Teachers Make the Leap

It's Our 1 Year Anniversary! Let's Recap This Year's Top 5 Episodes

• Kristin Macintyre • Episode 52

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Join Kristin and Hillary for a celebratory episode to mark the Teachers Make the Leap one-year anniversary. In this episode, Kristin and Hillary recap the years top 5 most-listened-to episodes, marking notable moments and key takeaways from each episode.

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Hillary:

Welcome to this episode of Teachers Make the Leap. Kristen and I are so excited that today we are celebrating our one year anniversary of our podcast, um, which is just such a huge milestone for us and something that we, have been looking forward to. It just feels like we've had a lot of really great conversations over the past year, and, um, we've had a lot of great teachers. Feedback from our listeners and people have asked us a lot of great questions. And so we're really, really excited, that we've been able to do this for a year and we're looking forward to many more years ahead. So in honor of our anniversary today, we thought we would just kind of revisit our top five episodes from the past year and talk a little bit about. What we loved about those episodes, what we've learned from those episodes. And, what people can really get out of those episodes, if they haven't listened to them yet before, and they want to go listen to it for the first time, or if they're just feeling kind of, you know, have some extra time in their days and they want to go re listen to them. So, Kristen, I will pass it back to you and maybe you can tell us what our, our top five episodes were from this past year.

Kristin:

Okay. So our top five episodes are how Deanna left the classroom and built a six figure tutoring business. How Kristen left the classroom and tripled her salary. 4K months and 20K months in the same year. How Cassidy Horton navigates fluctuating income as a freelancer. Helping teachers explore the potential of online business. And last but not least, how Hillary earns 20, 000 a month from one client. I am so excited to dive into these episodes and just kind of relive them a little bit and talk about them with you.

Hillary:

Yeah, me too. Um, as you were reading off these names, I was kind of struck. Like, I have 1 clear favorite out of these episodes and I'm curious. Did you have a favorite that from these 5 that we recorded?

Kristin:

I don't know that I have like a top line favorite, but I will say the two that stand out to me are the episodes we recorded with Deanna and Cassidy just because hearing their stories were so inspiring to me and just kind of getting it to ask them about how they left the classroom and to hear their journeys. From how they started to where they're at now I, I loved having those conversations. What about you?

Hillary:

Yeah. Same. My particular favorite. I mean, I love both of those episodes too. And my particular favorite was the one with Cassidy just because, well, number one, she's such a dear friend of ours and she's so darling. but number two, I loved recording that episode because it was a really big fear of mine in the beginning of like not knowing exactly every single month, like how much I would be paid. That was a really big, Leap for me going from W to work, knowing exactly how much I would be paid, to then, like, taking a little bit of a leap of faith and realizing, like, my income could fluctuate. And so I just really appreciated all the depth that Cassidy gave to, her journey with that as well. And I think it's just a question. That's top of mind for a lot of people who are thinking about entrepreneurship for the 1st time. So, Maybe we start with that one. Maybe we kind of rehash that one a little bit and then we can move on, to Deanna's episode.

Kristin:

I love that. So just for everybody listening, the episode we're talking about right now is episode number 27, and it was published December 11th, 2023, just in case you want to go back and give it a listen. another thing that stands out to me about this episode and why I think it's so, so pertinent for folks who are just getting into freelancing is You know, I talk about this and think about this a lot, but when we're moving from a teaching position to being an entrepreneur and starting a business and like, you know, working for ourselves and, and really shifting how income kind of comes into our lives. There is some getting used to the fact that owning a business is really not at all like having a W 2 position, when you have a W 2 job and you're an employee. Really, you go, you apply for a job, you get that job, and there's a contract that says, This is how much I'm going to be paid every year, or this is how much I'm going to be paid every month. And then every month you show up and you get that amount of money. So you start to rely on that, predictability, I'm going to get this much in my bank account every two weeks or every four weeks. And when you switch to owning your own business, it's not that transactional at all, right? There's a lot more variables in place. and that can definitely take some getting used to, especially in the beginning when you're just starting the business and there is nothing telling you that you're going to show up that month and you're going to get paid X amount of dollars. For so many of us, that is like very scary. And then as you grow in business, You start to really kind of like that aspect of business because sure, there's not a guarantee of how much you'll bring in that particular month. But instead of being scary, once you learn how to get clients, it starts being really, kind of fun. And like, wow, nobody's telling me how much I can make this month, you know? And like, let's see where we can go with this. and. When you start to surprise yourself and you start to see those really high income months, that feeling is just pretty unbeatable.

Hillary:

Yes, I appreciated that aspect of our conversation with Cassidy. So, so much. She did such a great job of just kind of walking through and being really transparent about what, several years of, Her income kind of looked like, like from year one to year two, year three, year four, and so on. She did a really great job in that conversation of saying like, yeah, some months I made 3, 000, you know, other months I made 8, 000 and then I started to make 16, 000 and then I started to make over 20, 000 and like, that wasn't necessarily a linear progression, right? And so I just really appreciated that conversation that we had with Cassidy. So if that is a fear of yours, if you are like, I don't know how I would handle those fluctuating months. go give that episode a listen. It was a really, good one. And we just loved having that conversation with Cassidy.

Kristin:

One more fun plug for that episode. our guest Cassidy Horton, not only is she, like, academic advisor turned copywriter, but she's really, uh, she's like you, Hillary. She's in the finance space, right? She writes for folks in the finance space. So just to make this conversation like doubly awesome. Cassidy is also approaching the income and freelance conversation from the lens of personal finance, which she is quite obviously an expert in. Um, so she's just got some really great advice and her perspectives and her. approach to managing the fluctuating income is so inspiring and so refreshing. So go give that one a listen.

Hillary:

Well, let's talk about Deanna next because that was, I think both of our Next favorite episode, if not, you know, right up there with Cassidy and Deanna was also a really fun person to talk with. Deanna is someone that we actually met in a Facebook group of teachers turned entrepreneurs. and what Deanna did was she basically took her teaching expertise and she turned it into a. Six figure tutoring business, which, was such a fun conversation for me, particularly Kristen, because before I started my copywriting business had also been considering this tutoring aspect and ultimately didn't go that route. And I, and I don't regret that by any means. I love what I do now, but to see someone who did take that and be really successful with it, I think was really inspiring. So, I would love to talk about this episode.

Kristin:

Yeah. So for anybody listening, this is episode number 20. It was published on October 23rd, 2023. just in case you want to go give that one a listen. So just a little background on Deanna first, before I dive into what I loved about, the episode. So Deanna was a, a teacher who also became a speech language pathologist while she was in the classroom. So she has this kind of added expertise, that she took into her tutoring business. So she she has skills in two really amazing areas, right? She's a teacher and she's also a speech language pathologist. and it was so cool to hear her story about how she felt really kind of fed up and kind of hit a wall with what she was doing in the school system, but still wanted to serve children and still wanted to teach kids how to read and how to navigate, learning language and phonetics and things like that. So. One of the most fun parts about Deanna's story is that not only did she start a tutoring business and then reach a six figure revenue number in her first handful of years in business, but she also did this neat thing where she started out virtually, and then she ended up getting a brick and mortar location too. So she still meets kids in person and has that really in person touch. They also still have a virtual element to the business, which is super fun and really leads to that scalability. and she ended up hiring one of her teacher besties that she worked with you know, when she was a teacher in, in her tutoring business. So she's been able to kind of give back to teachers in that way and invite them into her tutoring world. And that was just such an inspiring conversation.

Hillary:

Yeah. The other thing I love about Deanna, not only is her demeanor and personality, just like, so inviting and warm, but her passion for teaching and working with kids is. It's just really infectious. And what I love about her in particular and her starting this tutoring business is that she clearly has a love and a passion for teaching and for working with kids. Right. And so it was right for her to start a tutoring business and keep doing the work that she loved doing. And this just kind of brings to mind, it kind of contrasts With some other conversations that I've had with other teachers who are wondering what kind of business they can start. And they say, well, I guess I could start a tutoring business. And it's clear that they're not actually excited about starting a tutoring business. You know, that, work, doesn't actually excite them, but for some teachers, it does. Some teachers truly do love teaching and just don't want to be stuck in the systems that be anymore. and Deanna is such an embodiment of that. Um, so again, if that's you, I really encourage you to go listen to that episode. It was such a great episode. and it's also just really a testament of what is possible for teachers right out there. You know, um, it really, you know, Kind of breaks that glass ceiling, so to speak of like, we're teachers, we have degrees in teaching and all we can do is teach. Um, but there are truly so many possibilities that you can do with teaching skills. Now, the next episode that I would love to chat about with you, Kristen is actually your episode, which is how you tripled your salary. from classroom teacher to copywriter. So this was actually one of our earliest episodes. I don't remember exactly. Maybe you can tell me which number this was in our queue.

Kristin:

Yeah, this is episode number two, actually, and it was published on June 10th, 2023, which was when we really just first published a little bundle of episodes. this one's called How Kristen Left the Classroom and Tripled Her Salary. And what was so fun about this episode for me was that, This was one of our first kind of introductions of ourselves, to our listenership. And, we were just starting to kind of tell our stories in public, um, and share what it was like to go from classroom teacher, you know, to make that leap to entrepreneurship and starting a freelance business. So this was so fun just to recount my journey, And to get into the particulars of how I went about, you know, starting, starting a business and scaling that business a little bit and just to recount some of the struggles and successes I saw in the very first three years of my business. So that was such a joy.

Hillary:

Yeah, I don't think we realized when we recorded that episode, like how core it would become to you and I kind of telling our stories and It has been fun for me to watch, you know, over the months as you've kind of told this story more and more of like, how many more details you've kind of revealed. I mean, not only did you triple your salary, you actually more than tripled your salary. And we, we just use the word tripled your salary because you didn't quite quadruple your salary, but you almost did. Really? Um, so it's been really fun for me to also, even though I've heard this story before, story at this point, several times now, I still feel like I learn more about you and your journey kind of every time you share more and peel back a little bit more of the layers. So I'm really glad that that was one of our earliest, like coming out into public and sharing our stories, experiences that you and I had. And, I think you're right. I think it's a testament. You know, it's 1 of our earliest episodes, but it's also 1 of the most listened to. And I think that you have just been such an inspiration to so many teachers out there who are feeling stuck by their income potential and and all of those things.

Kristin:

Yeah, and I honestly think that when we talk about our stories, what it really does is just kind of like, Crack open what's possible for folks. Um, in the beginning for me, that was really, really important just to look around and say, Oh, wait a minute. People are having success in the freelance and online business world. Why can't I? Right? And without the stories that I heard in the beginning. I would not have even considered it possible for myself. And this kind of leads me to another episode that's in our top five. And that is an episode that was focused on you and your journey, of earning 20, 000 a month from one single client. That, just for everybody who's listening, is episode 17, aired on October 2nd, 2023. Hilary, what was it like sharing that story with our listeners?

Hillary:

Yeah, you know what? Well, one thing I'll say before I, before I kind of jump into that aspect of it was, I also really love how different our freelance journeys have been, even though we started around the same time, and we started very similar businesses. I really love the fact that we both get to share our stories kind of side by side, because it just shows that, like, your entrepreneurship journey is your entrepreneurship journey. And it's going to look like. What it needs to look like for you. Right? And so, I, I just kind of love that. 2 of our top 5 episodes from the 1st year are both various aspects of our story. Like, I think that also is, really. Something that's kind of cool. now what was it like to tell that story? This is actually a really fun question for me to answer because when we recorded that episode, I had just started working with that client. And so it was a little bit scary and vulnerable for me to share that story. because there was a lot of, Parts of me that were like, what if it doesn't work out with this client? Like I've never built a team of this size before. Like, you know, there was, there was a lot of scary things. And of course, when, when one client comes to you with that amount of revenue, at least for me, it was like, okay, I don't want to get used to this because what if that client leaves? Right. And so now at this point, it has been. Six or seven months since I first started working with that client, eight months and something really, really cool has happened. So, um, I worked with that client for several months. We did really, really great work with that client and it was such a fun project. And then, because of things changing in the content landscape and things like that, we kind of ramped work down with them a little bit, but instead of losing revenue and having to go back to something that, like. You know, was working fine before, but wasn't as much. I've actually ramped up my revenue doing work with other clients since then. So it has been just this incredible period of growth for my business. And like, it just has opened so many other doors that wouldn't have otherwise been opened, um, since I had that experience. So, I really loved recording that episode and I loved every moment that's come after, that experience as well.

Kristin:

You know what's super fun about this, too, is I remember recording this episode with you and asking you some questions about this, and one of the things that you had said on the episode was, you know, if I would have thought about this, You know, a handful of years ago, five years ago, when I was still in the classroom, if I would have somebody would have told me, you know, hey, and in less than five years, you know, you're going to be bringing in from one client working for yourself a 20, 000 in revenue per month. would have never believed them. Which is like, yeah, of course, most of us would never believe that, right? That is just a wild, wild thought, but it's such a testament to just keep, you know, continuously saying yes to things that scare you or put you out of your comfort zone a little bit or things that you kind of don't think are that possible but kind of still chasing that Dream and keep going in that direction. And all of a sudden you turn around and kind of like, there you are. so this episode is just amazing to listen to. If you are somebody who's like, that sounds amazing for Hilary. I don't think that'll ever happen for me. Listen to this episode and then keep taking small steps in this direction. Because if we can do stuff like this, Any teacher can do stuff like this. It's a, there is no secret sauce. There's nothing that we have that, other teachers do not. It's really about putting one foot in front of the other, upskilling a little bit, and then just getting out of your comfort zone.

Hillary:

I, um, just want to say one more thing about this. Hillary did not think this would ever be possible for Hillary, even in the moment that it came, that it fell in my lap. So, um, it's such a testament to, you have no idea what's possible for you. If you just like, start taking small steps towards the next iteration of what you want your life to look like. so I think this takes us. To our final top five episode, which is actually the first episode that we ever recorded, um, which doesn't surprise me that it's in our top five. Cause I think it's where a lot of people start when they find our podcast. Right now, Kristen, can you remind me? Obviously, we, we published that episode on June 10th alongside your story about tripling your salary. What, what is the name of that episode?

Kristin:

Yeah. So this is episode number one, published June 10th, like you mentioned, it's called Helping Teachers Explore the Potential of Online Business.

Hillary:

I have some thoughts and feelings about this episode. Do you have any thoughts and feelings about this episode?

Kristin:

I'll let you kick, kick us off.

Hillary:

Okay, my thoughts and feelings are that when I go back and listen to this episode, which I've only done 1 time, is I actually kind of cringe a little bit because We were so new to podcasting at that point and we didn't know what we were doing and I remember you and I really kind of agonized over, like, do we need a script? How do we write a script for a podcast episode? We don't want to sound like we're reading off a script, you know? And I just think that from, from that day that we recorded that episode to now, you know, a year later, We have learned and changed how we podcast so much in all of the best ways. And so while I think that the message of that first episode still rings, totally true. We still believe everything that we said in that episode. It's, it's core to who we are. There's a little part of me that wishes we could go back and redo it. but with that said, I was at a conference last October. And I was sitting in a room, um, it was a panel presentation of some of the most successful podcasters in the finance industry. 1, in particular, Paula pant, who is the host of the afford anything podcast. She's a legend in the finance industry. she said. Your first few podcast episodes will make you absolutely cringe. And that is a badge of honor. Like you have, whenever you're starting something new, you have to do the messy iterations. You have to do the first iteration so that you can then learn from those and move forward and things like that. And she's like, not only will it be your first few episodes, but then it will be your entire first year of podcasting. And then it will be, you know, Your entire first three years of podcasting, because you will just continue to grow and evolve and get better and better and better. Um, and I, and I can really see that playing out for, for me with our podcast.

Kristin:

Yeah, and I love how you're drawing this parallel between not just like podcasting, but and like how we feel about our very first episode, but but also doing anything new, right? Um, I can say the same thing about my first year in business, you know, or my first client, or my first client project, or my first website, um, every first thing that you do, what definitely has that like newness to it. You know, you don't really know what you're doing. Uh, that's okay. and I think that's just such a great lesson to carry into starting a business. It doesn't have to be perfect. It just has to exist. And then you can iterate on that and grow and grow and grow. And then sooner or later you look back. Yeah. And you do probably cringe a little bit of the first iteration, just like we're doing about the first podcast episode. And in the same exact vein, it makes it all that much more special, right? It's like, aww, it was that first episode and, you know, we were reading off of a script that we wrote, you know? There is kind of this, this innocence and sweetness to just kind of like putting yourself out there and just kind of like going for it. And that's admirable, I think, in any situation.

Hillary:

Yep. I have to share one other story from this experience. You know, we published our first 2 or 3 episodes at the same time, I think, and I can't remember what episode, This happened in, but one of your friends, I think, reached out to you and was like, Oh, love your podcast episodes so far. Like they're really great. I also love the mistake you left in at the end of, you know, and you and I were just like, Oh, that was so unintentional. We didn't mean to do that. So of course we went back and edited it out and then re uploaded the episode and it was just, it's so embarrassing,

Kristin:

I honestly cannot imagine how many mistakes are in all of these episodes just because I mean, for anybody who's listening, like, this is a full, like, passion project DIY situation. Like, Hillary and I. Think of the episode topics, record the episodes ourselves, edit the episodes ourselves, upload them ourselves. Like, we do, we do all of the things for the podcast, and there is inevitably going to be some mistakes in there. And I, just for like, sheer fear of like, I don't want to hear my voice, don't listen back to the episodes unless they're there. Like, there are some exceptions, but, um, yeah, if you're listening and you hear something in the episode, like, go ahead and give us a nudge, because it's just a mistake.

Hillary:

Yes, we will be more than happy to edit and re upload because we're, like Kristen said, we're doing all of this ourselves, um, which we kind of love. I mean, we have, again, learned so, so much and I'm just really excited for everything that's going to come in the next year of podcasting and what we might learn a year from today.

Kristin:

Yes, I cannot wait for that. Well, this has been so fun just to kind of look back and recap our topics. Five episodes from the year, and we are so excited to continue putting episodes out this next year and to continue interviewing teachers who made the leap to freelancing and entrepreneurship and to share more of our own stories with you all. thank you so much to all of our listeners, and we'll catch you next time. On the next episode of Teachers, make the Leap.