Welcome to a transformative episode where we delve into year-end financial strategies to optimize your retirement planning. Join us as we discuss tax-loss harvesting with Erin Coe, a seasoned planner and tax expert. Learn how to strategically sell capital assets at a loss to reduce your tax burden and explore the nuances of capital gains, wash-sale rules, and more. Plus, we answer listener questions about Roth conversions and annuities. Don't miss this insightful guide to maximizing your financial health! PRACTICAL PLANNING SEGMENT (00:25) Today on the show we begin to explore year-end action items. (02:23) So now that we're into tax season, we're going to do a primer on tax-loss harvesting with Erin Coe. (03:59) Tax-loss harvesting is the act of intentionally selling capital assets at a loss (05:25) Defining what a capital loss is (08:42)The intent is to reduce taxable income and reduce taxable liability  (10:12) How do you gauge the impact of this? (13:34) Leave some buffer room to be careful on tax cliffs (15:35) The wash-sale rule means you can't sell a capital asset and claim that loss and then repurchase it within 30 days (21:27) What are some gotchas that we need to watch out for when evaluating portfolios? (22:24) Another problem is those carry forwards, you need to track it every year whether you are using it or not. (25:38) Tax loss harvesting is not just a December activity, it’s a year-round sport LISTENER QUESTIONS (28:05) Greg asks a question about Roth conversions for his older relative (34:24) Stanley says his wife has a taxable MYGA, multi year guaranteed annuity, and wants to know if he should take the lump sum or roll it into something else. (40:28) Jay asks about the pie or bucket approach SMART SPRINT (46:50) Review your after-tax accounts looking for unrealized losses and examine whether you can use them productively  Join our live event on Roth conversions at livewithroger.com or sign up for the replay at sixshotsaturday.com. REFERENCES  Dinkytown.net Turbo Tax Retirement Podcast NetworkSix Shot Saturday Retirement Answer Man