Listener Michael asks about how Social Security is taxed, the rationale behind the 50% and 85% tax thresholds, and the implications of these taxes on Social Security and IRA withdrawals.

James responds by explaining how Social Security is taxed at the federal level, highlighting the concept of provisional income and the thresholds that determine the taxability of benefits. He notes state taxation of Social Security, explaining that most states do not tax these benefits and naming the ones that do.

He also explains practical strategies for managing Social Security taxes, including the Social Security tax torpedo, and how to incorporate these considerations into broader retirement and tax planning.

Questions answered:
How is Social Security income taxed at the federal level, and what are the provisional income thresholds?

What is the Social Security tax torpedo, and how does it impact the effective tax rate on retirement income?

Timestamps:
0:00 - Michael’s question
1:06 - How SS is taxed
3:15 - Provisional income thresholds
5:21 - Another example
7:13 - Thresholds for married filing jointly
8:41 - SS state taxes
9:59 - How to pay taxes on SS
12:26 - SS tax torpedo
14:27 - Effect on Roth conversions

Create Your Custom Strategy ⬇️

Get Started Here.

Listener Nael opens up a discussion about Roth conversions. There are benefits to doing Roth conversions, but can you do too many? Are there any downsides to Roth conversions?

Reaping the tax benefits from Roth conversions requires hitting a specific sweet spot. If you convert too little or too much, you’ll be leaving money on the table.

So, how do you find Roth-conversion the sweet spot? James lays out five things you should consider as you plan when and how much to convert:

1. Macro and micro tax environment
2. Required minimum distributions
3. State tax brackets
4. Charitable giving
5. Legacy planning

Questions answered:
How might a future out-of-state move impact Roth conversion decisions?
What impact might Roth conversions have on charitable giving or legacy gifts?

Timestamps:
0:00 - Question from Nael
2:20 - The wrong
4:27 - The right way
7:21 - The reality
9:12 - Macro/micro tax environment
11:19 - RMDs and state taxes
15:36 - Charitable giving
17:12 - Legacy and life expectancy
21:22 - Wrap-up

Create Your Custom Strategy ⬇️

Get Started Here.

David has a question about taxes in retirement: When you’re retired and no longer getting a regular paycheck from which your employer withheld tax payments on your behalf, how do you estimate the taxes you’ll owe?

To answer this question, it’s important to understand where income in retirement will be coming from and how that income is taxed. Once you have an idea of what you’ll owe, you need to make estimated tax payments throughout the year.

James explains how Social Security, withdrawals from pre-tax accounts, pensions, and brokerage accounts are taxed, and he explains how and when to make estimated tax payments to the IRS.

Questions answered:
What is the Safe Harbor Rule and how is it relevant to estimated taxes?
Is all income in retirement taxed the same?

Timestamps:
0:00 - David’s question
2:09 - Estimated tax payment options
5:28 - Back to David’s question
7:48 - Types of income – SS
11:02 - Pre-tax retirement accounts
13:53 - Average vs marginal tax rate
15:50 - Pensions
17:26 - Brokerage accounts
21:20 - How to make estimated tax payments
23:23 - Other considerations

Create Your Custom Strategy ⬇️

Get Started Here.