Ready For Retirement

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.22:56 - Plan D26:11 - Dental and vision28:25 - Fear about coverage33:09 - Denied coverage?35:19 - What Medicare doesn’t cover37:24 - Other options39:08 - MOVE Health PartnersCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 single position5:43 - Identify biggest risk8:00 - Tax gain harvesting and Roth conversions12:14 - Tax strategy15:14 - Two variables to consider20:44 - Max out 401k plans?22:07 - A question of tax24:52 - Tax plan in action26:44 - Concern about emergency savingsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 saving for retirement?What introspective questions should I ask now to help me live well pre- and post-retirement?Timestamps:0:00 - Drew’s question2:07 - Two mindsets6:08 - Assess current and future needs7:33 - Projection exercise11:28 - Working backwards14:50 - Working 10 more years18:21 - Back to the initial question19:47 - Considering growth rate21:38 - A philosophical question23:52 - 3 Levers26:07 - Check spending/saving habitsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 potential inheritances or property downsizing to more fully and confidently evaluate when you can retire.Questions Answered:How can I determine if I’m financially ready to retire?Is the 4% Rule sufficient for determining retirement readiness?Timestamps:0:00 - Consider withdrawal rate2:14 - 4% Rule5:12 - Not a perfect strategy7:39 - Straight line projection 9:09 - Downside of SL projection 11:07 - Monte Carlo test13:07 - Understand severity of failure16:20 - Defining success, 18:25 - Looking aheadCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 Jennifer maximize her retirement savings in light of her current financial situation and future tax implications?What factors must Jennifer consider when deciding whether to convert her traditional retirement accounts to Roth or change her contributions to Roth 403b?Timestamps:0:00 - Jennifer’s question4:46 - Retire early for tax benefits?6:05 - Roth conversion strategy8:43 - Consider future expenses 12:38 - Assess SS strategies13:56 - Consider living situation15:54 - The conversion question17:54 - Main takeawaysCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 penalties before age 59 and a half.Questions Answered:How are non-qualified annuities taxed upon distribution, including both lump sum and annuity options?What strategies can be implemented to keep the tax burden as low as possible when withdrawing from non-qualified annuities?Timestamps:0:00 - Joe’s question1:52 - Non-qualified annuity overview5:11 - Potential tax strategies10:02 - Annuitization option12:31 - Annuity regret13:22 - 1035 Exchange14:33 - Things to knowCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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. Teaming up and talking it out, whether with your partner or a financial advisor, is always beneficial.Questions answered:How can I determine whether working with a financial advisor is worth it for me?What factors should I consider when deciding if I need a financial advisor beyond just my age or income level?Timestamps:0:00 - Not an age-related decision2:43 - Value and pricing structure4:12 - Natural conflicts 7:24 - When benefit exceeds cost10:02 - Cost of mistakes12:18 - Cost of missed opportunities14:16 - Cost of anxiety 16:02 - Thought partnership21:36 - SummaryCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 deciding whether to sell, rent them out, or explore other options?Timestamps:0:00 - Ray’s question1:56 - Why a home isn’t an investment4:38 - Do you want to be a landlord?8:22 - The financials10:14 - Asset appreciation11:30 - Cashflow15:04 - Leverage19:02 - What should Ray do?20:33 - Reverse mortgageCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

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 gain harvesting, Roth conversions, and other tax strategies.Questions Answered: What is tax gain harvesting?What is the tax planning window and how do I use it to my advantage?Timestamps:0:00 - Drew’s question2:50 - Determine use for each asset5:59 - Tax gain harvesting11:10 - Back to Drew15:30 - James’ priorities for Drew18:41 - Usually not either/or20:07 - Working backwards24:50 - General principles29:50 - Tax planning window32:16 - SummaryCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

James responds to listener Jerry’s question about the optimal time to distribute inheritance or charitable gifts: before or after passing away. James walks listeners through four important things to consider when it comes to gifting and inheritance: your gifting goal, whether you have a strong desire to see the assets gifted within your lifetime, the tax implications of various types of gifts, and what to do with assets you plan to retain for now but are intended for future generations.Questions Answered: Should I give my children and grandchildren their inheritance before or after I die?What are the tax implications to my children when I gift them my assets?Timestamps:0:00 - Jerry’s question2:20 - What is your gifting goal?3:38 - Gift during your lifetime?6:51 - Timing and priorities9:17 - Different tax implications12:08 - Exemption amounts14:13 - Tax implications to child15:33 - Proper beneficiary designations21:41 - The right time horizon24:45 - SummaryCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!