Harsh realities of life can very quickly change your retirement plans and your entire financial future. In this episode, Joe and Big Al spitball on dealing with these realities. What financial strategies can they suggest for William and his 33-year-old wife, who has metastatic breast cancer? Debbie and Emily each experienced the unexpected sudden passing of their partners. Is it possible to minimize the capital gains tax on Debbie's son's inheritance, and can Emily retire in a year? Josie has lousy longevity in her family and wants to plan for the worst case scenario of dying before her husband. Alfred is 81 and concerned that he's going to run out of money before he runs out of time, and Richard has a sobering story that changed his thoughts about when to collect Social Security. Finally, Irene is subject to the Government Pension Offset (GPO) - can she withdraw the money she paid into Social Security? Timestamps: 01:03 - Financial Strategies for the Young and Disabled (William, TX) 08:16 - How to Minimize Son's Capital Gains Tax on Inheritance (Debbie, HI) 14:37 - Can I Quit Work in a Year? Should I Do Roth Conversions? (Emily, Rochester, MN) 20:22 - Worst Case Scenario Retirement Spitball Analysis (Josie, Atlanta) 28:45 - Are We Going to Run Out of Money? How Much Can We Safely Withdraw? (Alfred Pennyworth) 32:35 - Life Lesson on When to Take Social Security (Richard) 40:15 - Can I Withdraw the $17,000 I Paid into Social Security? (Irene, Bremerton, WA) 46:00 - The Derails Access this week's free financial resources in the podcast show notes at https://bit.ly/ymyw-443: Estate Planning Organizer - free download Social Security Handbook - free download 6th Annual YMYW Podcast Survey - one randomly-chosen participant will win a $100 Amazon e-gift card! Episode Transcript Ask Joe & Big Al On Air for your Retirement Spitball Analysis