Good to Great: Transforming your career!

Foreign. Hello, I'm Katie McManus, business strategist, leadership coach. And I am delighted this evening to have Jackie o' Rourke from Outermost Education from Cape Cod. Jackie and I go way back. I'm always confused because this isn't mirror. I'm like, am I going the right direction?

You're perfect.

But doing this long enough, you'd think that. I know. Jackie, thank you so much for coming on with me tonight.

I am so glad to be here. Thank you for inviting me.

Of course. So the topic we're going to be talking about is Good to Great. And the reason we kind of came up with this is because we've both had these arcs in our. Our careers where we had good careers.

You know, we were.

We were making money, we had respect. We, you know, checked all the boxes. But also, we're like, this isn't cutting it. Yeah. And I'm so excited about what you're doing because you've really, like, taken creative, like a creative edge of what you. All your experience has been and have really just designed work that fits you.

Yeah, yeah, yeah. It's. And I mean, I know we've talked about it, but it's really. It keeps coming back to this idea of I'm just keep designing the things I wish I had. Had.

Yeah.

You know, and it feels. It feels really good. I was just talking with a colleague the other day about the way that everything when I was a teacher, when I was a. An administrator, advisor, like, it keeps coming back into my work, and not just in the way that I inform people, but just in the way I talk to people and the way I think about schools and the way I parent in the way I go about all the aspects of my business. It just keeps kind of circling back, which I didn't. I had no idea would ever be.

Well, I love this, but I know, I know we're jumping over, like, this huge thing because the audience doesn't know what you used to do. So do you mind starting from the beginning and just telling the story of what you've done? Sure.

Yeah. So, I mean, I, like, I knew in fourth grade that I was going to be a teacher.

Right.

Mr. Corny's fourth grade class at Orleans Elementary School. I decided to be a teacher. Right. And that was my path, and I trusted that path, and I went to college to honor that path. And, you know, I thought it was a big shift when I decided that maybe I should be an English teacher instead of a science teacher. Right. That was my first big, like, whoa, maybe I can change. And, you know, boarding school. I attended a boarding high school. And so that was that click moment of, I want to be a teacher in a boarding school. Okay, Now I know that next step. And I did that. And I love that work. I love the classroom. I was an English teacher. I was a history teacher. I was an advisor to students. I coach multiple sports. I lived in the dorm with as many as 50 kids at a time. I shared my life with teenagers every day.

And I love this. You also had a child while you were in this environment?

Yeah, yeah, I was. Not only was I in it, my. I had a child right after I accepted the job to become the dean of residential life at a boarding high school. So I started my career in administration at the exact same time, literally, exact same time that I started my career in mothering. And it was insane. It was just insane doing those two things together. And again, like, incredibly fulfilling. And the things I love the most about boarding school. I just blogged about this recently, that it was such a privilege to have my daughter around all of these kids and with these incredible colleagues, all these resources, and. And I was so tired and so burned out, and it's like I'm surrounded by people and things that I love, and I'm also exhausted, right? And I feel like I need a break from this, which everyone around me at the time, right? They're like, but you're a lifer. This is who you are. This is what you do. And so there was that moment of my identity from the age of nine, was teacher. Yeah. This is the plan. This is the path, right? And love them. I come from a family of people who have had the career since they were 20 something, right? And that's what you do. You pick a job, you do it, you retire.

I admire people who can do that. I think I've had, like, 10 careers up until this point, Right? You just can't even imagine.

I know. And even, like, my mother was a school nurse and. And she worked in a couple of schools, but up until she retired, she was 25 years in that school. Right? So even the fact that in my education career, I jumped to three different schools in 12 years already felt bouncy to me. And then I was like, ooh, big leap.

I think. I think this is also the difference between, like, east coast mentality. Cause I grew up. I mean, like, I became an adult in San Francisco. And, like, you can stay in a job for a year. No one cares if you. You only stay a year, right? It's bounce Bounce, bounce, bounce, bounce. It's do whatever you need for your own career. So, like, it's just two different worlds of mentality.

Yeah, yeah, absolutely. So it did. It. It felt. And I remember justifying that a lot, right. Where I was like, well, I'm still. Now I'm an educational consultant. I'm helping schools. I'm helping boarding schools. I'm taking my education, my talents, my skill set, and just. I'm still where I'm still in my path.

Yes.

I just sort of, like, looped it into the woods a little bit, but. But needing, you know, feeling like I have to justify this shift into business ownership as. But it's still education, so it's. All my other stuff still counts.

Yeah, you're still in the same bucket. You're just, like, floating around with different parts.

Right.

Yeah.

And that was. You know, those are the early. Now I'm some four years into owning the business, and now I'm like, I don't need to justify it.

No, it just.

It just is what it is. I help schools. It's what I do. And not because I decided in fourth grade to be an educator, because I decided at 34 to be a business owner. And so that's what I'm doing.

Well, what I love about what you do is that, like, you actually get to touch so many more children's lives.

Yeah.

Through the teachers that you're supporting. And through the teachers you're. You're helping, like, avoid burnout and be better for themselves so that they can then be better teachers.

Yeah.

Like, your. Your impact is actually, like, that much expanded out.

Yeah. And that's where it stemmed from for me. Right. Is working at a professional development conference, working for a larger organization while I was still in a school. And just that huge moment of, okay, I'm working with 25 schools at once, which means 25 schools are getting that good work. That's hundreds of kids who, thinking really loftily, like, are benefiting from the work that I'm doing.

Yeah.

Right. And I just said this in a call with a prospective client today. Like, I, you know, I hear you talking about your institution, and. Yeah. I value your institution, and I want it to continue to exist. Exist. But I care about your kids. I want you to get better for your students.

Right. Right.

They're still where it all comes from. They're still the heart of the work.

Yeah. I'm curious, you know, not just with your work. Like, where have you seen. Since you've really taken the reins in.

Your life, in your Work.

Where have you seen that kind of trickle over into your life?

You know, I. I think that. I think where it comes up a lot is in parenting and in conversations with other people who have kids around my same age.

Right.

And so with friends or people in my community who sort of there's this adjacent, like, well, if you're an expert in the world of education, you're probably also an expert parent.

But.

Right. But it's the same, like, people who come to me to say, who just, again, like, out at coffee with moms who feel like I can hold space for them to say what they need to say to run stuff by somebody else. I'm not going to judge them. I'm going to laugh along with them. And I. If people ask for my advice, like, I'll put in my 2 cents. Doesn't mean I'm right. But I think it comes up in a lot of. Of parenting conversations with friends, which is fun and a little terrifying because I am not a parenting expert. I'm not a child psychologist.

What I love about this is that you could be. You could honestly, like, be a little evil and, like, try parenting experiments with their children through them. You're like, yeah, do this. This is the best thing that parents can do. And then just take notes as they, like, explain how it went.

Good psych. You're a subject for a book. Didn't tell you. That would be really fascinating. Yeah, no, it's. You know, I think it's also that thing and it comes up with schools, right? Where when you step in and people start to call you an expert or thought leader, which, you know, are titles I'm super uncomfortable with and trying to learn some. Some level of comfort with, but that the reason for that discomfort in all, in both of those realms is that we're not perfect. Right. So people ask for my advice as my kid with her hair unbrushed and, like, no shoes on is running down the street, warrior, screaming at somebody. I'm like, let me tell you how to do this. You know, we're imperfect. Our kids are all who they are. It is what it is. So it's the same. Then it comes back to schools.

Right.

And I think that's where the overlap is headed in the other direction, where I can say to schools when we're talking about, you know, how to build great relationships with students, like, I was in schools for 12 years. I didn't build a perfect relationship with every kid.

Right?

Right. I messed this up probably more times than I got it right.

Right.

Which is Where a lot of what I now teach and try to help others do comes from, hey, I really stepped my foot in it over here. And here's what I learned from that experience. Here's how you can avoid it. Right, right. So it's, it's getting comfortable saying, actually the expertise is in being not an expert.

Yeah.

And then trying again and just trying to get better at it.

Well, it's funny because like, you look at money experts and a lot of them have this story of, you know, rags to riches and not just rags to riches. It's like, here's how I burned my life down first, and then here's how it got worse. And here's how I made an even worse decision and then I figured it out.

Yeah.

And then I can turn around and show people who are in similar situations to me that, you know, they can find their way back.

Yeah, yeah. And that's, it's a little, it's a little scary. It's a really vulnerable place.

Yeah.

But, you know, I think it's true too. And your work isn't that different in that you have to be ready to be vulnerable with people because you're asking them to be really vulnerable with you. You know, coaching and consulting, it's like because we're peeling back the layers to figure out what's going on. You got to be honest. So it requires a lot of honesty from us too. And that's. It's scary.

Right. Well, I think one of the what that ties into is that in like pushing yourself to be better in anything.

Yeah.

Requires for you to peel back the shame. And one of the most shame inducing things is thinking that you're the only person who struggles with this thing.

Yes.

Right. And it's so reassuring when you hear someone else say, oh, no, I dealt with that all the time back in the day, or I still deal with this. Or here's my report on how 67 of educators also struggle with this.

Right, right, right. Yeah, yeah. And we do, you know, when I'm at a school, I or consulting with someone, I'm like, oh, yeah, you know, and it's always the first question, do you see other schools dealing with this? Yeah, yeah. Everybody's dealing with this. Everybody is grappling with the fact that kids mental health is a mess. That's not just your school, that's not just you. You know, whatever the topic is, I guarantee you I can find a colleague or friend or neighbor who is dealing with it, has dealt with it, is going to be dealing with it tomorrow. And there is, there's real comfort in that solidarity.

Yeah. Yeah. Well. And I love how you've transitioned a lot of your offering because you're just adding more and more services and more and more experiences to your repertoire. And it's all stuff like you said in the beginning that you would have wanted back in the day.

Yeah.

Right.

Yeah. Yeah. It's. I mean, I think about what would have kept me in it.

Right.

A lot of the times and people ask me that, what would have kept you in boarding school?

Right. You were a lifer.

Because I was a lifer and then I wasn't. Right. So that's where it started with individual support. Right. If I had somebody outside of my bubble to talk to.

Yeah.

Gosh, that would have made a huge difference. Right. So now I get to be that person for people. And it's. It's incredible. Right. It's so fulfilling. You know, I. I've got this new plan. It's bubbling, it's not fully formed yet, but I have learned to just put things out in the world and make it happen.

Right.

So we. I talk to people a lot about. And for me, it was always the left side of my desk. So for years as a dean of res life, like the things I got at conferences, the big ideas, the notes, because I like to write notebooks and it was. It would pile up on the left hand side of my desk.

Yeah.

And it was the strategic work pile. This is the stuff that if I could just get to it is going to totally change how we do things. It's going to make people's lives easier, it's going to make kids happier, it's going to make our school better. And I'm going to get to it. Right after I get this crying kit out of my office, I get through my next leadership team meeting, I talk to that dorm parent who was late for duty last night.

Like, right.

Right after I put out every fire that I can find. Oh, and by the way, go teach a class and go coach a practice and pick up my kid at daycare and then go to formal dinner and that, like, it's. It's just wild. Right. So I talk about it as that the pile on the left hand side of my desk that's so hard for people to get to in schools because you have daily realities.

Right.

So talked to some people and said, well, what. What would it look like if we got a group of people together who all had a similar goal for this year? Right. So let's say your advising program at your School is just, it's underperforming. It doesn't feel like it's really working. Well, you have a sense of what you want to do. You've gone to conferences, you have a bunch of great ideas, but you're stalled. What would it look like to go for two days, phone off, zoom off. No meetings, no interruptions. Get in a room with a cohort of colleagues who are also working on the same part of school. Because our schools, we love to say that they're unique. They are. They're also incredibly similar. Right. So we all have advising, so let's work on advising together. And so it's this notion of these strategic work retreats to help particularly the people who work in student life because it's the place where, honestly, schools shouldn't compete. If you talk to any dean of students, any dean of res life, we want kids to be happy, healthy and safe. I want that for the kids at my school, but I want that for the kids at your school too. No educator was like, well, I hope the kids down the road, I hope.

They'Re running with scissors and playing with live wires in the walls. Yeah.

It's one of things I love about student life. People and student affairs, as it's called. Lots of higher ed. But a lot of colleges are adopting. High schools are adopting that language too. Like we're really collaborative because it's all in service of the kids having a better experience.

Right.

So why wouldn't we work on that together? Why wouldn't we beg, borrow and steal to make those parts of our experience better for children? These are people's kids.

Right, right. Inboarding. I mean, I don't have to say this but you know, regular high school, you go there for eight hours a day. It's still a huge part of your life. Boarding school, you're living there for most.

Yeah, yeah. And your lives are so integrated, faculty and kids, because. And not everybody knows this. Right. But most faculty live on campus at most schools.

Well, I think most people know that from, from like Harry Potter, you know, in Hogwarts. Live on, on campus.

Yeah. Do they realize that all the professors are right there in the castle?

I don't know. I think they do. I loved there was a meme once. It's like, you know, could you imagine being like a pre teen Slytherin and having to go to Severus Snape for a tampon?

That's awesome.

Like all the awkward moments that you can imagine as a teenager.

Yeah.

Having to go to your head of house and having it Be like this grouchy, surly, like, angry potion master.

I got my first scary head.

Do you have a potion for this?

Oh, can we make a Harry Potter spin off about just that, please? Just the awkward, awkward moments of teenage. With your school adults in your life.

Oh, my God. Oh, my God. Well, and I would also love to just see, you know, the, the teachers in the teacher's lounge at the end of the day, like, oh, my God, this happened. You know, like, how many times did Flitwick get like, thr across the room because someone messed up the charm or whatever outing my. Like, this is how nerdy I am. If you're watching. Yeah, I'm following you.

Even if not everybody else is. I'm with you. I love it. No, it's. It's the thing I miss about. It's funny, right? It's the thing I miss about the life, that integration and also the thing that was exhausting.

Right, right. Well, you have to be on all the time.

Yeah, yeah, yeah.

I mean, how you do it. I was, I came from a sales background and in sales, like, you have to be on so much of the time. I remember I came home, I had this one roommate, and I get home and he'd work from home and he would just want to talk and he would want to connect and have human time. And I just say, hey, you have five minutes. You have five minutes while I put my dinner together. And then I'm going to my room and you can't speak to me again. Tell me what I need to hear or what you need to get out from your day. I can't. I can't give you more than that. My max of on time is like four hours a day.

Yeah, that for me, it was decisions, especially as an admin.

Right.

I would get home and I, I didn't understand it at first. And then when I finally heard the term decision fatigue, I was like, oh, my God. I have a name for it. Because I could not make the most basic decisions.

Right.

When I would get home at the end of the day, which sometimes was 10 o' clock at night.

Right.

And there's my darling husband who's like, would you like a cup of tea? I'm like, well, utterly paralyzed.

Heaven forbid. He offered. Would you like tea? Would you like wine? What flavor tea would you like? Would you like soda? Would you like some water?

Our basket of like a variety of teas was the most overwhelming sight. I'm like, I can't possibly process that decision because you're just. It's all day. Right. And so, yeah, those, those parts. I think it's one of the amazing things about business ownership that I honestly feel guilty about the control that I have over that. Like, I get to say, I think I've had enough today. Yeah, I think I'm done, you know, or, you know, I think I need a longer walk at lunch today. I need a break.

Yeah. Right.

I get to just decide that for myself almost all of the time.

Yeah. Well, and that's the goal. We talk about freedom and flexibility. Like, that is what you're going for when you start a business. And for some people, yeah, it's the freedom and flexibility to go live in Italy for a year or to live out of a camper car and to travel around. But for most of us, it's, I want to take my dog to the dog park. I can't even for two hours. Broken up.

Yeah.

I want to go hang out with friends. I want to, you know, I want to read instead of writing.

Yeah, yeah. It just, you know, it's. And I think I had that vision too. And I said there are still moments, right. Where I'm like, oh, my, we could uproot everything and we'll live in Costa Rica and, you know, we'll send the kiddo to like a bilingual school. And it's just all sounds so cool. And it does. But honestly, we've settled into just those little joys. Like, I'm in a garden today. I don't have stuff that I absolutely need to get done. I don't have a call. I'm in a garden. Right. So one of the things that I did made a decision about six months ago to block Fridays on my calendar. And for me, it's an opt in day. So sorry, clients, unless there's something going on, you can't schedule with me.

Right.

And they all know that I'm upfront with them. Listen, I don't do Fridays.

Yeah.

If you really have something going on, send me a text. But most of the time it's, do I want to come to Brave Biz Lab?

Yes. Always.

Always. But do I, do I need to clean my house today? Do I want to sit on my deck and read a book? Do I want to have coffee with the girls? Like, I just get to make a choice. And the really cool. It's obviously really cool when I get to do the fun stuff, but it feels really good on the days where I'm actually opting into work.

Yeah.

Because it was my choice.

Right, Right.

Yeah. I'm doing work you know, because it. The first couple Fridays, I'm like, oh, boo.

Work.

Like, well, no, this is the work I'm opting into. This is what I want to be doing with my time.

Right.

Nobody forced me into that. Yeah. So it's. It's that kind of freedom for me that has become really transformational.

Yeah. You know, this, this sparks a question for me. Do you think that we have an inherent drive to do work that matters, or do you think people are kind of inherently lazy or is there some. Some belief in.

In between? Yeah, I think it's both. Right. Like, I think both exist. So I think, and I know that there's a ton of research that exists on purposeful work, and I don't know any of it to cite, but I know it exists. I know for me and for most people I know the worst days are when you feel like what you're doing doesn't matter. It doesn't matter to anyone. And I still have those days.

Right.

I still have moments where I'm like, this is selfish. I don't even know if this matters. And then I've got to talk myself out of it. But then there are the days where it's like, this really feels good, this feels impactful. This feels like it's changing in a positive way. Something for somebody.

Right.

Whatever that is. And it's all about the approach. I think I could find that behind a grocery store counter, Right. Because I talked to you while I rung up your groceries today, and that made you happier. And, like, I think we can find meaning where we can find it. But I'm totally honest. If I won the lottery and like, big, like, mega bucks big, tomorrow, I would train somebody else to help boarding schools, and then I would move to Costa Rica.

Like.

I think there's other places to find that meaning, right?

Let's just check. So Powerball is currently at 112.4 million.

Oh, that's not enough.

That's not enough. Mega millions is at 137.4, but it actually is enough if you're. If you're investing it properly and paying yourself out, you can absolutely make a lot more money.

I want a big pool.

Yeah, you want like the billion dollar win?

Yeah, yeah, yeah. No, I already know where it's all allocated and it needs. It needs to be bigger. I also don't actually buy lottery tickets, so.

The first step probably should be there.

The first step is there, but, you know, I'm cheap and I don't like to spend money unless I know it's going to get a good return.

So. Yeah.

No, it's not the lottery. I think it can be both. And it's funny because I remember my mother always saying that if she won the lottery, she wouldn't change a thing. Yeah. And she's a school nurse. Yeah. Works so meaningful every single day.

Yeah. I probably wouldn't stop. I would probably buy like a bigger place in an area that had like more. More space around me.

Yeah.

But I probably wouldn't. I wouldn't stop working. I wouldn't. I would probably like get fancier equipment than this janky standing desk that I have up against my desk. I'd probably have like my own little studio where I produce videos and things and have someone like edit things for me.

Yeah. It's funny. Right? And I think that really, again, like, meaning is where you find it. Right. So I love to volunteer.

Right.

I'm on the parents group at my kids elementary school. Not because I have a particular expertise in being the communications director for the pto. I can post on Facebook. Right. But I just like, this is a way to help the school and volunteer for my community. I'm on a town committee. I coach youth sports. I think I would probably do a lot of that. But again, those are all things that now I get to opt into. I get to choose to do I have the time to do.

Yeah.

Which feels like winning the lottery.

Yeah, totally.

Oh, that's really cheesy, Katie.

No, I know, but it came out of your mouth. And it's true.

I said it.

Don't regret it. What's the coolest thing that you've been able to do since you started working for yourself?

Oh, coolest thing. Like, like for me, for us, just.

In general, for you, for your family. You can have a couple things.

I mean, it's just starting again. But integrating travel with work, you know, obviously Covid kept everything super remote. Boarding schools were like on extra heavy lockdown. Nobody in, nobody out. So just, just in August, right. I got to go train at schools, which meant I got to fly to Honolulu and spend my afternoons because they only wanted to work in the morning. So I had to go to the beach.

That's awful.

And then the week, and then the next week I was working in California, so I spent the weekend on Maui where I have some family in between. I'm like, I get to do this.

That's so cool.

This is so cool. Right. And there have been times where my family has joined me for those work trips.

Yeah.

And we get to do it Together. You know, I think honestly, the like, recently not top secret thing that I'm doing now is probably the next coolest thing. Right. So I'm about to buy another business, which is actually where I'm standing. So we've rented offices in this co working space for a couple of years. It's a really cool little space. It's in my hometown. It's been an awesome resource for small business owners.

I used to rent an office there. It's amazing.

And so when the current owner asked if we'd be interested in buying it, I was so surprised at how quickly I said yes in my own head.

Yeah.

Because five years ago, when I was a school admin, working 100 hours a week in that life and only saw that life, I knew nothing about business. Right. And now in just four years in my head, that conversation was, well, yeah, I know how to run a business.

Right.

I am a business owner. It's a thing that I do. Who knew?

Right? Whereas, right.

That teacher path. Yeah.

You got the badge. I started a business, I'm running a business.

I can do this. And it was just as Devin and I were talking it over, I'm like, I, this is so cool that I, I know what systems we need to set up. I know the little things. Yes. I know how to invoice people. Yes. I know how to go set up the bank account that we need to have.

Like, right.

I know how to do this now. And so I can take on, even if it wasn't this, if something else had come up, the notion that we can take on a new challenge that.

Way.

And really approach it as a family. It's just such a cool new opportunity. And it still links with oes, it still links with what I'm doing. It's just in a different space. So it's exciting to think that I have the capacity to add without having to take away.

Yeah.

Right. And I didn't have that capacity five years ago.

Well, no, you can even decide what kind of tea you wanted. Now I know.

Now I just know.

It's like a fun decision you make every day.

Right. Right. Yeah. Yeah.

So here's, here's another question, is what would your advice be to a teacher who thought this was their end all, be all and is like getting to the end of the road. Their end of the road.

Yeah.

And thinking like, I just can't do this anymore.

Yeah. Oh, it's such a scary thing for me because working with teachers, I am not. And it's a thing that scares out of Schools. I'm not like, good, quit. Go for it, right? Because we need teachers. We need teachers not to be burned out. So usually my. My answer. I mean, that's not even a hypothetical. That's like a daily conversation is exploring why, what you do about it. Do you actually want to leave the profession of education, or are there shifts inside education that you could make.

Right.

That feel good for people? And then I'm really honest, right? I get a call probably once a month from someone saying, someone in education saying, I'm watching what you're doing. I think this whole consultant thing looks really cool. How do I do it, right? How do I jump in and start a business? Because it looks, you know, I'm like, well, I have a marketing agent. That's why it looks like it looks like.

Right?

And I'm. I will lay it all out. Okay? You're gonna need insurance. You're gonna need this, you're gonna need that. You're gonna need. And you can see them like, oh, my. Don't dive into it blind. It's not easy just because somebody on social media makes it look really smooth. There's a lot behind it, and it has its own stress. Right. I also think that we're now in a culture, at least in North America, where it's okay to jump around more, and that's not just in San Francisco anymore, Right? So that's a lot of people. The conversation is, what if, for now, you just took a break? You just took a break from education, gave yourself a year or two and a lot of this, because most teachers who I know, it is a part of their identity, right? It's not unique that I knew I wanted to be a teacher in fourth grade. Most teachers knew long before they went to college that they wanted to be a teacher.

Right.

And so it's this thing that's been so foundational to your identity for so long that that change it for most people is not a simple change. It is truly. Okay? My entire identity feels out of whack, Right. And if I go right, I'm walking away from a piece of my identity. So a lot of times it's. Let's. Let's look at a break. What's a break? What's education adjacent that you could do? That's using your skill set.

Yeah. And also if it's speaking to bigger problems in their institution. Hi, I'm Jackie o'. Rourke. I can help with that.

Yeah, yeah.

Right.

And it really depends on who I'm talking to. Right. If I'm talking To somebody who's in a decision making position, it's, well, what if we partnered to work on the strategic and systemic issues at your school so that you're not burned out and other people aren't burned out. But I have other people who won't. Nobody at their school knows they have a coach they're paying for out of pocket. Even though the coaching that they're getting is directly supporting the mission of the school, they do not want to tell anybody at their school that they're using a coach. And it just like. But they don't know it's broken if you don't talk about it. Yeah.

Right.

And yet those are people who are really experiencing an identity shift.

Yeah.

And it's scary.

Yeah.

Right. But that's, it's like my first clue to someone when they say, oh, no, no, the school's not going to pay for it. I don't want to tell anybody. Oh, okay. We're in really deep on this one. Right. Whereas, like, I mean, I have another client who said, I've already gotten approval from my head to hire a coach, so now I just need to pick one. Hey, that's a super healthy culture. Right. That you can go to your head and say, I feel like I need more support. I'm looking into a couple of coaches. What's my budget for that?

Right.

Because it's professional development.

Yeah. Well, it's interesting you say that like for schools, but it happens in businesses too. You know, when I used to take leadership clients.

Yeah.

You know, if they came to me and booked a call, I'd be like, cool, Are you paying for this or is your company paying for this? Yeah, like, oh, yeah, I have a budget within my company. This is the budget there. I'm happy to go over whatever. Cool. I was shocked how many people were like, no, I. I don't even want to tell them that I'm struggling.

Yeah.

I don't want them to know you can't look weak.

Like, there's no right.

It's that culture of bring your full self to work.

Yeah.

Just the good parts. Just the parts that we enjoy seeing.

Right?

Yeah.

Right. Yeah. And it's. Unfortunately, it is like that still in a lot of schools, too. And whether that really is the culture or that's someone who's carrying that with them from elsewhere, that's part of their personality. But, yeah, that, that sense of, I don't want to tell anybody. Right. Which is funny in a coaching conversation, like, well, you're gonna have to tell me. And on the other hand, like, I love that because those are the people who. My hope is, after some time working, they've learned to put some language around what's going on.

Right.

And we find ways for them to start communicating with their school, with their leaders. That still feels good for them. Doesn't feel like it's compromising their position, but, like. Yeah, it is actually okay. It is actually okay to go to your boss and say, this isn't working.

Yeah. It's back to that. You know, demystifying the shame.

Yeah.

And it's not just you. It's a lot of people. A lot of people go through this. It's very typical.

Yeah, yeah, yeah. And in education right now, it's. It feels like almost everybody.

Yeah. Well, I mean, teachers get a bad deal in most places of our. In most regions of our country.

Yeah.

And it's unfortunate. They don't get enough support, naturally. No.

And. And don't get enough respect. Yeah.

Right.

You know, I think. And I hear it. I hear it online chatter, but I hear it, like, live in the world. Right. Sort of. Teachers as glorified babysitters, especially early ed teachers. I'm like. And I. I mean, during the pandemic, you know, I homeschooled a then third grader, kindergartner, and preschool teacher, and I have a master's degree in education. I was sinking. Drowning under the weight of teaching kids how to read.

Did I.

That's so hard.

Did I ever tell you about my senior year of high school? I. So I did diploma plus, which is where you do instead of your senior year at your high school, you go to Cape Cod Community College.

Okay.

And it's great. So you went to classes Monday, Wednesday, Friday, and Thursday, Tuesday, Thursday, you had an internship. And I was pretty sure I wanted to be a teacher also. And I wanted to be a French teacher. And so, like, God bless this. This woman who coordinated this. She found me an internship at the Waldorf School in Born.

Yeah.

With a French teacher. Because it was really the only. Like, I wouldn't be able to go and intern at another high school with a French teacher. It'd be weird. Right. And so I went and I realized I like children. Like, one at a time.

Yeah.

But on Mass, like, it is too much. I like, they are. They're awful.

It is hard. I subbed one day at my daughter's preschool, and it was the hardest. I was like, how do you do this every day? They never stop talking. There's so many of them. They need so much. And you're responsible for these. This moment when their brain is taking in so much. Like, no high school kids are easy.

Well, I just remember there are two instances, you know, I'm like, monitoring the recess that was happening, right. And I watched. I don't remember anyone's name, so let's just say Johnny and Evan. So I watched Johnny kick Evan, right? And then Evan punches Johnny. And Johnny comes over and he's, like, crying, and he's like, evan punched me. I'm like, you kicked him first. He's like, no, I didn't. I'm like, you are a liar. And the teacher came over and she's like, you can't call the children liar. But he is. And then this other instance was I walked into the classroom, and it was second grade, second graders, and this other little boy, wolf whistled at me. And it was so funny. But you're not supposed to react. No, you're not supposed to react. And I'm just like, excuse you.

Not built for teaching.

No, not built for teaching at all. Anyway.

Such a hard career.

Well, I actually only did it for two months, and they had to find me a different internship because I hated it so much.

Oh, my gosh. But imagine if more people had that opportunity in.

Oh, yeah.

No, in high school and in college to figure that out.

Yeah. Oh, I could have gone. I could have spent a fortune going to school to become a teacher. Gotten my first job. Hated it, and then felt like I just stunk so much money into this. I have to, you know, stick with it for a little bit.

Yeah.

Be awful.

It is awful when that happens, and it's awful for the kids and they.

I know they would have been called liars. Still lying to me.

You can say it to high school kids. Maybe you should have. I'm a high school kid.

Yeah, maybe.

We'Re.

We're coming up on time. But I wanted to hear, like, if you had a final word of wisdom for someone who, like, is wanting to uplevel their life by starting their own business, by going out on their own, what would those words of wisdom be?

I think it is ask all of the questions on, you know, as soon as you know what they are. And it's hard when you're starting. You don't know what you don't know. I guess in retrospect, I wish I had talked to more consultants and coaches to say, what's your job? Like, what are those things that you have to do? What should I be thinking about? So really getting informed and going in with your eyes open. And understanding that it can be amazing. And it's hard. Those two things are happening at the same time. And so it's not the magic solution to every problem. But if you are asking the questions on the front end and getting support, this is a blatant advertisement. But, like, everything changed for me when I got a coach whose name happened to be Katie McManus because it helped me understand the things that I didn't know. Right. Oh, I didn't even know I needed to be thinking about that. I didn't even know that that was a thing. So whether that's coaching support or reaching out to groups, reaching out to people who have the job you want and asking them about it is just so tremendously helpful. And I think sticking with it.

Right.

I mean, I. I started this business like 18 months before the pandemic set in. Like I was just getting going.

Right.

And. And so easily could have given up. And so having the fortitude to stick with it for a couple of years, even if it means a part time job bagging groceries or flipping pizzas or doing whatever you have to do.

Yep.

Knowing that it takes years to really establish in most industries. And that's okay. That's normal.

Yeah. Yeah. There's just this. This mindset of I have to start it. It has to be immediately successful.

Yeah. No.

Who said that? No one said that.

Yeah, I'm right. I mean, I was, like, honestly flabbergasted that the first time I went to a conference that I didn't leave with like six people who wanted to give me all of their money.

Right.

Wait, isn't that how this works? I just show up and then they're like, we're so glad you're here. Here's a contract and a budget. Oh, no. I have to establish relationships for years with people.

Yeah.

Before we're in that place. And that's gonna be okay.

Yeah.

Right. But. But without the support, I would have given up. Right.

I'm so glad you didn't.

Me too.

Well, Jackie, thank you so much for coming live with me today. It really helps me out. I don't know if you've been paying attention. I've been doing a live every day for September.

I have seen your wild.

It's so nice to share the live with someone and with someone who I admire so deeply.

Thank you. I was really glad to be here. And this is like my one live for the next year, so.

Okay, great. Well, we'll have you back. Well, everyone, if you happen to work in boarding schools or you're a teacher and you want some support, please reach out to Jackie O'. Rourke. I'm Katie McManus, business strategist and leadership coach. You've just watched our 14th live for the month of September. Well, actually, I think there are more because I've doubled up some days, but this is day 14. Just gonna lose, lose count there. You'll see me going live tomorrow, the day after, the day after until October 1st. If you have any topics you'd like me to talk about, please DM them to me, because coming up with topics is one of the main things that I struggle with. Anyway, Jackie, again, thank you so much for being here today.

Thanks, Katie.

Yeah. And everyone, thank you for joining in. Have an amazing Wednesday night, and we will see you soon. Nah.

Good night.