Ready For Retirement

Chris has been retired for a little over a year while his wife has continued to work. Now that Chris has “tried on” retirement and found the fit good, his wife will likely join him within the year. In his conversation with James, Chris, who could be described as goal-oriented and one who likes to be prepared, talks about the pros and cons of retirement. He’s found that by staying flexible, maintaining an adventuresome spirit, and focusing on giving back, retirement can be quite fulfilling. And he’s paved the way for his wife to retire with confidence.Questions answered:What sort of conversations could spouses be having before and during retirement about goals and expectations?How will relationships with colleagues shift and change in retirement?Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Chris3:50 - Impressions regarding retirement6:17 - Preparatory conversations9:09 - Decompressing and adjusting12:24 - Purpose and mystery15:59 - Exploring and serving21:19 - Missing colleagues25:57 - One spouse retiring first29:41 - What’s next and final adviceCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Meet Joe Sullivan, who found the first few years of retirement very difficult. Community is important to Joe, but he wasn't getting sufficient, routine social interaction to make meaningful connections while living in rural Virginia. He found his groove once he moved to a retirement community in Florida.James and Joe discuss the phases of retirement and what those phases have looked like for Joe. Joe emphasizes the importance of remaining flexible and trying new things as retirees explore who they will be in retirement and what will bring them the most satisfaction and joy.Questions answered:How can I test the waters to see if a retirement community is a good fit for me?What is Joe's advice for new retirees?Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Joe Sullivan3:07 - The decision to retire5:28 - Impressions vs real retirement9:11 - Needing something else10:39 - Retirement community decision12:05 - Before and after the move14:32 - Finding purpose17:16 - Phases of retirement20:08 - Joe’s advice22:05 - Emotional preparation24:32 - Next phase of Joe’s retirement26:07 - Final thoughtsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Ready for Retirement is on a mission to be the most valuable source of retirement information in the world. In that light, we’re making some changes. The biggest change is that rather than James doing all the talking, he’s inviting people like you to be part of the show. Some of you have real-life retirement advice to share. Others of you have questions that James can address. Ready for Retirement is poised to be a place for both. Get all the details in today’s episode.Questions answered:How will the format of the Tuesday YouTube video and the Saturday podcast change?How can I participate? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps:0:00 - A new format1:41 - Upcoming podcast changes2:56 - Retirement makeovers on YouTube4:23 - How to participate6:39 - How to apply7:43 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Gary is a 73-year-old with $8 million in savings. Despite having substantial assets, he’s concerned about missed opportunities for Roth conversions as he faces significant required minimum distributions.James encourages Gary to reassess his investment strategy, particularly the bond funds in his Roth IRA, and align his tax planning with his broader financial goals. By doing this, Gary could make more informed decisions that support his retirement goals and charitable aspirations.Questions answered:How can I give money to friends and family without them incurring a huge tax bill?What advice do you have for someone who has more than enough but has a hard time switching from saving mode to spending mode? Timestamps:0:00 - Gary’s question2:04 - More wealth = less freedom?5:16 - The controlling factor7:22 - An exercise10:09 - Living life; investment allocation 12:49 - Giving considerations16:09 - Medical expenses considerations18:45 - Modeling 20:40 - SummaryCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Connor plans to retire soon and wonders if he should pay off his mortgage of $300,000 or invest those funds, especially since he has a low interest rate. James gives a detailed response and reveals why there is no one-size-fits-all answer. When it comes to having a mortgage in retirement, math and spreadsheets can help with part of the question, but emotions and personal values should be considered too.Questions answered:Should you pay off your mortgage as you head into retirement, especially if you secured a low interest rate mortgage in recent years?How should you weigh the financial benefits of investing available funds versus the emotional peace of mind of being debt-free in retirement?Timestamps:0:00 - Connor’s question1:36 - An example scenario4:51 - Interest rates6:22 - Tax considerations9:13 - Tax-adjusted mortgage interest rate 12:13 - Sequence of returns15:27 - Peace of mind17:07 - ConclusionCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 burdens in retirement?Timestamps:0:00 - Jody’s question3:54 - The home7:06 - Inflation and tax thresholds11:04 - Cash flow vs taxable income15:07 - Withdrawal strategy19:30 - SummaryCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 question1:06 - How SS is taxed3:15 - Provisional income thresholds 5:21 - Another example7:13 - Thresholds for married filing jointly8:41 - SS state taxes9:59 - How to pay taxes on SS12:26 - SS tax torpedo14:27 - Effect on Roth conversionsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 planningQuestions 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 Nael2:20 - The wrong4:27 - The right way7:21 - The reality9:12 - Macro/micro tax environment11:19 - RMDs and state taxes15:36 - Charitable giving17:12 - Legacy and life expectancy21:22 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 question2:09 - Estimated tax payment options5:28 - Back to David’s question7:48 - Types of income – SS11:02 - Pre-tax retirement accounts13:53 - Average vs marginal tax rate 15:50 - Pensions17:26 - Brokerage accounts21:20 - How to make estimated tax payments23:23 - Other considerationsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 question3:12 - Pros of pulling from IRA7:24 - Lower tax rate today9:27 - Cons of pulling from IRA first11:38 - Charitable giving13:58 - Pros of brokerage pulls 18:40 - Other potential pros 21:39 - Cons of pulling from brokerage 26:03 - Things to consider30:50 - Wrapping up Create Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!