April 23, 2025

Transition Period Strategy Part 2 – Positioning and Repositioning: EDU #2517

1 hour 18 minutes

Chris’s Summary:
Jim and I are again joined by Jacob as we continue exploring transition period strategy—the years just before retirement when you’re not yet withdrawing but want to prepare. We cover how near-retirees can manage emotional reactions to volatility while positioning assets to support early retirement spending. For those using our Minimum Dignity Floor and Fun Number approach, we walk through how to identify which dollars need protection and where a degree of principal protection fits.

Jim’s “Pithy” Summary:

Chris, Jacob, and I pick up where we left off last week—diving even deeper into what we call the “Venn diagram” years. That’s the messy overlap between accumulating assets and using them, when you’re still working but close enough to retirement that your portfolio better start shaping up for showtime. This is where a solid transition period strategy can make all the difference. We dig into the emotional side of repositioning, including why I think “locking in a loss” is more of a mental roadblock than a financial catastrophe, and why trying to time your way back to some magical high-water mark is a recipe for regret.

I take a bit of a detour into prospect theory, sequence of return risk, and what I jokingly call the 11th Commandment (spoiler: it’s not “thou shalt not sell unless at an all-time high”). Chris breaks down how DIYers can map out future spending in those first critical retirement years, Jacob walks through investment timelines and buffered strategies, and I try not to spill coffee on my laptop mid-rant.

Show Notes: As promised here is the photo of the foot space on Jim’s flight. According to our helpful listener, the space shown in the red box between the aisle and middle seats belongs to the middle seat passenger. This is because the middle seat loses space to the window seat due to the fuselage curve, and regains it on the aisle side. The aisle seat has slightly less space overall but can extend into the aisle if needed.

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