Eps 658: Lisa Woodruff helps us tame home chaos

Episode 658

We don’t parent in a vacuum, my friend. Midlife and the teen years pile on the paperwork, the appointments, the mental load—and so many of us are drowning in reactive mode. In this episode, I sit down with organization expert Lisa Woodruff to talk about the invisible work of running a home, moving from reactive to proactive, and her game-changing Sunday Basket system. If you’re a parent of teens craving calm and grounded systems, this conversation is for you. 🌱

Guest Bio: Lisa Woodruff is the founder and CEO of Organize 365 and host of the top-rated Organize 365 Podcast, with 24 million downloads and counting. A former teacher and professional organizer, Lisa is on a mission to prove that organization is a learnable skill. She helps women reduce overwhelm, clear mental clutter, and build the operational systems a household needs to actually run. She’s the author of the new book Escaping Quicksand: 10 Steps to Overcome the Overwhelm of Modern Home Life.

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Takeaways from the show

https://www.besproutable.com/wp-content/uploads/2026/06/Lisa-headhsot.jpg
  • You are the common denominator—start there.
  • Move from reactive firefighting to proactive planning.
  • The mental load is real and invisible.
  • You’re the CEO, not the only worker.
  • Make invisible work visible to delegate it.
  • This is a season—you’ll get through it.
  • Care for yourself like you care for others.
  • Writing by hand encodes it in your brain.
  • Capture interruptions, then return to your plan.
  • Organization is a learnable skill, not innate.

“Joyful courage to me, especially the older I get, is allowing myself the permission to take time and resources that is going to make me joyful—and being courageous enough to talk to my spouse about it. Like, I want to spend this much money and this much time getting a PhD, and I don’t even need it… I just want to do it because I want to do it. That’s joyful courage to me.” – Lisa Woodruff

 

Resources Mentioned

  • Organize 365organize365.com
  • Organize 365 Podcast
  • Lisa on Instagram@organize365
  • Escaping Quicksand: 10 Steps to Overcome the Overwhelm of Modern Home Life (book, releases June 23; audiobook in July; pre-order for early audio chapters + live book club)
  • The Sunday Basket system (under $200, includes physical box + lifetime co-working)
  • Productive Home Solution (binder system replacing file cabinets)
  • Trimester Planning (CEO-style quarterly planning for the household)
  • YNAB (You Need A Budget) — mentioned by Casey as her budgeting app
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Transcription

[00:00:05:17 - 00:01:18:07]
Casey O'Roarty
Welcome, welcome, welcome to the Joyful Courage Podcast. This is a place where parents of tweens and teens come to find inspiration, information, and encouragement in the messy terrain of adolescence. This season of parenting is no joke. And while the details of what we're all moving through might be slightly different, we are indeed having a very collective experience. This is a space where we center building relationship, nurturing life skills, and leaning into our own personal growth. And man, the opportunity's abound, right? My name is Kasey O'Rourdy. I am a parent coach, positive discipline lead trainer, and captain of the adolescent ship over at Sproutable. I'm also a speaker and a published author. I've been working with parents and families for over 20 years and continue to navigate my own experience of being a mom with my two young adult kids. I'm so honored that you're here and listening. Please give back to the podcast by sharing it with friends or on social media, rate and review us on Apple or Spotify. Word of mouth is how we grow. Thank you so, so much. Enjoy the show.

[00:01:23:22 - 00:02:05:19]
Casey O'Roarty
Hey, listeners, welcome back to the show. I'm really excited to be sharing this interview with you today. You're in for a treat. We don't parent in a vacuum. Midlife and the teen years bring a lot of stuff. Stuff like paperwork and books and things that end up cluttering our space, not to mention all the stuff that we're keeping track of in our heads. I have a guest on today that has some real solutions for those of us that feel like we're drowning and constantly trying to keep track and catch up on all that stuff. Lisa Woodruff is the founder and CEO of Organize 365.

[00:02:06:20 - 00:02:38:12]
Casey O'Roarty
Lisa and 87% of Americans believe organization is a learnable skill. Thank God. Yet less than 18% of those same Americans feel like they are organized. Very relatable. And as the host of the top rated Organize 365 podcast with 24 million downloads and counting, Lisa shares strategies for reducing the overwhelm, clearing the mental clutter and living a productive and organized life. I am so glad that she's here. Lisa, welcome to the

[00:02:38:12 - 00:02:42:09]
Lisa Woodruff
Joyful Courage podcast. Thank you so much for having me.

[00:02:42:09 - 00:02:50:03]
Casey O'Roarty
Will you start with your origin story? How did you find yourself the queen of organization? I've just crowned you queen.

[00:02:50:03 - 00:03:59:00]
Lisa Woodruff
Yeah, I was not queen. I was drowning at the bottom of the pit of despair and quicksand. I was not organized at all, about to turn 40. And I was like, how is this my life? I had set and achieved goals in the first four decades of my life. And I just felt like everything was crumbling around me. You know, was that like everything you touch turns to dust? Like that was like my story. My kids were in middle school and life just kept getting harder and harder. And I kept thinking like if you got older, like things were supposed to get easier. And it wasn't like things were not getting easier. Finances were getting harder. Balancing the kids was getting harder. Marriage was getting harder. Like everything was getting harder. And so in 2011, I had nine schedule C's on my tax return. Meaning that I told the IRS there were nine different entities that were paying me more than $600 a year. Like I was cobbling together from everywhere how to make money. I was teaching, I was cleaning houses, I was tutoring, I was in multiple direct sales companies. And I realized that I could not sustain this pace any longer. Like I was literally going to break and I couldn't break because everybody was relying on me for all of their care needs, right?

[00:04:00:02 - 00:04:58:10]
Lisa Woodruff
But as I was turning 40, I decided that I had to do what I always knew I should do, to start my own company and be in charge of, you know, the buck stops with me. Like start a company that could flex around my family and also bring in more income. So I started the company Organize 365 as a blog. No idea how I would monetize it. I just knew that it was time to put more skin in the game. And you know, if it's going to be, it's up to me, I just keep going and figure out what was going to be my next story. But I find that women often end up in this place, whether it's their kids needs become more significant, their parents need help, their spouse or their sibling needs help, or they themselves get sick. And you just get to this point where you have to opt out of the normal ways of earning money and going through your day to day because the demands on your time are so unpredictable and real. And you're the only one that can meet these needs that you have to create a new path. So that's where I was as creating a new path. My kids were 11 and 12 at the time.

[00:04:58:10 - 00:06:24:09]
Casey O'Roarty
Yeah. God, that's so real. I was just having a conversation with somebody, well, my sister-in-law who's got this insane job in New York city, and she's telling me about her day. And she also has a three and a five year old. And I'm just like, how do you do that? You know, and last year I spoke at a conference for women lawyers who are also moms. And again, it's like, they walk out the door early in the morning and get home late in the evening. And then they work this insane job. I mean, I'm a woman who's a full time out of the house person. You're amazing to me. Cause I don't, I can't, I mean, I work from home. I'm doing my thing and I really resonate with what you said, like something that flexes around my family. That was so important to me. And, um, and still, even with that, it still can feel like, ah, there's so much to hold. And you talk about moving from reactive to proactive, which I adore in so many contexts. And I think every parents of teen listening is nodding along because yeah, reactivity is basically our default. It's like that feeling of chasing, right? Of putting out the fires. What does it actually cost us personally? And in our relationships when we're constantly living in that catch up mode.

[00:06:25:12 - 00:07:53:20]
Lisa Woodruff
So I also was a stay at home mom for a decade, loved every minute of it is my whole life's goal was to be a stay at home mom. And while I was a stay at home mom, I could not fathom how corporate women did it with children. Like I, I just, I didn't have that part of my brain installed. Now my daughter has two children, single mom with two children. And I am a working grandmother. And now having had that grandchild in a really great daycare and now a really preschool Montessori because I can afford it as a CEO. I see how I would have been able to do it possibly if I was a lawyer or if I was earning enough income to be able to provide the supports that I can provide for my grandson. When I was in my late twenties and thirties, I kind of now could see how corporate women are able to do it. But I was a private school teacher. There wasn't enough, like daycare center cost more than my salary was. So part of it was the money thing. So I think sometimes your perspective really changes as your environment changes and a lot of it is proactive versus reactive. So when you are a corporate professional and your children in daycare, like you have contingency planning, but also you have a place that your kids go every day or you have a nanny that comes to the house every day. You're not like watching the child and doing that corporate job, right? And you have to be very proactive and schedule what you're doing at work and what you're doing at home. It's not easy, but it is a lot of planning. Whereas when I was the stay at home mom, it was like, who do you want me to be today? Like maybe go to the library. Maybe we do this. Like there's a lot of loosey goosey.

[00:07:53:20 - 00:07:59:12]
Casey O'Roarty
And so what I found the longest days too. Oh my gosh. The longest shortest days, I guess they say.

[00:07:59:12 - 00:08:28:17]
Lisa Woodruff
Every activity is like five to 15 minutes. I'm like, Oh my gosh, how can you be done with 14 activities in two hours? Cause I'm like doing my preschool thing. So this reactive to proactive thing really hit me hard as I was turning 40. I had been proactive when my kids were younger. I was a trained preschool teacher. The younger years weren't a problem. It was this late grade school, middle school years that were harder. The school was 30 minutes. The school my kids went to is 30 minutes away from our house each way. So on an hour round trip twice a day. So that was killing me.

[00:08:30:09 - 00:09:01:00]
Lisa Woodruff
My energy level was really low. My weight was the highest it's ever been. My parents had gotten divorced and I had settled my dad's estate with my sister. So I was depressed and on antidepressants, like my physical health was the worst that ever ever been. And I had spent all of my thirties just putting out fires, putting out fires, putting out fires. And the fires just kept getting bigger and bigger and bigger. Instead of stopping and figuring out where these fires were coming from and maybe getting firefighter training for myself. I just kept trying to put out all the fires and I got to the point where I just couldn't do it anymore. And that's when I realized, okay,

[00:09:02:07 - 00:10:28:17]
Lisa Woodruff
I am the common denominator of all these things in my life, good or bad. And the women in my family live into their nineties and hundreds and I'm turning 40. So if I'm gonna live another 40, 50, 60 years, I can't live in this worn out, stressed out body. Like I have to make some physical changes here. Now I'm 54 now and I'm just now starting to work out. So I didn't make it a physical like workouty changes then. I made mental changes in my forties because that's what I had the time for. And the first thing was I could be in charge of my attitude. I could be in charge of like, there are a lot of things I'm not in control of, but inside of your house, you're in control of everything, your attitude for sure. And then how the schedule runs. And it really started to look at everything where I was like, what was me like, this is happening to me. How can I become proactive? And the ways in which I started becoming proactive was, well, okay, let's not drink 14 Coca Colas a day. Let's try water. I hear it's good for you. You know, switching from Coca Cola to water, you know, getting up 10, not an hour before the kids, 10 minutes before the kids and actually getting a shower in the morning, not waiting until they were already at school, coming home and shower. You know what I mean? Like starting to put whatever you do for your kids doing for yourself, which is the theme of my new book is like, how do you once you have given of yourself so much that you don't even remember what you need anymore? How do you start to rediscover what care is for yourself, just like you would care for other people? And that's being proactive. It's not going to happen.

[00:10:28:17 - 00:12:29:22]
Casey O'Roarty
Yeah, I love that. I think that's such a powerful message, especially for those of us with kids that are adolescents, because so much of it does feel reactive because, you know, they're unpredictable in their teen brain development. And I really appreciate the message of taking care of ourselves. I know for me, you know, I've gotten to the point where I am getting up. My kids are out of the house now too. They're 20 and 23 and doing well. And, you know, before my workday starts, I need a nice juicy time with my journal and to listen to something that's inspiring. And, you know, maybe if I can do it, I can always do it. Maybe if I'm willing, this morning I was, to get out, go to the gym, you know, get my exercise in. Because, yeah, I'm 52 and, you know, menopause and all the things we've got to stay active. And it did feel impossible. There was a period of time where all of this did feel impossible. And, man, when I am taking care of myself, I'm showing up so much better. Like you said, we have so much control. We are, you know, you said common denominator. I talk a lot about, we are participating in any dynamic that we are a part of. And so we always can shift the dynamic simply by shifting ourselves. I really, really appreciate that message. And you've done a lot of research around what you call the invisible work of running a home. What does research tell us about parents? And especially what falls on moms about what we're carrying in our heads and why does this matter so much for how present we're able to be? And bonus question, how do we articulate that to perhaps a partner that just doesn't have, like it just feels like it's so hard to explain just how much we're carrying in our mental load?

[00:12:29:22 - 00:13:20:23]
Lisa Woodruff
Okay, so many thoughts. I promise I'm answering the question. I'm going to do like three little hops. Perfect. Love it. Okay. Just letting you know where my rabbit trail is going so you know I'm actually on a path. I believe in you. The first thing I would say is I love that you say that you have a juicy morning routine right now. In your 40s, 30s, 40s, you feel like you are never going to have enough time to go to the bathroom by yourself alone again or have a complete thought. And I'm 54. I'm like two years ahead of you. My kids are two years older than your same, all the same, except I have grandchildren. And what I would say is I wish I would have heard, maybe people said it and I didn't hear it. I wish I would have heard in my late 20s and 40s, you literally will have time when you're older. Like, because I just didn't think I would. I don't know why. I had so much time that when I turned 50, I went back and got my PhD. So I'll be done in two months with my PhD. My dissertation is almost done.

[00:13:20:23 - 00:13:27:04]
Casey O'Roarty
Oh my gosh. Congratulations, Lisa. That's incredible. That's incredible. That's so crazy.

[00:13:27:04 - 00:15:35:12]
Lisa Woodruff
If you'd have told me, first of all, that I'd go back to school at all, but that I'd get a PhD in my 50s, I've been like, that's not a thing. It's a thing, you guys. When your kids are older, you have so much time and capacity. So plan for it, dream for it, write it down, get ready. Okay. Now let's talk about the invisible load. So yes, I was studying the cognitive under roots of cognitive overload. So cognitive load theory is actually an educational theory. That's where it was started. And it's basically how do we remove as much extraneous as we can so that students can learn more? How do we open up as much of their working memory as possible for them to learn new information? So working memory is trying to buy something on your phone and you need a passcode that they just sent to your email. Now you have to go over to your email, find the six digit passcode, remember the passcode, come back to where you're shopping, input it, ding, you get a message from the kids school. Okay, well, obviously we have to go over. Now this is perspective memory because something's interrupted our working memory. Now we're over here checking out what the kids school has to say. The kids school has now become your working memory task and buying the thing that you were going to buy has now become a prospective memory task. Our executive function is balancing between things that we're remembering for our prospective memory tasks and what we're actually doing working memory tasks. This has not been studied very much in the literature like prospective memory has research but not very much working memory lots and lots. So as women especially we are in a constant state of okay that was no big deal they were just saying that there's going to be like a Mardi Gras parade tomorrow. Wonderful. Now here's the trick. Do you remember to go back to buy what you were buying? I mean 50% of the time yes, no, maybe you're like what was it then you go what was I doing? Now the dog barks to go out. You're like okay I'll go let the dog out. What was I doing? Oh yeah I think I need a coffee next thing you know why is this package not arrived? Because you didn't buy it. You didn't buy it okay. So that's just as simple if you wash a woman any woman like she's like bing bing bing bing bing bing. So you're going between what was the plan what's the interruption? What was the plan what's the interruption?

[00:15:35:12 - 00:15:36:06]
Casey O'Roarty
Yeah.

[00:15:36:06 - 00:16:54:05]
Lisa Woodruff
So when you're living reactive life you're just going from bing to bing to bing and at the end of the day you have no idea what you did because none of it was on a plan to begin with but you did a lot of things but you can't tell us what you did. Okay so now the mental load that I believe is what people are calling the mental load. Now there are thousands of studies on housework and hundreds probably thousands of studies on the invisible load and this cognitive load theory. So the invisible load is all of this stuff that you do in your mind that you can't see it's not laundry dishes and meal planning you can see that that is housework. The invisible load is the management of the house. It is your CEO and CFO and COO responsibilities as the female head of household. Now here's where my dissertation comes into play if it's okay that I nerd out just a little bit. Please do. Okay so I did a survey and I was testing prospective memory just in a survey. I wasn't like actually like putting nodes on your head or anything and my question was this if your perspective memory strength is higher like if you have a system for writing down these interruptions or some way capturing the interruptions and keep going on your working memory plan do you have less anxiety from all this detritus of American life? And I found out that you didn't however I disagree with my own research so what

[00:16:55:19 - 00:18:21:04]
Lisa Woodruff
I found out was women who have higher perspective memory are able able to take all these things into their head. They actually have a start a sharper increase in the amount of anxiety they have as they become overloaded. However you have to look at the whole graph. Women who have really good systems for not getting overloaded with all these extra tasks start with an anxiety level of negative below zero. Women who don't have good perspective memory start at an anxiety level of 20 and women who have poor perspective memory start with an anxiety level of 40. So when you get to the highest cognitive load the women that started with negative below zero perspective memory anxiety ended up with a with an anxiety of 23. Okay well that's like three points less than the person who started with no, see what I'm saying? So scientifically I found a bad finding or whatever that you but I'll take it any day because I'm starting with no anxiety. Women who can plan and have plans for interruptions of what they do with those interruptions and can stay on their course of their working memory don't have anxiety. I'll be doing more research in order to support those findings and testing it in different ways. Now this mental load is scheduling, calendaring, remembering, reminding, knowing whose birthday it is, knowing what people's food preferences are, being at the grocery store and knowing that my grandson's allergic to sesame. So I've got to check everything for sesame like all these things that we do.

[00:18:21:04 - 00:18:27:22]
Casey O'Roarty
Now

[00:18:30:10 - 00:18:34:18]
Lisa Woodruff
let's take it to the last question you asked me which was basically how do we get men to do this?

[00:18:34:18 - 00:18:58:21]
Casey O'Roarty
Well it's not so much how we even like I've come to find out that I actually like my role. Yes, right. And so it's not so much that I want to farm it out as much as I want to be able to highlight because he can't see it what it is that I'm doing. So that's really because

[00:19:00:06 - 00:19:28:03]
Casey O'Roarty
and I am blessed with a guy who does a lot of stuff but it's so gender-rolled like he is the outside guy, he is the car guy, he is the fixer, you know I'm the laundry folder and the dinner maker. It's very gendered and like I said I can push against that but I actually am not, I'm okay with it in a lot of ways. It's just the try because it's we start to get like well I did this, well I did this, well I'm doing this. So and that's where it kind of breaks down.

[00:19:28:03 - 00:19:34:07]
Lisa Woodruff
Here's what research says research says you're right on all counts. You are doing more.

[00:19:35:11 - 00:22:56:12]
Lisa Woodruff
Research says women do indoor tasks, men do outdoor tasks. You're right. Okay but let's look at the population that is surveyed for that research and it is 100 percent married couples with children under the age of 18. All genders, all ethnicities, even all that but it's always married with kids because we're looking for a discrepancy in gender and in the 80s that's 43 percent of the United States population was married with kids under the age of 18. Do you know what it is today? I do not. 17.9 percent. Wow. Meaning that 82 percent of the population isn't even in these studies. Now personally in my family no one I know is would be in these studies. My husband and I our kids are over the age of 18 so we aren't in the study. My daughter is a single mother not in the study. My son is a single not in the study. My sister never married not in the study. My mother-in-law and my mother widowed not in the study. So everyone that I know they aren't even in these studies because you're looking for a gender difference. You can't have a gender difference if there's not another gender there. And there is definitely more load when there are kids. So when the kids are older you have more bandwidth so there's not as much load. So it's helpful to understand that this is definitely a lived experience especially for your audience right now. They're probably married and they definitely have teenage kids because they're listening to this podcast. So you are the 17.9 percent. However when we take this now we're in our 50s and our kids are older you and I and we think about this mental load. I love that you said that you love the responsibility because I do too. There is one study that I found it had that married couples with kids under 18 and there was one subset population that did not feel burdened by this mental load and it was women who chose to be stay-at-home moms. Like they chose to be a stay-at-home mom and they saw that as part of their job and so they did not mind that they had the burden because they loved it. And that is what I want to do. Like in my research what I hypothesize is that in cognitive load theory we need to reduce extraneous load in order for you to learn new things. But what happens in cognitive load theory when you get to level three is once you've learned something new then you create a schema for it. So you take some time and you think about it and then you create an internal little code for yourself and you put it in your long-term memory. And then the next time you do it you just pull out that little long-term code and you just run that script instead of doing it from scratch like Groundhog Day every single day. And what I think happens is I think that female household managers over time continue to create more and more schemas in their brains for things that they experience in housework. Then when you get to the years where the kids are teenagers and you are at your max amount of work that you do as a parent until that youngest one drives. That's like the delineator. Until that point you are carrying such a huge huge huge burden you feel like you're gonna break and then that youngest one drives and it all starts to flow away. When we get to that point where we're feeling like we're gonna break we need help but the problem is we are the ultra expert in our household because we have all these schemas created in our brain. We don't even remember why we do what we do or how we do it because we've created schemas over decades of years. And then we look to our spouse and we're like help me and they're like uh what do you do? And you're like I don't know you should know figure it out and they're like but I don't know because you've always done it. You're like tell me and you're like well if I have to tell you I might as well just do it myself because we can't articulate.

[00:22:56:12 - 00:22:59:20]
Casey O'Roarty
And if you can't do it the way I want you to do it then why am I having to do it?

[00:22:59:20 - 00:23:40:12]
Lisa Woodruff
Right so it is very real and it's where a lot of divorce comes from I think. It is very the lived experience is very real on both sides. So my thing is how do we equip and support household managers so that they can be the CEO of their household and when they want to make it possible and they want to help out in their household. And then we can figure out how to explain and or delegate something completely like I just can't even do vacations right now. I just figure it all out tell me where we're going and I'll pack and you just give the whole thing over. This is why my husband I abdicated the role of cooking to my husband about 10 years ago when I was in this phase of life I was driving 25 hours a week and I said to my husband "I don't go to the grocery store anymore." He's like what do you mean you don't

[00:23:44:10 - 00:24:56:18]
Lisa Woodruff
all the way. I don't even like food. I don't like cooking. You have a car. You know where the grocery store is. I mean, feel free to go there if you want to. I literally don't go to grocery stores anymore. It was very easy to delegate. He goes, Lisa, 80% of the people in the grocery store are men. I'm like, yeah, because men like to eat and they will figure it out. If you tell them, I will go hunt and kill something and bring it home. And if you don't like it, don't eat it. But I'm going to eat it. That's very easy to delegate who they get. My husband still doesn't know who the kids doctors are. And they go to hundreds of appointments, like the doctor stuff, the school stuff, the college stuff. I want to be in charge of this. And also, most companies have one CEO. You're the CEO of your household. It's just you're in a really heavy, intense season. You need support, but you don't need to be replaced as the CEO and you don't need a co-CEO. So I really want to kind of change the narrative about this invisible load. How do we make it visible so that it's easier for female household managers to do it? How do we find chunks that we can give to our beginner that they would willingly do and are going to be successful at? They don't need all of our hidden schemas that we have. And then how do we realize that this is a season and we actually will get through the season and then you'll get hit with other ones like being a caregiver or something like that. So yeah, the strategies are necessary.

[00:24:56:18 - 00:25:31:13]
Casey O'Roarty
Yeah. And I love that you say we're in a season. I talk about that a lot and it's a messy season for sure. And like I like to say too, it right now is a snapshot and who our teens are today is not who they're going to be forever. Just like who we were at 16, 17 is not necessarily who we are now. And yes, to the kids getting more independence with driving and things, but I'm also thinking about like college applications seasons and deadlines and

[00:25:32:20 - 00:25:58:23]
Casey O'Roarty
even as I say that out loud, I'm thinking and all the over-parenting we're doing through all of that. It's a time to really give them space to muddle through, to transition into what comes after high school for them. And we're trying to stay connected to these kids who are like, "Bye." So when we think about all of this from this organizational lens, what are people doing that are actually making it worse?

[00:25:58:23 - 00:26:04:00]
Lisa Woodruff
So I definitely over-parented. So I'm not a good example of that.

[00:26:05:01 - 00:27:29:12]
Lisa Woodruff
Yeah, my kids are 24 or 25 and I'm like, "Okay, I need to be like, "Oh, that's interesting. Like, what do you want to do with that information?" Like I'm just now doing it now. So I don't give parenting advice. I would say one thing I did well, if you're still in the driving the kids everywhere season, I did driving the kids everywhere season well in that I was available to talk. So this was for me a decade ago and we had wired AirPods at that point. They were, you know, earbuds. And I would just put one earbud in and I would be listening to a podcast. In our car, everybody had a phone and you were like playing a video game or whatever you were doing, watching a TV show. And so when my son wanted to talk, I would just pop the earbud out and we would talk. And when he didn't, we didn't because we were in the car so much. It's the same with my daughter. Like being in the car, those conversations in the car were probably the best conversations we ever had. And I was always available to have a conversation. But being a busybody, I always had something else on in my ear if they didn't want to talk. I would say that's probably and those conversations in that time for my daughter actually came when she was pregnant later, you know, we would have conversations on the back patio every night about her pregnancy. I was never pregnant so my kids were adopted. So we talked about her pregnancy and we gave her a baby and all of those things and we really bonded during that time. So finding times when you have a commonality or you have the time and capacity to really live through an experience with them really helps bridge the gap from adolescence to adulthood for me.

[00:27:29:12 - 00:28:33:11]
Casey O'Roarty
Yeah, yeah. You know, I appreciate your honesty too because we all live a very distracted life. Yeah. You know, and I'm wondering how does that fit in because you've got, I want to talk about Sunday basket. I'm so excited to talk about that. And I mean, I know that part of my problem, I had one of these days on Monday where I had a lot of space to do a lot of things and I didn't really do anything. I was, I could feel that energetic distraction in my body like throughout most of the day and these little fucking phones, these screens, the media, the content that we're constantly like, I mean, what have you noticed in your you know, like you said, this isn't about parenting. You're deep into this systemic organization. What have you noticed over time? How does the organization work intersect with our distractibility and our screens?

[00:28:33:11 - 00:28:49:00]
Lisa Woodruff
So I don't, not speaking as a PhD right now, just normal human. Yes. I'm like, now that I get a PhD, I'm like, I have to put a disclaimer on everything now because apparently I'm going to be a doctor. Like don't come to get your medical things. Although I probably can do that. I didn't have Google research. So

[00:28:50:05 - 00:31:20:10]
Lisa Woodruff
as an entrepreneur, and as a goal oriented person, I believe the number one thing is not our phone. It's just our lack of discipline. Like, it's so easy to not be disciplined. It's more easy to not be disciplined today than it was yesterday and the year before. And it's going to get easier and easier and easier. Like AI, like I've worked with multiple companies where I had great work with them. And then they started integrating AI into it. And now the work is horrible. I'm like, go back to what you used to do. We don't know how to do it anymore. Like, what do you mean? You just did it three months ago. Like we're checking out mentally in every single way we can. And I am such a purpose driven, future oriented person. I want to do things that are of significance, future significance. And so my word of the year is discipline. And to me that is like, okay, yeah, I mean, I'm on Instagram lately. I'm on x learning all about the war. Like I'm like, I'm all about politics and stuff like that. I love to learn about that stuff. And I do that at night. But during the day, I stack my calendar so tightly, that I don't have the ability to be distracted, because then I'll get behind in the work that I'm doing in organized 365. Back when I started the company, and I was an in home professional organizer, I would go to people's houses and organize and I mean, about 50% of the time they would cancel. Like that was the cancellation rate for an in home professional organizer. And at that time, I could have those days exactly like you're talking about like, well, they canceled, I don't know what to do, there's nothing on my calendar. So I had an organizing partner. And she and I both always had things our kids needed done medical and all that. And then we were also trying to earn extra money. So we started creating what I called the A B calendar. So we would have a our day blocked out like we were going to do an organizing job. But if that organizing job canceled, we would go to calendar B. And we have a second day fully orchestrated to go on. And I think, you know, I keep going that way, because I'm always trying to stay ahead, stay ahead of my podcast, stay ahead of my work. Because what if I get sick? What if the kids get sick and I get taken out for a week or two? Can the company keep going? Can we keep earning the revenue? Can we keep everything going? So I'm always trying to stay one to two to three weeks ahead at work and at home. And that working ahead and knowing that my future life, if this was already done, and that I've accomplished and I've gotten a PhD, then if I didn't, I keep going. So like the PhD was going to take 25 hours a week, I figured out where I could find 25 hours a week on my calendar for three years. And then I blocked it out. And if anything else came, I had to move that three hours because it's $2,500

[00:31:21:11 - 00:32:20:20]
Lisa Woodruff
a month to get a PhD. And I look at my colleagues and they're like extending it. They're in like year four, year five, I got done three years. I'm like, where's this money coming from? Then I found out they're getting loans and the loans aren't due until you graduate. I'm like, oh my gosh, this is real money, you guys. Like this is like an exorbitant amount of money that you're going to need to pay back. But I was paying every single month. So you better bet I was finding those hours because every single hour was worth $25 of tuition. Like, and you see what I'm saying? Like, you have to take seriously your time and your money and your energy. And when you put that importance on it and you realize what they say, you only have 18 summers and all that stuff. I don't believe in all that. Like your time is important. You need to be disciplined. What are you becoming? And is what you're becoming bigger and more exciting than, you know, just blowing off the rest of the day. I should relax more, but I don't, obviously. I'm a really terrible vacationer. I'm a wonderful trip person. I'm so good at vacationing. I'm not good at vacations.

[00:32:20:20 - 00:32:26:00]
(Bell)

[00:32:30:12 - 00:32:40:21]
Casey O'Roarty
Let's talk about the Sunday basket. I said before we got on listeners, I was looking at Lisa's work and I'm poking around and I see Sunday basket and I think,

[00:32:41:22 - 00:33:10:00]
Casey O'Roarty
"Wait a second. I know about this. I know about this. I got into it for a hot minute and then life happened and COVID and all sorts of distractions." So Sunday basket, this is one of those things that almost sounds too simple when you first hear about it. And then, you know, you found over the years, people try it and love it and it changes their week. Walk us through what it is and why you found Sunday as kind of the magic day.

[00:33:10:00 - 00:34:24:17]
Lisa Woodruff
Okay. So I am a trained preschool, kindergarten, elementary school teacher. Favorite is teaching kindergarten. I love teaching kindergarten. So basically I'm a kindergarten teacher. That's why it's simple and it literally works. It just works. The other thing is one of the things I'm able to do as a teacher is to take an abstract concept and make it real for you. So like in the A-B calendar, you're now picturing two calendars, right? I love to make time concrete in some way and also take all this invisible work that we do and make it real so that you can touch it and manipulate it and take some of that anxiety and the emotion out of the work that we're doing and make it more visible to you and to everyone else around you. That's how the Sunday basket was created 24 years ago today. It's when I created the Sunday basket. It was a Sunday night and my two-year-old and my six-month-old were asleep and my husband had gone to bed early. And I had this huge stack of papers on the end of my kitchen counter bills to pay, phone calls to make, orders to place, just all the things. And so it's 2002. We had a lot more paper and I spread it all out on my family room floor and it was 40 distinct actionable piles of things to do.

[00:34:25:22 - 00:37:33:03]
Lisa Woodruff
Now it was time to go to bed and the kids were going to be up tomorrow. I had to put them somewhere. So I am a self-professed office supply hoarder and I had slash pockets, which are binder inserts that have tabs on them and they're colored and office supplies. Okay, everybody, everybody onboard. So I put everything in a different slash pocket and I grabbed a Longaberger basket because I had a collection and I dropped them in there. So that was a Sunday basket. I mean, you know, it's not rocket science. It's a basket. I made it on Sunday. The next day my son takes a nap. He only took 20 minute naps. I went over to the Sunday basket, grabbed out a slash pocket, made a couple of phone calls. He went up and I was like, it's going to work. It's going to work because every single other time he fell asleep, I would spread the papers out. And as soon as I knew what to do, he woke up and I would just come back up again. So I was like, okay, now I can actually use my pockets of time for production, not to figure out what it is I'm going to do. And I have made lists after lists after lists. I don't use lists anymore. I just use the Sunday basket. All those prospective memory tasks that come your way, pick up milk on the way home, make sure the dog gets new flea and take medicine, all that stuff. I write each one on an index card and I throw them in the Sunday basket. Here's where the discipline comes in. The Sunday basket takes time to process it. Anywhere from 90 minutes to three hours. Stick with me. Do not turn this podcast off. You're already doing way more of this work. You're just ping ponging around like you are inside of a ping pong machine. The Sunday basket helps you set a path, go on your daily path and take every single request of your time, things you're thinking about, things you want to do, be, and have, and put them over on Sunday. And then you make all of the decisions once at a time. So, for example, when my kids were a little bit older and they would come home from school and you need marshmallows tomorrow or we need to go get this thing or can I go to Susie's birthday party or can we sign up for gymnastics? I used to make those decisions in the moment and we didn't have a lot of money. So then I'd make a decision. Yes, you can do gymnastics, which was a lot of money. And then there were a whole bunch of other things that would happen that I'd have to say no to because I already allocated our money. So I realized with the Sunday basket, I also started to become a better steward of my CEO duties as household manager. I made all the financial decisions on Sunday, then I would do all the shopping on Tuesday. So if you didn't have your request in by Sunday, it didn't get in the queue this week. And I didn't decide if we had enough money to buy that and all buying decisions happened on Tuesday. Same thing as I was doing the grocery game, you know, the couponing game back in the day and making your grocery list to match the sales to match the coupons to match like all those things. I did all of those calculations. And I really started doing a lot of that deep work and decision making and planning on Sunday. And the and the week just starts to flow better and better because you'll start to notice things that distract you now or you have to make decisions in the moment. You usually don't have to make that in the moment once. It's the same kinds of decisions that are coming at you all the time. And if you could start deferring those to Sunday, then you can make all your financial decisions at once, all your time decisions at once, make sure all the calendars are working and all the uniforms are clean and all those things on the weekend and then your weeks run so much more smoothly.

[00:37:33:03 - 00:39:00:03]
Casey O'Roarty
So in a nutshell, Sunday basket is really this system of capturing what needs to happen throughout the week in an organized way so that as you move through the week, you're just kind of checking boxes versus so I have my system. I have a planner which I created myself because I was never satisfied with the planners that I was seeing. And each week has a blank sheet where I am a list girl, but I kind of can I feel like it's also really connected to what you're saying. Where I'm writing my tasks for the podcast this week. I'm writing my tasks for my membership. I'm writing everything down with little box, little square boxes. It's so satisfying. And when I do that, the following week is so much smoother. And I have these moments of like, "La, la, la, ooh, I have an extra hour." Because yeah, sometimes clients cancel and then it's like, "Oh, I have an extra hour." And rather than, I mean, I would like to say all the time, but hopefully more often than not, instead of picking up my phone and deep diving into hot guys jump roping or baby swearing, I go

[00:39:02:07 - 00:39:12:12]
Casey O'Roarty
to my list and I can see, "Oh, perfect. I can get this done. I can get this done." So is that kind of what you're talking about? It's basically just containing so that it's easy to drop into.

[00:39:12:12 - 00:41:32:02]
Lisa Woodruff
Yes, and this works totally with the planner. This does not replace the planner. It does not replace the Google calendar. So this works in conjunction. When you are writing things down, you are encoding. That is the first step of cognitive load. Remember I said, making the schemas with the lapse step. The first step is to encode new information. It has been scientifically shown that when you write with your hand, not with a stylist, not a computer, with your hand on physical paper in a planner, you literally encode that deeper into your brain. And I don't know about you, but for me, I often don't even need to look at that again because now it's part of my memory and I'm going to actually get it done. It moves it from working memory into a deeper part of your memory. That has been scientifically proven. That's why I think we're all moving back to paper. And the more you get overloaded, you can write it out. Now, the Sunday basket is an additional support because you can get a lot of things in your planner, but planners are for this week, this month, maybe even the next couple of months. But there are a lot of things in my Sunday basket. There's something I've been working on for my daughter for four years. And there's substantiating documentation for that. I have in a Sunday basket for my daughter, we have like all the different swim lessons and all the different lessons that the four year old is in everything has its own slash pocket and has the little sheets in there. So you can find out all that information. I signed up for a nanny service, we didn't even use it, but I've got all that information in there. You know, so it's like a tickler system. It's all the supporting documentation for what is in your planner. You could have this digitally. Also, I do it in a Sunday basket because a Sunday basket is when I use things in paper, instead of on my computer, I don't get distracted and all of a sudden I'm in my email and why was I here? I'm literally looking at the piece of paper and I can write the notes on there. The other thing people find with the Sunday basket is one of the problems with having a digital only system or your planner is when you leave the house and your planner leaves with you, your family's like, Hey, mom, hey, mom, can you find this? What's the answer? Like you are, you are Google. Like, how are you doing, mom? I was wondering about this. When you have a Sunday basket and they call you, Hey, what about this? You go, yeah, it's in the Sunday basket labeled homeschool or college application. Now your family could go get the information because this is an information. They can get the information they need. They can add things in there. So it supports a planner. You still need a planner. This is the additional things.

[00:41:32:02 - 00:41:56:23]
Casey O'Roarty
Yeah. And I just want anyone who's listening who's like, whoa, I am intrigued. This is a lot. I don't really get it, but I want to get it. I just want to let you know, you guys, I'm going to give you Lisa's website. She's got a whole situation going on for Sunday basket where she really holds your hand through the creation, the use, all of it. So don't worry if you're like, ah, wait, what Lisa's got you covered.

[00:41:56:23 - 00:42:21:23]
Lisa Woodruff
And to your point, you said you created a planner because there wasn't a planner that worked for you. I created a Sunday basket because every single household manager bar none has created their own system because Casey, they don't exist. There is no operational system for a household start an entrepreneurial business. You're going to choose from 2000 different operating systems, a household you're on your own. So we got to get to the teens and setting up their household system.

[00:42:21:23 - 00:42:48:10]
Casey O'Roarty
Yeah. And if somebody's listening right now, and they have, they're realizing like, oh shit, I have zero systems in place. Right. What are two or three foundational things that they could just step into this week? Not a full overhaul, but what's like a baby step into just feeling a little bit, not only like a little bit more calm and groundedness, but also like, oh, this little thing was so useful. I can do more. What would you suggest?

[00:42:48:10 - 00:43:32:06]
Lisa Woodruff
So that's essentially what I've created. I've created the four operational systems. You need to run a household like you would a business. You start with a Sunday basket, which removes you from reactive proactive, takes a couple of months to really get that solid. Then you decide if you want to do your information and binders, which replaces your file cabinets, your whole house, which is the productive home solution. And then you start to plan and do trimester planning three times a year, like you would a CEO of quarterly planning in a business. So those are the four systems. You can all at once in one big package, like you're going to school, like you're going to get your PhD in organizing, or you just buy them one at a time. And if you buy them one at a time, I always suggest to get the Sunday basket first. It's less than $200. It'll change your life. It comes with lifetime co-working. Like it's amazing. A physical box, everything.

[00:43:32:06 - 00:43:42:07]
Casey O'Roarty
I love that you just mentioned the side note, the binder replacing the file cabinet. We are recently shifting into using binders.

[00:43:43:07 - 00:43:46:02]
Casey O'Roarty
Will you talk about why it's useful?

[00:43:46:02 - 00:45:08:02]
Lisa Woodruff
Yes, I organized hundreds of file cabinets. And the problem was the homeowners couldn't organize the file cabinets, which was great for me, because I kept getting to go back and getting paid to organize their file cabinets. But in 2018 or 17, we had the Houston hurricane, and then we had the California wildfires. And I had clients in both of those cities. And I'm in Cincinnati, Ohio. And so they were evacuating. And they said, what do we do with our file cabinets? And I was like, oh, crap, like I never even I live in Ohio, like we have tornadoes, like good luck, you're not going to evacuate. I was like, this is a terrible solution. You've organized all your information. Now you have to leave it. So I was like, okay, it needs to be portable so you can evacuate. But also, whenever you need your information, you need it with a lawyer or a doctor or a school or like, your information needs to be portable. And I realized that there are only really five kinds of information in anyone's file cabinet. It's financial, medical, household reference that relates to the house, household operations, which relates to your family, and kids school paperwork, if they have an IEP. That's it. They fit in these five binders, you might have more than one binder if you have a lot of paperwork. But for the most part, you can get your file cabinet down to these four or five binders. And they all have workbooks in them. Because when I had to settle my dad's estate, the problem was the information wasn't in the file cabinet. It was on his computer that I never got. And in his brain, that was no longer available to me. So I had to go on a scavenger hunt in order to settle the estate.

[00:45:08:02 - 00:45:34:21]
Casey O'Roarty
Oh my gosh, I'm both overwhelmed and really excited. Sorry, I don't know why. No, no, no. Sorry about the stomach gasket. Sorry about the stomach gasket. It's okay. I've been doing this a long time. But it's all real, like, especially for those of us in midlife. I mean, I've have multiple friends who've lost parents in the last couple of years and watching them, like you just said, you've experienced this try to navigate. I mean, just thank you. I just want to say thank you for your work. I am excited.

[00:45:36:07 - 00:46:51:07]
Casey O'Roarty
And it's funny too, right? Because I feel like, well, I use YNAB, you need a budget. I use an app for budgeting. And I know when I'm not using it, I start to feel really agitated about our money, scarcity mindset shows up. Because you don't know. And then the thought of organizing it all to get back on track can feel overwhelming. But I have to remind myself of how good it feels on the other side. So even as you're talking about all of these things, listeners, I want to remind you, this is all movement in this direction of feeling solid and grounded and being more available to the people that we love because it's spinning out. So one last thing I want to talk about, I realized time we're like sliding by. So positive discipline, that's what I teach. That's the foundation. And we talk a lot about kids and problem solving and the importance of contribution, not just with chores, but actually like giving them an opportunity to feel connected and responsibility knowing that they matter. So I know you haven't answered this. What is the role that you see for teens in these organizational systems of the household? How do we bring them in without it being a battle?

[00:46:52:09 - 00:47:29:02]
Lisa Woodruff
So there's a lot of research that shows the children who do chores have higher executive function. So it's super important to do chores for sure. My kids had issues with executive function. And so they were not able to do chores. And I recognize that as an educator and as a mom, like their job was to go to school. When they came home, they did not have capacity to run my house for me. I babysat a lot of kids that did. I know a lot of kids that do, but if your kid struggles with executive function of school is really hard, they're going to have a hard time coming home and doing additional chores. So I never required that my kids did chores. Again, don't take parenting advice from me, but

[00:47:30:06 - 00:50:09:12]
Lisa Woodruff
I really wanted my kids to be independent adults and they are independent adults. And I knew it was going to take a lot of teaching and structure to make sure that that happened by the time they were 18. So starting when they were about nine, 10, 11, I would start on Saturdays organizing their bedrooms with them, cleaning and organizing their bedrooms. My son learned really early on that if he just didn't acquire any more stuff, this would go very fast for him. My daughter loves stuff. So it took us a long time. And I took time I created a book called How ADHD affects home organization, these specific executive functions and what I saw in the houses that I was organizing, and it also relates to children. So I created a script for them. And it took me over a year to teach this to them. But this is the script. First of all, we go in our bedrooms and we collect all of the dirty laundry and we go take it wherever the laundry is. I did not require my kids do laundry. But if your kids do have them start the laundry, get rid of the dirty laundry. Second, we scan the room for any food or dishes because we eat food all over our house. If you don't, you're better than me, but we did. So all that goes back into the kitchen. Third, we start picking up anything that is trash. And this is like the every single week we did those things. Now after that, I would organize the room and I would make them watch me and then slowly over time I had them organize it. I have a whole kids organization system where I teach kids how to organize their rooms. I call their bedrooms so starting at the age of 12. These were their mini apartments. I'm the landlord. You can petition me for things if you want for your room or ask permission. But this is your space. And so it needs to be organized for you and kids rooms are little apartments like they do so much in there. They sleep, they dress, they play, they do school, they like crafts. It's all in there and they're all their own little microcosms. So we got new paint and we redo their rooms every three years. And they really took ownership of their spaces and we could upgrade things. But over time, they learned how to establish zones in their room and to maintain those zones. Now my kids are adults and they will get overwhelmed sometimes to this day and they'll be like, Oh my gosh, I can't get my apartment, you know, organized. And I'll say, Okay, well, get the laundry started and call me back. And they don't call me back anymore because they do the laundry, they do the dishes, they do the trash. And they're like, next thing you know, Mom, I was done. Because I created this script for them. Organization is a learnable skill. It's not programmed at birth. So you have to learn it. If you never learned it, then your house may be kind of chaotic. If you have three children, one child is kind of born organized and you rely on that one to kind of set up and run the systems. But every child needs to learn how to organize their bedroom. Because if they can't organize their bedroom, how are they going to be able to organize and run a household?

[00:50:10:17 - 00:52:01:17]
Casey O'Roarty
I love that. And it's interesting next week, I have days blocked off on my calendar to go support my daughter in her studio apartment. She's like, Mom, will you come and help me, you know, organize, declutter. So Lisa, I'm going to get on your website, and I'm going to find some tools to support. And we do need help. Yeah, we do. And it's, and I'm happy to do it. One, I'm glad that she reached out. And, you know, listeners, I, you know, I was raised by a pretty intense mom when it came to clean and organize. It was kind of rigid and scary sometimes. And I noticed as a mother how easy it was to swing into that. And so I worked really hard to let it go, let it go. I remember one day I said to my son, I would love to come chat with you, but I can't walk in your room because when I walk in your room, I feel rage. So you can, you know, and I'm available if you want some support, it seems a little out of control. So I really probably could have offered a little bit more tools to them. However, they are now, you know, living on their own and really capable of handling their space, which I'm really grateful for. But I am excited to look at your resources and to see what can help me help my daughter next week. So thanks for that. And I love that. I think that one, permission everyone for your kids helping out, looking however that works for your family and finding those places where they can practice systems, like you just mentioned, scripts, like you just mentioned, find places where they're practicing what you want them to ultimately be able to start to do and embody when they're outside of the house. Absolutely. I really appreciate that.

[00:52:03:09 - 00:52:10:02]
Casey O'Roarty
We are nearly out of time. I have two questions for you. The first one is, what does joyful courage mean to you? That's the name of my podcast.

[00:52:10:02 - 00:52:42:21]
Lisa Woodruff
So I think joyful courage to me, especially the older I get is allowing myself the permission to take time and resources that is going to make me joyful and being courageous enough to, you know, talk to my spouse about, you know, I want to spend this much money and this much time getting a PhD and I don't even need it to get a promotion because I already own the company. And he's like, what? And I'm like, yeah, I just want to do it because I want to do it. That's to me, that joyful courage. Like, yeah, I love to learn and this is what I wanted to do. And he said, of course, go for it.

[00:52:42:21 - 00:52:50:09]
Casey O'Roarty
Yeah, I love that. Choosing you, right? Oh, I love that. Where can people find you and follow your work, Lisa?

[00:52:50:09 - 00:53:00:09]
Lisa Woodruff
So everything's Organized 365. The podcast is Organized365.com and I do hang out on Instagram, Organized 365.

[00:53:01:10 - 00:53:04:04]
Casey O'Roarty
And your book, tell us the name of your new book.

[00:53:04:04 - 00:53:13:08]
Lisa Woodruff
My newest book is called Escaping Quicksand, 10 Steps to Overcome the Overwhelm of Modern Home Life. These are the mental shifts that I made in my 40s.

[00:53:13:08 - 00:53:18:08]
Casey O'Roarty
Love it. Love it. And is that out? Is it on your website? Can we find it wherever?

[00:53:18:08 - 00:53:31:12]
Lisa Woodruff
It is everywhere that books are sold. The Audible will not be available until July. It comes out on June 23rd, but if you get it as pre-order, then you will get the audio chapters as a pre-release in our live book club that we're doing.

[00:53:31:12 - 00:53:39:18]
Casey O'Roarty
Awesome. Awesome. All right, listeners, you know where to find Lisa. Thank you so much for hanging out with me today. This is really useful. Thank you.

[00:53:44:09 - 00:54:25:08]
Casey O'Roarty
Thank you so much for listening. Thank you to my sproutable partners, Julieta and Alana. Thank you, Danielle, for supporting with the show notes, as well as Chris Mann and the team at Podshaper for all the support with getting the show out there and making it sound good. As I mentioned, sharing is caring. If you're willing to pass on this episode to others or take a few minutes to rate and review the show on Apple Podcasts or Spotify, it helps other parents find this useful content. Be sure to check out what we have going on for parents of kids of all ages and sign up for our newsletter to stay connected at BSproutable.com. I see you doing all the things. I believe in you. See you next time.

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