This episode is an inspiring conversation for any educator feeling disheartened by the system and looking for a new path forward. You’ll walk away with practical insights, encouragement, and a clear vision of what’s possible when you take your teaching online.
Connect with today’s guest:
https://www.instagram.com/reclaimyourclass
https://outschool.com/teachers/Tara-Laczynski
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Read the transcript:
[00:00:00] Joining us today for a guest conversation is Tara, a veteran educator, business owner, and Outschool expert who’s helping fellow teachers reclaim their careers through online education. After losing her online teaching job overnight, Tara had to pivot quickly and what started as a scramble became a six figure success story.
[00:00:22] She built Mathletes, a thriving Outschool organization that combines rigorous math instruction with interactive tech and gamified learning, and has since replaced her teaching salary several times over. Through her signature program Reclaim Your Class, Tara now teaches other educators how to replicate what she’s done, designing high quality online classes, building sustainable income, and growing their own organizations on Outschool.
[00:00:50] She’s passionate about how teachers feel empowered, creative, and confident in a space where they are in control of both their time and talents. Today’s conversation is unique because Tara has a teachers pay teachers store as part of her teacher business, and she has some online teaching, so she is diversified.
[00:01:12] She also has experience hiring help, and she has hired contractors, 10 99 freelancers, and she has hired employees. And so contractors and employees are very different. This episode should not act as legal advice, but it’s interesting to hear from someone who currently has both contractors and employees as part of their teacher business.
[00:01:37] And in today’s conversation, Tara will share a little bit about the pros and cons and how you decide which one might be right for your situation.
[00:02:12] Janice: Tara, thanks for joining me today.
[00:02:14] Tara: Thank you for having me.
[00:02:16] Janice: For anyone who listens to this show that might not already know you, can you tell us a little bit about how you got started with your teacher business?
[00:02:24] Tara: So I was teaching on VIP kids just trying to make a little bit of extra side income, as I feel like so many of us were at some point. And then there was talk about changes in their education system and what they were gonna allow. And instead of kind of going down with the ship, I decided to jump to Outschool, which was the popular thing to do in that moment.
[00:02:47] Just trying to continue to bring some income into the house and four and a half years later, here we are.
[00:02:55] Janice: I have a question about timing because I obviously went on that wild journey too. Were you already like a little bit diversified and partly in Outschool and partly in VIP kid, or did you start your transition to Outschool when we saw that ship start to go down?
[00:03:12] Tara: I didn’t even know what Outschool was. I started with them in March. Everybody was already jumping ship and it was kind of like, I don’t wanna have to do that. You have to figure out what you’re teaching and I kept dragging my feet and then I felt kind of forced into the decision and just figured I would fake it till I make it and jumped in the end of March.
[00:03:33] Janice: Interesting. So you got into Outschool later than I did. I had a very brief Outschool era, but I was mostly VIP kid and then a little bit Magic Ears and a little bit Outschool and a little bit GoGoKid. And I was like playing with the percentages over time to see what was making the most money in the least amount of time.
[00:03:52] And you got onto Outschool after I had left. , I wasn’t sure the timeline of that.
[00:03:56] Tara: That’s odd. I didn’t realize we were that different.
[00:04:00] Janice: I think we all have a VIP kid era. There are a lot of listeners to this show who also met a lot of other people who are interested in the world of online business by collecting in that VIP kid space. So that’s really exciting.
[00:04:15] Tara: You have to have the T-shirt and the dinosaur though, to prove it.
[00:04:17] Janice: Absolutely. Well, and I had a whole uni collection from, uh, go-go kid and then Bonnie from magic ears, I had all the swag.
[00:04:24] So yeah, you were working from home and you were teaching from home and it was working, but you were in someone else’s marketplace and they stopped being a good option.
[00:04:33] So you shifted to someone else’s marketplace, but you were still teaching online and teaching from home. What were the big differences for people who might not know these companies well? What are the two big differences between something like VIP kid and something like out school?
[00:04:47] Tara: Uh, number one VIP kid you were teaching at the butt crack of dawn, like 3:00 AM because of the time difference. But the nice thing was that it was very hands off. You just show up, open the slideshow, teach, and be done. So in that way it was very low cost other than the lack of sleep. With Outschool, it was something that I thought was gonna be very similar and had to really learn along the way that it was completely different in that you had the opportunity to teach whatever you wanted, whenever you wanted, do whoever you wanted, um, which sounds really exciting, but is insanely overwhelming because then you have to make all of those decisions.
[00:05:29] And on top of that, you have to be business-minded. I love to teach about unicorn sparkles, but no one cares about unicorn sparkles. Or how do I create a class listing? How do I build a business model that’s sustainable? How do I keep students in my classes? How do I compare to other people? And all of a sudden it was like trying to get a Google business degree when I just wanted to show up and teach.
[00:05:55] Janice: That’s such a good point. And I think there were pros and cons to like showing up and teaching and having it be in such a small box because there were also people with kind of that victim mindset where they were like, well, I showed up and I opened slots and no one’s booking me. Oh, woe is me. And there are only so many things that you could do.
[00:06:14] And there was no guarantee that anyone was gonna sign up for your class. There were so many choices. There were like a hundred thousand teachers. There was no promise. It didn’t mean you were doing anything wrong. There were just things that you couldn’t control, and so that was good and bad I think when you compare it to Outschool, because out school did give you more choices, you could teach literally anything at literally any time of day.
[00:06:36] But there’s also some paralysis and decision fatigue about that for sure. You have a little more control, and also you are in charge of your own success and failure in the best and worst way.
[00:06:48] Tara: A hundred percent. There was a lot of mentality shift between initially feeling like I was doing the same thing and then realizing that if I went in with that mentality, that I was absolutely going down with the ship and that there was no point. So it was kind of learning with my feet to the fire and trying to figure things out.
[00:07:10] And there was a lot of accidental success. Things that I had in my personality characteristics that I didn’t realize made me a good fit for that business model. And just not having anyone to compare myself to was also a positive and a negative because
[00:07:30] you really have no idea how your business is running comparatively to anybody else because you’re very much just in this void of doing your own thing, but also being a part of a group in a lot of ways.
[00:07:42] Janice: Yeah, that makes a lot of sense. And I think you have to be very humble , if we talk about character traits that are really helpful for Outschool, I think as a business owner you have to be like, oh, I was in love with that class that I made, I really wanted the market to love it too, it’s not going to. Or I really wanna teach on Saturday morning while my kid’s at horseback riding.
[00:08:04] Well, nobody wants to take a class. I just have to be honest and humble and take the data and pivot and I think that’s something you do very well. I also think you have the appropriate amount of risk tolerance. I think there are people who came out of VIP kid that just would not have been willing to make like
[00:08:21] six classes, throw spaghetti at the wall, throw them out for a million times, and manage it from there. And they would start with like one at a time. And if it didn’t work, they didn’t know, should I do more, should I do less? I think there’s a certain amount of risk tolerance that you have to have to be successful as a business owner.
[00:08:38] Tara: And there was also a blessing and a curse because. At some point I was writing five or six levels of curriculum at the same time thinking, what in the world did I do? How did I set myself up in this situation? Because in a lot of ways, you’re excited that you know you’re your own boss and you have control of your schedule.
[00:08:53] But like you said, your control really only extends to what people wanna do. If you don’t want to teach at night, but everyone wants to take classes at night, well, yes, you can decide not to do it, but you’re walking away from that income and the idea of you having to earn every single dollar. Not that you don’t in a traditional job, but you have to continue to show up and be your best, and you can’t really show up and have a bad day because
[00:09:20] that might make or break it for one of your families and they might decide to walk away. And just a lot of that paradigm shift of what does it mean to be self-employed, what does that actually look like, and what type of things can I afford myself and what type of things do I just have to kind of, tolerate and adjust to, to make it work?
[00:09:41] Janice: That’s a really good point. And so you got started with Outschool, you probably started with just one or two classes at the beginning. How did you kind of transition, to be the income level that you needed? Because I believe you were teaching online full time. Is that correct?
[00:09:57] Tara: Um, yes and no. I was very much trying to figure out how to make it a full-time thing. Um, but I did not know what that looked like because I feel like, again, that traditional idea of a full-time job, is very different than what it looks like to earn a full-time income online. , My first year, which was 2021, I started at the end of March.
[00:10:20] And it was very much just trying to throw things up of what I thought would work. Throwing up math camps, trying to decide what I was interested in, I like social studies, so I made some social studies listings and trying to figure out where I wanted to settle in, and the math just seemed to get the most attention and I just kind of focused in on that and went from there.
[00:10:45] Janice: I think that’s really interesting because I think you’re willing to teach many different things, and a lot of people teach electives at first. They think, oh, this would be fun. I’d love to teach a class about X. But there are families there looking for the core curriculum to be taken off their plates for different reasons, and there aren’t a lot of people willing to raise their hand and say, oh, I would love to teach upper level advanced math.
[00:11:06] I think I would really excel at that. And so it’s nice that you were able to match with this gap in the market where that was a need for so many families.
[00:11:16] Tara: I think a lot of it too selfishly was I missed being in the traditional classroom, but I wasn’t willing to walk away from having that stay at home mom role. And this was a way for me to feel like I had success out of, like aside from catching up on laundry, like I needed something outside of those mom moments where I still felt like I was being true to myself, but also not having to deal with all of the nonsense that comes along with being in a traditional teaching situation.
[00:11:48] Janice: And I think that’s a really important conversation because a lot of times when people leave teaching, it’s really confusing. It’s not that you don’t like teaching. It’s not that you don’t wanna do it anymore, you don’t wanna do it within that broken structure. You’re just looking for a structure that works better for you, but you
[00:12:02] still would love to spend every day teaching math, and it’s really nice that Outschool has allowed that to be possible for you.
[00:12:08] Tara: Exactly. It allows you to have that freedom back.
[00:12:12] Janice: Going back and rethinking my full-time, part-time conversation. The more I think of it, you couldn’t really be full-time when you left VIP kid anyway because we were just fighting those China hours and it didn’t matter if you wanted to work during the day.
[00:12:25] If China was asleep, you didn’t have access to their students. So I wonder if maybe your first target was like matching your VIP kid income. Was that like kind of the first stepping stone?
[00:12:36] Tara: I went into it with, I wanted to make $2,000 a month. That just in my head was like the perfect amount. There was no rhyme or reason. It just felt like an amount where I would feel like I was contributing to the household. I could sign my girls up for dance or, you know, what have you, and not have to think twice about it.
[00:12:56] I just wanted to give us a little bit of breathing room, but it was very much an arbitrary number.
[00:13:01] Janice: Nice. So you knew what breathing room you needed and what that looked like, and you were like, Hey, this will be fun. Let me see what I can make happen.
[00:13:08] Tara: Exactly. It was like, oh $2,000 is $500 a week. And in my head, that felt manageable. So that was my first goal. I was gonna make $2,000 a month and I was gonna bring that extra income in and I was gonna be able to say yes to things that I wanted to say yes to, without having to think about it as much.
[00:13:28] Janice: Most of the Outschool classes pay out weekly. Is that correct?
[00:13:31] Tara: Yes. So they pay about two weeks after they run. So once you get into a consistent, um, class schedule, you get paid every Sunday.
[00:13:40] Janice: Nice. That’s really helpful for people who are trying to make progress towards a goal and stuff too. I forgot how frequent the pay is and the dopamine of that is so rewarding.
[00:13:50] Tara: it is, you wake up on Sunday morning and as much as you have the Sunday scaries, it’s payday. And that’s so exciting.
[00:13:56] Janice: So you were able to consistently hit that 2k a month goal, and were you like content with that? You had arrived, you had won the game, and you just chilled there?
[00:14:06] Tara: Yeah, it was very much like I hit the goal and I was like, wow, this is awesome. And I really didn’t have that urge to do more. It just became, oh, more parents are asking for more classes. Oh, I could add a class here or there, or. Oh, this third grade group is finishing and they want a fourth grade class.
[00:14:26] You know, I could throw a fourth grade class together. And then just continuing to make those decisions that felt right in the moment. And then it kind of got to the point of like, oh, I have blasted my goal out of the water. Is this normal for this situation? Because again, you don’t really have anyone to compare it to.
[00:14:46] And it’s not like I can show up and be like, Hey Janice, how much did you make this month? Not a lot of people wanna have those financial conversations in general. Um, so it was very much like an island of my own. Just kind of doing the next best thing and seeing where that took me.
[00:15:05] Janice: Amazing. And I love that you were really listening to the market, accommodating what clients and customers wanted, and letting that lead your path. At the beginning, you have to start with what you wanna do. But if we’re following the money, you eventually do have to create things as people are asking for them.
[00:15:21] But you probably can’t be everything to everyone, right? There must be some sort of a tipping point where it’s great that clients, customers, families, are getting all of their dreams come true. But how did you start to decide where that line was for you, where you had to start saying No? That must’ve been like a really tough transition.
[00:15:42] Tara: It was really hard because I even now find myself saying yes to things, and then after the fact being like, why did I add, you know, this one-on-one session, I really didn’t want to. But I genuinely love the families and the kids and it’s really hard not to yes yourself into a bad situation. So it got to the point where I was realizing like, Hey, I’m teaching 11 classes a day, and I don’t feel like I’m getting outside of this square, and I am exhausted and the benefits aren’t there.
[00:16:14] As soon as I leave class my whole body just falls. It was very much like such a small process of adding and growing and growing. It was like one day I woke up and realized that my schedule was absolutely asinine. And having a conversation with someone who was outside of that space and having them be like, that’s a lot.
[00:16:36] And kind of getting that validity to it.
[00:16:39] Janice: Because it feels like a lot.
[00:16:41] Tara: But in a lot of ways I just kept telling myself, like, if you look at the calendar, I wasn’t teaching 40 hours a week, so I’m still not working full time discounting all the time I was spending on prep and everything else. And I feel like in education, we’re so used to working more than we’re paid for and working outside of what
[00:17:00] We need to, and always just making it work that I wasn’t allowing myself to take a step back and be like, this is awful. This is too much and you don’t have to do it at this capacity because this is something you’re creating. This isn’t being inflicted on you , this is your decisions.
[00:17:21] Janice: Right. And I think when you leave a traditional classroom role, it’s like, well, I can’t make that structure work, but it’s like, oh no, I’m back in the same situation. Except there was no structure. But it makes sense, like that’s all you know, and we all end up following into the same patterns.
[00:17:36] I think paying attention to how you feel is such an important part of the process as you develop your boundaries and your idea of what capacity is and start to get ready to practice saying no. One of the things I struggled with in online teaching was almost the gambling addiction of it.
[00:17:52] Like I open up 10 slots, I wonder if they can fill, I open up six seats, I wonder if I can fill them. And so it’s so fun to see that like, oh yeah, I did fill them all. Wasn’t that exciting. But if when you actually show up to like fulfill that commitment and teach the class, it doesn’t feel good, you have to notice that and be really humble and be like.
[00:18:11] Well, that’s really cool that I could fill this slot, but also I hate teaching at this day or time or this many in a day, and you do have to really notice those things and be very honest about them. You certainly fulfill your commitment, but you have to learn from it so that the next time you at least have an end goal.
[00:18:29] Like, okay, after 14 sessions of this, I’ll never open up this time slot again.
[00:18:35] Tara: Exactly, and looking at it as you know it’s great that you can work whenever you want, as often as you want, as many classes as you want, but that doesn’t mean you need to, and that doesn’t mean that you should. And having to set your own boundaries, being self-employed is incredibly difficult because you have to hold yourself accountable, and some of us are not very good at that.
[00:18:59] And bringing people in to be like, Hey, I need you to help me create these boundaries and almost like police me in a way. Like, I need you to tell me that this needs to get done and just almost kind of bringing in like a mom role was really important to me to have someone be like, no, we’re not doing that because I’m not gonna disappoint somebody else . But bringing someone in that is like, Nope, we’re not gonna do that was really helpful in realizing that it’s okay to outsource those kind of things.
[00:19:30] Janice: And I think the neat thing about bringing another person into the puzzle is that they’re not mind readers. They’re not making up what they think your schedule should be. They’re mirroring back and reflecting at you the wishes that you’ve probably previously stated. If you said you didn’t wanna work during dinner.
[00:19:47] And they see you opening up a class, they have to slap your hand and be like, I think you told me you didn’t wanna do that. Can we like get ahead of that before you hate yourself? If you say, I don’t wanna work on Sundays anymore, but they see you putting tasks on your calendar on Sundays, they’re mirroring back your own wishes in a way that at some points in our journey, we’re just not great at doing that for ourselves.
[00:20:10] Tara: Exactly, and that was just realizing the scale of humans out there that can really support your business in really intentional, in different ways that you probably are not aware of unless someone has presented it to you, was really interesting to me because in all of my time of building my business up until, honestly, pretty recently in the last like two years, I was a one person show.
[00:20:36] I did everything. Because as a classroom teacher, like you do everything. And it took someone saying to me like, Hey, have you thought about hiring that out? Because in my brain it literally was not even an option to be like, oh, wait, I can pay someone to do that?
[00:20:53] Janice: It just does not compute. It wasn’t a thing in the previous career.
[00:20:57] Tara: It literally did not even cross my mind. And to them it was like, why aren’t you doing this? And to me it was very much. I didn’t even know that this was a thing. I didn’t even know that this existed as an option, and
[00:21:10] that was almost like the gateway.
[00:21:12] Janice: I think that’s really exciting because a lot of times people find themselves scrolling the gram say when they’re overwhelmed and it’s like you don’t even know what you’re looking for. You just know that you feel crummy and you wanna feel better. And that could be with business, it could be with anything in life, right?
[00:21:26] When you have nothing left to give the world you had to social media, you start scrolling and you just hope a solution will get fed to you because you have no idea. And I think that as we network and we bravely talk to other people too, then people start to say like, Hey, I have a girl for that.
[00:21:41] I have a person for that. Uh, I know someone who did that. Do you want me to connect? And you’re like, oh my God, please, please, I wanna meet all your unicorns, all your magic people, everyone. And that’s when you start to realize like, oh, I might be making this harder for myself than it needs to be. I didn’t know that.
[00:22:00] Tara: Yes, and all of my solutions have come from a friend of a friend or a business contact. And there has been so many supports that I’ve put in my business over the past few years that I did not even know existed. I did not even know that there was a person for that or a solution for that. And networking and having those really open and honest and raw conversations of like, I’m drowning in this.
[00:22:25] Has allowed me to find those people and in turn it’s put me in a position where I can also be that person for someone else of, Hey, I see that this is something you’re struggling with. This person is really great and I highly suggest, you know, hiring out things that are not your strength, they’re not in your wheelhouse.
[00:22:45] And finding the solution instead of just continuing to kind of suffer and float along through that frustrating moment.
[00:22:54] Janice: I think it comes back to that humble character trait we talked about at the beginning that you need I think to be successful in business. You have to be willing to reach out to someone and be like, I’m not crushing it. I am not thriving right now. Here’s what I know is broken. I don’t have the first idea what I’m even looking for or what the solution is. Because you can’t find a solution if you don’t even know what’s on the menu.
[00:23:18] And I think that’s the deal with us running businesses that we never saw ourselves in. You can. Identify what’s broken and what’s sticky and what doesn’t feel good, and the more times you’re willing to bravely say that out loud to the right person, the better chance there is that they can connect you with whatever the solution might be.
[00:23:37] Tara: Because I could honestly say, I never anticipated being a business owner. I never wanted to be an employer, to hire people, to know what payroll looked like. I just wanted to teach and I wanted to pay my bills. And as things continued to grow and I was getting into spaces and places that I never anticipated and never really wanted to be, it was very much, okay, how can I pivot to bring people in that know the things that I don’t know.
[00:24:08] Or enjoy the things that I don’t enjoy so that I can continue to focus on the things that got me here, that brought that passion and kind of like joyfully ignore the things that I don’t want to have to have my hand in and that maybe I don’t need to.
[00:24:28] Janice: And maybe things that aren’t getting done anyway. You know, we all have things on our list. We put 10 things on our list, knowing we have time to do three of them. There are certain things that even if I wanted to do them, it’s just not happening. We’ve had things that sit on our to-do list for embarrassing amounts of time and at some point you’re just like, but that really is important and I’m obviously not going to ever do it.
[00:24:48] So there’s gotta be someone else. So let me put that into a timeline. So 20 21, 20 22. Running your business solo. Sounds like maybe some of 2023 also. And then you’re completely, there’s just no more Tara to go around. There’s just no more classes that you can teach. You have more requests rolling in from families.
[00:25:06] There’s just no more hours that you can offer, and people still want things. What’s the first hire? What’s the first, like lifeline, life Raft, life preserver. What’s the first step?
[00:25:20] Tara: So the first thing I did was just to hire a virtual assistant, a VA, to take those time sucks off my plate. To go through my Canva slides because I create all of my curriculum within Canva and do the edits and make it pretty and upload it into Nearpod, and just taking those small menial tasks that didn’t need to be a CEO task,
[00:25:42] Janice: but they did have to happen.
[00:25:44] Tara: right.
[00:25:44] But just having the ability to reclaim that time and knowing that I can confidently give that to somebody else without it affecting my business and my brand. I didn’t realize because I was not time tracking at that point, I did not realize how much time was being invested into that. Because again, at that point I was still looking at, I’m only teaching 26 hours a week.
[00:26:08] Why am I so tired? I’m only teaching 26 hours a week. Why are things not getting done? And when I handed them off to someone else, it was like, oh my goodness, how was I getting all of that done? And where is this time coming from? And realizing that I didn’t have to work in every single free pocket because I could bring someone in to take those tasks off my plate.
[00:26:32] Janice: And it’s so interesting to follow the mindset mess of like, you keep saying 40 hours a week, like 40 hours a week came from somewhere, right? Someone said that a full-time job is 40 hours a week, but like that didn’t resonate for us as a classroom teacher. That’s not how it worked then. And it’s not that if you show up somewhere 40 hours a week, you magically make enough to pay your mortgage like it’s
[00:26:54] such an artificial goalpost that we had just heard enough times. I know in the freelancer world, I talk to a lot of people that are trying to get to like 5k a month and then it’s 10k a month and I know in the TPT space, it’s like I wanna make six figures this year, or I wanna match or exceed my teaching salary.
[00:27:13] There’s all of these artificial goalposts that soak into our mind in such a bad way, and you’re like, why am I raising towards a goal? Just because it’s been repeated a lot by other people. When do I get to see what did I actually want? What am I trying to accomplish? We kind of end up on this runaway train just from numbers that other people have repeated so many times.
[00:27:37] Tara: Exactly, and I have found that this year where I’ve had people in the business space saying to me, you know, what’s your goal for your business this year? And very candidly, I told them like, I don’t have one. Because I feel like in so many ways every single year it’s been, I need to push myself, I need to do more, more, more.
[00:27:56] And I finally realized that like at some point I need to be content in where I am at and stop continuing to push myself to do more and to have more of an output. So, as much as I’m being realistic this year and I have, you know, things that need to be done and I have quarterly goals, I’m taking away that financial goal of I need to meet X dollars.
[00:28:19] And just kind of saying, let’s see what this year looks like. What does 2025 look like? Because there’s so much that’s unknown and there’s so much that’s out of my control and I’m trying to take that stress off myself of just, I want this year to be the best that it can be.
[00:28:35] And I’m not gonna put an arbitrary, number or benchmark on that.
[00:28:40] Janice: You’re taking an above average amount of risk this year, I think you have some new adventures in the mix, and that’s very positive. And so you can’t make goals for an uncharted path, but you can remember why you’re taking those steps and what your like minimum baseline is. It’s like as long as I’m making
[00:28:58] at least say 2000 a month, that target you talked about before, and all my team members are happy and nothing bad is happening. I’ll be grateful because I’m here for the adventure of this new thing that I’m doing. Right? You just have to change what success looks like. Success can look much different than year over year growth.
[00:29:17] That’s not the only way to measure being successful.
[00:29:21] Tara: Exactly, but I feel like for me specifically, it was really hard for me to measure what I thought success looked like without having a number attached to it because I didn’t really know how else to conceptualize it. Like what is that goal, if it’s not making X dollars or hitting this level.
[00:29:42] So this year has been very uncomfortable in that, um, but also trying to just lean into it and own the fact that this year is just gonna be its own beast and whatever it is, it’s gonna be.
[00:29:54] Janice: Yeah, I think you feel more comfortable when you have a goal that you can name, so that you can say, yes, I’m doing that, or No, I’m not. But like having dinner with your family instead of teaching at night is a valid goal. Being able to say yes when your kid wants to sign up for an activity is a goal, right?
[00:30:09] We just have to change the menu of what goals get to be because we’re the boss.
[00:30:13] Tara: Exactly.
[00:30:14] Janice: So it sounds like your virtual assistant experience this first brave hiring experience went pretty smoothly. Was it enough of a relief to even things out so that you could teach and they could do some admin?
[00:30:26] Or did you still feel like you were slightly over capacity?
[00:30:30] Tara: I was still definitely over capacity that year. I was writing, I wanna say five levels of curriculum at the same time. It’s when things really took off and I truly had no idea what I was doing in so many ways. I knew what I was doing was working really well. I knew that what I was doing was well received. But there were so many components to the business that I did not have any background in or any capacity to learn because I was very much in survival mode.
[00:31:00] So it was trying to figure out what can I hand off? What does this person have capacity to take over? But also not really having a way to verbalize what I needed because I had no idea what I needed. I was so overwhelmed that it was just, okay, get to Friday, get to the next week, get past this class, and I feel like I never was really able to catch my breath that year and figure out
[00:31:26] what I needed or what was available. And it was very much having conversations with people and trying to piecemeal, almost like a team together and figure out who my people were going to be and what I needed. And it changed so much over the year of, this is what I need in this moment. No, it’s not working.
[00:31:46] This is what I need in this moment. Oh, I don’t know if that’s really what I want. Um, it was very chaotic.
[00:31:51] Janice: Yeah, and I always preach the importance of getting systems in place before we hire team members whenever possible, just because that survival place is such a scary place to be. It’s almost an out of body experience. When you truly have pushed until the limit, it’s really hard to even let people in and help ’cause you don’t even have time to identify what you need.
[00:32:14] You don’t have time to make them an SOP. You don’t have time to get them a password. You don’t have time to even access help if we push it too far. And that doesn’t mean that anyone who hires in a different order did anything wrong or that they can’t access help. It’s just, man, it’s a lot harder if you push past that point.
[00:32:33] But we’ve definitely been there. I work with some people who like to slow and steady build their systems, and I work with other people that are just like, my world is on fire right now. We have to do this as soon as possible. And so like sometimes I’m working with people in a DIY course environment and we hold their hand and other times they’re like, all right, it’s one miserable week.
[00:32:52] VIP week. Let’s buckle up, put on a pot of coffee, and if you think you can save my life, let’s do it.
[00:32:58] Tara: Yes, and in a lot of ways I was very, very blessed to have people that understood the way that my brain process and were able to come to me and be like, Hey, I need you to give me this so that I can do that, and keeping my life organized when it very much was not. So finding people that understood my process and were willing to jump in and be like, look, I know that it is a disaster, but I need this and I need you to give me that and focus.
[00:33:26] Janice: And
[00:33:26] if you give me 30 minutes to gather these things, I can do 20 hours of this task for you. Well, then you can process that and be like, well, okay. ’cause I definitely don’t have 20 hours.
[00:33:37] Tara: Right, and I very much needed the people to be like, Hey. You’re paying me to do a job. You’re not allowing me to do it ’cause you’re not giving me what I need. And having those people that were like, we’re gonna have a hard conversation right now because I can’t help you until you let me in. So I was very thankful with the people I surrounded myself with in the beginning, who their only goal was to help me win.
[00:33:58] Janice: Right. And you have to feel that way when you invite people inside your business. It’s so important and worth it to find that perfect fit. So a virtual assistant can help a little bit at the beginning. What does your team look like now if we fast forward to 2025? What is your current kind of team structure?
[00:34:16] Tara: I have some people that I use on the day to day. I do have a VA that comes in and does a lot of tasks and behind the scenes. I have people that come in and will support me in pockets of time when I have projects that’ll come in and support me in organizing something.
[00:34:32] But really my day to day is just my main VA who luckily can wear 900 hats at the same time, um, and keep things very, very organized. And then I also have four teachers that are teaching for me, which started in January. So very much trying to keep a lean crew, as I figure out what it’s like to have W2 employees and keeping as much of that business profit as I can because with W2 employees and having employees in general, still learning what that looks like.
[00:35:05] So running a very lean business in this season.
[00:35:09] Janice: I’m really glad you called out that they’re W2 employees ’cause we are talking about two different things at the same time. There’s hiring out contractors that are ongoing, like you’re behind the scenes VA, there’s hiring out contractors on a popup project basis, that’s really what we talk about when we’re talking about hiring out.
[00:35:25] And then when it comes to these teachers, these employees, that’s something totally different. So when you started on Outschool, if someone wanted to take your math curriculum, they had to sign up with you as a math teacher, and correct me if I’m wrong, as an Outschool organization, there are now multiple teachers who work under your organization that are teaching your same slides and curriculum.
[00:35:47] Would that be accurate?
[00:35:48] Tara: Correct. So they are teaching my materials. It’s basically, they’re a stand in for me. I give them all of their materials, I create their schedules, and it’s a fine line between with the hiring and having to look in to what you want, because what I was asking of them was very much within that W2 wheelhouse.
[00:36:08] And it’s really important that it goes back to hiring people that know what they’re talking about and knowing that I needed to hire employees. And a lot of people within the business space were saying, you know, you could do a 10 99, it’s easier. But knowing that I needed to go to an accountant and I needed to go to that business
[00:36:31] minded person and realize that just because I wanted to do a 10 99 doesn’t mean that it fit into that situation. And just being able to navigate those is important.
[00:36:43] Janice: No, and I think it makes sense because when we talk about where that line is, you know, as a freelancer, myself, as a contractor, you can give me a project and I can tell you I’ll get it to you at the end of the month or the end of the week. But if you start saying, okay, but you have to do it on Friday at 10:00 AM, you have to be here every Friday at 10:00 AM, Well that’s where the line is.
[00:37:04] That’s a JOB. Like now I’m an employee and that is the situation in a math class.
[00:37:10] Tara: Exactly. Exactly. And then, you know, from my perspective, I’ve gone from, oh, I just scheduled classes and I teach what I want to. Now I have to consider when is this person going on vacation and when are they available?
[00:37:22] Janice: What are we doing about that? What are we doing when they get sick? That sounds a lot like an employee situation.
[00:37:28] Tara: Exactly, which falls into that wheelhouse of things I never wanted.
[00:37:32] And here we are.
[00:37:33] Janice: But isn’t that funny how it’s not what you wanted, but in a different season, you also didn’t want to say no to families that needed a math teacher. You also didn’t want to say, I’m gonna stay in this burnt to a crisp schedule. It’s funny how what we want gets to change over time.
[00:37:55] Tara: Yes, A hundred percent.
[00:37:58] Janice: So I love hearing your way of hiring out and your path to hiring out is so individual. There are many teacher business owners where their business looks totally different from yours, and hiring an employee might not be the solution for them, but it’s the same problem solving path, and that’s why I think it’s so empowering to hear these win-win stories.
[00:38:18] You could have been past your capacity, burnt out, let your family reviews start to dip, and then close your classes, bounce, and never open them up again and decide going back in the classroom sounds fabulous, and go do that again. There are definitely people who make different decisions at that same pivot where life does not feel like a win-win.
[00:38:39] So I’m just so grateful for you sharing your story. It’s messy, it’s brave. I’m sure you’ve tried things along the way. We didn’t go through the timeline sequentially because there’s of course things in there that we try that don’t work, I assume, right?
[00:38:53] Tara: Oh a hundred percent. For everything that has been successful, there are 900 things that are just an absolute dumpster fire.
[00:39:00] Janice: That’s just normal. And I think that we can’t hear that from other business owners enough. None of us are crushing it seven days a week. We are all having our humble moments along the way.
[00:39:11] Tara: And I think it’s really important to share that because I think it’s really easy for people to see things like there was an article that went out, on entrepreneur.com that just highlighted you know, the good things about, oh, this is how much money I’m making in a year. And then I have people come back to me like, that’s amazing.
[00:39:29] How did you do it? And it’s like, I was working 24 7, I was exhausted. I wasn’t seeing my family. And I think it’s really easy for people to see the highlight reel and not to share the messy. So I try and really lead with, yes, I make a great amount of money. I am so thankful for where my business is, but it has been so hard and so messy, and I have failed my way to the top in so many ways.
[00:39:57] And I think that if you don’t share that and you don’t lead with the hard, I think it’s really unfair to other people that see your year four or year five when they’re in, you know, day one.
[00:40:09] Janice: And growing a business is not for everyone. There are personality types who are just risk averse, who this would not be a lifestyle that makes them happy. It’s not a fast food menu. It’s not, oh, I have a business that makes this much money. Oh, cool. Can I have a number four? Can I have one of what Tara has?
[00:40:25] No, you may not, they would not like the steps to get there. Some people would. It would sound exciting and fun for them. And there are, we all know people we’ve chatted with in our community, in our neighborhood that are like, yeah, I don’t think that’s for me. We certainly met some of those people when we were teaching at butt crack of dawn VIPkid, right?
[00:40:42] Tara: Oh, a hundred percent. You were teaching at two 30? Yeah, because that’s when the demand was there. It’s not always pretty
[00:40:49] Janice: And they’re like, oh, I don’t think I would like that. No, that’s true. You probably wouldn’t then you shouldn’t do it, and that’s totally fine, but it’s working for me in this season. Not that I think our cortisol will ever recover from that season, but it was a fun adventure.
[00:41:04] Tara: Definitely not. And there’s some days where I wake up and I’m like, man, I would love to be an employee. I would love to have somebody else make the decisions and show up and, you know, at five o’clock, clock out and be like, not my circus, not my monkeys. But I wouldn’t be able to have and do what I am in this moment.
[00:41:23] But I will say there are definitely days where I wish I could just do the quote unquote normal job. I could just work for somebody and get vacation time and have sick days and you know, not have to worry about all of the tiny little minute details.
[00:41:41] Janice: It’s fun sometimes though, to browse job listings and I can feel my nose wrinkle up as I start to read about like the things they would require, and I’m like, no, no, no, no, no, no.
[00:41:52] Tara: Anytime I get frustrated I will look at job listings to see what it would be like to work for somebody else. And I’ve never found anything that I’m like, you know what?
[00:42:01] Janice: Right, like a little
[00:42:02] 15 minute scroll on Indeed does a body good? Right?
[00:42:06] Tara: exactly. I look at it and I’m like, Nope, it’s not that bad. It’s not that bad. Close it down.
[00:42:12] Janice: Sometimes you just need that reminder. So Tara, I work with a lot of business owners who love running a business, but they still have that teacher part inside them and they might be interested about Outschool. If someone wanted to get started learning more about being an independent teacher on Outschool, uh, what would be the best place for them to get more information?
[00:42:33] Tara: So that’s actually a really good question because one of the things that’s hard to get started on Outschool is that you are an independent contractor. There’s no training. And as much as they give you a lot of options of things that you could dig through, you have to do the digging. So I actually created a course that takes you step by step through how to set up a schedule and how to find your families and how to build a class listing.
[00:42:56] Because that was something that I realized that as I had people coming to me wanting to replicate what I did, it wasn’t out there. So I’ve actually built a course, and it’s on my Instagram at Reclaim Your Class, and it takes you step by step through how do you build your business and what are the moving pieces that you need to keep in mind, and how do you continue to come back and cycle through to make sure that your business is strong and that you are able to be successful.
[00:43:29] Janice: How would I know if I want to be an Outschool teacher independently, or if I might like one of those employee type roles that we talked about today? How do people determine if that’s even an option on their menu?
[00:43:42] Tara: I think it really comes down to what your interest is. If you still want to teach, but you have that creative outlet of, I want to write the lesson plans and I wanna decide what I’m teaching, and you want that extra work on your plate because it’s exciting, then you wanna go into that independent teaching situation.
[00:44:00] But also know that you have to start from the bottom. You have to find your first families. You need to build your reviews. And it’s very, very rewarding, but you are very much coming in from the bottom. If you want to teach because you’re excited about it, but you don’t wanna have all of the decision making.
[00:44:20] I wanna show up and teach what I’m told, or I want to come in and work with someone who’s already established on the platform so that I don’t have to be as scrappy in the beginning of finding my families and kind of having that leg up, then going into the organization might be a better situation for you, but there’s definitely a cost difference because if you’re willing to go in and be an individual teacher, you know, financially you have more opportunities available to you.
[00:44:48] Whereas if you’re going into an organization, you don’t have as much of an opportunity in most situations because you are in a lot of ways utilizing all of that work that somebody else did. So it really just depends on where your passion is, what you have capacity for, and realistically what you’re willing to do.
[00:45:08] Janice: I think it’s been really exciting to see Outschool as a marketplace grow over time because when I was in Outschool back in the day, you didn’t have the two paths and you didn’t have that decision. And if I did think I wanted to be an employee, there isn’t any sort of like job board where organization jobs are posted,
[00:45:23] right? It’s just kind of a networking, you just have to know people, situation?
[00:45:28] Tara: In a lot of ways there is a Facebook group, for organizations on out school where you can put in that you’re, you know, wanting to teach but in a lot of ways it’s not super organized and it’s really reaching out to people in that space, knowing someone that knows of an organization. Some people will put listings up on Indeed, um, or other, you know, job listings, but there’s no, it’s not really organized in that way.
[00:45:55] Janice: It’s new, so there’s no standardization yet because it’s very much a building the plane as we’re flying its situation, right?
[00:46:01] Tara: A hundred percent.
[00:46:02] Janice: Yeah, and that might sound exciting to some people and that might sound like not anything people wanna get into and that’s totally okay. I will make sure to put the link to your course and your Instagram down in the show notes.
[00:46:14] I think Outschool can be a great opportunity, especially if say you have like a teachers pay teacher store and it’s like a hundred percent of your eggs are in that basket, and that’s starting to feel a little scary. I think it can really give people that breathing room, like you said before, to be like, I think I’d be really happy actually to teach two days a week and see some kids and use my products to develop curriculum and spin them in another way.
[00:46:38] And then maybe run my TPT thing three days a week in my business. I think we’re definitely in an era where we’re all calculating our risk tolerance and figuring out what feels like the win-win for us.
[00:46:51] Tara: A hundred percent. And I think it’s just kind of embracing the chaos in a lot of ways. And I feel like if it’s something that you wanna jump into, one of the things that I learned year three, is finding people that are like-minded but different. I have gotten some of my best ideas from having conversations with people that do things completely differently.
[00:47:11] I have a friend who runs classes that are video games. All video game based. I know nothing about video games, but we’re able to have those business conversations and because there is no office, because there is no water cooler, you have to be really intentional with who you’re bringing into your space and finding your people because it’s very difficult to do if you’re an island and you really want to find that way to just embrace other relationships and really bringing people in that could, just help you grow in ways that you did not think were even possible.
[00:47:51] Janice: I think that’s something so beneficial about your reclaim your class course is you could absolutely spend years trying to figure it out on your own and hoping that you meet a couple other teachers and they each share one tidbit and one secret. But in reclaim your class, you’re gonna give them a step by step,
[00:48:08] here’s what you need to do and why to help them really understand how the Outschool marketplace works. And I know when I got into the Teacher’s Pay Teachers marketplace, I was so glad we started with a course right within that first three months because I’ve met so many people that have wasted time backtracking, taking steps that they would’ve avoided if they knew.
[00:48:29] But I think a lot of us as teacher business owners know the value of having that step-by-step expert path from the beginning.
[00:48:36] Tara: Absolutely. And you wanna seek out people who are not gatekeepers. I have never been one to say. I’m not gonna share that with you. I’m not gonna tell you, how I did that. I think it’s really important to just surround yourself with people who want to see you win, because me helping somebody else grow in the Outschool space is never gonna be a negative to me.
[00:48:54] And I think it’s really important to lead with that mindset of if we build everyone else up in that space, all we’re doing is creating a better product for the families that are there. It doesn’t really help to just keep yourself on that individual level. I think the more that we can do to really bring quality teachers into that space and help them grow is just gonna continue to make Outschool better for everybody.
[00:49:17] Janice: And it’s everyone’s responsibility shared to make sure that when families head to the out school marketplace search bar, they have a great experience and they tell other people. Because your job will only be around as long as people are having a positive experience in that search bar. And in that sense, it’s very similar to the TPT marketplace.
[00:49:37] We talk about the same thing. We want to help other people make high quality listings because if when teachers go to that search bar, they’re not finding things that are truly helpful, they’re not going to come back to the search bar again.
[00:49:49] Tara: Exactly
[00:49:51] Janice: Tara, this was such a great conversation. I learned new things about Outschool, so selfishly, that was cup filling for me.
[00:49:57] But your story is so unique and I love the different eras of your hiring journey that you went through, and we always love to hear about a win-win where we come out the other side. If people wanna chat Outschool with you more, can you let them know what your Instagram handle is before we leave?
[00:50:14] Tara: it is reclaim your class.
[00:50:16] Janice: Amazing. And just in case, I do have a student or a child that’s looking for a math enrichment experience, what would they search for on Outschool
[00:50:26] Tara: So our school in on Outschool, our organization is Mathletes with Tara.
[00:50:31] Janice: And so at the end of this conversation when this podcast ends, go ahead and head over to Outschool and check out all of the incredible reviews and offerings that your amazing math organization, since it’s 2025, is offering for learners. Tara, thanks so much for taking the time for our coffee chat today.
[00:50:50] Tara: Thank you so much for having me. I appreciate it.
Here is a playlist of other win-win teacher business stories that I think you’ll enjoy:
