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

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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

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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

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Mark asks a common question – What should I do regarding my withdrawal strategy? Should I first pull from my brokerage account or my IRA?

There is no one-size-fits-all answer, but James provides a framework for creating a strategy to increase your odds of getting the most out of your money saved. He walks through the pros and cons of first pulling from your IRA versus a brokerage account, taking into consideration required distributions, tax rates and strategies, capital gains, Roth conversions, tax gain harvesting, and charitable giving.

Questions answered:
What are the tax implications of giving to family members versus charities?

How should capital gains affect my withdrawal and tax strategy?

Timestamps:
0:00 - Mark’s question
3:12 - Pros of pulling from IRA
7:24 - Lower tax rate today
9:27 - Cons of pulling from IRA first
11:38 - Charitable giving
13:58 - Pros of brokerage pulls
18:40 - Other potential pros
21:39 - Cons of pulling from brokerage
26:03 - Things to consider
30:50 - Wrapping up

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Dr. Riley Moynes, author and creator of a popular TED Talk joins James to discuss his own retirement which led him to become the author of The 4 Phases of Retirement. While Dr. Moynes was financially prepared for retirement, he wasn’t prepared for the boredom and depression that followed the first two years of retirement fun. As it turns out, his retirement path was far from unusual.

Dr. Moynes shares what leads to a truly meaningful retirement and how you can prepare now for a meaningful, deeply satisfying retirement, one that is about much more than vacations and golf.

Connect with Dr. Riley Moynes:
Website: https://thefourphases.com/
YouTube Channel: https://www.youtube.com/@rileymoynes545
TedX Talk: https://youtu.be/DMHMOQ_054U?si=wr1B3lw5ysc05GPS
Book: https://thefourphases.com/buy-the-book/
The Workshop: https://thefourphases.com/book-a-workshop/

Questions Answered:
Why are some people unhappy in retirement, and is there a way to prevent that?
What are some reflective questions that can set me on the path to a satisfying retirement?

Timestamps:
0:00 - Dr. Riley Moynes and his research
4:55 - Phases 1&2 - vacation and boredom
9:57 - Phases 3&4 - trial and reinvention
12:45 - Ask the tough questions
16:06 - Skip Phase 2 and 3?
18:39 - Pre-retirement preparations
22:52 - Service to others
26:05 - Summary

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Listener Sherry asks a good question: How do large, one-off expenses (like a new roof, new car, etc.) fit in the 4% Rule?

James explains the concept of the 4% Rule and its limitations while demonstrating how it can be an effective guideline in planning and forecasting retirement success.

He addresses the importance of anticipating one-off expenses and, depending on your portfolio withdrawal rate, using sinking funds to get a reality check on where you stand.


Questions answered:
Are one-off expenses covered in the 4% Rule?
Who should be concerned with creating sinking funds for one-off expenses?


Timestamps:
0:00 - Sherry’s question
3:19 - Shortcomings of the 4% Rule
5:30 - Look at income and outcome
6:58 - Portfolio withdrawal rate
10:51 - Example of no margin
13:02 - Sinking funds
16:57 - New reality check
18:49 - Consider the duration of expenses
20:17 - The wrap-up

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Healthcare subsidies are like a tax break and should always be optimized, right? That seems like an easy question that should have a straightforward answer. But the correct answer is, “It depends.”

Cole from Move Health is back, as he and James explain how advanced premium tax credits work, when you might not want to take them, and why it’s imperative to have a financial plan and a tax strategy in mind as you make healthcare insurance decisions. They share case studies and remind listeners that we don’t need to feel intimidated regarding healthcare in early retirement. We just need to be informed.


Questions Answered:
Who is eligible for advanced premium tax credits?
When should I not try to optimize healthcare subsidies?


Timestamps:
0:00 - ACA coverage
2:19 - Advanced premium tax credits
4:59 - Determining subsidies
8:09 - Modified adjusted gross income
9:36 - Estimating income
13:17 - Optiming premiums and subsidies
15:28 - Tax/subsidies strategies
18:56 - A case study
21:43 - When to optimize subsidies
27:10 - Another case study
29:34 - Tips and takeaways

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We meet many people who are in a position to retire early. But when they think about healthcare in retirement and not being eligible for Medicare until age 65, they feel stuck, even though they’re ready for retirement in every other way.

Cole Craven of Move Health Partners chats with James about the healthcare options that are available for early retirees and why there is no one-size-fits-all, “best” solution. He also lays out a general timeline for ensuring a smooth transition between your current healthcare, early-retirement healthcare, and post-age 65 healthcare.

Questions Answered:

What are my healthcare options if I retire before age 65?

What are advanced premium tax credits, and how can I make the most of them?

Time stamps:
0:00 - Cole Craven on early retirement
4:05 - 5 pre-65 retirement healthcare options

9:35 - Determining the best option

11:38 - Advanced premium tax credits

13:27 - Upcoming ACA changes

16:16 - Is low-income strategy a good idea?

18:50 - How/where to get coverage

22:03 - Timeline for pre-and-post 65

24:32 - Wrap-up

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