She.E.O Episode 10 – Anna Skelton | Organizing by Anna

She.E.O Series

For 2026, we are continuing our She.E.O Series with local motherhood focused businesses, their stories and how they achieved success through interviews and photography. This ongoing series highlights small business owners in Metro Detroit who provide valuable services that support, educate, and empower mothers.

Each episode I interview and photograph a local small business owner in the Metro Detroit area. I can’t wait to share the story of every business that has stepped forward — together, we’ll explore the amazing services they offer to support, educate, and empower your journey into and through motherhood.

As a mom myself (my little is almost 3!), I’m constantly learning about the changes and challenges that come with this phase of life. My goal is to share this valuable information with others who may benefit. Let’s get started…

P.S. Don’t forget to check out our Branding Portfolio to book your next session!

About My Guest

Anna Skelton is the professional organizer and owner of Organizing by Anna, a Southeast Michigan-based organizing business dedicated to helping families create functional, realistic spaces that work for real life. In business for over 3.5 years and now fully focused on it full time, Anna brings a no-judgment, no-pressure approach to every home she works in, because she believes your space should feel like a breath of fresh air, not another source of stress.

Q&A

Q: Can you tell us more about your professional organizing services at Organizing by Anna? What inspired you to start the business, and what are its main goals for clients in Southeast Michigan?

Organizing by Anna is all about helping families create functional, realistic spaces that actually work for your everyday lives. When I’m working with a client, I truly get to know them, to really understand what’s working, what’s not, and I create a system that makes sense for them instead of something that just looks beautiful but doesn’t fit how they actually live.

I started this business because I saw how overwhelming clutter can feel. I’ve been very organized my whole life but growing up and seeing how much things can weigh on people; I wanted to create a company that helps families feel calmer and have more control over their homes. I’m big into no judgment, no pressure to be perfect, at the end of the day, I’m just here to help you feel better in your space.

Q: You emphasize creating functional spaces tailored to family needs. What were some of the key successes or transformations you’ve seen in clients’ homes after completing a project?

The biggest change I see is how people feel. There are massive physical transformations, I had a client whose basement I organized, and just one month later a pipe burst and water was everywhere. She texted me and said, “I just want you to know that if we hadn’t organized a month earlier, we would have lost everything.” You hope those things never happen, but with basements in Michigan, they do. That moment really showed the real-world impact of having things in order.

But beyond that, the biggest transformation is emotional. My clients always tell me they feel lighter, less stressed, and more confident in their homes. I grew up in a household where unorganized rooms just got the door closed on them, and I think we spend way too much on our homes to feel like we have to hide parts of them. No one should have to do the ten-minute throw-everything-in-the-closet scramble when guests arrive.

Q: How do your organizing services address the unique challenges that busy parents, especially mothers, face in maintaining an orderly home amid daily chaos?

I design systems that are simple and realistic for busy families. The goal isn’t perfection; it’s making everyday life easier. And I create systems that the whole family can actually use. I’m big into getting input from everyone in the household, because a lot of the time it is busy moms hiring me, but I want the systems to be functional for kids, spouses, and partners too. That way it’s not just mom carrying the load of maintaining it all.

There’s also a real emotional piece with moms specifically. If you have older kids and their outgrown things are still living in your basement, there’s so much memory tied up in that stuff. I work through that gently with my clients. I often say: you have amazing memories with that item, and you can also give it to someone else who will make those same memories with it, instead of it collecting dust. I’m not here to tell anyone to throw anything away. But if something is bringing guilt instead of joy, it’s okay to let it go.

Q: Your approach includes decluttering, renewing spaces, and establishing easy-to-follow systems. Can you elaborate on how these components contribute to the overall peace of mind for your clients?

Decluttering clears both physical and mental space. Once the excess is gone and everything has a clear home, daily tasks just feel easier. People spend less time searching for things and more time actually enjoying being in their homes.

When I’m working through decluttering with clients, I always start with the easiest category first; something like office supplies, because very few people have an emotional attachment to a stapler. We work through it logically: realistically, how many do you need? That process of going through something easy first makes it so much more manageable to tackle the more emotional categories later. Once you realize, “this isn’t as bad as I thought,” the momentum builds. I take it in small chunks to make it easier to digest. And it works every time.

Q: Setting up sustainable systems and reducing overwhelm are central to your work. Could you share some specific strategies or techniques you teach clients to maintain organization long-term?

I focus on simple habits, category-based storage, labeling, and easy routines that actually fit how a family lives. The key is that the categories have to make sense to the client, not just to me. Some people would look for a stapler near hole punchers. Others would look for it near the tape because in their mind those things belong together. So, I build the system around how they actually think, not how an organizing book says it should be done.

I’ve seen people work with other organizers who asked zero questions, and within a month everything was back to square one, and they were frustrated the entire time because they couldn’t find anything. What is the point of hiring an organizer if the system doesn’t work for you? The whole goal is that after I leave, your life is genuinely easier.

Q: Can you discuss how your services help with time management and preventing clutter buildup for families juggling work, school, and home life?

When your home is organized, you save time without even realizing it. Mornings run smoother, cleanup is faster, and things are easier to put away, which naturally prevents clutter from building back up. I always say: if something takes five minutes or less, just do it now. When you know exactly where something goes, that becomes effortless.

I recently came across a statistic that in the average household, people spend about a full day per year searching for lost items. A full day! And if you’ve ever bought a duplicate of something because you couldn’t find the original, that’s real money out the window. With proper systems, overspending stops because you know exactly what you have. Less stress, less spending, and more time for the things that actually matter.

There’s also the mental weight of visual clutter. If something is sitting on your counter that doesn’t belong there, you’re thinking about it constantly even when you don’t realize it. Having systems where things have a home, and get put there, gives you genuine mental rest.

Q: How do you foster a positive environment during organizing sessions to build client confidence?

I lead with kindness and encouragement, always. Organizing can feel incredibly vulnerable; you’re inviting someone into the most private corners of your home and your life. So, I make sure clients feel supported and never judged, and we celebrate progress, even the small wins. We move at whatever pace feels right for them.

Some clients need more time, more encouragement, more check-ins. I’m completely fine with whatever my client needs. I remind them: I don’t get overwhelmed in spaces, so they don’t have to either. We start at point A and we’ll work all the way to Z together. I also call it what it is, hiring an organizer is an act of self-care. If clutter is causing stress, getting support is incredibly freeing. It’s giving yourself your home back.

Q: Can you tell us more about your garage or basement organizing projects and how they complement larger home transformations?

Basements and garages are often the spaces that hold the most, not just stuff, but unfinished dreams. I had a client who wanted to start selling things on eBay, but her basement had become so chaotic she couldn’t even walk in without shutting down. She said, “When I come down here, I’m just so overwhelmed.” We created clear sections, a spot for items to be listed soon, and a simple screen to keep the catch-all area out of sight. Suddenly she had a workspace she could actually use.

For Michigan families especially, organized basements also provide real protection. When everything is sorted and off the floor, you have a fighting chance if water ever gets in. And as anyone with a Michigan basement knows, that’s not a question of if, it’s when. These spaces also connect to the rest of the home’s transformation. When you finally tackle a basement or garage, the whole house breathes differently. It’s often the final piece that makes the home feel completely under control.

Q: What kind of ongoing support options are available to clients after a project ends to ensure they continue benefiting from the systems you’ve helped implement?

I offer what I call “tidying up”, maintenance sessions and refresh visits. Clients can always reach out when life changes, a new season hits, or things start to feel a little overwhelming again. Those sessions are much shorter because the system is already in place; it just needs a little refreshing.

I also remind clients that it’s completely okay if a system needs to evolve. What makes sense for your family today might not be exactly right in a year, and that’s normal. If something isn’t working the way we designed it, let me know and we can absolutely adjust. I have a strong memory of my clients and their spaces, so even if someone reaches out and says, “I can’t find this one thing, where would you have put it?” I can usually walk them right to it. My clients are my clients for life. Whatever they need, I’m there.

Q: For homeowners who are considering hiring a professional organizer but feel hesitant about the process, what would you tell them to help inform their decision?

Please do not prepare, and please do not feel embarrassed. That is literally what I am there for. You are hiring an organizer; you do not need to have it together first.

Hiring an organizer is an act of self-care. Full stop. When clutter is causing stress and holding you back from fully enjoying your home. From being creative in your craft room, from running a side business out of your basement, from having people over without anxiety, getting support is what breaks that cycle. It gives you your space back. And more than that, it gives you your peace back.

I am a safe space for every client, no matter where they are starting from. Some people know exactly what they need help with. Others don’t even know how to start the conversation. Either way I’m here, I’m not going to judge you, and we are going to make your home feel like yours again.