Listener Q&A where Andy talks about: 

• Correction to a previous Q&A episode regarding taxation of lump sum Social Security benefits paid in one year for benefits attributable to the prior year ( 9:54 )
• His thoughts on artificial intelligence and how it can impact the financial planning industry ( 13:00 )
• The "withhold and replace" method of paying taxes when doing IRA distributions or conversions and using the indirect 60-day rollover approach to ultimately pay taxes out of your bank or brokerage account, but with the benefit of doing it via withholdings from the IRA ( 20:30 )
• Step DOWN in basis when inheriting assets that have declined in value from where the original owner bought them ( 31:46 )
• When having a pension available, instead of selecting a payment option that lives on for your spouse upon your death, instead taking the payment option that stops when you pass, and using the difference in the larger payment amount to buy life insurance for the benefit of your spouse ( 40:00 )
• His thoughts on using a TIPS ladder ( 45:29 )
• Whether to invest money or instead use it to buy long term care insurance. Such as deciding between making an $8,000 Roth 401(k) catchup contribution, or using some or all of that $8,000 to buy long term care insurance ( 50:48 )
• At what point does larger investable asset size or net worth start to lead to the need to have a more complex portfolio, or to invest in non-traditional assets like private investments, alternatives, etc. ( 54:31 )

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Links in this episode:

• Tenon Financial monthly newsletter/blog - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

Special edition 200th episode where Andy shares some of his observations about the financial services industry from his time working in it:

• Creating good and consistent content is hard to do and do well ( 9:32 )
• A lot of content is just clickbait to get your views and/or advertise something to you, and not actually good content ( 13:15 )
• Personal finance is a lot more personal than it is finance ( 17:40 )
• The vast majority (all?) of long-term retirement planning is ultimately just a lot of educated guesses and there is no way to create a perfect or infallible retirement plan ( 21:46 )
• Roth conversions are given too much attention and emphasis ( 28:15 )
• There are a lot of reasons to not like the financial services industry, and most (all?) of the industry is ultimately out to get you to buy something from them ( 33:30 )
• Most of the people in the industry are really good people and do really good work, but they just might not be working in a company or structure that prioritizes the client ( 37:52 )
• There is continued growth and momentum in financial advisors providing planning-focused services at more logical fee structures and service offerings ( 42:17 )
• Tax planning is getting more attention and more advisors are learning about and offering tax planning ( 43:50 )
• The percent of assets under management model doesn't make sense. There are other fee structures that are less illogical, less unfair, less arbitrary in what they charge ( 46:46 )
• The financial services and advisory industry is unfortunately really fragmented between different "factions" of companies, services, products, etc., and it ends up being a disservice to consumers ( 53:12 )
• Tax return prep is a hard business. Please be kind and considerate in dealing with tax preparers, especially in February, March and April! :-) ( 1:00:36 )
  
  

Links in this episode:

• Episode 100 of the Retirement Planning Education podcast - #100 – 100th episode celebration!!! Andy's 100 words of retirement planning wisdom

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

• My company newsletter - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

Andy and Jonathan Vance from Vance Financial Planning share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: 

• Given current world affairs and their impacts on the markets, should you do anything different with your investments, or are there any other planning opportunities to consider ( 14:20 )
• Tax updates for 2026, and some recap of tax takeaways for 2025 now that the 2025 tax return season is mostly behind us ( 26:27 )
• Using in-kind gifts to family and friends to get rid of appreciated non-qualified assets you no longer want, but don't want to sell and realize the gains ( 38:45 )
• The importance of having a good grasp on your future expenses and how that impacts virtually all aspects of retirement planning ( 46:00 )
• The practicality of the "die with zero" concept, and how Monte Carlo can help try to put it into practice ( 1:00:48 )
• Questions to ask when interviewing a financial advisor ( 1:11:54 )
• Options for what to do with permanent life insurance policies or annuities you might no longer want, or are no longer in your best interest ( 1:23:10 )

Links in this episode:

• Vance Financial Planning website - https://www.vancefp.com
• Manuka Financial's article, 9 Questions to ask a Flat Fee (or any!) Financial Advisor as you Near Retirement - here

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

• My company newsletter - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

Andy discusses the pros and cons of taking a lump sum vs taking monthly payments for your pension, questions to ask yourself to help figure out if it might be better for you to take one vs the other, and other considerations to keep in mind in making the decision

Links in this episode:

• www.ImmediateAnnuities.com
• www.PBGC.gov
• Tenon Financial's April 2026 newsletter - Whether to take a pension as a lump sum or monthly payments

• Tenon Financial monthly e-newsletter - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Listener Q&A where Andy talks about: 

• How often to check your accounts for rebalancing, and how often to check on your bigger picture finances and plan ( 2:32 )
• What to do with old positions you no longer want in a brokerage account but they all have large unrealized gains ( 16:03 )
• How Medi-Cal benefits interact with a high deductible health plan and an HSA (spoiler alert...I don't know!) ( 22:20 )
• Are there any good reasons to leave old/prior employer 401(k) plans where they are ( 25:31 )
• Tracking Roth IRA contributions (including money inherited from a deceased spouse's Roth 401(k)) ( 29:50 )
• The mechanics of separating the cream from the coffee when rolling pre-tax money in an IRA to a 401(k) to leave behind in the IRA just the after-tax basis, and potential gotchas with that process ( 33:41 )
• Are potentially large RMDs really a threat to someone's financial plan, or just a pain ( 42:37 )
• Additional thoughts on whether to pay off a mortgage before retirement, particularly if using pre-tax funds (like from a 401(k)) to do it, even if the interest rate on the loan is really low ( 49:45 )
• Why Roth money within a 401(k) isn't actually in its own separate account, but is instead just an internal accounting record type of "sub" account ( 53:04 )
• Tax-free conversions of mutual fund share classes to ETF share classes of the same fund, where available ( 59:02 )
• Thoughts on rental property vs bank CD's for purposes of estate transfer, tax implications and general retirement plan considerations ( 1:03:23 )

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Links in this episode:

• My article about pros and cons of rolling over old employer plans to an IRA - here

• My company newsletter - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

Andy chats with a real person (not an advisor) doing their own retirement planning. In this episode, Andy talks with Jim Kellerman. They talk about a wide array of retirement planning topics such as when he started getting serious about planning for retirement, how he now spends his days in retirement, what he's doing for health insurance since he's not yet on Medicare and why he's at the local prison each week...
 
 Links in this episode:

• Puritas tax prep software (including for Form 709 gift tax returns) - here

• Tenon Financial monthly e-newsletter - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Andy chats with fellow retirement planner Bradley Hilton, CFP®, TPCP®, MBA from Sonas Financial Planning. In this episode they talk about a wide array of retirement planning topics such as tax planning, distribution strategies, investing, annuities, long-term care insurance, what consumers often overlook in retirement planning and much more!

Links in this episode:

• Bradley's advisory company website - https://www.sonasfp.com/ or https://www.sonasfinancialplanning.com

• Tax Foundation summary of state-level estate and inheritance taxes (as of 2025) - here 

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

• Tenon Financial monthly e-newsletter - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

Andy discusses the ins and outs of gifting, the annual gift exclusion, gift splitting, gift taxes, gift tax returns (IRS Form 709) and more!

Links in this episode:

• Tenon Financial's March newsletter/blog about gifting - here
• IRS Form 709 - here

• Tenon Financial monthly e-newsletter - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Listener Q&A where Andy talks about: 

• Income tax treatment of buying bonds in a normal non-qualified brokerage account when you buy or sell bonds in between coupon periods ( 8:37 )
• When still working, are 50 or older, are maxing out your 401(k) contributions, and are high income and therefore would need to have your catch-up contribution go into your Roth (instead of pre-tax) 401(k), would it be better to skip the catch-up and instead put that money in a normal brokerage account ( 14:40 )
• Taxation of Social Security lump sums received for prior month's retroactive payments; is it taxable in the year received or in the prior year that the payments were attributable to ( 17:56 )
• Does the imputed wage income from employer group life insurance in excess of $50,000 death benefit qualify as earned income for purposes of making Roth IRA contributions ( 24:26 )
• Deciding how/when to sell out of appreciated assets in a brokerage account you no longer want but don't want to have to deal with realizing taxable gains ( 29:11 )
• Thoughts on direct indexing, and whether it's a strategy worth considering ( 37:01 )
• Whether or not to pay off a mortgage, especially now that interest rates are higher than they were a few years ago ( 44:07 )
• Thoughts on when to stop saving if/when you've saved "enough," balancing planning for the future you vs the present you, deciding how much to sacrifice now for saving for the future, etc. ( 49:24 )
• The differences in step-up in basis rules for spouses in community property states vs common law states, and how that impacts federal taxes (even if the gains aren't taxable at the state level) ( 55:10 )
• What to keep in mind when spouses want to maximize gift giving and not have to file a gift tax return ( 1:01:44 )
• Deductibility of donating appreciated securities vs cash and how to plan large donations in years of doing Roth conversions to help manage taxable income ( 1:07:47 )

To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Links in this episode:

• My company newsletter - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

Andy chats with a real person (not an advisor) doing their own retirement planning. This week Andy is joined by Kevin Sebesta from the Rock Retirement Club

Kevin retired at 43 as part of the FIRE (Financial Independence, Retire Early) concept. He shares his planning and retirement journey, and discusses more about FIRE including the FIRE community and thoughts everyone (not just FIRE folks) should consider when planning for retirement.

 
 Links in this episode:

• Kevin's blog - www.LifeInFIRE.com
• The Rock Retirement Club - www.RockRetirementClub.com

• Tenon Financial monthly e-newsletter/blog - Retirement Planning Insights
• Facebook group - Retirement Planning Education (formerly Taxes in Retirement)
• YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)
• Retirement Planning Education website - www.RetirementPlanningEducation.com

To send Andy questions to be addressed on future Q&A episodes, email [email protected]