Category: Retirement

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Year-End Tax Planning Checklist for 2025 (Ep. 75)

Year-End Tax Planning Checklist for 2025 (Ep. 75)

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The final months of the year are the perfect time to review your finances and take action before December 31st. 

New tax laws bring both opportunities and risks, making this year’s planning even more important.

In this episode, I walk through my year-end tax planning checklist to help you understand the key areas that can impact your retirement, your taxes, and your long-term goals. I explain how to approach contributions, distributions, and deductions strategically while also touching on family gifting and estate considerations.

Key points:

  • Why reviewing your tax plan in October and November helps maximize opportunities before the year ends
  • How to use retirement accounts, Roth IRAs, and HSAs to reduce taxes and grow long-term wealth
  • The importance of required minimum distributions (RMDs) and qualified charitable distributions (QCDs)
  • Family gifting strategies and the unique advantages of 529 contributions
  • Deduction changes, charitable giving rules, and new provisions under the current tax law
  • And more!

Resources:

Connect with Eric Blake: 

Roth IRA earnings grow tax-free, and qualified withdrawals are also tax-free, provided certain conditions are met (e.g., the account has been open for at least 5 years and you are age 59½ or older, or meet another qualifying condition). Eligibility to contribute to a Roth IRA phases out at higher income levels. Non-qualified withdrawals of earnings may be subject to income taxes and a 10% early withdrawal penalty. Converting a traditional IRA or other tax-deferred account to a Roth IRA is a taxable event and may increase your current-year tax liability. Roth conversions cannot be undone.

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Social Security Claiming Strategies: Beyond the Breakeven Calculator (Ep. 74)

Social Security Claiming Strategies: Beyond the Breakeven Calculator (Ep. 74)

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Deciding when to start Social Security is more than a math equation. It’s about balancing life expectancy, risk tolerance, and long-term income needs.

In this episode, I explore the trade-offs of claiming early versus delaying for larger benefits. I explain how investing early benefits might change the picture, why survivor benefits matter, and how taxes and policy changes could influence your strategy. This conversation highlights the importance of tailoring the decision to your unique situation.

Key Points:

  • Why breakeven calculators don’t tell the full story about Social Security timing
  • The potential of investing early benefits into accounts like a Roth IRA
  • How spousal benefits and survivor planning influence claiming strategies
  • The role of taxes, risk tolerance, and other income sources in the decision
  • Possible future adjustments Congress may make to Social Security rules
  • And more

Resources:

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Roth IRAs and Retirement: What You Need to Know (Ep. 73)

Roth IRAs and Retirement: What You Need to Know (Ep. 73)

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Roth IRAs can feel confusing—but when you understand how they work, they can become one of the most powerful tools in your retirement plan.

In this episode, you’ll discover how Roth IRAs may give you more control over your taxes in retirement, create flexibility for future withdrawals, and help protect your income for the long run.

We’ll cover the basics—what Roth IRAs are (and aren’t), how the rules for contributions, conversions, and withdrawals really work, and why Congress has been pushing Roth accounts more in recent years. You’ll also hear how Roth IRAs may help you avoid hidden tax traps like higher Medicare premiums or unexpected Social Security taxes.

Key takeaways:

  • Why Roth IRAs are not investments themselves, but tax-advantaged account types that act like umbrellas shielding money from future taxes
  • How Congress is encouraging Roth contributions through Secure Act 2.0, giving retirees long-term tax-free opportunities
  • The importance of tax diversification, comparing it to and even elevating it above portfolio diversification
  • Four ways to fund Roth accounts: contributions, conversions, rollovers, and backdoor strategies
  • The five-year rule, distribution order, and how Roth IRAs can help control tax brackets, Medicare premiums, and Social Security taxation
  • And more!

Resources:

Connect with Eric Blake: 

Roth IRA earnings grow tax-free, and qualified withdrawals are also tax-free, provided certain conditions are met (e.g., the account has been open for at least 5 years and you are age 59½ or older, or meet another qualifying condition). Eligibility to contribute to a Roth IRA phases out at higher income levels. For 2025, contributions begin to phase out at a modified adjusted gross income (MAGI) of approximately $150,000 for single filers and $236,000 for married couples filing jointly. Non-qualified withdrawals of earnings may be subject to income taxes and a 10% early withdrawal penalty. Converting a traditional IRA or other tax-deferred account to a Roth IRA is a taxable event and may increase your current-year tax liability. Roth conversions cannot be undone.

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Exit Planning for Business Owners: Preparing Financially, Personally, and for Legacy (Ep. 72)

Exit Planning for Business Owners: Preparing Financially, Personally, and for Legacy (Ep. 72)

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Exiting a business is more than just a financial transaction. It’s a life transition that can affect family, legacy, and the future you envision.

In this episode, I sit down with Renita Wolf, MBA, founder and CEO of Poe Wolf Partners, to discuss how business owners can thoughtfully plan for a smooth and meaningful exit. We explore the importance of preparation, both financial and emotional, and what truly defines a successful transition.

Renita discusses:

  • Why over 80% of businesses never sell, and how to avoid being in that group
  • How emotions and identity play a big role in preparing for life after selling a business
  • The importance of early planning and cleaning up financials before going to market
  • How family members can influence and support exit readiness
  • Why a successful exit is about freedom, legacy, and choices, not just the sale price
  • And more!

Resources:

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Connect with Renita Wolf:

About Poe Wolf Partners:

Poe Wolf Partners is a boutique advisory firm that helps middle-market business owners, particularly those with companies generating between $10 million and $100 million in revenue, prepare for and navigate business exits. We specialize in aligning financial outcomes with personal and legacy goals, so owners can exit confidently and on their own terms.

About Renita Wolf:

Renita Wolf is the founder and principal advisor at Poe Wolf Partners, a boutique exit planning firm serving middle-market business owners. With a background in corporate finance and M&A at Fortune 50 companies like Wells Fargo, HP, and Cray Research, Renita brings over 20 years of strategic and financial expertise to business transitions.

At Poe Wolf Partners, she guides owners through complex exit planning, helping them define a clear vision, build a tailored strategy, and assemble the right advisory team. Renita’s approach is holistic and client-focused, addressing not just the financial side of an exit, but the personal, emotional, and legacy-driven aspects as well.

She is especially passionate about supporting women business owners and those navigating life transitions, such as widowhood or divorce, to ensure they exit their businesses with confidence and clarity.

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Can I Stop My Social Security Benefits If I Go Back to Work? A Listener Case Study (Ep. 71)

Can I Stop My Social Security Benefits If I Go Back to Work? A Listener Case Study (Ep. 71)

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Retirement rarely unfolds exactly as planned, especially when unexpected life changes occur.

In this episode, I share a real listener’s story involving Social Security, divorce, and the possibility of going back to work. I walk through step-by-step strategies to help women understand their Social Security options and prepare for future benefits.

Key points:

  • How to determine whether Social Security payments are based on personal or spousal benefits
  • The rules for withdrawing a Social Security application within 12 months (Form SSA-521) and the repayment requirements
  • The earnings test and how going back to work before full retirement age can reduce or later recalculate benefits
  • How additional work years can replace low-earning years and improve future Social Security benefits
  • The differences between ex-spousal benefits, survivor benefits, and how remarriage affects eligibility
  • And more!

Resources:

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Planning Beyond Documents: Building Support as a Solo Senior with Kathy McNair (Ep. 70)

Planning Beyond Documents: Building Support as a Solo Senior with Kathy McNair (Ep. 70)

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Too often, retirement planning focuses only on documents, but what happens when you don’t have the right people to rely on?

In this episode, I sit down with elder law attorney and founder of Solo Allies, Kathy McNair, to talk about the unique needs of solo seniors and why legal paperwork alone isn’t enough. We explore how to choose the right people for critical roles, when to consider professional support, and how to build a community for peace of mind in retirement.

Kathy discusses:

  • The difference between an estate planning attorney and an elder law attorney
  • What it really means to be a solo senior and why planning matters
  • Why “Planning + People = Peace of Mind” is a critical formula for aging well
  • How to choose and prepare a power of attorney, and what happens when you don’t
  • Resources, tools, and community programs like Solo Allies and the Aging Allies Club
  • And more!

Resources:

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Connect with Kathy McNair: 

About our Guest: 

Kathy McNair is an elder law attorney with over 25 years of experience serving seniors. She is the founder of Senior Solutions LLC in Boston and the national resource platform Solo Allies, dedicated to helping solo agers—those without reliable family support—plan for their legal, financial, and personal well-being.

Kathy is also the creator of the Aging Allies Club, a small-group planning program designed to provide both legal tools and meaningful connections. She frequently speaks to community groups and has written The Solo Senior’s Guide to Thrive, a practical guide to aging with independence and security.

Appointed by Governor Deval Patrick in 2008, she served 15 years as a Public Administrator of Suffolk County, managing estates with no known heirs. She also serves on the Board of Directors at McNamara House, an affordable senior housing community in Boston.

Kathy earned her J.D. from Boston College Law School and her bachelor’s in psychology from St. Lawrence University.

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Navigating Life After Loss – Part 3: Planning Your First Year with Clarity and Care (Ep. 69)

Navigating Life After Loss – Part 3: Planning Your First Year with Clarity and Care (Ep. 69)

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The first year after losing a spouse brings overwhelming emotions alongside important decisions. Knowing what needs immediate attention versus what can wait can make the difference between added stress and thoughtful progress.

In Part 3 of our Navigating Life After Loss series, I share how to approach both urgent and long-term planning after the loss of a spouse. I explain which financial and lifestyle choices deserve early focus, how tax planning can protect your future, and why building a supportive foundation is essential. Together, we look at practical ways to move forward with clarity and confidence.

Key takeaways include:

  • The impact of pre-death planning, wills, estate plans, and beneficiary designations on easing stress after loss
  • The key financial updates in the first year, including executors, trustees, Social Security timing, and income sources
  • How tax filing status changes after a spouse’s passing, and strategies like Roth conversions and capital gains harvesting
  • Rebuilding a financial foundation through account consolidation, investment updates, and income planning
  • The importance of lifestyle and emotional choices, such as housing, community support, and designing the next chapter of life
  • And more!

Resources:

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Navigating Life After Loss – Part 2: Financial & Legal Aspects (Ep. 68)

Navigating Life After Loss – Part 2: Financial & Legal Aspects (Ep. 68)

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In Part 2 of our Navigating Life After Loss series, I share compassionate, practical advice for the critical first weeks after losing a spouse. I walk through the legal, financial, and everyday matters that can feel overwhelming, offering clear action steps to bring order during a difficult time. From meeting with an estate attorney and understanding probate versus living trusts to retitling property, updating beneficiary designations, and addressing debts, we help you focus on what matters most. 

You’ll also learn how to protect against fraud, safeguard your privacy, and manage your loved one’s digital and social media presence. This conversation is about more than tasks; it’s about helping you prepare, prioritize, and protect your well-being while working through one of life’s hardest chapters.

Key takeaways:

  • Why meeting with an estate planning attorney early can prevent costly delays and probate complications
  • The importance of retitling property, vehicles, and accounts in your name to avoid future issues
  • How Social Security payments and survivor benefits work, including timelines and required forms
  • Steps for handling debts, protecting against fraud, and safeguarding your spouse’s digital footprint
  • When a living trust may be worth considering for privacy, efficiency, and avoiding probate
  • And more!

Resources:

Connect with Eric Blake: 

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Navigating Life After Loss – Part 1: The First Week (Ep. 67)

Navigating Life After Loss – Part 1: The First Week (Ep. 67)

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Grieving the loss of a spouse is devastating. During that fog, there’s still paperwork, decisions, and urgent tasks demanding attention.

In this episode, we open up a three-part series called “Life After Loss.”  I start by focusing on the first few days after losing a spouse, sharing essential steps to help with emotional healing and practical planning.

Key takeaways:

  • How to prioritize both emotional well-being and urgent financial responsibilities in the first week of widowhood
  • The importance of requesting 20–30 certified death certificates and why it’s better to order more than needed
  • Who to contact immediately, including attorneys, financial advisors, Social Security, and employers
  • The impact of joint vs. individual account ownership and how that can affect access to funds
  • How estate planning and clear communication can prevent emotional and financial turmoil for surviving spouses
  • And more!

Resources:

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Understanding The Widow’s Penalty and What You Can Do About It (Ep. 66)

Understanding The Widow’s Penalty and What You Can Do About It (Ep. 66)

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Losing a spouse is heartbreaking, but it can also trigger financial challenges that many women aren’t prepared for. 

The Widow’s Penalty is real, and it can have long-term consequences on income, taxes, and retirement.

In this episode, I walk through the Widow’s Penalty, what it is, why it disproportionately affects women, and what proactive steps can be taken to protect your financial future. We share real client stories, clear up tax myths, and offer strategies to navigate the road ahead with more confidence and clarity.

Key points:

  • How the Widow’s Penalty results in higher taxes and lower income due to filing status changes and reduced Social Security benefits
  • Why women are more impacted due to longer life expectancy, smaller Social Security/pension benefits, and caregiving interruptions
  • Real-life client examples, including challenging planning scenarios involving early widowhood and limited access to retirement assets
  • Important tax strategies, like using Roth conversions and capital gains harvesting during joint filing years
  • When couples should begin retirement planning conversations, emphasizing proactive communication before unexpected life events
  • And more!

Resources:

Connect with Eric Blake: 

Roth IRA earnings grow tax-free, and qualified withdrawals are also tax-free, provided certain conditions are met (e.g., the account has been open for at least 5 years and you are age 59½ or older, or meet another qualifying condition). Eligibility to contribute to a Roth IRA phases out at higher income levels. For 2025, contributions begin to phase out at a modified adjusted gross income (MAGI) of approximately $146,000 for single filers and $230,000 for married couples filing jointly. Non-qualified withdrawals of earnings may be subject to income taxes and a 10% early withdrawal penalty. Converting a traditional IRA or other tax-deferred account to a Roth IRA is a taxable event and may increase your current-year tax liability. Roth conversions cannot be undone

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