Retirement Planning

Listener Questions: I have Roth Conversion Questions! [Video]

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Listener Questions: I have Roth Conversion Questions!

Roth conversions, HSAs, pension choices, risk management: these are the topics of today’s listener questions. 

Susan, Gina, IM, and Daniel all submitted their questions to me via  and you can too! If you have any retirement questions, or even if you simply want to leave a comment about the show, click on the link to present your question. 

Whether you are looking to learn more about HSAs, Roth conversions, or evaluate your pension choices, listening to other listeners’ questions can help you learn how to frame your own questions and consider your options by always keeping your goals in mind.

How to evaluate the best way to take a pension? Susan recently asked her financial advisor how she should take her pension and wasn’t satisfied with his answer. 

There are several options to choose from when deciding how to take a pension. One choice is to take the pension for a larger monthly sum for the duration of the pensioner’s life. Another option is to take a smaller amount over the course of the lives of both the pension holder and their spouse. A third option is to opt for a lump sum payment and forgo the monthly payments altogether.

When making this decision there are a few ways to evaluate your choices. Create a what-if scenario to help you compare all the options. Then evaluate them next to your retirement plan of record. Listen in to hear how I perform this exercise with my clients. 

HSAs after age 65 HSAs are amazing tools that can help you reach your retirement goals. Gina’s question is about HSAs after age 65. She is still employed and plans to continue working for a few more years. She would like to continue to stay enrolled in her high deductible insurance plan so that she can continue to contribute to her HSA, but she isn’t sure how that would affect her Medicare choices. 

This is a great idea but navigating these waters is tricky since the rules surrounding Medicare are so complicated. Making a mistake could lead to a gap in coverage or even a lifetime penalty on parts B and D premiums. 

You’ll first want to check the rules surrounding your Medicare eligibility with your employee health insurance provider. Next, you should contact a Medicare navigator like Boomer Benefits . 

Should IM roll over her 401K to a Roth if she is worried about financial protections? IM writes in with a question about rolling over a 401K to a Roth IRA. She is worried about losing ERISA coverage when transitioning this money. ERISA stands for the Employee Retirement Security Income Act which was put in place to protect workers’ retirement plans. 401Ks are covered under this federal law; however, the protections for IRAs vary wildly from state to state. 

The first thing to do when considering this question is to check on the rules governing Roth IRA protections in your state. Next, you’ll want to evaluate your personal financial risk and how important this kind of coverage is to you. 

Make sure to scroll down to the bottom of the show notes to check out all the links to the resources mentioned in this episode.

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN LISTENER QUESTIONS • [4:41] Which pension choice best suits Susan’s needs?
• [13:40] A question about HSAs after age 65
• [17:23] Do the risks associated with Roth IRAs outweigh the benefits?
• [22:12] Daniel has a few Roth conversion questions
• [30:22] Daniel has a few HSA questions

Resources Mentioned In This Episode YouTube episode with Andy Panko on retirement tax bombs

Boomer Benefits

BOOK – Retirement Planning Guidebook  by Wade Pfau

Interview with Wade Pfau

The Retirement and IRA Show

Rock Retirement Club

Roger’s YouTube Channel – Roger That

BOOK – Rock Retirement   by Roger Whitney

Work with Roger

Roger’s Retirement Learning Center

Retirement Planning

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How to Avoid Tax Underpayment Penalties When Performing a Roth Conversion! [Video]

Do you have need experienced help optimizing and executing your Roth Conversion strategy? You can schedule an appointment with one of our Retirement Experts to look at your situation and help you plan for your future. Call us at (920) 544-0576 or go to Do you know you can't just wait until tax time in order to pay a balance you owe to the IRS? If you do, you may be subject to a tax underpayment penalty and have to pay future quarterly estimated taxes. Neither of which are very fun...Withholding the right amount for taxes is a problem throughout retirement but specifically is a problem that can arise with Roth Conversions. Roth Conversion taxes can be paid in numerous ways. From withholding taxes right out of the conversion to paying taxes from your checking or savings accounts. Regardless of how you pay taxes, the IRS will force you to pay those taxes at a specific time or face IRS penalties.In this video, we are going to clear up a hot button issue in regard to Roth Conversions - How to pay the right amount in taxes at the right timeWe will discuss: ✅ How to pay estimated taxes in order to avoid underpayment penalties✅ The way you withhold taxes will vary based on what source you are paying those taxes from✅ How to meet one of the three guidelines the IRS specifies you need to meet in order to avoid IRS penalties- - - - - - - - - - - - - - - - - - - - - - Always remember, "You Don't Need More Money; You Need a Better Plan"🍿 Subscribe to our channel:🏆 Join our 'Retirement Mastery' Facebook Group:📈 Talk with us about your retirement plan here:📚 The New 60/40: How the Next Generation of Retirees Can Achieve Radical Financial Freedom through Better Safe Investing - Wealth Management is a Registered Investment Advisor in the State of WI. Safeguard Wealth Management is not an insurance provider. All content on Youtube is for informational purposes only and should not be taken as personal advice for your situation. You can read more disclosures at