How to Build a Joyful and Sustainable Teaching Business - 5 Common Teaching Business Mistakes

In this episode, Rachel shares five common mistakes teachers make when starting their own teaching or tutoring business and how to avoid them. This episode offers practical insights on aligning your business with your passions, understanding your ideal students, and building a sustainable, joyful teaching practice.

Chapters
00:00 Common Mistakes in Starting a Teaching Business
02:14 Understanding Your Ideal Student
04:21 Creating Products from Passion
06:29 The Importance of Pricing
09:01 Authenticity Over Formality
11:07 Designing a Life-Supporting Business

Resources

Podcast Episode on Pricing Strategies: "What Your Pricing Says About You and Your Business" from April 27, 2026

Transcript

SPEAKER_00 0:01

Welcome to the Teacher to Entrepreneur Podcast. I'm your host, Rachel Siccioni, former classroom teacher turned entrepreneur and mentor to educators building their own unique teacher businesses. This is a space for teachers who are curious about alternatives to the classroom, exploring private practice and other multifaceted work, and for those who want to know what success can look like beyond the classroom. I'm glad you're here. Now let's get into today's conversation. And that's what I want to talk about today, as well as give you some guidance as to what you should or could be doing instead. So mistake number one is starting with your resume instead of your ideal student. Here's what I mean by this. When teachers start thinking about their business, the first thing that they do is think about what they are qualified to do. But they're thinking about what they're qualified to do based on their certifications or their experience. And the problem with doing this is that you're looking at your employability based on what your employability for a school would be, instead of looking at what your ideal student needs and whether or not you're qualified to meet those needs. So that's a big shift that I want you to make when you are beginning to conceive of your business and you're thinking about all the different layers, whether it's your marketing or even how you name your business, and when you're looking at the menu of services that you plan to provide or offer in your business. So instead of starting with your resume, starting with all of the things that you would put in your job application if you were applying to another school, I want you to start your thinking about your ideal student and the problems that they would be having, and then how you could help them overcome those obstacles and struggles and challenges that they have. And that is a really great place to start, not just when looking at your own abilities and what you are qualified to do and capable of doing. It also allows you to speak directly to your ideal student and their lived experiences rather than confusing them with a whole bunch of edu jargon that they aren't necessarily going to be able to make sense of. The fact that you have all of these different certifications and experience and these different levels, that doesn't make a lot of sense to a lot of most people who are not in education. That doesn't make a lot of sense to people that are outside of the education world. The second common mistake that I see teachers making when starting their businesses is creating products, services, offers from what they think will sell instead of what they really love to do. And this is problematic in a couple of ways. One, what you think is going to sell doesn't always sell. In education, we see problems and solutions in ways that most other people don't. And so when we're looking at some of the biggest struggles that our students have and we're thinking about the different solutions, we're looking at it from our point of view. And that's not necessarily going to be recognizable from your parents' or ideal students' point of view. So you really need to be in their shoes in order to talk to them about what they are seeing. So that's one thing. The other part of it, though, is I've seen a lot of teachers create businesses, again, based on what they think will sell. And sometimes they're right. It is things that they that will sell, but it's not the things that they wish they were doing. I think a lot of times when I sit down and talk with teacher business owners, they are more motivated and driven by what they are leaving, i.e., the burnout, the stress, the unrealistic workload. And so they just create something that's like out of need, out of the need to get away from that, instead of creating something that's based on what they want to move toward. And that's why I tell all of my clients to think about what they really love to do. Think about when we're in the classroom and we have all of this genuine enthusiasm and excitement for that particular lesson. And the students can't help but to get caught up in our enthusiasm and our excitement, even the big kids, even the high schoolers, even college students. And so when you are creating a business that is based on the type of thing that you love to do and the way that you love to show up for your students, and in a way that you are passionate about showing up for them and helping them, that enthusiasm, that joy comes. It comes through. It comes through in everything. It comes through in your marketing, it comes through in your consultation, it comes through when you talk about your business. And it's very attractive. The your ideal student and their family members can't help but get caught up in that excitement and feel that as you're coming through. So that's one big side of it. And why I really push joy. I talk about joy a lot and why it's an essential part of your business. That's what gives you the energy to keep going. That's your renewable energy source as you're working in your business. And sometimes it's not always fun and glamorous. You know, it's just like teaching in the classroom, you know, working with the students, oftentimes, not always. I know we're seeing more and more behavior issues in classrooms, but when it's good, the actual teaching part, the actual face-to-face part with our students, that's the fun part. That's the life-giving part of teaching, not all of the back end stuff that goes into it ahead of time. Sometimes that can be enjoyable too if you happen to like planning like I do. And so there are less glamorous, less fun tasks to business ownership as well. But if you really love your business as a whole, the whole way through, and everything that you get to do, that's where you find the energy to do the parts that you don't love so much, like social media content creation. I don't know any teachers that are like, yay, I love this. Actually, that's not true. Sue, I see you. Sue actually is really good at that and she loves it. She has so much fun with it. But it comes through in her social media content how much she really loves what she's doing, why she's passionate about it, and the different ways that she goes about helping to make her content accessible to her learners. So by creating something that you don't necessarily love just because you think it's going to be more marketable, you are setting yourself up to have a business that you don't really enjoy showing up for. And that's a recipe for burnout. I mean, yeah, it can be better, a lot better, than what you're leaving, but it doesn't tend to be as successful. And mostly because you're not going to be able to bring the same heart and energy to it. The third most common mistake, underpricing. And I did a whole episode about underpricing. So I'm not going to dive super deep into that one here. But with pricing, underpricing in particular, two different things can happen. One, you completely fill up your schedule and you are working yourself back into the ground and barely getting your needs met. You schedule a student into every possible moment you have, but then that doesn't leave much time for the back end of your business. And you're so tired you don't want to do that. And it starts to feel very classroom reminiscent as far as the burnout level is concerned. So that is definitely not what we want to be accidentally recreating again. And I know I just talked about that recently too, is how if we're not really intentional in the front end of our business about what we're building, why we're building it, and who we're building it for, it is almost, I want to say it's almost impossible. I don't think it's impossible, but if you're not really mindful, it's more than likely that you're going to rebuild what you are already accustomed to and put yourself right back in that same setup for burnout. So that's one possible outcome. The other possible outcome of undercharging is that you are communicating such low value to what you have to offer that nobody wants it. Even though you know how great it is, it's kind of like that, you know, free chair on the side of the road. People are wondering what's wrong with it. Why is it there? Is there really, can they get a lot out of it if it's only free? And by undercharging, that can be what you are communicating to people. I had somebody that I had a consultation call with that they're, they said, I keep lowering my price and nobody's coming. And like, it's because you're communicating that you're not worth their time. You know, we we live in uh a society where we feel like we get what we pay for. And if a bargain looks too good to be true, then we keep going or we wonder what's wrong with it. And like I said, I had done a whole podcast episode just about pricing. So you can go back and look for that. I'll ask Mary to put in the show notes that what episode number that is so that way you can get to it more quickly. Mistake number four, trying to look quote unquote official instead of showing up as a real person. I totally get this one because I I kind of did the same thing when I first started My Friend You. I thought that in order to be taken seriously, in order for clients to trust me, I needed to look like a business. I needed to look like something more recognizable, like a learning center or a business or just really like a business instead of like a teacher. And what I found is that that's flawed logic because when it comes to who we want to trust our children with, we would rather trust them with a person than with a business. We, especially in today's climate, I find we are so used to businesses not actually caring about their consumers that we have more trust in people than we do in businesses. And that makes sense. So instead of trying to look like something other than what you are, look like, you know, the owner of this huge, successful learning center type of business, look like what you are. Present yourself as who you are, a dedicated, educated, professional teacher with years of experience and a passion for helping a specific type of student. And then talk to those people and let them know that you are there for them, that you see them, you see their struggle, and you know how to help them. And that is your specialty. And by talking to them like a person, you're giving them the opportunity to see you as a person. And that's who we really want to work with. We're seeing more and more of a move to wanting to work with small businesses who actually care about their customers, who care about their clients. And when it comes to choosing people to work with our children, that's what we want. We want people who genuinely care about them and care about what they do and care about the experience that they're having. Customers don't want to be a number. We don't want to be a statistic anymore. We want somebody to actually care about our experience. And as money becomes more and more of an issue for us, where we're becoming more and more intentional with how we spend our money and the types of things that we invest in, we're just pickier about how and where we spend our money. And last but not least, building a business before designing the life it needs to support. And this is really big because again, if I go back to that teacher that underpriced and completely filled up their book, even if you're pricing appropriately and you fill up your schedule with every possible moment that you can see a student, do you have time for the back end of your business? Do you have time for the reasons that you left the classroom in the first place? Do you have the time and energy left for your family? Do you have the time and energy left to volunteer in your kids' classrooms? Do you have the time and energy left to go away on long weekends with your partner? Do you have the time and energy left to invest in your own well-being and not just your preventative care doctor's appointments, which are very important, but in just making sure that you are living a satisfying, well-rounded life. So I always tell my clients, let's think about the life that we are trying to build. And then how can the business support that? Look at the whole vision. Look at your what you want your general, your average day to look like. I firmly believe that your life is made up of a collection of days. And so your day-to-day life matters. Your Monday through Friday life matters just as much as your weekend life matters. Your life in January matters just as much as your life in June. And so, what do you want your days to look and feel like? How many hours a week do you want to spend working, even in a business that you love? How much time do you want to have? How much time and energy do you want to have for the other parts of your life? And then put all of that together and plan that accordingly. You know, look at all the different pieces of your life. I actually have like a mind mapping or graphic activity that I do with my clients, where we look at all the different layers or categories in their lives, and we talk about all of the different pieces that are in there. And then we look at our 24-hour day and we look at our week and our month. And we're like, okay, so how do we fit in the amount of time for each of these things that we want that we want to have in there? And then we figure out, okay, so these are my hours that are available for working. And then these are the hours that are available to be client-facing. And then how do we price from there? You know, we do have some basic guidelines, but when we are looking at building a whole vision for the entire life as a whole, and we're breaking it down into the different pieces, we're also looking at, okay, what are our income goals? What are the number of hours available for working? And where do those intersect? What, what does our price point need to be? And then how close to national averages or the cost of living in our area? And then we we look at it from that way instead of starting with, okay, I need to make as much money as possible so I can get out of the classroom. Because that kind of thought process, while it makes a ton of sense, is also building from what you are running away from instead of building from what you want to be working towards achieving. And in order to create what we want to create intentionally, we need to be looking at what we are working towards, not what we are working away from. And I'm actually working on putting together a kind of a free mini workbook specifically on these five things. It's not quite ready for you yet. But as soon as I get it all put together, I will make sure that it is put out for you. So if you are not already on my email list, please see about doing that. I only email about once a month. Or if I have something new that I'm launching or sharing that I have created for you to help you, then I put it out there. But I'm definitely, I know you're busy. I'm also very busy, and I don't want to spam you or fill up your email inbox with a whole bunch of things that you don't need to look at. Thank you for tuning in this week. I hope you have a wonderful week. And if you are not already on summer vacation, I hope that you will be soon. Thank you for listening. If today's episode resonated with you, please share it with a colleague or leave a review. This helps the conversation reach other teachers who may need it. You can learn more about what I do and how to work with me at theprivatepracticeteacher.org. Best wishes always.