Pay ZERO Capital Gains Tax vs Roth Conversions in Retirement: How to Determine Which is Best

Ready For Retirement

Listener Drew asks about a tax strategy for juggling capital gains and Roth conversions. While it can be a complicated question – especially when large accounts are involved – James provides some general guidelines that can be helpful for anyone with similar gnarly tax strategy challenges in retirement.
In this episode, we’ll cover the extent to which required distributions will be an issue, what you need to alleviate that issue, and the timeframe within which you have to do that.
James explains how to work backward to project your various tax brackets and determine how to prioritize tax gain harvesting, Roth conversions, and other tax strategies.
Questions Answered:
What is tax gain harvesting?
What is the tax planning window and how do I use it to my advantage?
Timestamps:
0:00 - Drew’s question
2:50 - Determine use for each asset
5:59 - Tax gain harvesting
11:10 - Back to Drew
15:30 - James’ priorities for Drew
18:41 - Usually not either/or
20:07 - Working backwards
24:50 - General principles
29:50 - Tax planning window
32:16 - Summary

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Chapters

1. Tax Strategy in Retirement (00:00:00)

2. Tax Strategies (00:07:20)

3. Tax Planning Strategies for Retirement (00:13:31)

4. Roth Conversion Tax Planning Strategy (00:28:08)