#190 - All about "backdoor" Roth contributions

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.comTax 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] Financial monthly e-newsletter - Retirement Planning InsightsFacebook 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 discussed 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 - hereIRS Form 709 - hereTenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.comTo 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] in this episode:My company newsletter - Retirement Planning InsightsFacebook 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 ClubKevin 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.comThe Rock Retirement Club - www.RockRetirementClub.comTenon Financial monthly e-newsletter/blog - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.comTo send Andy questions to be addressed on future Q&A episodes, email [email protected]

Andy and Jason Cutitta from ToBa Financial share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: How to incorporate a potential inheritance into your retirement planning ( 12:30 )Limitations of the "Die With Zero" concept ( 18:55 )The upcoming ability to do in-plan Roth conversions in the federal Thrift Savings Plan ( 29:06 )Whose retirement accounts to take from first when spouses have a big age disparity ( 36:56 )When are you required to file a tax return. And even if you aren't required to file one, why you still should anyway ( 45:04 )How to try to project your income for the year when there are certain items you can't know for sure until later in the year ( 53:32 )When in the year is the best time to take your annual Required Minimum Distribution ("RMD") ( 1:01:02 )How much money do you need in retirement to justify hiring a financial advisor ( 1:08:21 )Links in this episode:ToBa Financial website - https://www.jasoncutitta.com/toba-financialThe Hawaii Retirement Show podcast - https://www.jasoncutitta.com/hiretirementshowTo send Andy questions to be addressed on future Q&A episodes, email [email protected] company newsletter - Retirement Planning InsightsFacebook 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 does a deep dive into everything about "backdoor" Roth contributions, which is where you make an after-tax contribution to a traditional/pre-tax account, and then convert it to a Roth account. Looks simple on the surface, but there are a lot of angles and gotchas to watch out forLinks in this episode:IRS Form 8606 - hereCongressional meeting summary from December 2017 meeting on the Tax Cuts and Jobs Act - hereTenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.comTo send Andy questions to be addressed on future Q&A episodes, email [email protected]

Andy shares his background and how/why that shaped his views, beliefs and approach to providing tax-efficient retirement planning and related content through the Retirement Planning Education website, podcast, YouTube channel, blog and Facebook groupLinks in this episode:Tenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.comTo send Andy questions to be addressed on future Q&A episodes, email [email protected]

Listener Q&A where Andy talks about: Can a spouse claim spousal benefits while delaying the start of their own benefit ( 10:40 )What's the best way to view your accounts in terms of how much of them are actually yours after accounting for eventual taxes you have to pay on them ( 14:08 )Can a minor be named as the beneficiary of a retirement account ( 23:28 )His thoughts on dividend stocks and funds ( 26:55 )Follow up thoughts about combining retirement account, in response to a previous listener question ( 34:43 )Considerations and gotchas around changing state tax domicile ( 39:30 )10 cognitive biases in investing, and which three I see the most in my practice ( 46:48 )Considering the present value of expected future Social Security payments when determining asset allocation ( 54:25 )Additional thoughts about the 4% rule and whether you can increase your distribution if your portfolio value increases ( 1:01:40 )To send Andy questions to be addressed on future Q&A episodes, email [email protected] in this episode:NASDAQ's summary of 10 cognitive biases in investing - here Retirement Planning Education podcast episode - #002 - What's the 4% RuleMy company newsletter - Retirement Planning InsightsFacebook 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 episode is a bit different from our normal real people chats though. Andy is joined by Kevin Lyles from the Rock Retirement Club. Kevin is a retired corporate lawyer who has since become a certified retirement coach, focusing on helping people with the non-financial aspects of retirement.In the episode, Andy & Kevin talk about six "Retirement Truths:"You never know when you have enough; there are too many uncertainties and too many changes in lifeThe 90/10 rule; before retirement, planning is often 90% financial, 10% non-financial. In retirement, planning is often 90% non-financial, 10% financialSearching for purpose can lead to frustration and failure to find itOptimization is great. But don't let the elusive quest for perfect be the enemy of good. Don't let yourself get stuck in analysis paralysisTo thrive in retirement, we must continue to grow and achieveRetirement isn't about money; it's about time. Tomorrow is not promised  Links in this episode:The Rock Retirement Club - hereTenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.comTo send Andy questions to be addressed on future Q&A episodes, email [email protected]

Andy and Cody Garrett from Measure Twice Financial share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: Affordable Care Act ("ACA") tax credits and income "cliffs" in tax planning ( 08:13 )Doing Roth conversions vs tax gain harvesting ( 22:30 )Paying taxes in retirement; estimated payments vs withholdings ( 31:33 )Rushing into Roth conversions ( 38:50 )When to start doing HSA distributions ( 51:31 )Should you be worried about tech stocks ( 58:23 )Timing Required Minimum Distributions ("RMDs"); when in the year to take them ( 1:08:26 )Retirement spending anxiety ( 1:17:37 )Links in this episode:Cody's website - https://www.measuretwicemoney.com/To send Andy questions to be addressed on future Q&A episodes, email [email protected] company newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com