The Modern Retirement Playbook

Would you trust a house built on a single support beam? Then why build a retirement plan around just one source of security? In this episode of The Modern Retirement Playbook, Jason Matthews explores the five essential pillars that support a stable retirement: income, investments, taxes, healthcare, and legacy planning. He explains how each pillar works together and why a weakness in any one area can affect the entire plan. From creating reliable retirement income and managing investment risk to planning for healthcare costs, minimizing taxes, and leaving a meaningful legacy, Jason discusses the practical steps retirees can take to build a more resilient financial future. Retirement success requires more than one strategy. It requires a comprehensive framework.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

AI can generate a retirement strategy in seconds, but can it understand the emotions, relationships, and life decisions behind it? In this episode of The Modern Retirement Playbook, Jason Matthews explores the growing role of artificial intelligence in retirement planning and where its limitations become most apparent. From investment ideas and tax strategies to retirement income planning and estate considerations, Jason discusses why AI can be a valuable research tool while still falling short of personalized advice. The conversation highlights the importance of human judgment, empathy, behavioral finance, and understanding a client's unique goals. Technology is changing quickly, but when it comes to retirement planning, the human element remains difficult to replace.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

Could the wrong Social Security strategy cost you more than you realize, even if your benefits never get cut? In this episode of The Modern Retirement Playbook, Jason Matthews breaks down some of the biggest misconceptions surrounding Social Security and retirement income. He explains how different income sources are treated, when Social Security benefits can be affected by earned income, and why claiming too early may not always be the best move. Jason also discusses the importance of tax diversification, planning for potential future benefit changes, and how Gen X investors can prepare for a retirement landscape that places more responsibility on the individual. Understanding the rules today could help you make more informed decisions tomorrow.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

What happens to your retirement plan when lawmakers decide to change the tax rules? In this episode of The Modern Retirement Playbook, Jason Matthews discusses California's proposed billionaire tax and uses it as a springboard for a bigger conversation: the uncertainty of future tax policy. Jason explains why retirees and pre-retirees should focus on tax diversification, the role of Roth accounts, required minimum distributions, Medicare premium surcharges, and Social Security taxation. He also shares common tax planning mistakes and why retirement often brings more tax complexity, not less. When tax laws can change unexpectedly, building flexibility into your retirement strategy may be just as important as growing your savings.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

What's the bigger retirement risk: running out of money, or worrying that you might? In this episode of The Modern Retirement Playbook, Jason Matthews explores the concerns that keep many retirees up at night, from longevity risk and market volatility to the challenge of turning savings into reliable income. Jason discusses the difference between reacting to headlines and following a well-designed plan, why guaranteed income can provide more certainty, and how simplicity often leads to greater confidence in retirement. If you've ever wondered whether your retirement strategy is built to weather the unexpected, this conversation highlights the value of planning ahead rather than reacting in the moment.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

What do rented swans, air-conditioned lawns, and a dog with its own inheritance have to teach the rest of us about retirement? In this episode of The Modern Retirement Playbook, Jason Matthews explores the surprising financial lessons hidden behind some of the extravagant habits of the ultra-wealthy. From creating reliable income streams and planning for long-term care to protecting assets through estate planning and avoiding unnecessary spending, Jason explains how principles used by the wealthy can apply to everyday retirement planning. The conversation also touches on legacy, financial stewardship, and why true joy isn't tied to a bank account balance. Sometimes the biggest retirement lessons come from the most unexpected places.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

What should you actually do with your 401(k) when you retire and could the wrong move cost you more than you think? In this episode, Jason Matthews breaks down the key choices retirees face: leaving money in a 401(k), rolling it into an IRA, or cashing out. He explores the potential tax implications, investment flexibility, and hidden risks behind each option—including why cashing out may create unintended financial consequences. The conversation also highlights the dangers of “set it and forget it” thinking in retirement and why actively managing income, taxes, and inflation becomes essential. It’s a practical look at turning your savings into a strategy that supports your retirement goals.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

What should your finances look like at every decade of your life? In this episode, Jason Matthews walks through a decade-by-decade approach to building financial health, from your twenties to your seventies and beyond. The conversation highlights how early habits like saving and automation can shape long-term outcomes, and how priorities shift as life evolves through family, peak earnings, and retirement. Jason also explores key turning points, including tax strategies, long-term care, and transitioning from saving to spending. It’s a look at how financial decisions compound over time and how each stage of life presents a new opportunity to strengthen your long-term strategy.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

Is the American Dream still within reach or just getting more expensive? In this episode, Jason Matthews explores how rising costs, longer lifespans, and shifting financial responsibilities are reshaping what retirement looks like today. From the realities of multi-generational households to the growing gap in retirement savings, the conversation highlights the challenges many families face. Jason also discusses key considerations like housing decisions, income planning, and long-term care, especially for those navigating retirement on a single income. It’s a practical look at how evolving economic pressures are changing the path to financial stability and what it takes to adapt.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.

Could a future cut to Social Security reshape your retirement income? With projections pointing to a 2032 shortfall and potential benefit reductions, this episode breaks down what it could mean for retirees and those planning ahead. Jason Matthews discusses how to prepare for uncertainty, including stress-testing retirement plans, understanding claiming strategies, and exploring ways to supplement income. The conversation also covers tax considerations, the role of diversified income sources, and how inflation and market risk factor into long-term planning. It’s a timely look at how shifting policies and economic realities may impact retirement decisions.

We have a special focus on serving single women age 50+ with at least $250,000 of investable assets — especially those navigating retirement, inheritance, or widowhood. These are pivotal moments where clarity, compassion, and smart tax and retirement planning matter most. Schedule your complimentary consultation today. Visit www.MFIS.biz or call (510) 288-3268 today!

You can also find us on Facebook or LinkedIn.

See omnystudio.com/listener for privacy information.