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Organize & Cherish with The Organized Flamingo
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Organize & Cherish with The Organized Flamingo

Author: Stephanie Deininger

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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 plenty of a-ha moments.

- Explore different combinations and ways on how to get and stay more organized and productive.

- Invite guests in complementary industries such as interior designers, habit coaches, mental health professionals, stylists, and more that help and enhance your organizing & productivity journey.


Ready to explore the right organizing and productivity solution for you? Let’s go!


You can find full show notes and resources for Organize & Cherish with The Organized Flamingo at http://theorganizedflamingo.com/podcast/


Connect with The Organized Flamingo:

Theorganizedflamingo.com

@theorganizedflamingo


Hosted on Acast. See acast.com/privacy for more information.

141 Episodes
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In this episode of Organize & Cherish, we continue the Fix It or Free It series with August’s project: electronics. From letting go of old headphones to tackling the bigger items like TVs and printers, we explore practical, compassionate strategies for clearing out tech clutter. Electronics can be sneaky sources of overwhelm—whether it’s tangled cables, outdated backups, or the promise of “someday” repairs. This episode offers tips for deciding what to keep, what to fix, and how to responsibly let go of the rest.In this Episode We Talk AboutHow to apply the Fix It or Free It method to electronics of all sizes Decluttering tips for cables, chargers, and accessories Responsible ways to recycle or donate unused electronicsMentioned in this EpisodeAugust’s Fix It or Free It challenge: letting go of old headphones Local e-waste recycling programs and retail drop-off options The mental relief that comes from fixing or freeing technology clutterReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
Life doesn’t always go according to plan. In this episode of Organize & Cherish with The Organized Flamingo, we explore how unexpected changes — from last-minute travel to sudden moves or local routine shifts — can throw us off balance.We’ll talk about how organization helps us meet these moments with less stress and more presence. By streamlining what we can control, we create the emotional bandwidth to focus on what really matters: supporting loved ones and showing up with compassion.In This Episode We Talk AboutWhy do unexpected changes (travel, moves, or local shifts) test our systems at home The difference between being streamlined vs. scrambling in urgent moments How organizing creates the emotional space to show up for loved onesMentioned in This EpisodeReal-life story of an unplanned trip to Mexico following a planned trip to Canada Practical tips for “future-proofing” your life against sudden changes How to create travel, move, or local readiness without overcomplicating thingsReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
The holiday season can bring joy, celebration, and memory-making—but it often brings clutter, stress, and an overwhelming amount of “stuff” too. In this episode, we share simple, compassionate strategies to help prepare your home and mindset before the holiday rush sets in.By picking nonprofits ahead of time, setting up sorting bins that actually work, and letting go of the dreaded “junk in the trunk” habit, we can approach this season with more ease, more intention, and more space for connection.This is not about perfection or overhauling everything before January—it’s about small, practical steps that help us organize with care and enjoy the season more fully.In This Episode We Talk About:Why the holiday season is also an “organizing season” and how to use it as a reset How to pick nonprofits in advance so donation decisions become effortless The power of labeled bins to keep clutter moving instead of piling up Why “junk in the trunk” delays progress—and how to stop it for goodMentioned in This Episode:The importance of choosing nonprofits ahead of time for holiday donations Creative naming ideas for sorting bins (freebie available in the show notes) Setting a 7-day rule for donation drop-offs to avoid clutter in the carReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
In this episode of the Fix It or Free It series, we recap July’s project: repairing and cleaning a travel backpack. We explore how simple cleaning can sometimes be the fix we need, why not every item is worth saving, and how to set boundaries around bags and backpacks that pile up. This is a reminder that caring for your belongings extends their life, but also that letting go is part of the process.In This Episode We Talk About:Why cleaning can be just as powerful as repairing when it comes to extending the life of belongings. How to set boundaries around bags, backpacks, and totes so they don’t pile up. When it’s time to fix, clean, donate, or finally let go.Mentioned in This EpisodeThe Fix It or Free It challenge series. Tips for repairing and cleaning bags, backpacks, and fabric items. Guidelines for donating vs. discarding items responsibly.Review full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
In this episode of Organize & Cherish, we take a compassionate but clear-eyed look at the true cost of storage. Whether it's a rented unit or boxes in the garage, storage comes with more than a price tag—it requires our space, time, energy, and emotional bandwidth. We explore national statistics on storage usage, how clutter impacts our stress levels, and why postponing decisions might be costing more than we think. This episode offers both insight and a gentle nudge to revisit whether the things we’re storing are still serving us.In this episode we talk about:The financial reality of paid storage and why the industry continues to grow The emotional toll and decision fatigue that comes with keeping things “just in case” How to evaluate whether your stored items are truly worth the space they takeMentioned in this Episode:The U.S. Self-Storage Industry Stats (2024) and average cost breakdown A UCLA study linking clutter to increased cortisol levels Other episodes in our storage seriesReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
In this episode, we turn our attention to the often-overlooked emotional experience of helping someone else declutter, downsize, or organize. Whether you're supporting a parent, a partner, or a friend, this type of work—while full of love—can also be incredibly isolating. We're diving into why it feels so heavy, what resources are available, and how to care for yourself as you care for others. If you’ve ever felt overwhelmed or alone in this role, this episode is a reminder that you're not the only one navigating it and you don’t have to do it without support.In this episode we talk about:Why supporting someone else's decluttering process can feel emotionally isolating The difference between organizing for yourself and organizing with/for someone else Resources and strategies that can lighten the emotional and practical loadMentioned in this Episode:Family Caregiver Alliance (https://www.caregiver.org) AARP Family Caregiving Resources (https://www.aarp.org/caregiving) National Association of Senior Move Managers (https://www.nasmm.org) Eldercare Locator (https://eldercare.acl.gov) Caring Transitions (https://www.caringtransitions.com)Review full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
In this episode, we challenge the all-or-nothing mindset around decluttering and organizing. Not everyone is a minimalist, and not every item needs to go in a donation bag to count as progress. We explore the emotional and personal work of deciding what to keep—not just what to toss—and why organizing is ultimately about awareness and alignment with the life you’re building today.This is a gentle reminder that organizing with intention doesn’t have to mean constant letting go. Sometimes, it starts with simply asking the right question: What still deserves a place in my life right now?In this episode we talk about:Why organizing doesn’t always mean throwing things awayThe importance of clarity, not speed, in the decluttering processA mindset shift from “What should I toss?” to “What do I want to keep?”Mentioned in this Episode:A seasonal mindset check-in: embracing where you are right nowThe emotional work behind identity and organizingWeekly organizing nudges from the Organize & Cherish newsletterReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
It’s the halfway point of the year, and we’re recapping our Fix It or Free It progress from January through June. In this mid-year check-in, we share what was fixed, what was let go, and what those small choices taught us. We also answer five of the most common questions we’ve seen from listeners and readers this year from how to start when you’re overwhelmed to what to do with inherited items that don’t feel like “you.”This episode is all about reflecting on what’s working, where you feel stuck, and how to move forward with clarity and compassion.In this episode we talk about:The six-month recap of our 2025 Fix It or Free It challenge How to start decluttering when everything feels overwhelming Scripts and mindset tips for helping loved ones without pressureMentioned in this episode:Our Fix It or Free It monthly challenge from January to June The Pomodoro method and 15-minute organizing sprints Tools for navigating inherited belongings and family dynamicsReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
In this episode, we’re exploring how artificial intelligence can support real-life organizing, not just as a tool for planning, but as a partner for taking action. We’ll share common ways people are using AI tools to declutter, make decisions, and communicate more clearly with family and loved ones. Most importantly, we’ll explain how to ask better questions so that AI can provide you with answers that align with your goals, energy, and bandwidth.Whether you're organizing inherited items, managing school prep, or just trying to get your paper piles under control, this episode will help you use AI in a compassionate, practical way. Additionally, we’re sharing a complimentary guide with 20 insightful prompts to help you get started.In this episode we talk about:How AI can become a helpful companion in your organizing journey What makes a “good prompt” that leads to actual progress not just planning When AI becomes a support tool and when it becomes a distractionMentioned in this Episode:A free downloadable guide with 20 AI organizing prompts Episode 127: The Power of Asking the Right Question Examples of how people are using AI to write scripts, plan projects, and get unstuck NAPO National Blog: Smart Ways to Incorporate AI into Your Organizing Journey (So It Doesn’t End Up Being More Work) Review full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
Back-to-school season can feel like a fresh start or a total scramble. In this episode, we explore how to approach this transition with compassion, not perfection. Whether listeners are managing their own lives or supporting kids, aging parents, or both, we offer small but impactful systems that reduce stress and bring ease to daily routines. It’s not about doing more, it’s about removing friction so life runs a little smoother. Because organizing is an act of care for the future you and the people you live with.In this episode, we talk about:How to reset your space and routines for a smoother school season Why compassionate organizing supports both you and your household Easy, sustainable systems to reduce morning chaos and paper pileupsMentioned in this episode:The Sunday Reset routine for weekly planning Creating functional drop zones for bags, keys, and papers A mindset shift from perfection to practicality in organizingReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
In this episode, we’re sharing a simple yet powerful organizing practice that helps prevent forgotten items, duplicate purchases, and long-term overwhelm: intentional labeling and list-making. This low-effort task is a great way to check in with what you’ve stored, bring awareness to what you’re holding onto, and set yourself up for smarter organizing decisions. We also share how this practice can be reflective, collaborative, and even AI-assisted — all while aligning with your values and vision for your home.In This Episode We Talk About:Why labeling and listing your storage is an intentional act of self-care and clarity How to use this process as a reflection or journaling practice, not just a task Ways to stay out of the “planning trap” and move toward progress with intentionMentioned in this Episode:The Pomodoro Method for short, focused organizing sessions Flow organizing and journaling techniques to support mindful decision-making Using AI tools like ChatGPT or Gemini to sort your list and uncover patternsReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
In this Fix It or Free It series and Community Garage Sale update, we’re recapping what got accomplished in May. From finally tackling that pile of tangled jewelry to hosting the Larkspur Community Garage Sale. This episode is about momentum, finishing what we start, and finding clarity through simple actions. Whether it’s repairing a clasp or parting with boxes of unused items, we explore how both fixing and freeing create space for what matters most.In This Episode We Talk About:How a small project—like cleaning and fixing jewelry—can bring surprising satisfaction Lessons learned from organizing and hosting a large community garage sale The shared theme of completion behind both personal and community decluttering projectsMentioned in this Episode:The Fix It or Free It monthly organizing series The 2025 Larkspur Community Garage Sale recap blog post The podcast episode on the emotional power of finishing things: Episode 125Review full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
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 swapMentioned 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 progressReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
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 stuckHow search engines and AI tools like ChatGPT reflect the power of well-worded questionsA practical framework to rephrase common organizing questions for better clarity and actionMentioned in this episode:A “Question Makeover” cheat sheet for reframing stuck points during organizingReal-world examples of how better questions lead to faster decluttering decisionsA free download: Better Questions to Ask When You’re StuckReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
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 overwhelmingMentioned 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 awayReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
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 purposeMentioned 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 itemReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
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 effectiveMentioned in this episode:Signs someone needs a coach vs. a guide The emotional stakes of helping someone declutter Tools to support others without oversteppingReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
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 youMentioned 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 organizingReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
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 thingsHow to recognize when storage is based on hope, guilt, or fearPractical ways to shift toward storage that serves the present momentMentioned in this episode:The “Review in 6 Months” strategy for guilt-free decision delaysTips 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 Hosted on Acast. See acast.com/privacy for more information.
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 2025The difference between making a plan and making progressHow AI tools can support, but not replace, hands-on action and emotional decision-makingMentioned in This Episode:Harvard Business Review article: “How People Are Really Using Gen AI in 2025” by Marc Zao-SandersAI tools like ChatGPT, Gemini, and other generative platformsCommon organizing tools of the past (planners, Pinterest boards, magazine clippings) and what they have in common with today’s techReview full show notes and resources at https://theorganizedflamingo.com/podcast Hosted on Acast. See acast.com/privacy for more information.
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