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Ready For Retirement

Author: James Conole, CFP®

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Ready For Retirement is the podcast dedicated to helping you learn the tips and strategies that will help you achieve your retirement goals. When it comes to retirement planning, it can quickly become overwhelming and easy to not take action. I designed this podcast because I want you to have the knowledge and confidence to create your secure retirement. My ultimate goal for all of my clients (and listeners) is to create peace of mind and that starts with having a strategy. I want you to spend more time thinking about what matters most to you in retirement. I post weekly episodes to keep you up-to-date on all the best tips and strategies to create a retirement that excites you. Everything from investing tips, tax planning, withdrawal strategies, insurance planning, Social Security, and that's just the start! Let's help you maximize your return on life. We use your money and the strategies I share in this podcast to do just that!
230 Episodes
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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. An...
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...
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 ...
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 ans...
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...
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 m...
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...
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 ...
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, wit...
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 conv...
Dr. Riley Moynes, author and creator of a popular TED Talk joins James to discuss his own retirement which led him to become the author of The 4 Phases of Retirement. While Dr. Moynes was financially prepared for retirement, he wasn’t prepared for the boredom and depression that followed the first two years of retirement fun. As it turns out, his retirement path was far from unusual. Dr. Moynes shares what leads to a truly meaningful retirement and how you can prepare now for a meaningfu...
Listener Sherry asks a good question: How do large, one-off expenses (like a new roof, new car, etc.) fit in the 4% Rule? James explains the concept of the 4% Rule and its limitations while demonstrating how it can be an effective guideline in planning and forecasting retirement success. He addresses the importance of anticipating one-off expenses and, depending on your portfolio withdrawal rate, using sinking funds to get a reality check on where you stand.Questions answered:Are on...
Healthcare subsidies are like a tax break and should always be optimized, right? That seems like an easy question that should have a straightforward answer. But the correct answer is, “It depends.” Cole from Move Health is back, as he and James explain how advanced premium tax credits work, when you might not want to take them, and why it’s imperative to have a financial plan and a tax strategy in mind as you make healthcare insurance decisions. They share case studies and remind listene...
We meet many people who are in a position to retire early. But when they think about healthcare in retirement and not being eligible for Medicare until age 65, they feel stuck, even though they’re ready for retirement in every other way. Cole Craven of Move Health Partners chats with James about the healthcare options that are available for early retirees and why there is no one-size-fits-all, “best” solution. He also lays out a general timeline for ensuring a smooth transition between y...
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 - ...
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 h...
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 f...
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 alo...
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 de...
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...
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