What if a garage sale was more than just a way to offload old stuff? In this episode, we explore how sorting for a sale—whether or not you actually host one—can offer powerful insights into what truly matters. From free boxes to family heirlooms, we share how the process of letting go often leads to surprising clarity and confidence. Whether you’re prepping for a big purge or just starting small, this conversation offers practical encouragement and mindset shifts for your next chapter.

In This Episode We Talk About:

• Why a garage sale is often the start of a deeper decluttering journey—not the end
• How sorting reveals what no longer fits your lifestyle or values
• Alternatives to selling, including donation, consignment, and community swap

Mentioned in this Episode:

• The power of letting sorting lead—not just organizing for the sake of it
• Common “aha” moments people experience when prepping for a sale
• Permission to skip the sale entirely and still make meaningful progress

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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In this episode, we explore why getting organized often has less to do with stuff—and more to do with the questions we’re asking ourselves. Whether it's searching on Google, using ChatGPT, or trying to help a loved one decide what to keep, progress depends on how we frame the problem. We talk about the subtle power of shifting from judgment-based questions to curiosity-led ones, and how asking better questions can unlock momentum in our organizing, decluttering, and downsizing journeys.

In this episode, we talk about:

• Why vague or emotionally loaded questions can keep us stuck
• How search engines and AI tools like ChatGPT reflect the power of well-worded questions
• A practical framework to rephrase common organizing questions for better clarity and action

Mentioned in this episode:

• A “Question Makeover” cheat sheet for reframing stuck points during organizing
• Real-world examples of how better questions lead to faster decluttering decisions
• A free download: Better Questions to Ask When You’re Stuck

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 summer is the perfect time to embrace a “do something about it” energy. Small actions count. Let’s get unstuck together.

In this episode we talk about:

• Why summer is the ideal time to embrace a “less thinking, more doing” approach
• How to stop using planning, research, or AI tools as excuses for inaction
• A gentle framework for moving from idea to effort—even when the task feels overwhelming

Mentioned in this Episode:

• The Fix It or Free It monthly project as an example of micro-action with big results
• Ways to use AI to support—not sabotage—organizing efforts
• A simple weekly challenge prompt to help listeners take action right away

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 month? A quick 20-minute fix made a big difference—and we’re breaking down why.

In This Episode We Talk About:

• How small repairs can spark a sense of progress and empowerment
• The hidden weight of “wobbly” systems and unmade decisions
• A practical mindset shift for tackling your fix-it pile with purpose

Mentioned in This Episode:

• The Fix It or Free It challenge
• Why “just fix it” can be a powerful organizing tool
• How to assess when to repair, replace, or release an item

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 your approach to be more supportive and effective

Mentioned in this episode:

• Signs someone needs a coach vs. a guide
• The emotional stakes of helping someone declutter
• Tools to support others without overstepping

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 helpful tips and a fresh perspective.

In This Episode We Talk About:

• The emotional and environmental benefits of hosting a garage sale
• Why garage sales get a bad rap—and what’s actually true
• Tips for deciding whether this decluttering method is right for you

Mentioned in This Episode:

• Free Garage Sale Planning Checklist on our Resources page
• Blog post Garage Sale Tips: In-Person vs. Online Reselling
• Garage Sale Tips: How to Make the Most out of Your Sale
• Garage Sale Tips: Shopping with Intention to Avoid Overwhelm
• Episode 87 on outsourcing vs. doing it yourself when organizing

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 store things
• How to recognize when storage is based on hope, guilt, or fear
• Practical ways to shift toward storage that serves the present moment

Mentioned in this episode:

• The “Review in 6 Months” strategy for guilt-free decision delays
• Tips for talking with loved ones about items “saved for them”
• Episode 114: Storage vs. Stalling—Are You Keeping It or Postponing a Decision?

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 the emotional, human element still matters most.

In This Episode We Talk About:

• Why “organizing my life” is now one of the top AI use cases in 2025
• The difference between making a plan and making progress
• How AI tools can support, but not replace, hands-on action and emotional decision-making

Mentioned in This Episode:

• Harvard Business Review article: “How People Are Really Using Gen AI in 2025” by Marc Zao-Sanders
• AI tools like ChatGPT, Gemini, and other generative platforms
• Common organizing tools of the past (planners, Pinterest boards, magazine clippings) and what they have in common with today’s tech

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 15-minute timer helped speed up decision-making
• What I learned from repairing items in January and February
• Why storage should align with your actual life (and goals!)

Mentioned in this episode:

• My February project: turning a dress into a skirt (Ep. 115)
• A reminder that "taking care of your stuff" also means making decisions
• My own slip-ups and what they taught me as a professional organizer

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 Series, where we help listeners reframe what it means to store things with intention—and how to move forward when storage starts holding us back.

In this episode we talk about:

• Why “out of sight, out of mind” doesn’t always work in our favor
• The hidden costs—emotional, mental, and financial—of long-term storage
• Small, actionable ways to reconnect with forgotten storage spaces without overwhelm

Mentioned in this episode:

• How to set a “review date” for anything stored in bins, attics, or garages
• Tips for creating a visual inventory using quick phone photos
• Questions to ask yourself before deciding what stays and what goes

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 meaningful ways.

In this episode, we talk about:

• Why storytelling is a powerful tool when decluttering sentimental items
• Questions to ask that help clarify whether to keep or release something
• Creative ways to honor the story without holding onto the entire item

Mentioned in this episode:

• A client example of using one story to keep one special item
• Tips for creating a “story shelf” or curated memory zone
• A simple practice for letting go with clarity and compassion

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 unnecessary.
• Six reasons why storage can positively impact your life.
• How intentional storage empowers decision-making and enhances daily routines

Mentioned in this Episode:

• Practical examples of seasonal storage solutions.
• Real-life success stories about thoughtful storage decisions.
• Tips on preserving family heirlooms and sentimental items.

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 decision-making to hands-on sorting and specialized services.

Whether you're sorting through generations of family items or supporting someone else who is, this episode is a compassionate reminder that the right help makes all the difference.

In This Episode, We Talk About:

• The three types of support you might need (emotional, logistical, and specialized)
• How to match the right kind of help to your current situation
• Why asking for help is a strength, not a shortcoming, especially in the sandwich generation

Mentioned in This Episode:

• A breakdown of support roles: organizers, therapists, appraisers, and more
• Common mistakes people make when trying to “go it alone”
• Where to find reputable help when you're ready to ask for support

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 key factors to consider when deciding whether to fix or replace an item.
• The value of revisiting "fix it" projects to reassess what’s truly worth keeping.

Mentioned in This Episode:

• The Fix It or Free It challenge and why small repairs can be a game-changer.
• How local community recommendations helped find a great tailor.
• Why it’s important to check in on old repair projects and reassess what’s still worth fixing.

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 time.

If you're wondering whether you're holding onto something for the right reasons—or just avoiding the decision—this conversation is for you.

In This Episode, We Talk About:

• How to recognize the emotional signs that you're postponing a decision with storage.
• Why certain life phases and time constraints shape how we approach organizing and decluttering.
• Practical strategies to shift from stalling to intentional storage decisions.

Mentioned in This Episode:

• Five observations to help determine if you're stalling or intentionally storing.
• Quick tips for creating storage strategies based on life phases and how much time you realistically have.
• How to build awareness around storage choices and why it's okay to revisit decisions over time.

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 considerations to smart storage strategies. Plus, hear about upcoming events and resources designed to support caregivers and those navigating the overwhelming task of downsizing and decluttering.

In This Episode, We Talk About:

• The common reasons people put things in storage
• The upcoming Storage Series topics, including storage costs, emotional attachment, and inherited storage units.
• How storage fits into the bigger picture of decluttering, downsizing, and organizing with intention.
• Updates on our upcoming events!

Mentioned in This Episode:

• The Organize & Cherish Expo on May 28th in Colorado and the upcoming virtual summit.
• The Fix or Free It series, featuring monthly updates on items that were either repaired or released.
• The free Organize & Cherish Chat happening on April 16th, a supportive space to discuss storage, downsizing, and organizing challenges.

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 actually works, this discussion focuses on making thoughtful choices rather than reactive purchases.

Tune in to discover how small shifts can make a big impact in both your home and the spaces of those you assist.

In This Episode, We Talk About:

• Why decluttering first makes seasonal transitions smoother and prevents unnecessary purchases.
• How to set a seasonal timeline that fits your life instead of following retail’s fast-paced cycle.
• The ‘One In, One Out’ rule and other simple strategies to keep clutter from sneaking up on you.

Mentioned in This Episode:

• The benefits of creating a “holding zone” for potential purchases to curb impulse shopping.
• Questions to ask before buying something new—whether for yourself or a loved one.
• How to gently encourage downsizing when helping a parent or family member refresh their space.

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 disputes in real-time, this episode offers actionable strategies to keep family relationships intact while making progress.

Whether trying to prevent conflicts before they arise or dealing with tension in the middle of the process, this conversation provides valuable insights for anyone facing family disputes over belongings.

In This Episode, We Talk About:

• Why family disputes over belongings happen and how emotions, fairness, and decision-making play a role.
• How to set expectations before organizing shared belongings to reduce conflict before it starts.
• What to do if tensions rise mid-process and how to de-escalate disputes while still making progress.

Mentioned in This Episode:

• Episode
• Strategies for fairly dividing sentimental items when multiple family members want the same thing.
• Tips for mediating family disputes when disagreements arise over inherited or shared belongings.

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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 struggling with personal belongings, these expert-backed tips will make the process easier and more intentional.

In This Episode, We Talk About

• How to lead with curiosity to understand why an item feels valuable.
• Practical ways to shift the focus from keeping everything to making thoughtful choices.
• When to seek professional support, including estate experts or mental health professionals.

Mentioned in This Episode:

• Questions to ask a loved one when they struggle to let go of an item.
• Tips for using estate appraisers and online marketplaces to determine true value.
• How to recognize when decluttering struggles may require professional intervention.

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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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: how a simple bag strap replacement made a big impact
• How small repairs can prevent unnecessary clutter and save money
• When to repair, repurpose, or finally let go of an item

Mentioned in This Episode:

• The Fix It or Free It challenge and how listeners can join
• Episode 82: Decision Making: Keep, Repair or Toss? https://theorganizedflamingo.com/82-decision-making-keep-repair-or-toss/
• Episode 89: The Fix It Dilemma: Are Those Nostalgic Items Worth Mending?https://theorganizedflamingo.com/89-the-fix-it-dilemma-are-those-nostalgic-items-worth-mending/

Review full show notes and resources at https://theorganizedflamingo.com/podcast

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