Ready For Retirement

James Conole, CFP®
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7 snips
Jan 11, 2026 • 18min

I’ve Never Seen So Many Retirees Make This Same Mistake

Retirement mistakes are often made by the most careful planners. With people living longer and markets fluctuating, many retirees cling to outdated strategies. Whether it’s sticking with growth stocks or relying on cookie-cutter portfolios, these choices may prove costly. Through case studies, the risks of sequence-of-returns are unveiled, highlighting the importance of aligning portfolios with actual cash-flow needs. A tailored approach, rather than generic templates, can significantly enhance retirement success.
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Jan 4, 2026 • 15min

This Is What a $10M Retirement Actually Looks Like

Exploring a $10 million retirement reveals unexpected complexities. The focus shifts from lavish spending to smart financial planning, addressing income needs, taxes, and lifestyle choices. James highlights how high-net-worth retirees often struggle with defining their spending and managing withdrawal rates. He explains the importance of estate planning, charitable giving, and the critical role of Social Security. Wealth doesn't ease the burden; it amplifies it, necessitating intentional strategies for a fulfilling retirement.
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Dec 28, 2025 • 17min

Retiring After 65? The Rules Change (Hint: You Can Spend More)

Retiring after 65 reshapes financial strategies and priorities. With potentially higher Social Security benefits and fewer years to plan, retirees can often afford to withdraw more. The podcast highlights the importance of optimizing your 'go-go years' for travel and experiences. It delves into the risks of market downturns and emphasizes careful cash flow management. Key topics include navigating required minimum distributions, Medicare surcharges, and investing in health as a priority for a fulfilling retirement.
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Dec 24, 2025 • 36min

18 Months Into Retirement, This is What Surprised Me Most | Retirement Reality

Christian candidly shares his first 18 months of retirement, revealing how the stress of a demanding job slowly dissipated, akin to shedding a heavy coat. He found liberation in stepping away from an 'always-on' mindset, allowing for healthier habits and deeper connections. Reflecting on personal experiences, he emphasizes the importance of prioritizing quality time with loved ones over financial gains. As he navigates newfound passions and hobbies, he encourages others to embrace the emotional journey of retirement beyond just financial planning.
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Dec 21, 2025 • 12min

Here's the Most Unethical Thing Advisors Do

Exploring the darker side of financial advising, the discussion reveals how seemingly sound advice often prioritizes fees over clients' true goals. A case study illustrates how tax strategies can mislead by focusing on numbers rather than quality of life. Listeners learn the importance of aligning financial plans with personal values and desires, rather than getting lost in spreadsheets. Ultimately, good advice should support life’s objectives, ensuring that retirement is not just about saving money, but about enhancing freedom and experiences.
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Dec 17, 2025 • 40min

The Hardest Year of Retirement: What No One Warned Me About | Retirement Reality

James "Jim" Selvey, a retired software engineer and author, opens up about his unexpected early retirement and the identity crisis that followed. He shares how a sudden layoff turned into an opportunity for clarity and self-discovery. Jim discusses navigating the emotional challenges, finding purpose through volunteer work, and exploring new creative outlets like writing. He emphasizes that retirement can be a chance to embrace new chapters and encourages others to view it as a liberating transition rather than a loss.
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Dec 14, 2025 • 10min

The Hidden Cost of Roth Conversions: Avoiding Surprise Medicare Charges

Roth conversions can significantly reduce taxes but may also lead to costly surprises with Medicare premiums. The discussion highlights how a single dollar increase in modified adjusted gross income can trigger IRMAA surcharges. A compelling case study illustrates how strategic conversions can save a couple nearly a million in taxes, yet if mismanaged, could cost them tens of thousands in premiums. Key strategies for navigating Roth conversions effectively call for careful planning to balance tax savings with Medicare expenses.
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Dec 10, 2025 • 38min

Freedom at 60 Why He Left a Job He Loved (and Doesn’t Regret It) | Retirement Reality

Steve's story of early retirement reveals how a heart attack shifted his perspective on life. After two decades in video game programming, he embraced freedom at 60, trading stress for hobbies like jazz bands and improv. His health journey included losing 70 pounds through innovative fitness routines, including VR workouts. Moving back to Arizona to support his mother during her illness deepened the value of his newfound time. He emphasizes that retirement is about finding joy and purpose, not just finances.
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Dec 7, 2025 • 13min

Most Retirement Advice Fails Singles (Here’s What to Do Instead)

Most retirement advice quietly assumes you have a partner: two incomes, two Social Security checks, someone to split expenses with, someone to catch the slack if something goes wrong. But for singles, the margins are tighter and the freedom can be much greater. Planning alone means every decision carries more weight, but it also means you have full control over the life you want to build.This video centers on Tina, a 62-year-old single woman with roughly $2.2 million across investment accounts, employer stock, a 401(k), and a Roth IRA. Her situation highlights something many single retirees face: the rules for married couples don’t apply. There’s no second Social Security benefit, no shared expenses, no fallback income — just her plan, her goals, her decisions. Once her “freedom number” becomes clear, the entire plan shifts. Reliable income fills part of the picture, but the rest depends on how her portfolio supports the exact life she wants to live. Simple choices — retiring sooner, traveling more, inviting friends on those trips, or designing a lifestyle that actually reflects what matters — completely change her projections and expand what’s possible.The heart of this conversation isn’t about budgets or perfect withdrawal rates. It’s about giving singles permission to build lives that match their values, not someone else’s template. When the numbers align with the life you want, confidence follows naturally.If this perspective helps you rethink how retirement looks when it’s just you, tap like and share what resonated. Your retirement doesn’t need to look like anyone else’s, it just needs to support the version of life that feels right to you.-Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsementsParticipation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.Create Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!
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Dec 3, 2025 • 38min

Retired at 50 Freedom, Guilt… and What No One Tells You | Retirement Reality

Retiring at 50, Kent shares his journey of financial independence, shaped by early saving and unexpected inheritance. He dives into the guilt of accepting family wealth and the urgency that family loss brought to his decision. Nine months in, Kent relishes newfound freedom: quality time with his daughters, travel, and pickleball. He candidly discusses the identity shift and the importance of redefining productivity beyond work. With intentional planning, he embraces simplicity, prioritizing family over societal expectations for a fulfilling retirement.

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