In the inaugural episode of the Organized 365 Teacher Podcast, host Lisa Woodruff introduces herself as the founder of Organized 365, sharing her transition from a public‑school teacher to an entrepreneur focused on organization and productivity for all ages. She then welcomes Jayme (spelled "Jamie" in the transcript), a longtime school principal, to discuss her personal and professional journey. Jayme recounts her early love of school, subbing experiences, and her first teaching positions in Arkansas (middle‑school science, elementary 6th‑grade, and first grade). She describes moving to Indiana, teaching middle‑school science for eight years, earning two master’s degrees (counseling and administration), obtaining a principal’s license and a superintendent’s license, and progressing through roles as counselor, assistant principal, and finally principal of Greendale Middle School for a decade. The conversation pivots to a broader theme: educators enter the field driven by passion, yet systemic pressures, layered regulations, and invisible work often lead to burnout. Lisa frames the podcast’s pilot program as an effort to explore how to extend the “passion” phase and mitigate burnout. They compare the duties of assistant principals and principals, noting state‑specific differences (Ohio’s discipline‑focused AP role versus Indiana’s collaborative data‑driven approach) and the interplay of IEP responsibilities. Jayme also shares the personal organizing challenges of juggling a demanding leadership role with two school‑age children, emphasizing her reliance on both paper and digital calendars. The episode concludes with a preview of upcoming podcasts that will delve deeper into Jayme’s personal organizing journey and broader school‑leadership topics, positioning the series as a “curtain‑pulling” look into the hidden work of education leaders.
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Welcome to this special edition of the Organized 365 podcast, which will also be turned into its own playlist for the Teacher Workbox. In this first podcast episode, I'm going to introduce you to Jamie, the principal who took a chance on us and let us do a pilot inside of her school, and also a little bit about me, my history in education as well. So my name is Lisa Woodruff. I'm the founder and creator over here at Organized 365. I started this company in 2012 when I turned 40, and that's when I left the teaching career. So I got a degree from Miami University in early childhood and elementary education. I spent 4 years teaching in the public school and then adopted my children and was a stay-at-home mom for about a decade. And then I went back into teaching for 18 months before I left teaching entirely to start my own business. And now Organized 365 teaches the skills of organization and productivity to people throughout the entire lifespan from age 5 all the way to 105. Jamie, I'd like to introduce you to the Organized 365 podcast. You've already been on the podcast before and shared your organizational story, but here we're going to talk about your educational story. Can you just tell us a little bit about your experience in school as a child to start?
Well, I'll have to say school kind of came easy to me. Um, I loved school. I was the one that was, you know, teaching all of my stuffed animals and that type of thing. Um, so school just came easy to me, and, um, particularly math, science, and social studies. Not as much language arts, um, just because I would love to read, but I didn't like to necessarily do all the the grammar and that, that kind of thing. Um, but the spelling and that type— my mom always laughed because I, I, I totally understand your floating C. Mine was a floating B, but it was still— but it was always my mom would say like, you did so well on this, but why can't you spell? Like, I still can't spell. Um, they make fun of— students make fun of me at school sometimes because if it's a word and I'm like, I don't know how to spell it, I just ask Google. So it's still a weakness that I have. But I've always loved school. I think I knew from an early age that I was gonna go into some type of education.
That's so fascinating. I didn't realize our stories were that similar. I too had all the stuffed animals. Luckily, I have a younger sister, so she had to be my willing/unwilling student. So everything I learned at school, I came home and taught my sister. I am better at math and science. I cannot spell at all, but always wanted to be a teacher. Like, always, always, always wanted to be a teacher. So tell us about your teaching experience. You were a classroom teacher before you were a principal. Tell us about the different kinds of classrooms that you were a part of.
So I first, I started off subbing. I was, I would be what some people might call a workaholic. It's not something that I necessarily, I just say I'm passionate and that we all find things that we're passionate about. But even through college, I would sub on Fridays because I had a lighter, lighter schedule. And then towards the end, I just made sure I didn't have anything because schools always needed subs on Fridays. So I got a lot of experience with subbing, and then I did my student teaching in 5th grade and 1st grade.
Okay.
And then I got my first teaching job. That was It was all in Arkansas. So I did my original. So if you guys pick up on my accent, even though I've been in Indiana for 20+ years, apparently I still have a southern accent. And that— it was all in Arkansas was where I did my first 3 years. So my first year was middle school science. I did not have middle school science on my license. I had elementary ed. But You take whatever job you're offered, right? And, um, and I ended up loving it. Um, the only thing I didn't love was the commute. It was an hour and 20 minutes without traffic. So it was into Little Rock, and I lived in Conway at the time. And so it was about an hour and 40 minutes during a heavy traffic day. Um, so I also don't think that helped with my workaholicness, Because at the end of the day, if I didn't finish in time to leave by about 4:40, I stayed until like 7 because I didn't want to end up in the traffic.
Right.
So then my second year, I actually transferred. I still had a— I've always had a decent commute. I think without realizing it, my mind needed that time. And I never— because everybody's always like, oh my God, you have a 45-minute commute. And I'm like, I always have. And so anyways, I took a job at an elementary. It was 6th grade, but it was at an elementary setting. So it was a completely different experience. I taught everything— PE, health, art, music. Well, I brought people in to do art and music. I should have said that at the beginning. Those are also things that I'm not good at. I love music. I just can't do anything with it. But then my second or my third year, I taught First grade, which was a drastic change from middle school and 6th grade down to first.
Yes.
Um, that was also the year I met Joe online. Um, and so one thing led to another, and one of us had to move if our relationship was going to move forward. And so I was the one that chose to move. And so I moved to Indiana, and, um, my job there I taught 8 more years in the science classroom of a middle school, 7th and 8th grade. I taught both. And then within there, I finished my— I got a master's and finished that right when I was pregnant with Pierce. And then found out that what I wanted to do was school counseling and found out that was a separate master's. So I got a second master's, and then I got my principal's license because with my first master's, I only had to take like 3 classes to get my principal's license. And then I transitioned into middle school counseling. Loved it, but felt like I had a way of helping more people if I was in administration. Had a chance to move into administration, also middle school, and I did assistant principal for like 2 and a half years, and then I moved to my current job, which was 10 years ago, principal of Greendale Middle School, which is in Lawrenceburg. And then while I was there, I got my superintendent's license, which I don't know that I'll ever use it. Um, but again, it was, um, some, some PD opportunities that I had. And again, I think it was like 3 or 4 classes. And so I got my superintendent's license. So.
Okay. First of all, I just want to rephrase workaholicism because I also have it too with passion. Like when you are passionate for something and you love what you do, it does not feel like work. And because it doesn't feel like work, like why would you go like out to the movies to watch a movie when you could keep doing your work, which is like your unique gifting and calling in the world? So I understand why you're saying workaholic, but also I think pretty much 99.9% of people get into the education profession because we have a passion for it. Like, yes, we're good at it, but also no one's getting an education for the money.
Right? Oh, yes.
You know what I mean? So there is a— not that you don't get paid, but I'm just saying that there is a service component there. You're drawn to education. It is part of who you are. Like, it's just the way you think and you're wired and what you want to do. So I love that you mentioned that a couple of times because that is going to be a theme as we go through this podcast series. We as teachers or those in the education field, from, from teachers all the way up to administration, we feel called to where we are and we want to be where we are. I, I want to be very clear. We want to be where we are. But along the way, there is so much invisible work that we need to do, and additional rules, regulations, responsibilities that come at different levels and different buildings in different states and different eras and different administrations in the White House that come our way that usually do not get removed. They just kind of get layered on as if you're like painting a little bit more paint on the wall. But we're not taking away the first layer of paint or the 18th layer of paint under the new layer of paint. And so our passion— I think we all go into education with a passion. And I think the majority of us leave education in burnout. And somewhere between that coming in with this passion and leaving with the burnout, that's what we want to address in this pilot that we did and in this podcast series. So what happens from the passion to the burnout? And is there any way that we can lengthen the amount of time that you stay in passion, remove some of the things that would cause burnout? And, you know, you and I are like, how do we change the world? As I think all teachers, like, we all have that, like, we could change the world one student at a time, whatever at a time. So that's the passion that we bring to this conversation in this pilot that we did. Um, can you also just like more succinctly, as if you were applying for a job interview, how many years did you spend like in the classroom, in counseling, as an assistant superintendent, assistant principal, and as a principal? Yeah.
Okay. So in the classroom, it was 10 years because it was 3 years in Arkansas, 7 years in Indiana. And then counseling was 4 and a half. And then that half, I moved into assistant principal that year. So 1 and a half there. I jokingly said the first time that I ever signed an 8th contract was at Lawrenceburg. Everywhere else it was 7 years. And I always laughed and said, is that like the 7-year itch that I felt like I needed to move on or what? And then I've been the principal at Lawrenceburg for 10.
And as we've done this pilot and we've been talking to other schools, other school districts, other principals, other administrators, other teachers, other superintendents, every single person says to me, we want to talk to Jamie. So that's great, Lisa, that you're a teacher and you've created this product and you think you've solved this problem. We could care less what you have to say. We would like to talk to Jamie. Just so you know, Jamie would like to also talk to everyone. So Jamie's like, I could talk to him. Put me on a plane, put me on a call. I'll talk to him. I'll talk to him. We can go to this conference. We could do this. Jamie and I are going to do all of those things. However, Jamie is also a full-time administrator at a real live high school or middle school. Sorry.
Yeah.
So she does have a full-time job. I don't think she sleeps. So she does have a lot of time, but she can't talk to everyone possibly in the United States. So we are creating this podcast series so you can get to know Jamie more. You could get to understand what we're doing in this pilot. So just frankly, you could do anything else you would do with the podcast. Where you could just listen and see, is this even anything you want to explore further for your building, for your district, for your state? That's why we're recording this. Okay, so I want to segue from the teacher to the principal part of your story, Jamie, because I left school and did not move into administration, and I think it is a unique perspective that you have. In that you've been an assistant principal and that you've been a principal. Um, I would like to talk about the differences between an assistant principal and a principal as well, and with the caveat that you're in Indiana right now. I'm in the state of Ohio. I've always lived in Ohio, taught in Ohio. My kids have been taught in Ohio, so I really only know Ohio state law. Education is done on a state-by-state basis.
Yes.
There are federal funds for children who qualify for IEPs, and there are federal rules and regulations, but there are also state rules and regulations. So both have to be met, and it's very, very— every state is very different. They're all very different. So if you're like, oh, I want to do that in my state, it— your rules and regulations may be different. But the role of assistant principal and principal, if you have both in a building, which sometimes you don't, sometimes you only have one, In Ohio, my observation was that the role of the assistant principal in the schools I was a part of was more of a discipline role, coordinating of the IEPs role. And so they were usually in those meetings, and the principal was not in those meetings. That's what I observed in Ohio. What have you observed in Indiana?
Well, I'll have to say that's probably the roles. Most of the time when you have an assistant principal, their ultimate role is usually dealing with discipline of some sort. I will say that has probably increased to where both people kind of deal with it some, especially because a lot of times the IEPs are on that assistant principal as well. I did a lot of data meetings and that type of thing. Because I was the one dealing with the behaviors and the academics and that type of thing, and it, it freed the principal up to be able to run the building and do what she needed to do. But we both observed staff members. We split them up, made sure that we saw different ones each year. But I think it's, it is very different, the roles and my responsibilities. I will say I was probably very lucky in the aspect that I have always worked well with whoever I'm with. So we were more of a collaboration. Whatever I did well, I took over. Whatever that person did well, they took over. I've always been a very strong data person, which laughs because my calendar, I make my own because I have to have paper pencil calendar. Everything else I do is data, or is— I'm sorry, digital. But I have to have a hand, a hand-done calendar. So they make fun of me all the time for that at school. But I think like the role of the principal, I remember when I took the principal job, the principal, I love her. She's a great friend of mine. She had a lot of, a lot of family things, a lot of health things. So there was a lot of times that I was doing both roles because she was out a considerable amount of time, just because of, you know, life. And so I remember when I decided to go ahead and take that leap and go for the principal's job that I was like, well, I've kind of been doing it. Oh, no, no, no, no, no, no, no. It was not the same. It was definitely an eye-opening experience when it really did fall all on my shoulders. And I, I still always had that side of me that was dealing with the scheduling because I feel responsible for it all. I definitely keep my hands in it. It does make you— I've heard you say before, like, it's, it's kind of like I'm the CEO of that building and I care for all of the kids very much. And I do think going back to what you said earlier about passion, one thing That made me think of that is everybody has— if you're a teacher, you know where your passion is. Like, yes, my degree was elementary, but once I found middle school, that was my passion. And so everybody— and just know that you might be really good at elementary, but other people are really good at middle school and other people are really good at high school. So, and it looks a little different at all of those levels. And so that's one experience that I've also had. Where I, I've not ever done high school, but I've had enough friends that have. But I think that you have to own where you are in the whole realm because everybody has their own role. But the principal side, I think that's when I felt like I had to get organized in both places. between the house and school, because at that time my kids— I have 2. I mentioned Pierce earlier, but I had Kennedy somewhere in the middle of all those degrees too. And so I— when I took the principal job, Pierce was going into 6th grade and Kennedy was going into 3rd grade. So not only did I make a jump professionally, But my kids were going into very significant different grade levels. And, um, I had to be a mom and, and, and a principal. And so I, I really do have a lot.
So I think that's a great place for us to end this first podcast episode. That's your, your history as being a teacher. And also you added a couple kids in there, added a spouse, added all those things into the mix.
Yep.
We're gonna go in the next podcast episode and we're gonna talk about your personal organizing journey. And then we'll pop back out in the 3rd episode and we'll talk about school leadership. Assistant principals, principals, superintendents— how does it all fit? Having only been a teacher, you know, to me it's just like the man behind the curtain. I don't know what they do, and I don't know what I can ask for, and I don't know what they know or don't know or what they're looking for. We're going to kind of pull back that curtain and take a look. Thanks, Jamie.
