Bob and Shawn delve into the complexities of deciding when to take Social Security. They discuss factors to consider when taking Social Security such as your current age, anticipated lifespan based on family history, potential income sources, and whether you're still working. Bob emphasizes the importance of calculating the breakeven point for starting Social Security benefits early versus later, factoring in the time value of money. They also touch on political implications and uncertainties surrounding the future of Social Security. As always, Bob and Shawn reference Biblical scriptures, tying financial decisions to faith-based values.