Welcome to Widows That Wine Together!

Today, I am bringing you a conversation that every widow, and anyone who loves a widow, needs to hear. My guest is Mitch Simkins, a wealth advisor, host of Wins for Widows, and author of Finding Your Footing, a financial workbook designed to help women navigate life and money after loss.

In our conversation, Mitch shares why listening must come before financial planning, how to recognize and respect your capacity while grieving, and why you do not have to make every financial decision immediately. We talk about moving from financial survival to creating a plan for the future, understanding what needs attention now versus what can wait, and ultimately using money to support the life you want to build and the legacy you want to leave.

What I especially appreciated was Mitch’s reminder that widows are so much more than their financial portfolios. We are women navigating an unimaginable loss while learning to find our footing again.

So, if you have ever felt overwhelmed by the financial responsibilities that come with losing your person, this episode is for you. Let’s talk about how to take things one step at a time, give ourselves grace, and begin to see the possibilities ahead.

Let’s get started!

In this episode of Widows That Wine Together, Jen Newberg—widow and founder of It’s Lifey and HopeHub—shares a meaningful conversation about grief, connection, and rebuilding life after loss.

After the sudden loss of her husband, Jen turned toward connection as a way to navigate her grief. Today, she creates spaces where widows can feel supported, understood, and less alone.

This episode explores the realities of early grief, the power of community, and what it looks like to move forward while still honoring your story.

If you have any questions regarding this episode please reach out to me at widowsthatwine@gmail.com.

What does healing look like just three months after losing your spouse?

In this powerful episode of Widows That Wine Together, I share the story of a widow who said “yes” to connection earlier than most — booking a flight and joining a Temecula wine country weekend only three months after her husband’s passing.

While many widows are deep in brain fog, shock, and survival mode during those early months, this guest chose movement and community. But her story does not stop there.

After a transformational weekend surrounded by women who truly understand grief, she experienced what I call the “widow’s crash” — the emotional drop that can happen when connection fades and loneliness returns.

In this episode, we explore: • The courage it takes to show up early in grief • Why healing timelines look different for everyone • The power of safe community • What the widow’s crash feels like — and why it is normal • How connection can accelerate healing without eliminating pain

If you are newly widowed, feeling alone, or wondering if you are “behind” in your grief, this episode will remind you: there is no right timeline — and you do not have to do this alone.

If you have any questions on this episode you can reach me at widowsthatwine@gmail.com.