Taking time to reflect can bring perspective, clarity, and renewed intention. Looking ahead with purpose helps turn lessons into meaningful action.

In this episode, Peter Raskin is joined by the team at Raskin Planning Group, Kathryn Broy, Alexander LaCroce, Tony Araujo, and Declan Davis for the annual Raskin Planning Group year-in-review and outlook conversation. 

The team shares personal moments from 2025 that inspired growth, including travel, family milestones, creative pursuits, and career development. They reflect on lessons learned through routines, responsibility, and professional change. The discussion also looks ahead to 2026, focusing on motivation, relationships, teamwork, and intentional planning.

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

A new year often brings pressure to make changes, but thoughtful planning can be a far more useful starting point. Rather than focusing on rigid resolutions, a structured review can help households feel organized and prepared.

In this episode, Peter Raskin walks through a comprehensive planning checklist to help individuals and families prepare for the 2026 calendar year. He explains how reviewing the prior year, setting new goals, and anticipating life events create clarity before making financial decisions. The conversation covers age-based milestones, cash flow awareness, assets and debt, tax preparation, insurance reviews, and estate planning, all framed as manageable steps that can be revisited over time.

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

Life can change quickly, and those shifts often leave us reassessing what matters most.

Moments of uncertainty can feel heavy, yet they also open space for renewed direction. Thoughtful planning gives structure to those moments and helps guide steady decisions.

In this episode, Peter Raskin reflects on the many transitions clients experienced this year and how planning supports clarity through change. He shares real examples of families dealing with retirement questions, concentrated stock positions, charitable goals, and market anxiety. Peter highlights how planning offers direction, keeps people grounded, and creates a path forward no matter what life brings.

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

Turning 65 comes with many decisions, and few are as important or confusing as Medicare. 

Between Parts A, B, D, Medigap, and Advantage plans, it’s easy to feel overwhelmed by choices and costs.

In this episode, Peter Raskin explains how Medicare works, what each part covers, and how to make informed decisions during open enrollment. He breaks down the differences between Medigap and Medicare Advantage, highlights how income can affect premiums, and shares tips for staying flexible as your health or lifestyle changes.

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

Investors often look for ways to balance cost, performance, and control, but what if there were a method that let you own the actual stocks behind an index and tailor them to your needs?

Technology has made that possible through direct indexing, a strategy that’s reshaping how investors think about diversification and tax management.

In this episode, Peter Raskin explains how direct indexing works, who can benefit from it, and why it’s becoming an increasingly popular option for investors who want more flexibility, personalization, and tax efficiency in their portfolios. He also compares it to ETFs and mutual funds and shares how his firm integrates this strategy into comprehensive financial planning.

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

As the year closes, financial planning opportunities emerge that can set the stage for a stronger future.

How do you make the most of tax strategies, savings tools, and estate planning before the calendar turns? What should be reviewed now to avoid last-minute stress in December?

In this episode, Peter Raskin shares a practical year-end checklist covering investments, tax strategies, cash flow, insurance, and estate planning. He explains how timely action helps families and business owners finish the year prepared and step confidently into the new one.

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

Insurance can feel like a maze of jargon, rising costs, and confusing policies, but it’s also one of the most important tools for protecting wealth.

How do you know if your coverage is enough? When should you shop around, raise deductibles, or consider umbrella protection?

In this episode, Peter Raskin talks with longtime friend Robert Mansfield, CPCU, Senior Vice President at HUB International New England, about the essentials of property and liability insurance. Together, they unpack the reasons behind soaring premiums, the critical role of umbrella coverage, strategies for handling claims, and the growing need to protect against scams and fraud.

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About Our Guest:

Robert Mansfield, CPCU, Senior Vice President at HUB International New England, is a seasoned insurance advisor with more than four decades of experience in property and liability coverage. Starting his career in the mail room of his family’s agency in 1977, he gained hands-on knowledge of every part of the business. Today, he works with individuals, families, and organizations, helping clients protect their homes, vehicles, valuables, and assets with the right coverage and guidance.

This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

From new tax rules to little-known retirement plan strategies, 2025 is shaping up to be a year of significant changes for many taxpayers.

In this episode, Peter Raskin unpacks timely provisions from the “One Big Beautiful Bill Act,” explains a tax-saving approach for employer stock, and addresses the impact of Massachusetts’ Millionaires’ Tax. With practical examples and forward-thinking strategies, he shares how clients are adapting their financial plans to take advantage of new opportunities and avoid costly surprises.

Peter discusses:

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

Taxes may be inevitable, but how you approach them can make a meaningful difference in your long-term financial path.

In this episode, Peter Raskin unpacks the recently signed “One Big Beautiful Bill” and what it means for families and individuals. More importantly, he breaks down how to think about taxes not in isolation, but in the broader context of your goals, values, and peace of mind for your family’s future.

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.

Love and finances often intertwine in unexpected ways, especially in later-life marriages. 

From tax strategies to estate planning, every decision reflects a delicate balance between personal connection and practical considerations.

In this episode, Peter Raskin explores the unique financial challenges faced by older couples tying the knot. With stories and strategies, Peter offers guidance to help navigate the complex decisions surrounding later-life marriages.

Peter discusses:

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This is not intended to be a substitute for professional investment advice. Always seek the advice of your financial adviser or other qualified financial service providers with any questions you may have regarding your investment planning.

Securities and investment advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. Osaic Wealth is separately owned, and other entities and/or marketing names, products, or services referenced here are independent of Osaic Wealth.

Osaic Wealth, Inc. and its representatives do not offer tax or legal advice. Individuals should consult their tax or legal professionals regarding their specific circumstances.