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Ruthie Gray welcomes Lisa Woolery, author and founder of The Widow’s Comeback, for an honest conversation about healing childhood wounds while caring for an aging parent. Lisa shares how losing her husband, grieving her father, and having her mother move nearby brought old emotions to the surface. Together, they explore forgiveness, complicated faith, grief, and the process of learning to show up as an adult daughter rather than as the little girl still hoping her mother will meet unmet childhood needs.

Lisa also offers practical guidance for preparing for difficult visits, including healthy boundaries centered on kindness and encouragement. She explains the mindset shift from expecting a parent to fill your emotional bucket to choosing to fill theirs instead. The conversation also highlights Lisa’s widow-focused ministry, memoir, grief calendar, guided journal, and upcoming workshops designed to help widows process painful emotions with honesty and self-compassion.

Resources:

• The Widow's Comeback
• The Widow's Comeback 365-Day Grieving Calendar
• The Widow's Comeback Grief Journal
• Lisa’s Website
• Coaching with Ruthie

Bio:

Lisa Woolery is an award-winning author and founder of The Widow’s Comeback, a ministry dedicated to helping widows navigate grief, rediscover who they are, and build a life they genuinely want to live.

After the unexpected death of her husband, Eric, in 2019, Lisa found herself raising two children while learning how to make a life—and a future—on her own. Her award-winning memoir, The Widow’s Comeback, shares that journey with honesty, humor, faith, and hope.

Today, Lisa creates books, practical resources, workshops, and an online community designed to meet widows where they are and help them take the next step forward. At the heart of everything she does is a simple message: your life is not over.

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In Part II of her conversation with Ruthie Gray, bestselling author, speaker, and Clutter Free Academy host Kathi Lipp returns to tackle the deeply personal work of helping a loved one declutter and downsize. This episode moves from managing your own home to stepping into someone else's — with all the emotional weight, family dynamics, and safety concerns that come with it. Kathi and Ruthie navigate the tension between getting things done and honoring a parent's dignity, reminding caregivers that function and safety matter far more than aesthetics.

• Start with safety, not sentiment. Fall risks, floor clutter, and tangled cords are the first priority — and Kathi shares a practical hierarchy for moving items out of a loved one's space in a way that respects both the person and the process.
• Begin where there's the right level of pushback. Rather than tackling the most emotionally charged rooms first, Kathi explains how to read the room — literally — and start where you'll make progress without creating conflict.
• Sentimentality is grief in disguise. Kathi unpacks why aging parents hold onto belongings, connects it to a longing for the past, and shows how understanding that changes how caregivers approach the conversation.

Listeners will come away with a room-by-room framework for helping a loved one downsize with grace and without guilt. More than a decluttering strategy, this episode reminds us that peace — not a perfect space — is the real goal of sandwich season.

Resources:

• Clutter Free Academy Podcast - Clutter Free Academy
• Kathi’s Website
• https://www.nytimes.com/wirecutter/accessibility/aging-in-place/
• https://youtu.be/i6FSfXp4eWI?si=1Zn9lxKP3T-bQ7oe
• Coaching with Ruthie

Bio:

Kathi Lipp is the bestselling author of Clutter Free and The Clutter-Free Home and host of the Clutter Free Academy podcast. For more than a decade she has helped overwhelmed people clear their homes and their heads, one small step at a time — proving you don't need a perfect house to have a peaceful one.

Visit Ruthie's Website at RuthieGray.com

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Read Ruthie's book, Empty Nest Awakening; Weaving the Threads of Your Passions into Purpose

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Ruthie Gray talks with bestselling author, speaker, and Clutter Free Academy host Kathi Lipp about simplifying life when caregiving leaves little time, energy, or margin. They cover practical decluttering strategies for overwhelmed caregivers.

Kathi brings refreshingly honest, practical wisdom for caregivers running on empty — reframing the goal from perfection to function and offering small, stackable strategies that fit into the margins of an already-packed day. From naming how much energy you actually have to building a nightstand routine that lets you rest without a bathroom trip, this conversation meets caregivers exactly where they are.

• Triage is a season, not a failure. Kathi explains why caregiving often means simply keeping life from falling apart — and why choosing one "sacred surface" to keep clear can anchor your entire day when everything else feels chaotic.
• Think systems, not piles. Through a concept called "value stacking," you can attach a small clutter task to an existing habit — like unloading the top dishwasher rack while your coffee brews — so progress happens without demanding extra time or energy.
• Perfectionism is the real culprit. Kathi identifies the deeper issue behind caregiver clutter: the belief that if you can't do everything, you shouldn't start at all — and why paper plates and grocery pickup are accommodations, not shortcuts.

Listeners will leave with practical, guilt-free strategies they can use today, no matter their energy level. Most importantly, they'll have permission to stop chasing perfection and start choosing progress.

Resources:

• Clutter Free Academy Podcast - Clutter Free Academy
• Kathi’s Website

Bio:

Kathi Lipp is the bestselling author of Clutter Free and The Clutter-Free Home and host of the Clutter Free Academy podcast. For more than a decade she has helped overwhelmed people clear their homes and their heads, one small step at a time — proving you don't need a perfect house to have a peaceful one.

Visit Ruthie's Website at RuthieGray.com

Get Ruthie's Sandwich Season Pieces Newsletter

Read Ruthie's book, Empty Nest Awakening; Weaving the Threads of Your Passions into Purpose

Click here to send a text and tell us how you like the show!

In this episode, Ruthie Gray talks with Jodi Snowdon about the grief and complexity of sandwich season, where caregiving for an aging parent overlaps with launching adult children and navigating major life transitions. Jodi shares how her own journey through divorce, miscarriage, loss, and caregiving led her to write Depth and develop a framework for moving through heartbreak with faith.

We discuss how to sit with grief without rushing past it, why trust can coexist with unanswered questions, and how pain can become a place of deeper purpose and perspective.

Resources:

• Jodi’s Website
• Jodi’s Depth Book

Bio:

Jodi Snowdon is an author, podcaster, and speaker who serves women through her podcast, Depth, and her blog, Heartbreak to Strength. In August 2022, she released her first book, Depth: Growing Through Heartbreak to Strength. Having walked through multiple heartbreaks (divorce, miscarriage, & cancer), Jodi now inspires women to grow deeper in their faith and to find hope, joy, and purpose through their unexpected storms. She lights up the most when she shares her testimony using her cracked clay pot, a visual reminder that God shines brightest through our broken places. She is raising two sons (one in college and one adulting) in Southern California where she teaches science to elementary students in the STEM Lab. Jodi would love to connect with you on her website, jodisnowdon.com or on Instagram @jodi.snowdon

Visit Ruthie's Website at RuthieGray.com

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Read Ruthie's book, Empty Nest Awakening; Weaving the Threads of Your Passions into Purpose

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Celebrate one year of the Sandwich Season Sanity Podcast with us!!! This episode highlights the top five most-downloaded episodes, shares updates on coaching and upcoming seasons, and offers practical advice for caregivers and parents navigating multigenerational relationships.

Resources below are highlighted in this special episode. Please listen and share the podcast, so we can reach more multigenerational caregivers with the message of peace, even in multigenerational mayhem!

Resources:

• Exchanging Expectations of Adult Kids for Peace in Empty Nest ft Jill savage
• Jill’s Podcast
• Jill’s FB Group
• Building Healthy Connections with Adult Children and In-Laws ft. Suzy Mighell
• Suzy’s book
• Overcoming Old Wounds While Caregiving ft. Laura Acuña
• Still Becoming Hope, Help, and Healing for the Diet-Weary Soul
• Lisa Serugo’s Trauma Tree
• Caregiving Special Needs Children and Aging Parents ft. Kelly Hall
• Kelly’s podcast
• Kelly’s website
• Practical Ways People Pleasers Can Balance Identity and Daily Demands ft. Lori Schumaker
• Lori’s resources

Enter to win a free coaching package with Ruthie! To enter, fill out this form. Giveaway closes Monday, May 4, at 12:00pm, est.

Visit Ruthie's Website at RuthieGray.com

Get Ruthie's Sandwich Season Pieces Newsletter

Read Ruthie's book, Empty Nest Awakening; Weaving the Threads of Your Passions into Purpose

Click here to send a text and tell us how you like the show!

Ever felt caught in a struggle between your beliefs and that of your adult children and your aging parents? You're not alone. In this episode, Michelle Rayburn and Ruthie open up about their own struggles and wins in bridging those generational divides with kindness and faith. If you're juggling family differences, craving peace, and seeking practical ways to stay grounded, this conversation will help.

Resources:

• Book: This Reimagined Empty Nest
• Midlife Repurposed blog and podcast
• Michelle’s Website

Bio:

Michelle Rayburn is an author and podcaster who blends humor with honesty in the midlife season. She writes Midlife Repurposed on Substack, where she explores wisdom, wonder, and the laugh lines that come with growing older and growing up at the same time. She’s a boy mom, grandmother of six, and lives in the northwoods of Wisconsin.

Visit Ruthie's Website at RuthieGray.com

Get Ruthie's Sandwich Season Pieces Newsletter

Read Ruthie's book, Empty Nest Awakening; Weaving the Threads of Your Passions into Purpose

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Ever feel like mornings are just too overwhelming to handle? Trust me, I’ve been there. Whether you’re caring for loved ones, managing a busy household, or navigating life's chaos, establishing a morning ritual can be your anchor. In this episode, we explore practical ways to make mornings matter—no matter what season you're in.

In this episode, we delve into how the biblical concept of mornings as new beginnings can transform your day. We discuss the four archetypes of morning routines—are you a doer, mover, meditator, or social seeker?

Tips for connecting your routine with your unique temperament and season of life are provided, alongside the science behind God-centered thinking and its brain-changing power.

Practical ideas for busy caregivers to prioritize self-care through morning rituals are also included. Remember, only you can choose to prioritize your peace each morning—because mornings are for new mercies, and your day is waiting to be transformed.

Resources:

• How to Love Your Morning + Free Resources

Bio:

Jennifer Dukes Lee is a bestselling author, speaker, and morning evangelist from Iowa. She is the author of several books, including How to Love Your Morning, Growing Slow, and It’s All Under Control. She lives on a fifth-generation family farm, where she and her husband have made a life of growing crops, pigs, two beautiful humans, and an enduring faith.

Visit Ruthie's Website at RuthieGray.com

Get Ruthie's Sandwich Season Pieces Newsletter

Read Ruthie's book, Empty Nest Awakening; Weaving the Threads of Your Passions into Purpose

Click here to send a text and tell us how you like the show!

Ever feel like caregiving is wearing you thin? You're not alone—and the good news? You can find moments of joy, hope, and even peace amid the chaos. In this heartfelt episode, Kim shares honest stories and simple strategies that help caregivers like us keep dreaming, connecting, and nurturing ourselves. In this episode:

• The power of creating a bucket list to nurture hope and joy
• Practical ways to incorporate small, meaningful activities into daily life
• How using your home as a supportive space can lift your spirits
• The importance of honest sharing and protecting your peace
• Simple ways to manage your feelings and prevent overwhelm
• Embracing creativity—painting, writing, gardening—as a form of self-care
• The art of being unoffendable and extending grace in caregiving relationships

Remember, you’re not just surviving—you're creating moments of joy and peace. Take that first small step today. Dream big, protect your peace, and lean into what refreshes your soul. Because, friend, your well-being is just as important as those you care for. You’ve got this—one small act of kindness to yourself at a time.

Resources:

• 15 Ways Caregivers Can Protect Their Mental Health
• Moments of Grace for Teachers
• Moments of Grace for Moms
• This Reimagined Empty Nest: Stories and Poems for Moms Embracing New Chapters
• Life in the Estrogen-Free Zone: Humor and Heartfelt Wisdom from Boy Moms
• Kim's Facebook Profile
• Kim's Instagram Profile
• Full Joy Ministries Website

Bio:

Kim Cusimano is a collaborative author and mother of adults with special needs. Beyond her family, she spends time encouraging others to reach their full potential through hospitality, mentoring, and the arts, weaving in the faith lessons she learns as a wife, mother, and caregiver.

Visit Ruthie's Website at RuthieGray.com

Get Ruthie's Sandwich Season Pieces Newsletter

Read Ruthie's book, Empty Nest Awakening; Weaving the Threads of Your Passions into Purpose