Episode 24 From Teacher to Solopreneur with Cat O'Brien

Christina: [00:00:00] Welcome to episode 24, From Teacher to Solopreneur with Cat O’Brien. Teachers can create meaningful businesses as solopreneurs, using education in ways that causes a ripple effect of change in the world. Today I welcomed Cat O’Brien to talk about her journey from teacher to creating her own business as a solopreneur.

Christina: Cat is a curriculum designer who’s on a mission to raise the bar for online education. By developing programs rooted in evidence based and innovative strategies, she helps her clients cultivate student success and become go to experts in their respective fields. In this episode, we talk about Cat’s journey from teaching to a full-time solopreneur, how freedom and flexibility are not the only requirements to feel successful.

Christina: And how meaning, purpose, and the quest to deliver life changing results are essential to building a sustaining business. We coached on the common fears of being seen and visible when creating a new identity, and how the fear of being salesy can often impact educators and other helping professionals [00:01:00] when starting businesses as solopreneurs.

Christina: Find the full episode and transcript at richlysuccessful.com/24.

Christina: You’re listening to Richly Successful Solopreneur with host Christina Renzelli. Helping you learn to trust your gut and follow your heart so you can set your business up for success. Podcast episodes will help you build better business relationships, network in an authentic way, and learn to love selling as you grow your business beyond the time for money model.

Christina: Subscribe to this podcast so you don’t miss a thing.

Christina: Hi Cat, podcast.

Cat: Thank you. I’m so happy to be here.

Christina: I’m so happy to have you. I’m also excited to hear your story of how you became a solopreneur.

Cat: Yeah, I, I’ve been binging, [00:02:00] um, your past episodes and I love listening to, it seems like everyone has a different journey to becoming a solopreneur, um, and I just love seeing all of the different paths people have taken.

Christina: Yes, thank you. It’s, I, that’s why I like doing these episodes because it shows all the, the fun ways people can create their own businesses.

Cat: Yeah, definitely.

Christina: So what’s your story? How did you decide to become a solopreneur?

Cat: Yeah, I, you know, when I reflect on this, it really is a winding path for me. I, um, I used to be an English teacher, so I taught high school English for years and really loved it, felt Super fulfilled.

Cat: Very happy with, with most of my life as a teacher. Of course, um, teaching comes with a lot of, a lot of stuff that isn’t super lovable, but for the most part, I was really happy until the pandemic hit. And, you know, I think if there’s any educators out there listening to this, they’re like, [00:03:00] yep, I know where this is going.

Cat: Um, so I live in Chicago and here we were remote for like the whole time, right? Like the year, like the, the end of the first year and then the entire second year. So I had not been in my classroom for what felt like a lifetime, um, by the end of the pandemic. And so much of what I loved about teaching, like the relationships with my students, the mental stimulation, the challenges, they’re like really fulfilling pieces of actually seeing students learn in front of you, they were all just gone just overnight.

Cat: And the struggle to do online learning and all of that, we all know that story, but you know, at that time about halfway through the second, well, like the, the first full year, anyway, A little while after we went remote, I was just going mad. I, I was like, I don’t feel fulfilled. I don’t feel challenged. I [00:04:00] frankly felt a little bored, um, with the way we were learning online.

Cat: And so, um, you know, we all picked up hobbies at that time. I never got into bread baking, but I did. Get into copywriting because I saw like an ad online, someone was like, Hey, do you like to write? Do you want to make money online? And I was like that sounds like a fun thing to learn how to do right now with all of this extra like You know mental and emotional energy that I have pent up and so that’s how I started that’s how I first was introduced to this whole like world of online business and At first it was totally just going to be A little project, a little COVID project, um, just wanted to flex some mental muscles and then, you know, forget it and go back to the quote unquote, regular life.

Cat: Well, my husband and I actually decided to, he was a teacher at the same school and we both quit those jobs at the end of like the end of the school year, spring 2021 and decided to travel. So we put all of our stuff in storage, left the country for a [00:05:00] year and. Um, we had both built up savings at that point, so we were mostly living on savings, but I kept copywriting because it was so easy to do, um, while we were anywhere in the world really.

Cat: So, um, continued to copyright for mostly, like, You know, like pocket money. Like it was, I was not making big bucks while we were traveling because I didn’t want to prioritize spending the hours to do that. Um, but got to continue to like live that life. And then when it came time to come back to the States and we both started applying for quote unquote real jobs in education, I had kind of had a, I had had a taste of what it would be like to not You know, go back.

Cat: Yes. And I was like, wait, I just, I’m like applying to these jobs and I, my heart was not in it, which was so, such a surprising experience for me because being a teacher, I think this is true of a lot of, Service professions. Like I know I’ve talked to a lot of nurses who feel similarly, like it was such a [00:06:00] big part of my identity and discovering that didn’t really want to go back at least for now.

Cat: Um, it took a while for me to kind of come to terms with that, honestly. And so I eventually I did and, um, stayed. You know, with the freedom, I work from home in my sweatpants and continued copywriting. And then the second part of the story, I’m sorry, this is a little long winded answer. It’s good. Okay. Um, so as a copywriter, I was mostly working in launches.

Cat: So people who have online courses or group coaching programs and they launch periodically throughout the year, those. Like launches take so much marketing and copywriting and that was kind of my specialty as a copywriter. Part of that process is sourcing social proof, testimonials, case studies, talking to their students so that we could highlight and celebrate their student success and all of these juicy student transformations that they promise on their [00:07:00] sales page.

Cat: And it just wasn’t always very easy. More often than I expected. We were kind of grasping at straws, searching for the needle in the haystack for that, you know, a couple outlying students who really had these like phenomenal transformations and that we could highlight on the sales page. And I had like a, a few problems.

Cat: One, I was like, this doesn’t feel super transparent or. Even a little ethical, like we’re, we’re acting like everybody gets these transformations when really it’s only a couple, right. And people out of the whole group. And that feels wrong. And then the other piece was like, why, why aren’t more people, weren’t more students having success in your program?

Cat: Because. The business owners that I was writing for, they were really successful. They had been, you know, really successful as one on one service providers, and for some reason that wasn’t translating to their group education programs, whether it [00:08:00] was group coaching or an online course. Um, so. So it was

Christina: like the teaching part was missing.

Christina: Yes. The way they provided their lessons wasn’t reaching the students in the most impactful way.

Cat: Exactly. Exactly. And so I started digging in to their actual courses to look at how they were set up, what, you know, if you’ve got videos, what do those look like if you’ve got worksheets? So really looking at the curriculum design and seeing that it was, well, for lack of a better word, lacking.

Cat: And I, you know, I think there is this false Narrative in the online business space where if you are a successful one on one service provider, you can package up that expertise. And sell it for passive income. And that’s not, sorry, that’s not the full narrative, but the idea being that you just have to record what you know into a video and sell it.

Cat: [00:09:00] Right?

Christina: Well Cat, I think, I’m a former teacher too, so teaching is something that not everybody knows how to do. It’s a skill that takes so many years of practice and experience. So you’re right. It’s not just easy to throw up a course and. Say, oh, I can teach that.

Cat: Yeah, I mean, there is so much that goes into creating a strategic learning environment.

Cat: And, um, thinking about, so my big thing now, so I don’t know if I’ve said this, at this point in my business, I am a curriculum designer for online courses. So this is what I do now. I’ve moved, I still copyright, um, but the majority of my time is now spent curriculum designing, which I love. And the biggest.

Cat: shift that I try to help my clients in the curriculum design space make is most often I see people come to me and they’re, they’re telling me about the content they want to teach. And we have to flip the script and [00:10:00] think about what is. What are the learning experiences that your students need to have?

Cat: You can’t design a course just about what you want to say. It has to, you have to think first about your students. What experiences do they need to have to actually make that growth? Um, because you as a coach, obviously know that it’s not, you can’t just listen to someone else talk and then woohoo, the magic has happened.

Cat: Like you have been transformed. It just doesn’t work that way. So, um. So yeah, I just I saw this gap and I’m I’m I’m working with folks in the online space to create better online courses that get their students really. meaningful success, whatever that word success means for the each of these courses, which just has that such a good ripple effect in that you, of course, the number one and the number one, like positive impact of this is that your students actually make the growth that you want them to make.

Cat: But the other piece is that. All of a sudden you, you have a like flowing testimonials, [00:11:00] your sales cycles are easier. You’ve got this, you know, audience that raves about you and your program. You become known as this go to mentor. So it just kind of has this snowball effect where it’s so hard sometimes being an online entrepreneur.

Cat: Um, and when. When you’re, when you’re given these pieces that make it easier, like curriculum design, it makes it easier for you to do your job well, and then the momentum kind of takes off from there. Yeah.

Christina: It’s so important. And I love how you are still a teacher. You were like, I love teaching. I love connecting with the students.

Christina: And that was the part that was missing during the pandemic. And you use that to create this business. With that need to connect with students. I just love that story.

Cat: Yeah. Yeah. It’s been such a wild and unexpected ride. And I think that’s, I mean, I never, never imagined being here where I am today, where I am a solopreneur and like running my own [00:12:00] business that feels so far beyond what I could have imagined for myself even five years ago.

Cat: And, um, it, it does. It just, there’s so, you know, people always say, I feel like people often talk about like, okay, you, no matter what your life has been, you have all of these skills and you can use them for your next, whatever it is, stepping stone or journey. And this feels like a moment for me where things are really aligning and I, cause I do have this passion about education and I’m like, I can’t go back to, I would say nine, I was going to say to the nine to five, but as a teacher, it’s not nine to five.

Cat: No, it’s much more than that. So, um, yeah, it feels like a really. Special, just like alignment of what I feel passionate about.

Christina: Yes, that’s amazing. I loved your story. So, you’ve kind of answered all the questions I was going to ask you. I was going to ask, like, what motivates you, but I feel like you just explained that

Cat: so well.

Cat: Yeah, I think, I did explain it, and I think the [00:13:00] biggest piece for me, like, so, I will add here, And I don’t mean for this to sound, I don’t know if snobby is the right word. So I got to a point with copywriting where I was comfortable. I mean, I was not making, like I wasn’t making six figures or like huge, you know, buku bucks, but I was comfortable.

Cat: I could pay rent. I could, you know, I was living well in my sweatpants. Um, and I really missed. education. And so it was a weird, it was another like weird moment for me where I was like, I, I’ve worked so hard to get to this place and I thought that this is everything I wanted. And then I got here and I’m like, okay, something’s still missing.

Cat: And I don’t know, maybe that’s a forever ongoing journey as a, as a solopreneur, I don’t know to be determined. Right. But it has been eyeopening that I’m like, it’s more than just. Time and financial freedom for me because that’s what I got with copywriting now. It’s like the underlying like [00:14:00] passion which is for me education yeah, the

Christina: passion and how you can make a difference in the world and Create something with all those moving pieces.

Christina: I think that is what a lot of people find is the true motivation

Cat: Yeah, which is not Easy.

Christina: Oh no, it’s not. It’s a journey of, like, the soul, I think.

Cat: Yeah, yeah, and it’s, um, it’s so simple when we talk about it, but the reality is it’s really, well, for me, it’s been really hard and really messy.

Christina: Mm hmm. Yeah, it definitely is not just like, step one, do this.

Christina: It kind of takes all the detours of any kind of journey would.

Cat: Yeah, definitely. So

Christina: how do you, how do your clients work with you? How do you, what would that look like?

Cat: Yeah, that’s a good question. So it depends on, there’s really two main camps. One camp is the, [00:15:00] um, business owner who is building a course from the ground up.

Cat: And The value that I bring in that space, um, in the beginning is helping them organize because so often People are like I have this brilliant or this great or this I think it could be great idea for a program But I have no idea where to start. That is a really common thing that I hear It’s like I know I want to teach people this I just I don’t even know where to begin and So, uh, what I do is I help them, if any educators out there might know, well they will know the term backwards outline, right?

Cat: So we start with the very end in mind, which again, it does not come, it’s not an intuitive thing for you to, to do if you don’t have that background in education. And so we work on getting a full blueprint of start to finish, what do they need, because When designing a course people stuff way too much into it.

Cat: So I help them not just Outline the course, but make sure they’re not putting too much into it. And then [00:16:00] we we go step by step forward from there So it’s really like it’s hand holding start to finish That’s camp one camp two Is the business owners who already have programs and they’re not seeing results and they’re like maybe it’s everyone drops off after module three or no one comes to the live group coaching calls or they’re just having a Sticking points, and they don’t know why.

Cat: Then I come in as, um, an investigator as a problem solver. We look at what is working. We restructure, redesign, um, their program so that it responds to what their students need and just kind of fixes some of those problems.

Christina: So, how do they find you? How would we be able to, how would listeners be able to reach you if they need your course magic?

Christina: Course magic.

Cat: Uh, I have a website. It is still more copy branded, so it’s Catobryancopy. com, and it’s Cat with a C, Catobryancopy. com forward slash learning. That is where… The, [00:17:00] the course magic happens. I’m also on Instagram, cat O’Brien, but it’s cat O underscore Brian. So where the apostrophe would be, it’s an underscore.

Cat: Great.

Christina: Well, I’m sure I can list those in the show notes for the listeners so they can find you. So what have been your biggest challenges as a solopreneur?

Cat: Okay. So from day one, from, for me, it’s. It’s visibility, I think, uh, you know, coming from an education background and I, I’ve, I have a lot of solopreneur friends who are similar, even if they’re not in education, but coming from a place like, again, like I, I see a lot of parallels between teachers and nurses, and at least within my friends where.

Cat: We, you know, we don’t necessarily have to, a lot of the business stuff is taken care of, right? Mm hmm. You don’t have to negotiate, you don’t have to do all of this stuff that people in business learn how to do. Right. And you get a salary. Yeah.

Christina: You just go to, go to work.

Cat: Yeah. And do your job. And [00:18:00] another piece, so that piece, it was a learning curve for sure.

Cat: And I’ve dedicated myself to it and I feel decent about it, but the piece that I’ve, I feel like I’ve tried and failed repeatedly is getting visible. I have some kind of, I don’t know, I guess fear around showing up and people actually seeing me. And. In the times where I do show up and people see me, I have like this vulnerability hangover where it’s like, Oh my God, I need to go like lay in bed for a day and not see another human being and pretend like nobody knows I exist.

Christina: Yes. Like it takes all that energy to be seen that you then have to go recharge it, recharge that battery. Well, is that what you’d like coaching

Cat: on today? Yes. Yeah, I think so. Okay.

Christina: So you, so

Cat: what would you like

Christina: to change with this?

Cat: So [00:19:00] I, I mean, I’d like to change how I feel like in the moment and afterwards of being visible.

Cat: I, you know, I think for me, this is this. Pain point is becoming stronger the more I do curriculum design work, because as a copywriter I, if you have an online business, you need copy, whether or not you’re in a place to hire a copywriter, it was easier to pitch them, right? Because I knew, and it was a more of a done for you service as a curriculum designer.

Cat: I can’t do everything when they’re, when, you know, my clients are the experts themselves and this is their course. So pitching businesses. For a curriculum design, um, service isn’t, it’s just not as effective as it was for copywriting, which means I am trying to focus on more inbound marketing, getting visible, like, like on this podcast.

Cat: Um, and pitching podcasts is a focus of mine right [00:20:00] now and, um, guest workshops and guest blog posts and all of that sounds so great in theory, but it is. It is, it always gets pushed to be the last thing on my to do list, which means it almost always gets pushed off the to do list. And I’m like, oops, guess that didn’t happen.

Cat: It’s like my subconscious is like, like, we don’t want that.

Christina: It’s hiding. It’s trying to hide. Yeah. Yeah. So what feelings come up when you feel this visibility,

Cat: uncomfortableness, fear, embarrassment, um, I think, I think it’s a fear of judgment and yeah, it’s just like a, like, Oh my God, I’m cringing so hard that people are seeing me even when I feel like objectively. I can look at whatever that thing is and think, I didn’t do [00:21:00] anything super embarrassing. I’m just there.

Cat: I’m just visible. And I still cringe.

Christina: I feel like this happens with so many teachers and nurses, like you said. It’s the, the helpers, the helpers have this feeling, who, I guess, who are you afraid of seeing

Cat: you? Yeah, I know. That is the question, isn’t it? Um,

Cat: who am I afraid of seeing me? Who are

Christina: these judge, judgmental, critical people that you’re afraid of? They see you out there creating curriculums for students. Who are they?

Cat: It’s, it’s my, it’s not, so I want to say my peers, and I don’t mean Like my peers in business your high school peers. It’s like heist It’s like when you get on Facebook and you see someone from high school, you know, whatever it is there and it’s it’s there Selling something or [00:22:00] something on Facebook and I I don’t know I don’t get on Facebook anymore but that’s what I think that’s what the image that comes to my mind is and feeling like Yeah, I’ll be judged and I When I separate myself from that moment where I feel like they’re judging me I don’t care what they’re doing and I don’t and I know that I don’t really care what they it’s most of these people I don’t care right like most of these people.

Cat: I’m afraid of judging me. I never really speak to anymore Anyway, right and I know that but um I just don’t know how to get over it. Well, I think

Christina: that most people have this. It’s because our brains develop at a ti The limbic system is developing when we’re in high school. And this is all about the social part of our brains.

Christina: So this is how we relate to people. So when you’re in high school and middle school, You are being very vulnerable and you’re kind of like creating that identity. So it’s almost like you feel like you could [00:23:00] die if someone else from high school thinks something bad about you. It’s like a true feeling that your body thinks you could die.

Christina: So the only thing that I’ve found that works is make a list of those people and go through one by one and say, do I really care if, I don’t know, Jane from high school thinks that My curriculum designing career a business is silly or whatever like really break it


Cat: You know what just stood out for me when you said that too.

Cat: So sorry. Yes, right like and I think for me writing is always It’s always helpful and seeing some, seeing it on paper is like, it just changes the way my brain, my brain understands it. Right? So that is, that sounds very helpful. I think the other piece when you said that, you said the word career and I, I think, [00:24:00] um, This is also about me taking My career more seriously almost.

Cat: Mm-hmm. . And not like, it’s some, like in high school, when we were in high school, there were kids that were in, I think it was, I don’t know, everyone said it was a pyramid scheme that made it, it’s just been like high school gossip. But they were like selling like, like monster, not monster, but some energy drink.

Cat: And they were all selling it on ca, on high school campus or whatever. And I was always like, you guys are just trying to get like beer money or whatever. . Mm-hmm. . And I, I think, I’m afraid that that’s how I come off, but this also isn’t, Just for beer money. Like this is my career and I am skilled and I am making a living off of this.

Cat: And I think that I need to see myself a little bit more seriously in that way. Um, I feel like that would help me. I think also

Christina: we tend to worry about the sales piece and being like salesy. [00:25:00] And so if you’re thinking, Oh, I’m going to sell something or sell myself, um, or something that I’m doing. Everyone’s going to think, oh, you’re, she’s just selling like the monster drinks for beer money and now she doesn’t.

Christina: Have a real career. It’s just selling things instead. That happens with the service providing. So entrepreneurs that I’ve worked with, it’s like teachers, um, we don’t have to learn how to sell until we do until we create a business. And it’s that exposure to being thought of as. A salesperson that can be really hard.

Cat: Yeah, like I said, it’s a huge identity piece that is, is not that easy to overcome. Yeah, it’s so interesting because when I was a teacher, I was so proud to be a teacher, and I still feel pride that I was a teacher, even, you know, even though I didn’t stay in the profession, I, I felt really proud of that.

Cat: And, and [00:26:00] something my husband and I have, were recently chatting about is like, As a teacher, you are basically selling your kids every day. You’re selling, I mean, your students. You’re selling them on the importance of what you’re doing. You’re selling them on doing their homework. You’re selling them on why this is valuable and why this matters.

Cat: And it’s really, I mean, it is, it is different, but it’s a similar skill, um, as when you’re.

Christina: It’s the same skill.


Cat: Yeah. So it’s really, and I, I think I’m slowly learning that it’s just all about how you frame it. Um, including being visible, like selling, yes, and also attached to the selling pieces. People knowing that I’m selling services and people knowing that I’m doing this.

Cat: Um, yeah,

Christina: yeah. We want everyone to know what you’re doing because all the students of all the courses that you’re working on the curriculum development for need what you have. Like, it’s essential, like, it’s going to change lives. [00:27:00] You

Cat: know what? I believe that. Yeah, it’s really true. And I think I need to, like, write myself a little sticky note and put it on the, on the wall behind my computer so that I see that when, in those moments when I’m like, I thought I was going to pitch a podcast today, but I’m not going to.

Cat: Yeah.

Christina: Are you going to let Jane from high school stop the students of those courses from learning what they need to know to change

Cat: their lives? Yeah, that’s a powerful way of framing it. Oh, yeah.

Christina: Yeah, I think that’s, it’s a journey that all solopreneurs have to go through, especially when you come from these helping professions.

Christina: Yeah,

Cat: that’s, it’s such an interesting piece, isn’t it? Mm hmm.

Christina: We can help people when there’s no sales involved. But as soon as you put the sales word in there, it’s like, oh, I don’t want to do that.

Cat: Yeah, it’s all, it’s kind of like, things are starting to click with the, because I, I am so happy to help people for free.

Christina: [00:28:00] And, Oh, definitely. Like, it is like,

Cat: I am always happy and willing to like, do work beyond, I mean, not, It’s I was gonna say to do work beyond scope to do work for free and I’m happy until I’m like, okay I got to pay rent this month, but you’re right It’s just it’s coming from that service profession and I think to I’m just thinking out loud now, you know as a teacher so much of My work, it’s almost like there’s baked in unpaid labor as a teacher because you do so much work out outside of school outside I mean you but yeah, it’s just it is it’s that whole piece of like I never had to sell I never had to charge for my time.

Cat: I never had to worry about People seeing me because it was just, you know, my 16 year olds every day in the classroom who I had an intimate relationship with. Well, they had

Christina: to be there. Yeah, exactly. Well, I hope this helps because I feel every solopreneur and [00:29:00] you have a gift that you are giving to the world.

Christina: And it’s in exchange for sales, basically. Because if you don’t ask for money or ask for a sale, then it won’t… You’ll have to do something else.

Cat: Right. Then you’re no longer a solopreneur because

Christina: you’re broke Right. Yeah. Well, how does that feel? Do you feel like you can get visible now?

Cat: Well, I feel like I I feel like I am closer to be to getting visible.

Cat: I think We’ll see when this podcast airs. I may have to go into a little, uh, vulnerability. Uh, coma for a day or two, but then I, I think every time I do something like this, it gets easier and I am, I already made myself a little note to put a sticky note behind my, my computer not to let Jane from high school.

Cat: Yeah.

Christina: Jane doesn’t get to decide. What you do in life. Yes.

Cat: Yes. Amen.

Christina: [00:30:00] Okay. Well, thank you so much, Cat. I really enjoyed this conversation. Thank you so much.

Thanks for listening to Richly Successful Solopreneur. Remember, you can trust yourself and follow your heart. If you’re ready to find your flow and grow your business, I want to invite you to head over to richlysuccessful.com where you’ll find more valuable resources. If you’re getting value from this podcast, please leave a review and share it with a fellow solopreneur.