Widowhood – The Simply Retirement Podcast

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

By The Simply Retirement Podcast | September 10, 2025

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:

Connect with Eric Blake:

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

By The Simply Retirement Podcast | September 3, 2025

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)

By The Simply Retirement Podcast | August 27, 2025

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:

Connect with Eric Blake:

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Financial Tips and Support for Widows with Chris Bentley, MBA, CFP®, CLU®, BFA®, CRPC® (Ep. R36)

By The Simply Retirement Podcast | December 4, 2024

Widowhood often brings emotional and financial turmoil, leaving many unsure of where to turn.

Wings for Widows offers a lifeline to widows through personalized coaching and financial guidance.

In this episode, Eric Blake, along with guest Chris Bentley, MBA, CFP®, CLU®, BFA®, CRPC®, Founder and CEO of Wings for Widows, dive into the importance of financial preparedness and support for widows and widowers navigating the complexities of financial decisions post-loss.

You’ll gain valuable insights into the mission of Wings for Widows, learn about the coaching services they offer, and discover practical financial strategies to ensure stability during an emotionally challenging time.

Eric and Chris discuss:

The emotional and financial challenges faced by newly widowed individuals
The concept and impact of the “widow’s crisis”
Essential financial steps and resources for widows
Detailed coaching services provided by Wings for Widows
And more!

Resources:

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About our Guest:

At the heart of Wings for Widows lies the vision and dedication of Chris Bentley. Chris’s journey to establish this organization was sparked by a profound realization during his tenure as a financial advisor. He recognized a widespread and critical gap in support for individuals in the throes of early widowhood—a time when the need for compassionate, professional financial guidance is most acute, yet startlingly underserved.

Chris Bentley, whose career spans roles as a veteran, entrepreneur, retired financial advisor, author, educator, speaker, and unwavering advocate for the widowed, was moved by the struggles faced by those who had lost a spouse. He observed firsthand the detrimental impact of navigating financial decisions without expert advice during such a vulnerable time. The mistakes made in the wake of loss, often under the cloud of grief and confusion, can have long-lasting repercussions.

Driven by a deep sense of purpose and armed with expertise and empathy, Chris embarked on a mission to change this narrative. In 2017, his vision took flight with the creation of Wings for Widows, a pioneering nonprofit organization dedicated to offering widowed men and women the critical financial coaching and education they sorely need. Chris has since devoted his life to this cause, transforming his insight into action, and in doing so, has built a beacon of hope and empowerment for countless individuals navigating the path of widowhood.

Through Chris Bentley’s leadership, Wings for Widows stands as a testament to what visionary dedication can achieve. His commitment not only addresses the immediate needs of the widowed community but also fosters a broader understanding and appreciation for the unique challenges they face. Chris’s legacy is one of compassion, advocacy, and unwavering support, ensuring that no one has to face the financial aftermath of losing a spouse alone.

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