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PODCAST

Organize & Cherish with The Organized Flamingo

Stephanie Deininger

Welcome to the Organize & Cherish podcast with The Organized Flamingo, hosted by Stephanie Y. Deininger, a professional organizer and productivity expert. For those of you who love the thought of organizing & being more productive, but don’t know where to start or constantly up against hurdles that don’t let you advance the way you want to, this podcast is for you!This podcast will:- Cover a variety of topics within the organizing and productivity space, offering you tips, inspiration, and

leisure home & garden

All Episodes

18:53

126: How to Stop Overplanning and Start Decluttering

Organize & Cherish with The Organized Flamingo ·

2025/06/16

In this episode, we explore the mindset shift from overthinking to intentional action—especially during the months when decision fatigue and “I’ll get to it later” thinking tends to pile up. Whether it’s a storage bin you keep ignoring, digital clutter you keep bookmarking, or inherited items waiting for attention, we walk through how to break the loop of mental overwhelm and take the first doable step.We also touch on how AI tools can either support or stall your organizing goals, and why this

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22:55

125: The Power of Fixing What You’ve Been Avoiding

Organize & Cherish with The Organized Flamingo ·

2025/06/09

This week we reflect on the small but powerful act of fixing a broken wheel on an office cart—and what it taught us about decision-making, resourcefulness, and letting go of mental clutter. We explore how these “tiny wins” can create major momentum in your organizing journey, and how to know when it’s time to fix something, repurpose it, or move on.This is part of our ongoing Fix It or Free It series, where each month we take on a single item we've been avoiding and finally make a decision. This

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23:32

124: Decluttering Together? Know When to Step Back...

Organize & Cherish with The Organized Flamingo ·

2025/06/02

In this episode, we explore the subtle but important difference between coaching and guiding when it comes to helping someone through a decluttering or downsizing journey. Whether you're supporting a parent, friend, or managing your own stuff, understanding your role can make the experience more effective—and more compassionate.In this episode, we talk about:The difference between coaching and guiding during decluttering How to tell which role you’re playing (or should be playing) Tips for adjusting

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24:06

123: Garage Sales: Worth It or Waste of Time? Let’s...

Organize & Cherish with The Organized Flamingo ·

2025/05/26

Thinking about hosting a garage sale but not sure if it’s worth the effort? In this episode, we dive into the real-life pros and cons of garage sales—from the emotional benefits of letting go to the practical challenges of pricing and planning. This conversation explores whether a garage sale is the right fit for your organizing journey and how to make the most of the experience if you decide to move forward.Whether you’re a first-time seller or a seasoned garage sale pro, you’ll walk away with

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21:16

122: Living for Later? How Future-Based Storage...

Organize & Cherish with The Organized Flamingo ·

2025/05/19

In this episode of the Storage Series, we explore the sneaky ways future-based thinking affects what we keep. From saving items for the “next house,” “the kids,” or “retirement,” we often hold onto things that don’t reflect our current reality. This conversation invites listeners to challenge the stories we attach to stored belongings and offers thoughtful ways to reconnect with what we truly need today—not just someday.In this episode we talk about:The most common future-focused reasons people

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16:50

121: Using AI to Organize Your Life? Let’s Talk About...

Organize & Cherish with The Organized Flamingo ·

2025/05/12

In this episode, we dig into a surprising trend from a recent Harvard Business Review article: more and more people are using AI to “organize their lives.” But does organizing digitally mean we're actually taking action in real life?We reflect on how technology—from notebooks to planners to AI—has always promised to help us stay on track. But in our experience, clarity is only half the battle. The other half? Doing the work. We explore what AI can and can’t do when it comes to organizing, and why

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14:05

120: Fix It or Free It: The Power of Letting Go

Organize & Cherish with The Organized Flamingo ·

2025/05/05

In this episode of Organize & Cherish, we're diving into March’s Fix It or Free It moment—a month that turned out to be more about letting go than fixing. After trying my hand at repairing items earlier in the year, this month I faced my overflowing fix-it box with honesty and a 15-minute timer. Tune in to hear what stayed, what left, and the big reminders this month brought up about storage, sentimental clutter, and giving yourself permission to move on.In this episode, we talk about:How a

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27:48

119: Out of Sight, Still a Problem: When Storage...

Organize & Cherish with The Organized Flamingo ·

2025/04/28

Sometimes, the most overwhelming clutter isn’t what we see—it’s what we’ve quietly stored away and forgotten about. In this episode, we explore how on-site storage areas like garages, closets, and attics can slowly become emotional and financial burdens when they're used as long-term holding zones. These spaces may not feel like a problem at first, but over time, they carry hidden costs—monthly fees, decision fatigue, and a subtle weight of guilt.This conversation is part of our ongoing Storage

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17:55

118: Using family stories to decide what stays and...

Organize & Cherish with The Organized Flamingo ·

2025/04/21

In this heartfelt episode, Certified Professional Organizer® Stephanie Deininger shares how family stories can guide the decision-making process when sorting through sentimental and inherited items. For many in the sandwich generation, decluttering isn't just about making space—it’s about honoring memories without holding onto every physical object. Stephanie offers a compassionate, practical framework for using stories to determine what to keep, what to let go, and how to preserve legacies in

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25:58

117: When Storage Makes Sense: Smart Reasons to Keep...

Organize & Cherish with The Organized Flamingo ·

2025/04/14

In this episode, Stephanie discusses the often overlooked positive aspects of storage, shifting away from the idea that decluttering always means discarding. She highlights practical and emotionally beneficial reasons for intentional storage, reassuring listeners that storage can sometimes be the best solution for managing life's transitions, preserving memories, and simplifying everyday living.In this episode we talk about:The pressure people feel about constant decluttering and why it's sometimes

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14:03

116: Who Can Help When Feeling Stuck with Downsizing...

Organize & Cherish with The Organized Flamingo ·

2025/04/07

When you're faced with a home full of inherited belongings—or trying to help a loved one downsize—it's easy to feel overwhelmed. But just because it feels heavy doesn’t mean you have to carry it alone.In this episode of Organize & Cherish, Stephanie breaks down the different types of support available to help during emotional and logistical organizing challenges. Rather than just listing resources, she offers a thoughtful guide for knowing what kind of help is right for each stage—from emotional

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20:23

115: Was It Worth It? Altering a Dress Instead of...

Organize & Cherish with The Organized Flamingo ·

2025/03/31

In this episode, we share our latest Fix It or Free It update, where Stephanie transformed a green dress she loved—but never quite fit right—into a skirt. She walks through the decision-making process, the steps she took to find a tailor, and whether the alteration was worth the investment.We also introduces the March Fix It or Free It project, which involves revisiting a box of items she set aside to repair.In This Episode, We Talk About:How a simple alteration gave new life to an unworn dress.The

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27:38

114: Storage vs. Stalling—Are You Keeping It or...

Organize & Cherish with The Organized Flamingo ·

2025/03/24

This week we dive into the emotional side of storage and how to recognize when it's becoming a form of avoidance. Sometimes keeping things in storage is about preserving memories, but other times it's a way to postpone tough decisions.This episode helps listeners reflect on why they’re keeping certain items and how to move from stalling to intentional choices. We share practical strategies for evaluating storage habits and making decisions that align with personal values, life phases, and available

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17:11

113: Storage Series Kickoff: An Introduction to Our...

Organize & Cherish with The Organized Flamingo ·

2025/03/17

Storage can be a useful tool—or a way to postpone decisions. In this episode, the conversation kicks off a brand-new Storage Series, exploring the real costs, emotional weight, and decision-making process behind keeping things in storage. Whether it's inherited items, sentimental belongings, or everyday clutter, this series will dive into the pros and cons of storage and how to use it effectively.This episode provides an overview of the topics that will be covered, from financial and emotional

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24:46

112: Refresh Your Space Without Adding Clutter

Organize & Cherish with The Organized Flamingo ·

2025/03/10

Seasonal transitions often bring the urge to refresh our homes, but adding new items without a plan can quickly lead to clutter. In this episode, I share practical strategies for refreshing a space without accumulating excess belongings.Designed for caregivers, those in the sandwich generation, and anyone helping loved ones downsize, this episode provides actionable tips to create a more intentional, clutter-free home. From decluttering before shopping to setting a seasonal transition timeline that

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28:45

111: Who Gets What? Navigating Family Conflict Over...

Organize & Cherish with The Organized Flamingo ·

2025/03/03

When it comes to organizing shared belongings—whether it’s downsizing a parent’s home or handling an estate—family tensions can run high. Sentimental value, long-standing family dynamics, and unclear expectations often lead to disagreements about what stays, what goes, and who gets what.In this episode, Stephanie shares a professional organizer’s perspective on how to navigate these moments with clarity, fairness, and compassion. From setting expectations before the process begins to managing

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29:50

110: When Loved Ones Insist Everything Is Worth...

Organize & Cherish with The Organized Flamingo ·

2025/02/24

Helping a loved one declutter can be challenging, especially when they believe everything they own is valuable. In this episode, professional organizer Stephanie Deininger shares practical strategies for having compassionate and productive conversations about letting go.With over 20 years of experience, she provides insights into why people hold onto items, how to shift the conversation in a positive direction, and when to call in outside help. Whether assisting a parent, grandparent, or even

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19:11

109: Reviving What You Love: The Power of Small Fixes

Organize & Cherish with The Organized Flamingo ·

2025/02/17

In this episode, we dive into the Fix It or Free It challenge and how one simple $18 repair brought a favorite work bag back into daily use. We explore why small fixes are often overlooked, how to decide what’s worth repairing, and when to let go of items that no longer serve us. Plus, we discuss how this mindset applies to inherited or sentimental belongings—helping listeners create space for the things that truly matter.In This Episode, We Talk About:The first Fix It or Free It challenge of 2025:

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23:01

108: It's Your Home Too: How to Set Boundaries in...

Organize & Cherish with The Organized Flamingo ·

2025/02/10

In this episode we addresses the unique challenges related to setting boundaries faced by sandwich generation caregivers, particularly those in multicultural and multigenerational households. With practical strategies and compassionate advice, this episode helps listeners create personal boundaries and maintain their own physical spaces while juggling the demands of caregiving and inherited clutter.In This Episode We Talk About:How to communicate needs and set boundaries with family members in a

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20:18

107: How to Balance Family, Tradition, and Clutter:...

Organize & Cherish with The Organized Flamingo ·

2025/02/03

In this episode, the Organize and Cherish Podcast dives into the unique challenges of the sandwich generation—those navigating the complexities of caring for aging parents and younger loved ones. With a fresh perspective on multi-generational and multi-cultural family dynamics, we explore strategies for managing inherited items, balancing cultural traditions, and finding purpose in the process. If you're feeling overwhelmed by “the stuff,” this episode will provide clarity and actionable steps to

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