#564 - Retirement Year End Planning: Tax-Loss Harvesting

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.
(26:40) 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