Listener Questions: Should I Take Social Security Early and Invest It?
In this episode, host Roger Whitney shares two "Rocking Retirement in the Wild" stories—one about a retiree who finds joy in doing nothing and another about a Navy veteran fulfilling a lifelong dream of flying the longest nonstop flight. The main focus then shifts to listener questions about whether to take Social Security early and invest the benefits, with a detailed analysis of the trade‑offs, including earnings tests, investment return assumptions, life expectancy, and the value of guaranteed, inflation‑adjusted income. Whitney outlines scenarios where early claiming might make sense—high expected returns, no other income, or skepticism about Social Security’s future—while emphasizing the risks of market volatility, execution errors, and the security of delayed benefits. He concludes that for most people, especially those who value a risk‑free, inflation‑protected income stream, waiting until full retirement age or 70 remains the prudent choice.
Why Even the Best Retirement Calculator Is Wrong
In this episode, Roger Whitney critiques the overreliance on retirement‑planning software—especially Monte Carlo engines like Bolden, Money Guide Elite, and eMoney—explaining that they only measure the probability of a portfolio not hitting zero, not the quality of life in retirement....
Healthcare Before Medicare: Retiree Feedback
In this episode, host Roger Whitney shares real‑world retiree feedback on navigating health‑care before Medicare, highlighting strategies such as timing the COBRA‑to‑ACA transition to preserve deductibles, leveraging part‑time city jobs or student enrollment for affordable coverage, and uncovering employer‑sponsored extensions...
Healthcare Before Medicare: Creating Your Own Action Plan
Roger Whitney concludes his four-part series on pre‑Medicare health care by introducing the OODA Loop—observe, orient, decide, act—as a practical decision framework. He walks listeners through building a five‑year cash‑flow plan, estimating MAGI, and assessing ACA subsidy eligibility alongside COBRA...
Healthcare Before Medicare: How to Lower Your Costs
In this third episode of his four‑part series, Roger Whitney guides listeners through practical ways to lower health‑care costs before Medicare, from daily health habits to smart insurance shopping. He demystifies the ACA premium subsidy system now that the expanded...
Healthcare Before Medicare: Your Options
In this episode of The Retirement Answer Man, Roger Whitney walks listeners through the three primary health‑care options available before Medicare eligibility: COBRA continuation coverage, ACA marketplace plans, and part‑time employer group insurance, while also noting other alternatives like private...
