Show Notes
Episode Overview
Year-end planning doesn't have to become a giant project. Roger walks through the key items every retiree should put eyes on before December 31st -- not to do everything, but to avoid the unforced errors that sneak up on you. He also takes listener questions on coordinating Social Security survivor benefits, weighing a teacher pension lump sum against a higher annual payment, what happens to capital losses when there are no gains to offset, and how to build enough confidence to actually pull the trigger on retirement. Outline Of This Episode Of The Retirement Answer Man (00:00) Year-end planning is about avoiding unforced errors -- not turning the checklist into a project (00:42) Rock Retirement Club open enrollment runs October 15-21 -- rockretirementclub.com (01:40) October theme in the club: year-end planning PRACTICAL PLANNING SEGMENT (03:35) Life check: pull up your 2027 plan of record and ask what's changed (05:01) What spending ideas are floating around that aren't in the plan yet? (06:00) Re-check your retirement paycheck: is your contingency fund and income reserve where it needs to be? (08:24) Tax-related action items (16:18) Deadline-driven items: required minimum distributions (17:15) Annual gifting limits ($19,000 per person in 2026) (17:45) Charitable giving strategies: cash, appreciated assets, and qualified charitable distributions for those 70.5+ (18:42) ACA subsidies: if your income changed this year, now is the time to check -- not at tax time (20:38) ACA and Medicare open enrollment LISTENER QUESTIONS (22:49) Jim asks about coordinating spousal and survivor Social Security benefits (25:09) Brian asks whether to take a teacher pension lump sum or a higher annual pension (29:19) Rose asks what happens to capital losses when there are no gains to offset (32:36) Bacher asks how to assess confidence in being financially ready to retire SMART SPRINT (41:29) In the next seven days, run through a year-end checklist -- just to put eyes on things. You may not have to do anything, but you'll be glad you looked. ROCKIN' RETIREMENT IN THE WILD (42:26) Roger just got back from his annual golf trip to Traverse City -- a good reminder of why investing in friendships is worth it REFERENCES Rock Retirement with Roger Whitney — YouTube channel Submit a Question for Roger Rock Retirement Club Dinkytown tax estimator Boomer Benefits Medicare guidance Healthcare.gov -- ACA open enrollment
More from Retirement Answer Man
Roger welcomes Danielle Roberts, co-founder of Boomer Benefits, to discuss Medicare in 2026, including rising Part D premiums, Medicare Advantage versus Medigap, and what to review during open enrollment. Then, Roger shares a Rock Retirement Club case study about building an income reserve before retirement and finding peace of mind by focusing on what matters most.
Peter Lazaroff, Chief Investment Officer of PlanCorp and author of The Perfect Portfolio, joins Roger to explore what makes a portfolio “perfect.” The answer isn’t a mathematically optimized portfolio—it’s one that serves your life. They discuss how to align investments with your goals and purpose, manage risk, evaluate stocks and bonds, and create a simple investment process you can actually stick with.
Roger Whitney closes out his five-week Social Security series with a practical framework for married couples deciding when to claim. He explains how to coordinate benefits, avoid common mistakes, and make a decision that fits the household rather than relying on a single calculator or searching for a perfect answer.
Roger Whitney explains how solo filers can make a confident Social Security claiming decision without getting overwhelmed by complexity. He covers the biggest mistakes to avoid, introduces a practical decision-making framework, answers listener questions about survivor benefits, and closes with a simple action step for deciding when to revisit the issue.
Roger Whitney explains six levers that can influence Social Security benefits: reviewing your earnings record, choosing when to claim, managing retirement income, reconsidering an early claim, considering where you live, and coordinating spousal or survivor benefits. The episode emphasizes that the best claiming strategy depends on each person’s priorities, resources, and desired outcome. OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN PODCAST (00:00) Roger introduces the Social Security series and explains that this episode focuses on the factors individuals can control. PRACTICAL PLANNING SEGMENT (02:52) Roger walks through the six Social Security levers, including earnings history, claiming age, retirement income, application withdrawal, state taxation, and spousal coordination. LISTENER QUESTIONS (31:08) Planning for Social Security uncertainty: Roger responds to Turner, who asks how to model future benefits given uncertainty about possible changes to Social Security. (36:25) Coordinating benefits for spouses with different earnings: Roger examines whether a higher earner should delay benefits while the lower earner claims earlier. (45:27) Claiming benefits when retirement assets are growing: Roger discusses a listener’s decision to claim Social Security before age 70 because withdrawals from pre-tax accounts would otherwise be needed and how a spouse’s early claiming decision could affect future spousal and survivor benefits. SMART SPRINT (49:14) Review your retirement plan, identify the Social Security levers you control, and compare alternative claiming strategies with a “what-if” scenario. CLOSING THOUGHTS (50:15) Roger shares a personal story about his daughter and a listener’s positive experience with her work. REFERENCES Social Security Administration — Social Security Statement and earnings record Social Security Administration — Social Security Benefits Calculators Dinkytown — Social Security Benefits Taxation Calculator AARP — State Taxation Of Social Security Benefits Rock Retirement with Roger Whitney — YouTube channel Submit a Question for Roger Sign up for The Noodle