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Retirement tax planning should begin well before Retirement. Listener Jodie, with over $2 million in assets in various types of accounts, is concerned about the high tax bracket she anticipates she be…

Retirement tax plann…

Retirement tax planning should begin well before Retirement. Listener Jodie, with over $2 million in assets in various types of accounts, is concerned about the high tax bracket she anticipates she be in in Retirement. Is there a tax strategy that would put her in a lower tax bracket?  James explores some often-overlooked tax strategies that can save retirees thousands in Retirement, especially for those like Jodie with diverse portfolios.Questions answered:How could my home be part of my tax strategy?How can understanding different income sources and account types can help minimize tax burde…

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…

Listener Michael ask…

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 Se…

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 …

Listener Nael opens …

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 environment2. Required minimum distributions3. State tax brackets4. Charitable giving5. Legacy …

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 ta…

David has a question…

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 whe…

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 …

Mark asks a common q…

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…

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 …

Dr. Riley Moynes, au…

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. Ril…

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 demonstra…

Listener Sherry asks…

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?…

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.�…

Healthcare subsidies…

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…

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 r…

We meet many people …

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:Wh…

Drew Shockley of MOVE Health Partners joins James to address questions about Medicare. He overviews the Medicare system, explains Parts A, B, C, and D, and breaks down what Medicare does and doesn’t…

Drew Shockley of MOV…

Drew Shockley of MOVE Health Partners joins James to address questions about Medicare. He overviews the Medicare system, explains Parts A, B, C, and D, and breaks down what Medicare does and doesn’t cover, who is covered, and when/why you might want alternative coverage. Questions Answered:I’m 65, still working and qualify for Medicare, but I have health coverage through my employer. What should I do?Does Medicare provide good, reliable coverage?Timestamps:0:00 - Medicare overview5:28 - About enrollment9:49 - Part C, Advantage vs traditional16:26 - Switching plans19:26 - Plans F, G, etc.2…

Graham and his wife are in their early 50s and plan to retire in 5 years. He wonders if they should continue maxing out their 401ks, how their investments should change, and what they should do with s…

Graham and his wife …

Graham and his wife are in their early 50s and plan to retire in 5 years. He wonders if they should continue maxing out their 401ks, how their investments should change, and what they should do with savings accounts to best prepare for their Retirement goals. James addresses these questions, Graham’s biggest risk as he nears Retirement, and potential tax strategies for him to employ.Questions answered:Which is a better tax strategy – tax gain harvesting or Roth conversions?Do I need to have a dedicated emergency fund in cash? Timestamps:0:00 - Graham’s question3:16 - The move from sing…

Drew, a burnt-out, financially responsible 40-something father of two, hopes he can scale back from his stressful job and still be okay when it’s time to retire. James offers a practical and philoso…

Drew, a burnt-out, f…

Drew, a burnt-out, financially responsible 40-something father of two, hopes he can scale back from his stressful job and still be okay when it’s time to retire. James offers a practical and philosophical take as he tackles Drew’s question. He demonstrates how to determine when Drew and his wife will be in a good position to fully retire. He also challenges listeners to assess their spending and saving habits and to strike a balance between planning for an unknown future while still finding fulfillment, freedom, and purpose today. Questions answered:How can I determine if I can stop savin…

How do you know if you can retire? It seems straightforward, but the answer is far from simple. Beyond portfolio balances and age thresholds, there are other things to consider. James explains his thr…

How do you know if y…

How do you know if you can retire? It seems straightforward, but the answer is far from simple. Beyond portfolio balances and age thresholds, there are other things to consider. James explains his three-step test to determine your Retirement readiness.By pulling together principles from the 4% Rule, straight-line projection, and a Monte Carlo analysis, you can assess whether your portfolio can sustain your desired lifestyle over decades amid various market conditions. However, these tests alone don’t paint the complete picture. James emphasizes the importance of considering other assets like…

Jennifer, 54, plans to retire soon. Her husband, 70, is retired, on Social Security, and dealing with some severe health issues. Jennifer worries about possibly becoming single in Retirement, which co…

Jennifer, 54, plans …

Jennifer, 54, plans to retire soon. Her husband, 70, is retired, on Social Security, and dealing with some severe health issues. Jennifer worries about possibly becoming single in Retirement, which could result in a higher tax bracket for her. Jennifer is considering whether to convert her traditional accounts to Roth to lower future taxes or to change her contributions to Roth 403b, even if it means paying more taxes now. James walks us through several factors for her to consider and demonstrates why her future tax situation is likely not as dire as she thinks.Questions Answered:How should J…

Joe is planning for Retirement and wants to minimize his tax burden, especially on the interest earned from his three annuities. James explains that non-qualified annuities are purchased with post-tax…

Joe is planning for …

Joe is planning for Retirement and wants to minimize his tax burden, especially on the interest earned from his three annuities. James explains that non-qualified annuities are purchased with post-tax money and offer tax deferral on growth until withdrawal. When taking out funds, the principal is tax-free, but earnings are taxed at ordinary income rates. He explores strategies for tax-efficient withdrawals. He also touches on annuities, options like a 1035 exchange to transfer an annuity into a different product for improved performance, the tax implications for heirs, and early withdrawal pe…

Deciding to work with a financial advisor is about more than how much you've stashed away. It's also about determining whether an advisor's benefits outweigh the costs. In your higher …

Deciding to work wit…

Deciding to work with a financial advisor is about more than how much you've stashed away. It's also about determining whether an advisor's benefits outweigh the costs. In your higher earning years, finances become more complex. More money means more decisions and more chances to make mistakes or miss out on opportunities. That's where a quality advisor can come in handy. They help you steer clear of bad investments, seize the right opportunities, and keep financial stress at bay.Having more than one perspective to draw from is the key to well-informed financial decisions.…

Listener Ray is wondering what to do with his home as he embarks on a nomadic, van-life journey in Retirement. Should he sell it to finance his travels or retain it for potential appreciation and cash…

Listener Ray is wond…

Listener Ray is wondering what to do with his home as he embarks on a nomadic, van-life journey in Retirement. Should he sell it to finance his travels or retain it for potential appreciation and cash flow? James explores the nuances of home ownership as an asset versus an investment. He considers cash flow and leverage as he looks at Ray’s three options – sell, rent, or borrow – while emphasizing aligning financial decisions with personal goals and aspirations.Questions Answered:Why shouldn’t I consider my home an investment?What are the key financial considerations for retirees when…

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 …

Listener Drew asks a…

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…