Episode 57: How To Organize Your Home And Business For Freedom And Focus

In this inspiring episode of Main Street Success Stories, Jennifer Kok sits down with Lisa Woodruff, founder and CEO of Organize 365, to talk about how women entrepreneurs can create more peace, profit, and productivity starting at home.

Lisa shares her journey from teacher and mom juggling multiple roles to building a multi-million-dollar organizing brand and podcast that helps women everywhere regain control of their homes and schedules. Together, Jennifer and Lisa unpack why true organization starts with systems, not stuff, and how entrepreneurs can reclaim five extra hours a week by implementing simple weekly habits.

They also dive into Lisa’s fascinating concept of living and working by trimesters instead of business quarters  a framework that aligns with real life, family rhythms, and how women actually operate.

Whether your business is online, local, or still growing, this episode will help you rethink productivity and give yourself grace while still reaching your goals.

Key Takeaways

• Why women entrepreneurs need to create systems both at home and in business
• How to gain back five hours a week using Lisa’s “Sunday Basket” method
• The power of writing down one idea per sheet of paper to reduce mental overload
• Why trimesters — not quarters — are the real secret to sustainable growth
• How to align your business goals with life’s natural rhythms to reduce stress and guilt

About Lisa Woodruff
Lisa Woodruff is the founder of Organize 365, a company dedicated to helping women reclaim their homes and their time through proven systems and products. A former teacher turned entrepreneur, Lisa hosts the Organize 365 Podcast, runs a thriving product line, and is the author of several books — with her upcoming release The Art of Escaping Quicksand launching soon.

👉 Learn more at organize365.com
👉 Follow Lisa on Instagram: @organize365

Meet Your Host:
Jennifer Kok has been a business owner for over 25 years and is now a Small Business Growth Advisor. She turned her first business into a franchise and successfully sold it 20 years later.  She was passionate about building a business and a family at the same time.

I support women entrepreneurs in their second year and beyond as they build businesses and families, helping them achieve Clarity, Confidence, and Consistent Profits.  The reality is, you’ve built a Business You’re Proud Of— but it’s time for it to work for you.

The Earn More Stress Less 9-Pillar Blueprint helps women entrepreneurs with families create profitable, sustainable businesses that finally pay them back — in money, time, and peace of mind.

Join me for a Free Online Workshop:
3 Steps to Boost Profitability: Strategic Shifts to Help Small Business Owners Make More Money.  https://nextwavebusinesscoaching.com/webinar

https://nextwavebusinesscoaching.com
Facebook: https://www.facebook.com/nextwavewithjen
Instagram: https://www.instagram.com/nextwavewithjen/

You’ve Built a Business You’re Proud Of -But It’s Time for It to Work for You. You’re still wearing all the hats, working long hours, and not paying yourself what you deserve. You know there’s more possible. More profit, more clarity, and more freedom to enjoy the life you’re building.  The Earn More Stress Less 9-Pillar Blueprint helps women entrepreneurs with families create profitable businesses that finally pay them back. 

Transcript

Jennifer Kok (00:01.228)

Hi, Lisa, I'm so glad to have you on the show today.

Lisa Woodruff (00:05.101)

Thank you for having me, Jennifer.

Jennifer Kok (00:07.244)

I tell you what, so Lisa, your business, Organize 365, boy, where were you my whole life? Where were you 25 years ago when I first started my first business and had little ones at home?

Lisa Woodruff (00:13.731)

You

Well, I was at home with my little ones. And you know, that's so true with women. I think just to point that out, like a lot of us feel like if we can't get it done in our twenties and thirties, like our lives will pass us by. I'm in my fifties now. You guys just give yourself grace in your forties. You'll start to get traction fifties, sixties, seventies. This is where it is. So don't worry about the timing. What you are struggling with in your twenties and thirties, you'll be able to bring to the marketplace in your forties and fifties.

Jennifer Kok (00:44.872)

my gosh, thank you. I'm in my 50s as well, so hearing that is so refreshing. So first of all, Lisa, before we dive into your wisdom on how to organize our business and lives, tell us, how did you get here? Where were you before you started your business?

Lisa Woodruff (00:59.139)

you know, it's a long winding rabbit trail as is every woman's story. Like women are so like the spaghetti and men are waffles. You know, you hear that? Well, our stories are all spaghetti as well. So the highlights are I loved children growing up. I babysat like it was my job 40 hours a week. I went to college, I wanted to be a business owner. And my mother was like, you will get a college degree. So I was like, okay, well, I'll become a teacher because I love teaching and I love children. And then I'll be able to match my

work to my kids if I have to work when I have kids. We were blessed through adoption with two kids right before I turned 30. And so my 30s were in the you know taking care of my kids. I had taught so was teaching. I stayed home mom for a while. Big in direct sales for a couple of decades. And then I found myself sliding into the pit of despair by the time I turned 40 because I just I'd taken on so much and and things.

aren't as easy as they seem once you get into them. And I just had too many roles, too many responsibilities, not enough money. And so at the age of 40, I quit my teaching job, came back home again. My kids were in middle school at that point, started Organize 365, had no idea how I'd make money. I just knew that there was, know, I had blogged before, so I started as a blog. A couple of months in, realized I was an in-home professional organizer, didn't realize that was a thing. Started organizing people's homes for about three years.

And I was like, okay, there's something to this. The way I organize people's homes is a little bit different. It's from the lens of a teacher, like teaching the skill of organizing. And I was like, if I could figure out how to teach you how to organize your home through the internet, because most people can't afford professional organizers, that would be a business that would grow. And so that's what I did. I started the podcast 11 years ago and then started courses. And now I manufacture products that don't exist in the marketplace.

Because there are literally no school supplies for us at home, you guys. Like we literally cobble everything together from scratch. So when you say, were you 25 years ago, every single 20, know, woman in her 20s feels that way. Once you get the house, you're like, yes, this is it. Like I'm ready to go. Well, the house is just the dwelling. Like all the systems and processes, we have to cobble those together from scratch. It's exhausting.

Jennifer Kok (02:53.142)

you

Jennifer Kok (03:14.381)

You know, I love how you're teaching. It's kind of the old, I mean, every single person I know would love to hire a home organizer to come into their home. And a couple of my clients actually do that for a living. But that's a little bit, can be a little bit of a one and done, right? It looks great for a month, but if we don't have the habits, if we don't have the systems, it's soon going to go back to the way they found it. So I love how you're teaching people how to get to the root. It's not really just about, let's just get you cleaned up for the month. It's teaching us.

Lisa Woodruff (03:22.178)

Right.

Lisa Woodruff (03:38.403)

Mm-hmm.

Lisa Woodruff (03:42.955)

Exactly.

Jennifer Kok (03:43.635)

new systems. That's really cool. So what was the first thing you taught? Like when you started way back, was it something about your business or was it more personal in your home?

Lisa Woodruff (03:49.399)

Hahaha.

Lisa Woodruff (03:53.879)

So the Sunday basket, which we might get into, was an ebook I had and it was like the undercurrent. It's like the operating system that I've run my household on since I was in my early 30s with those little kids. But the thing that I would sell to people to service was the mommy makeover package. And that's where I would come in. I would do your home office. I would do your laundry room. I would do your kitchen and I would do your closet. And I thought if those spaces were going, then the woman could have her head above water and she could keep going.

Jennifer Kok (04:22.111)

Yeah, absolutely. OK, so let's fast forward a little bit. You have a really robust business, and it's really fun. I was poking around on your website today and just looking at all the different things you offer. And since we're a podcast talking to entrepreneurs, let's speak to the woman entrepreneur out there who is juggling her business, whether she's service-based, solo entrepreneur, online, or has a brick and mortar.

Lisa Woodruff (04:26.467)

Okay?

Lisa Woodruff (04:39.575)

Yep. Yep.

Lisa Woodruff (04:45.357)

Mm-hmm.

Jennifer Kok (04:50.047)

juggling home, whether she has children, empty nester, you know, fur babies, heck, you know, like, just before you and I hit record, I was letting my dog out for the 10th time today. So it's all got, we all got a lot going on. And, you know, for whatever reason, and I think it's the way we're wired, I think it's the way God designed us, the woman tends to be the one who kind of organizes the home, plans the holidays, plans the special occasions. A lot of it falls on her. So here she is.

Lisa Woodruff (04:58.433)

Ha ha ha!

Yep.

Jennifer Kok (05:19.021)

Organizing her business, running her business, organizing her home, running her home. And we know as entrepreneurs, it's really hard to leave one at the door and go to the other. It just doesn't work that way. Mentally, we're always thinking about our businesses, or we're always thinking about home. So you kind of have a system where you tell us about how do we create our weekly routine?

that's going to free up five hours during the week at home. So let's start at home. Because I always say to my clients as business owners, get help where you can. Sometimes getting help can mean hiring help for home or hiring help for your business. So what are some suggestions to help us get organized at home to free us up to focus on our business?

Lisa Woodruff (05:59.265)

I have so many things to say about this. I'll just give like bullet points and you could say where you want to go deeper. Okay, I have been always an entrepreneur. Yes, I taught, but I mean entrepreneur all the way through and through. And the thing about being an entrepreneur is in your business, you have to create every single system. Cause you're not going into corporation, you're not going into school where they have everything. So also in your household, it runs like an entrepreneur organization. You have to create every single system.

So you're double creating systems. is no structure anywhere. You're creating all of your own structure, which is exhausting, but also for entrepreneurs, we like it that way because we like to be in charge. So it's number one. Number two, I found that I was able to have more success in business if my household was organized and in my direct sales company, if my direct sellers, their households were organized, then they would make profit in their company.

If their household wasn't organized, they would miss the party, they would miss the order, they would miss the whatever, and they would not be profitable. So I've now come to realize, actually in my business, I'm getting rid of all of my work products, and we're only gonna focus on helping you organize the home going forward, because you will always default to organizing your business, and there are like thousands of coaches and programs that will help you organize business. There are only a handful that will help you organize your home. And when your home is not organized, even if you're successful in business,

you inside feel like a fraud, because you're like, yeah, but if you knew my house is a mess, even though it looks like I'm good over here, I'm not good over here. And you're personally judging yourself based on your house. So if you can get your house organized for the phase of life you're in, you have so much more confidence, clarity and time that you can devote to your business without being like, yeah, but I'm shortchanging my house or my family in order for my business to succeed. So you mentioned hiring help. There are two people I tell you as soon as you can hire them as an entrepreneur.

Number one, a housekeeper to do the actual like, you know, cleaning the floor, the toilets, all of that. And number two, a personal assistant in your business so they can help you with your email and your calendaring and putting things on your blog or anything that you could teach them administratively, just keep offloading because you are the only salesperson. You are the driver of the vision of your business. You're also the heart of your home. So if you can get these two people in your two different locations working for you on all the administration tasks,

Lisa Woodruff (08:17.037)

then you can be visionary in both. Now let's talk about getting five extra hours. Here's the thing, especially as entrepreneurs, we have lots of ideas and lots of visions and we want to do them all right now. And we think they're going to take like 10 minutes and they take like 10 years. So anyways, we have all that going on. You can do be and have everything you want just extend your time horizon. And the best way that I did that was I write every single idea I have down on paper.

Jennifer Kok (08:25.946)

Haha.

Lisa Woodruff (08:43.563)

specifically on index cards or little notepads. One idea per sheet of paper. And the reason why is because we have 8,000 ideas. And if you start making lists and then you want to go find your idea or your to do, you have to read through all your other ideas and then you get sidetracked and then you get absolutely nothing done. So if you write every single thing that's an idea or something you want to do on one piece of paper, then you put that in the Sunday basket if it's household related.

And right now through the end of the year, you could still get the Friday work box. You put that in the Friday work box or wherever you do your work. That way you can be your normal awesome creative self 24 seven. You have all the ideas you want. You capture them all and externalize them to the environment. And then you put them wherever that responsibility is. So when you are being your household manager, you do your weekly planning with the Sunday basket and you see all your brilliant ideas you've had all week, half of them are trash, just recycle.

And the other half you're like, yeah, I really did want to send my mom that card, book that vacation, get that haircut, order that thing on Amazon. And then you don't have to constantly try to use your brain to remember those things. Same thing with business. Like I'll get a podcast idea in the middle of the night, unfortunately. So I just write it down, then it's there for work. Next time you're doing podcast recordings or I have a new way to market something that I'm selling. Write it down, even though you're sitting in car line when you get that idea. But where do you put it if you don't write it down?

Jennifer Kok (09:52.205)

Always.

Lisa Woodruff (10:05.759)

I love it on paper because then you could sort them and you could put them in different places and things like that. For home, yeah. Yep. Yeah.

Jennifer Kok (10:10.411)

That's so fun and I love the old school approach to paper because there's a lot of studies that tell us.

that when we write things down, we're able to process better, we're able to remember better, we can just kind of think a little more clearly. So I'm loving that old school and I'm loving the one idea per sheet because I am classic, especially in this digital world that we live in, everything's on my phone. So I'm walking my dog and my 101 ideas come up about a podcast guest or a business idea or one of my clients, always thinking about what they need and where do I put it?

Lisa Woodruff (10:24.429)

Yep.

Jennifer Kok (10:44.139)

and I end up putting it in my notes or I do a voice memo. And then when I go back to it, I get so sidetracked by the other ideas. So I'm loving this one idea per index card or one idea per posty note or whatever it is. That's really brilliant because it's helping you compartmentalize what's going on in our brains.

Lisa Woodruff (10:52.109)

Yes. Yes.

Lisa Woodruff (11:04.555)

Yeah, and so along with that, so when I'm out, if I don't have my note cards with me, then I'll email it to myself and I'll print the email. So then it's one idea per email. So, and I'm in the process of getting my PhD. I'm just finishing my dissertation. Yes, so, so, so much science about handwriting. Even if you write with a stylus on a tablet, it's not the same as handwriting with paper and pen. Also, yeah, the handwriting is a big thing. Cognitively offloading to the environment, which is what we're in doing.

Jennifer Kok (11:11.297)

Okay.

Lisa Woodruff (11:33.463)

doing reduces the stress and the overwhelm of the mental load. We must especially as women like write down every single thing but then the key is you have to have a regular time to review those things.

Jennifer Kok (11:45.44)

Right, they can't just stack up and get ignored, right? No, love that. Really creative. You're the first person I've ever heard suggest that. And I've taken a lot of time management classes, and I've talked to lot of different people about, you know, getting help at home and in the business, and this one idea per piece of paper. To me, that's like, okay, mic drop, we're done. But I'll, you know.

Lisa Woodruff (11:47.713)

Yeah. Yeah.

Lisa Woodruff (12:04.035)

Great.

Jennifer Kok (12:06.477)

All right, so good, so good. All so let's talk about women entrepreneurs and their business. And I know your focus is a lot in the home, but you are a women entrepreneur. And so one thing that is interesting is the business world puts us into these buckets of quarters. And I do it. You we're always looking at Q1, Q2, Q3, Q4, 90 days, here's our goals, you know, where are we headed? And you had said something once.

Lisa Woodruff (12:13.219)

Thank

Jennifer Kok (12:35.691)

that someone shared with me and I thought, you know what, that is so spot on. For women, we don't have quarters in our life. We have what you call trimesters. Take us through that, what you mean by that.

Lisa Woodruff (12:43.415)

Right. Yes.

Lisa Woodruff (12:50.395)

So I am a mom. So this idea came because I'm a mom and I was working on the school schedule with my children and being an entrepreneur at the same time. But even if you're not a mom, if you are an American citizen, you run on trimesters because the school runs on trimesters and that's how you planned your entire life. These quarters are, they're arbitrary. They're created by accountants in order to make sure you have your accounting rights so that you can pay your taxes on time. That's really the only thing that is based on quarters at all in business. So the trimesters are

We naturally, as Americans, have this organizing, productive energy in August, because we're used to getting ready to go back to school. You started school sometime in August or early September, and so naturally your body's like, where's my new outfit? Like, what are we doing this fall? And once you get to Labor Day, you actually have the 10 most productive weeks of the entire year, are from Labor Day all the way until Thanksgiving. And once I realized that,

I was like, well, I need to really set myself up for success for taking advantage of these productive weeks. So if you're in business, you're doing things in September, getting you ready for whatever your Black Friday special is going to be, which is going to be Thanksgiving weekend. So you have like 10 weeks where you're like marching really fast and you're getting your audience ready for that. If you're physically sending products like we are, you're getting your warehouse ready for that, getting all your marketing ready for that. And then the end of the year, the last six weeks, you are

doing your Black Friday, your end of the year sales, and you're also spending a lot of time in the holiday merriment with your family. Thanksgiving, whatever your December holiday of choice is, which actually is another part-time job. So that's why you feel so crazy, because it's another 20 hours a week. And each of these trimesters ends with this like merriment, family oriented, chaotic time. Then you start January. So in January, we have the 16 most productive weeks or the 16 most organized weeks of the year.

January, we have the least amount of extracurricular activities. We have the least amount of sports. We have a lot of heads down, getting the big organizational work, reorganizing your house, reorganizing your business, starting new goals, starting new things up. You can have a ton of meetings from January to April and people will usually be there. You can have no meetings from the end of November to December and have people show up. You see what mean? It's totally different energy. We reorganize all the physical areas in our house. We do a lot of.

Lisa Woodruff (15:10.221)

crafting at this time. And then you have May, which you could also call May-Sember because it feels like December. If you have kids. Now, if you don't have kids, you're like, I don't know what people are talking about. But if you have kids, you know what I'm talking about. Mother's Day, end of the year, weddings, birthdays, know, babies being born, all that stuff. So May feels like December. That ends that trimester. And then you're going to start summer. Summer is a season that is state specific.

Jennifer Kok (15:15.521)

Yeah.

Lisa Woodruff (15:39.375)

and your life specific. So if you don't have children, summer is from Memorial Day to Labor Day. But if you do have children and your kids get out the beginning of May and they go back to school at beginning of August, your summer is the beginning of May until the beginning of August. That's what your summer feels like. If you don't have children, it's whenever the pool is open, which in Ohio is from Memorial Day until Labor Day and then they close the pools again. In Florida, don't use that because your pools are open year round. those are, I guess, the months where you stay inside.

Jennifer Kok (15:58.158)

you

Jennifer Kok (16:08.682)

Exactly, that's our winter, I always say. OK, so let's break this down a little bit more, because I'm really just loving this. And I'm thinking from a business owner perspective, how could we start to shift our strategy and, like you said, not follow what the accountants want us to do from a quarterly lens and plan our programs, our energy, our business around it? Because I owned a cookie and cupcake business for 20 years while my kids were in school, while they were growing up. And I can remember.

Lisa Woodruff (16:10.569)

Mm-hmm, mm-hmm, yes.

Lisa Woodruff (16:16.38)

Mm-hmm. Yep.

Jennifer Kok (16:37.152)

September was like my January 1st. I was super excited to get back into work, know, head down, let's, you know, get re-energized, let's finish strong. And I feel like if we were to look at our business and plan our goals around this, if you are a woman with a built in, building a family at the same time, that the stress would come off of us a little bit. Cause I feel like we're trying to run a race.

Lisa Woodruff (16:42.563)

Yes.

Lisa Woodruff (16:59.917)

Yes.

Jennifer Kok (17:03.518)

with other participants that aren't doing the same things we're doing. So I loved how you said September is kind of that go month, you know, to Black Friday, we're running like crazy. And then you're right, January through May. And I, it's funny, I've never heard that term May-Sember when my kids were little, but I'm hearing it all the time now. You know, so my thoughts are let's embrace this. Let's take away the guilt that comes with, I'm not doing enough over the summer, like.

Lisa Woodruff (17:11.255)

Yes.

Lisa Woodruff (17:24.129)

Yes.

Jennifer Kok (17:30.314)

maybe somebody we see on social media building their business. And let's just lean into these trimesters instead of fight them.

Lisa Woodruff (17:40.257)

Yes, because your audience is probably a woman. I mean, what they say? Like 85 % of buying decisions are made by women and women are running on this cycle. Like no woman is running on a quarter. So there are going to be seasons in your business where you make a lot of money and there are seasons in your business where you make no money. And once you've been in business two to three years, you need to just run through and be like, how much should I make in January, February, March, and April? And you will notice there are some months where you don't make a lot of money.

Jennifer Kok (17:43.703)

Right.

Jennifer Kok (17:51.565)

Right.

Lisa Woodruff (18:07.617)

traditionally June, July, and August are months where most businesses don't make a lot of money. And so now you're like, I got to work and I got like, just take the summer off. Like, know what your cashflow is and then follow your cashflow. Black Friday is a term that came up from corporate America and it's for retailers because they run their entire business in the red until the Friday after Thanksgiving. And then all the money that comes in from the Friday after Thanksgiving until December 31st.

is the actual profit in like Macy's or something like that. Hilarious that now Black Friday is like whatever, the week before Thanksgiving, like they're changing the date. Yeah, they just want you to buy more stuff. But the true thing, Black Friday is when does your business go into profitability? Because all the money you earn, like if you have a 30 % profit margin, no, you have a 0 % profit margin until October and then 100 % profit margin till the end of the year. So quarters, mean, go with your...

Jennifer Kok (18:42.21)

That's all year sometimes, doesn't it feel like it with Amazon?

Lisa Woodruff (19:03.075)

Don't try to make yourself earn, let's say $10,000 a month every single month. If naturally you'll make 20,000 some months, nothing some months, and 10,000 some months, figure out what they are and match those energies. If you're not making the $10,000 a month, let's say that's a zero month where you just know that your customers are not buying, stop sending the emails. Stop annoying them. Really wait so that they are looking forward to your next email and you're not trying to sell to them when they don't want to be sold to.

Don't try to sell everything year round when you know that this one product does well in the fall and this one product does well in the spring. If you need a summer product, make a better product for the summer. And then take advantage of those lower times. That's when I would, there's some seasons where organized 365 is a little bit quieter. People have bought the products and the services and they're now implementing them in their houses. So they're not buying new. That's when I would traditionally hire in new staff, train the new staff, reorganize the warehouse, develop new products that are going to come out later.

And then there are seasons where all you're doing is shipping and delivering to the customer. Once you recognize those seasons in your business and you match them to the seasons of the people who are buying from you, then you can be like, okay, well this month I'm gonna work 50 hour weeks and this month I'm gonna work 30 hour weeks or whatever and I'm gonna enjoy more of my family. I'm gonna enjoy this time because I know that this is not when I make the revenue and it's okay.

Jennifer Kok (20:24.287)

And I think that approach too is a lot of mindset, not only really good business strategy on when to lean in and do all that, but it's also, it's freeing. Because I hear a lot of guilt sometimes with women who are raising children at home. I should be at work. I should be at home. And when you know and go into it with intention and knowing that this is the season, the summer is the rest season for you.

Lisa Woodruff (20:28.407)

Mm-hmm.

Lisa Woodruff (20:34.913)

Yes, yes.

Lisa Woodruff (20:43.287)

Right, right.

Lisa Woodruff (20:50.317)

Yep.

Jennifer Kok (20:52.949)

there is a lot of freedom that comes in that. And one of the key reasons that people start their own business, especially women, is they want freedom and flexibility. But then we go about.

treating our businesses and not giving us permission to have freedom and flexibility. So, so, so good. So thank you so much, Lisa. I really enjoy just, you know, I'm a type A, a good list, love a good organization, you know, organized closet, that sets my day. So it's really fun to just kind of hear your approach and hear how you've built a business around this, because I think that's key too, that there's a business for everyone.

Lisa Woodruff (21:14.081)

Hahaha.

Lisa Woodruff (21:27.895)

Mm-hmm. Mm-hmm. Mm-hmm.

Jennifer Kok (21:27.937)

There's ideas out there for everyone. You took your skill set, you turned it into something really unique and look at it. It's just scaling and just, you know, amazing what you've built. So tell us about what's next for you. You've got a book coming out.

Lisa Woodruff (21:42.683)

Yeah, next year I'm writing the book The Art of Escaping QuickSand. It really talks about how do you move from reactive to proactive? What does modern self-care actually look like for a woman? It's not a spa or a bubble bath. It's actually taking care of your physical, emotional, relational, and spiritual needs. And we don't really have a good model.

Jennifer Kok (22:01.837)

want wonderful. And in the meantime, if anybody wants to learn more about Lisa and Organize 365, you have a free routine reset for us. And I will put the link to that in the show notes. And they can also head to your website. Is there anywhere else a good place to connect with you?

Lisa Woodruff (22:11.809)

Yep.

Lisa Woodruff (22:19.711)

I'm most active on Instagram and my handle is organized365 and a podcast by the same name.

Jennifer Kok (22:26.027)

Wonderful. Well, I will make sure I put all those links in there. So once again, thank you so much for being with us today. I really appreciate it.

Lisa Woodruff (22:32.695)

Thanks, Jennifer.