study to explain how to segment early retirement needs into time-based chunks, identify dollars that require principal protection, and distinguish between your Minimum Dignity Floor and Fun Number spending.
Jim’s “Pithy” Summary:Chris, Jacob, and I finish up our series on positioning assets during what we call the Venn diagram years or transition period. That’s that murky overlap between accumulation and decumulation, where you’re not retired yet, but you’re gearing up to live off your savings. This week, we dig into a listener’s question—he’s five years out from retirement and feeling nervous about market drops. He doesn’t know when or how to start making changes.
So, we build a hypothetical case to show what this might actually look like on paper. I walk through how to start allocating dollars across time without trying to do everything at once (because that’s how people freeze up or make bad calls). Jacob jumps in to explain why we don’t just ladder investments, we build what we call a liquidity timeline—an approach that gives you structure and flexibility. I dig into recency bias, the emotional hang-ups that stop people from spending even when they can—and should. We talk through which dollars need principal protection, which don’t, and why timing matters. And then I get into buffered strategies, laterals, the illusion of statement dollars, and, of course, my ongoing beef with growth-focused asset managers who don’t understand the first thing about distribution planning.

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