Social Security Claiming Strategies, Part 2: EDU #2544

October 29, 2025

If you would like to skip Jim and Chris discussing Jim’s travel plans and the guys’ frustration with low-cost airline pricing, you can skip ahead to (10:30).

Chris’s Summary
Jim and I continue our discussion on Social Security claiming strategies, revisiting the debate between Professors Derek Tharp and Laurence Kotlikoff. We explore how academic disagreements overlook the practical realities of retirement, emphasizing that Social Security is a resource, not a contest. We examine listener experiences, psychological factors, and portfolio interactions, highlighting how claiming decisions should reflect individual comfort, income structure, and long-term needs—not just mathematical optimization.

Jim’s “Pithy” Summary
Chris and I wrap up our walk through of Professor Kotlikoff’s response to Derek Tharp’s Social Security article—two academics with brilliant résumés and completely opposite opinions on claiming strategies. One says claim early. The other says delay to 70. But both, in my opinion, miss the bus when it comes to what actually matters to retirees: peace of mind.

We read two listener emails that bring the conversation back to reality. One listener puts it simply: “delaying Social Security is longevity insurance”. The second shares two real stories: a friend who claimed at 63, had a serious health event at 68, and passed away at 72, and a father who claimed at 62 but lived to 95. Same choice, very different outcomes. That’s why I say retirement is just a seesaw between the younger you and the older you—and you don’t know which one’s going to show up.

We also dig into some of the risks that get thrown around to justify early claiming—like sequence of return risk or loss of spending flexibility—and explain why they don’t hold much water if your retirement plan is structured the right way. The delay period isn’t something to be afraid of. It has an end date. You can plan for it.

For us, there’s no single right answer. The correct claiming strategy is whatever works for the person. But too many people focus on how to die with the most, instead of asking what their Social Security has to do for them.

Show Notes
Derek Tharp article

Laurence Kotlikoff article