From teacher to freelance copywriter

EP 35 – Sarah Mill: From Teacher to Freelance Copywriter


Copywriting has been one of those careers I’ve always received many inquiries about. I’m excited to chat with Teacher Career Coach team member and copywriter Sarah Mill for this episode of the Teacher Career Coach Podcast. Despite thinking teaching was going to be her life-long career, she ultimately left the classroom after teaching High School English for four years. Today, she’s successfully navigating the world of freelance copywriting while traveling around the country with her fiance. This interview is going to be a great lesson for anybody who wants to be a freelancer or a copywriter because we touch on both subjects almost equally. Follow along as we talk about everything from finding the right clients to marketing yourself as an expert. Sarah also shares the biggest lesson she’s learned since leaving the classroom. (For real, it brought a tear to my eye.) This episode pairs perfectly with Episode 13 How To Start Freelancing with Jay Clouse.

Recap and BIG Ideas:

  • Copywriting is an opportunity to rebrand your expertise utilizing many concepts and skills you used in the classroom, just in a different way
  • Writing sales copy is more similar to teaching than it sounds. It’s mostly about knowing the product or service, understanding the ideal audience, and promoting the product or service in a relatable way
  • Understanding and capturing a client’s desired voice is essential to successful copywriting. Ask about what that voice is before beginning any project. 
  • Writing proposals on a freelancing site like Upwork is a low-stakes way to practice rebranding yourself as a copywriter
  • Writing proposals is a great opportunity to showcase your writing abilities and make it clear why you are the right fit for the job. 
  • Freelancing provides financial opportunities and general freedom that a traditional career doesn’t. 
  • While there are risks to freelancing full-time, if you know what you’re getting into, plan around those risks and prepare yourself for the worst-case scenario, you’ll be okay.

Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.

Interested In Freelancing? Don’t Miss This Great Opportunity!

Daphne: Before diving in, I have an important announcement. For those of you listening in real-time, don’t miss the free freelancing webinar on June 24, 2021 hosted by yours truly and freelancing expert Jay Clouse. Join us live or catch the replay to learn how teachers can quickly learn the ropes and start freelancing full or part-time. If you’re even considering freelancing as an option, this is an incredible opportunity. Sign up here

Leaving The Classroom Vs. A Long-Distance Relationship. 

Daphne: Hi, Sarah, I am so stoked that you are here today. 

Sarah: Hi, It’s such an honor to be here. 

Daphne: Sarah, I just told my audience all about you prior to you hopping on this call. We have been working together for about seven months at this point?

Sarah: I don’t know. It’s one of those things where when you find the right person to work with, it’s easy to feel like it’s been forever. So, it’s hard to keep track. 

Daphne: For everybody who missed the intro, do you mind introducing yourself to the audience?

Sarah: Absolutely. So my name is Sarah and I was a high school English teacher for four years, including a one-year full-time internship working under another teacher. And to be fully transparent here, I want to start by saying that my situation is definitely a little bit unique. My fiance had a job offer at the time of me leaving that required us to totally move across the country. So, when it came to leaving teaching, I was in a little bit of a different scenario there. But I did leave after year four and now I am a full-time copywriter.

Daphne: That’s something that a lot of teachers who are looking to transition actually reach out to me about. In several cases, it’s not necessarily burnout that’s making them leave the classroom. It’s potentially moving to a new state and they don’t want to get new teacher accreditations. Or there’s a lot of military spouses that are moving from town to town and they need something that’s a little bit more flexible. It sounds like that’s kind of where you found yourself. Was he your husband at that point or fiane back then?

Sarah: He was my boyfriend then, is now my fiance, and my soon-to-be husband.

Daphne: So he has to travel pretty regularly, right? And staying in the classroom wasn’t really a great fit for you. 

Sarah: Yeah, so he has to move around every couple of months and spends months at a time in one location. So, it came down to if we wanted to do the long-distance thing or not. And it wasn’t just that. There were definitely things that I was feeling and things that kept coming up for me in teaching. His career opportunity was more of just the push that I needed to take that step. 

I was kind of like towing both sides there for a bit. I was definitely having these feelings that were confusing, and I couldn’t ignore them. Honestly, I don’t know that I would have taken the leap otherwise. I didn’t have resources like yours. I was just this lost little soul trying to figure it out. I really don’t know what would have happened if he hadn’t had that job opportunity. But, it was definitely a big push for me to pursue other opportunities. 

The Challenge Of Balancing A Passion For Creativity With Other Teacher Duties. 

Daphne: So were you always thinking of exploring something, like a more creative role or something with a little bit more freedom?

Sarah: Yeah. I mean, I was an English teacher. So in my mind, that was the way to really explore the creative side. Not that you can’t be a creative science teacher or math teacher, but I do think it’s a lot harder. So for me, the creativity side was really important even when I was teaching. 

As a child, I was always writing in journals, and this is super embarrassing but when I was little I used to write plays, and then make my family watch me perform them. I used to write stories and all of these things. So, writing was always something that was part of my life. I think once I got into teaching, I got so lost in the creativity, which was great, but so time-consuming. 

I know that on a recent episode of the podcast with Angela Watson, you were talking about getting lost and caught up in these creative elements. That creativity was definitely something that was always a passion point of mine. But it kind of started becoming unbearable in the teaching sense, because there were so many other unavoidable duties and expectations, like the grading and of these things, and it just became too much in a way. I felt like I had to start cutting out my favorite part, which was the creativity. 

To go back to your question, creativity was always there. It was always something that I was always super passionate about. So, I think it was a natural switch for me to go into something that was also creative, just in a different way.

From teacher to freelance copywriter

Learn What A Copywriter Is And What They Do. 

Daphne: Let’s get into copywriting. What is copywriting? Because for me, coming into the world of creating my own business and actually working with marketing in different capacities at various education companies, I’m really familiar with copywriting now. When I first started out, the first few times I saw the word copywriting I thought it involved writing legal documents for copyright or something like that. 

So, what is copywriting for those who have never heard the term before?

Sarah: No, that’s a good question. I mean, when people would ask me what I did when I was a teacher, they think they know what you do. Let’s be honest though, no one really knows what a teacher does unless you’re a teacher. With copywriting, I just kind of get that glazed-over look because no one really knows what it is, right? Even my parents are still like, “What do you do?” So great question. 

In some ways, it depends on who you ask and where you look, in terms of the nitty-gritty details of copywriting. But technically, a copywriter is just someone who writes words that are meant to sell. So, whenever you’re on a website or looking at a product, all of those words are called copy. And there’s someone behind the scenes who’s hopefully thinking about marketing and the target audience to help write those words. 

As a copywriter, you’re really just crafting words to get people to take that action of buying a product or whatever it is. But then there’s also content writing, right? And that’s more of writing the informational, educational, and entertaining copy. 

You can definitely specify in the sales-focused copy, and the advertising and marketing and all that. Or, you can do more of the informational and educational writing for content on a blog or something like that. I do both.

Learn What Led Sarah To Copywriting. 

Daphne: What made you realize that this was the path that you were the most excited about pursuing outside of the classroom? Where did you start learning about copywriting in general and realized that it was something you wanted to pursue instead of, let’s say, editing or creating curriculum?

Sarah: When I first left the classroom, I didn’t have a particular plan. I know that probably makes some people’s skin crawl. Looking back, I feel crazy that I did that. But for me, I was used to having the summer off as a teacher anyway. So, I really sat down that summer that I left and moved across the country and really thought about what skills I had. Because it’s easy to feel like you don’t have any, right? You’re like, “My skill was teaching. What do I do now?”

So, I started to think about what else I could do. And that’s when my fiance kind of was like, “Well, you like writing and you’re really good at writing.” I was always the person that my friends went to for essay help in college or application cover letters and stuff like that.  And so I thought I would try writing. And I literally think I started googling phrases like, “How to make money writing.”

I didn’t really know what a copywriter was, to be honest, until I started looking into ways to make money writing. And then it all kind of started with one of those freelancing websites. I used Upwork, but there’s plenty of other ones out there as well. I just started exploring different opportunities. I mean, I was writing everything from pamphlets to blogs. I wrote beauty blogs, financial blogs, and all sorts of topics. 

The Connection Between Copywriting And Teaching. 

I just started realizing that all it was was taking a big idea and breaking it down. And that’s what teaching is, right? I slowly started to realize they were way more similar than I thought. And funny enough, I am not a financial person at all, but my first client was a financial advisor. So I just kind of jumped in and got started. I know that’s not a super-specific pathway, but sometimes I do think it’s just getting yourself out there, trying something new, and going from there. And that’s really what I did.

Daphne: Yeah, I think a lot of times there is the common roadblock of imposter syndrome, or just people being a little bit unfamiliar with different opportunities. 

Copywriting And Sales. (And The Connection To Teaching.)

But I wanted to touch on something that you said a little bit before about how copywriting is focused on sales pages. When it comes to copywriting versus other types of writing, I think copywriters can charge a little bit more than other writers. Do you agree with that?

Sarah: Yeah, totally. I mean, it’s very value-based at that point. If you help them close the sale, that’s the most valuable thing you can do.

Daphne: Sales pages for businesses, small businesses or large businesses, are usually the most important feature. So for us, it’s the Teacher Career Coach Course sales page. Sales sounds intimidating but I want to pull back the curtain a little bit on what that looks like, and what that process looks like for me being the client and then then the copywriter. 

In general, it’s not you just typing something and being super salesy. It’s just talking about what is in the course and being able to clearly articulate what is inside the product. Why would people want to purchase this product? Who is it a good fit for? It’s about being really transparent about who it’s not a good fit for as well so people don’t accidentally purchase it. Then there are a lot of components of marketing involved as well.  For some people that’s intimidating, but I think it’s really easy to learn.

Sarah: Honestly, for anyone listening right now, if you go back and just rewind that little part right there, you’re basically describing teaching, right? As a teacher, you’re taking a concept that is complicated, or seemingly uninteresting to your audience, which is your students. And then you’re just thinking of ways to get them to buy in, right? So, when I had that doubt of, “Am I really qualified for this?” I started to think of how I stood up every day, in front of a group of 16, 17, 18 year olds, and had to sell English curriculum to them. That’s probably the hardest sales pitch you could ever make.

So, for anyone out there who’s intimidated by that word sales—I think everyone thinks of the pushy salesman knocking on your door or at the car dealership—and it’s totally not like that. And that’s the beauty of copy. And that’s what I think makes a good copywriter.  They’re not pushy. It’s all about relating to the ideal audience. For me, your audience is awesome, because I was your audience one upon a time. 

So, if you can find an audience that you really relate to that whole “sales” piece that might be intimidating will be less so because of that relatability aspect. I think that it sounds more intimidating than it is once you really get into it and understand that you don’t have to be perfect, you just have to be relatable and really understand what it is that you’re trying to sell.

There Are A Variety Of Industries With Copywriting Opportunities. 

Daphne: what other types of clients besides me, your ideal client and your favorite person to work for, do you work for?

Sarah: That’s an interesting question because in copywriting, sometimes you have clients where you’re just doing one project for them, or a small handful. And then others like you, you’ll work with them long-term. Personally, that’s my favorite type of client to have, because you really get to know the audience. You also really get to know the voice. 

An important part of copy is capturing that right voice. You can’t just always use the same exact voice for every client. I’ve written for a financial advisor. That was fun, because he wanted me to write an ebook that broke down the benefit of a financial advisor and some big financial terms for a general audience. I remember thinking, could that be more of a teacher-focused thing? Taking a big concept and breaking it down? 

I’ve written for educational nonprofits to help them get funding. I have a bookkeeping business coach client who you actually had on your podcast. I help her with a lot of her sales copy. I write for a lifestyle and business coach. I’ve done beauty blogging and written for a financial literacy project. I write STEM-focused educational scripts for kids, which is super fun.

I mean, the list could go on and on and on. But that’s what I think is fun. You can get as niche as you want. You could only search for clients in X, Y, and Z industry, if you wanted. I just think it’s fun to explore different options. So it’s all of these industries and things that you would never really think about. I’ve done so many things that I didn’t ever imagine I would do or think was even a thing to do. But everything that someone does or puts out there, someone has to write it. And that’s what I do. I write them. 

How to Capture A Client’s Voice When Copywriting.

Daphne: Let’s dig into that voice piece. So, you said that you have to mimic people’s voices. Even just writing for the Teacher Career Coach, you’ve mimicked multiple styles and voices. I think I’m a little bit more informal and when you’re typing something out, to mimic my voice and relay it to the audience, I think that you usually do some kind of quirky things that sound like something that I would say.  

We’ve really gotten to know each other where sometimes I read it, and I’m like, “Oh, it looks exactly like what I would say!” I don’t have to edit it for grammar, or it didn’t take me four hours to type it out or think about it. Then there are other times that you have to write about a more serious subject. Maybe we’re talking about going to therapy or writing letters for administrators to help them see why professional development about sustainable teaching practices is important. That type of email or resource needs to have more of a serious tone to it when it comes to voice. 

And that’s where I think copywriting is really important for you to understand that there are different times and different people who want different things. Was that something that you had to learn on your own?

Sarah: That’s a good question because it definitely is interesting to do. One thing that I’ve learned to do is make that one of the first questions I talk to a potential client about is regarding that voice aspect. I think when I first started working for you, I had written my proposal in a voice that captured your attention because I had an idea of what you were looking for. With other clients, they’ve been super vague about what they’re looking for. And I specifically ask, “What type of voice are you looking for? What are your goals for the voice of the copy?”

Again, going back to teaching and transferable skills, teachers have to do that all the time, too. It’s about time and place. Especially if you’re an elementary school teacher, think about having to go back and forth between speaking to your young students, and then your co-workers and parents. Even in high school education, you speak to one class differently than you speak to another. You speak to one student differently than you speak to another. So, I definitely think that helps because it did come a little more naturally to me than I would have thought. 

I think a big part of it too is finding those people whose voice you connect with. People might be skilled in switching voices, but for me, it’s more enjoyable when I connect to the voice that that person has. So, if they already have something out there, like a website or blogs or whatever, I would recommend looking at what’s out there seeing the voice that they already have. They might be looking to workshop that voice, but at least it gives you an idea of what you’re getting into. If you don’t like the voice they’re striving for, you don’t have to write it. So, that’s kind of a little piece of advice there. 

Again, everyone’s different. I just personally like writing invoices that are more natural fit to me, because to be frank, it’s just easier. Did that answer your question?

How To Book Copywriting Clients.

Daphne: Yeah. And I wanted to even describe the process of booking clients. You brought up a really great story. When I was looking for a copywriter, I had started hiring freelancers. The majority of the people who work for Teacher Career Coach are actual former teachers. So that is a big part of who I am looking for to help bring this community together and help keep this project going. Everybody on the team already understands what the struggles of the audience are and help me in different capacities. 

So, I put out this advertisement on Upwork. I was just kind of looking for someone with copywriting experience, but also someone who had education experience or was a former teacher. Now, I have had a lot of negative experiences with freelancers and I think that that’s something that a lot of small businesses struggle with. They don’t not know how to hire someone who’s a good fit. 

You went above and beyond, and instead of just saying, “Oh, I fit the criteria,” you basically wrote this blog that was like, Boy, am I the right fit for you. And I remember reading it and was just like, How can I not hire this person? I don’t know if you looked on my website or if you somehow lived in my backyard for a week. But you picked up my voice almost perfectly, and also did a great job selling yourself as well.

I got on the call with you and I think my first words to you were, “Listen, you have the job. I don’t even know what you’re charging me and I should bluff better. But you have this position just based on how above and beyond you went for that application.

Do you do that for every client?

Sarah: Yeah, that’s a good question. It’s funny because I remember that. I think before we got on that first call, you messaged me on Upwork something like, “Your copy, you killed it. Let’s get on a call.” I just felt that connection. But the funny thing is, there are clients where I’ve gone in and looked at their stuff before even writing the proposal, which I’ll talk about that whole process in a second because it’s important, but when it came to you, I think that—and this does happen sometimes—I just connected on such a deep level with what you were looking for.

On Upwork, unless the client tells you what their website is or something in their job posting, you might not even know what their name is when you’re applying for the position. So, I had no idea what your platform was. I just wrote from my heart. You know, I think that’s why we’re such a good match, not to get all mushy here.

In terms of other clients, and going back to Upwork and that proposal process, I have no idea what other people write for their proposals. But for me, and my advice for anyone going into a role where you’re writing, your proposal is your opportunity to showcase what you can do. So, not only do you want to explain why you’re a good fit, but it’s your opportunity to show your writing ability and try to write it in a voice that you think captures what they’re trying to get at. 

Again, we’re talking about proposals on those freelance websites like Upwork, which is what I used and still use to this day. That proposal piece is so important.

From Classroom To Copywriting: Rebranding Your Expertise.

To go off of that, I think your proposal is a great opportunity to practice rebranding yourself in a new area. You’re not going in for this big interview or applying for this big, full-time job. You can apply for a one off job and just use that proposal space to practice rebranding your expertise and highlight those transferable skills you have and why you would be a great fit. I even think that that’s a great thing to do even while you’re still in the classroom because it is so low stakes.

Daphne: For anybody who is interested in learning all about starting a freelancing position, I have a previous episode that you can listen to where I chat with Jay Clouse who created Freelancing School. In that episode, he talks about booking clients and how to book clients. One of the best practices that I’ve seen you and other freelancers do is exactly like you said. Your proposal is your moment to actually showcase what you can do. So, if you’re trying to be a graphic designer, and you have a template already created, you can really quickly create something that looks like what they’re asking for. Even if that’s not going to be the final product by any means. 

The blog that you wrote to me was never copied and pasted or put up anywhere. It’s not free work. What happens is it helps alleviate the fears of whether or not you’re hiring the right person. They’re already able to actually envision them working at your team. That’s what’s happened for me. Anytime somebody has actually created something of value that’s in my voice or for my company as part of their proposal, it’s a lot easier for me to make that commitment and see them actually inside the company. 

If you gave me a bland resume that said, I’m a copywriter, these are my copywriting skills, I would have probably had to have two or three phone calls with you to see what you were actually capable of if you didn’t take that time to write that blog.

Sarah: Yeah, that makes sense. And I just want to touch upon a quick thing that you mentioned, because I think it’s important. I know that I’m a copywriter and this episode is about copywriting. But you know, when it comes to those freelancing websites, it’s not like Upwork is specifically for copywriting. So you know, if you’re listening to this and words aren’t your thing, you can do so many things on those websites. You mentioned graphic design, I think there’s even like podcast editing and just so many different things that you can get from those websites. So even if you’re not interested in copywriting, it’s still a fun and useful platform to explore, especially while you’re still in the classroom and are having these feelings that you might want to leave the classroom.  

I just want to clarify there are plenty of full-time copywriting roles in a business. You don’t have to do freelancing if you don’t want to. So that’s just an important side note there. 

Going back to what you were saying about using that proposal to your advantage, it’s way more fun than a resume. You’re not just bulleting things in a list. You’re really showcasing what you can do and what you have to offer. I think that that can be really fun and build confidence in the meantime.

There were proposals I wrote that I never heard back from the person or they wrote back and said they were going with someone else. But just writing that proposal and going through that whole process or rebranding myself as an expert in not only writing but whatever it was that they’re asking about, whatever their company or industry is or whatever. That just built confidence in general. It’s been a good process as I learn and grow as a copywriter, whether I get the job or not. 

How To Prepare Yourself To Move From Teacher To Freelancer Full-Time. 

Daphne: I wanted to kind of pivot a little bit and talk more about freelancing because it feels very risky. This is especially true for teachers who are already feeling all these stressors or fight or flight syndrome telling them that any change is bad. Freelancing and being an independent contractor is not necessarily a stable career. You’re going to need to always find clients. 

Were you nervous about taking on freelancing as a full-time job?

Sarah: Oh my gosh. Yeah. Nervous is like an understatement. I can think of a couple of things that helped. One, my fiance is very entrepreneurial and actually runs his own little business. But he also has a more traditional job, where he gets the paycheck every two weeks and stuff like that. So that definitely helped. 

Two, I am very frugal and a big saver. That helps because I know that if I had a break in employment or a decrease in income for a certain month or whatever, I would be okay. So, it’s definitely not for people who live paycheck to paycheck, because you don’t always know what your next paycheck will be. 

But I also think that COVID and the whole pandemic helped. Before I went full-time, I was doing other things on the side. I did the waitressing thing, after-school nannying, other things that were really fun for me. But once COVID happened, I had this opportunity. I couldn’t do the restaurant thing anymore because it shut down. There was no need to do the after-school nannying because the kids weren’t in school. So, it really was a unique opportunity for me to step into it full-time, because there really wasn’t another option. And again, I had done things ahead of time to make that feasible, like saving up a lot of money, and stuff like that. 

You know, I definitely think that it’s risky. But if you know what you’re getting into, and can properly prepare for it, and plan on those risks and prepare yourself for the worst-case scenario, you’ll be okay. Like what happens if I have a month where I have no work? That’s never happened to me, but there have been months where I am used to making a certain amount, and then suddenly I have a dip because it was a slow month, or it was like a holiday month or whatever. 

I just think you have to know what you’re getting into before you fully dive in. And it makes the risks a little less scary because you’ve taken the flashlight and shined the light in their eye, right? And then it’s just being smart and just always kind of like being a step ahead. 

Daphne: Yeah, absolutely. You have been doing it long enough where you have at least a few clients that you know that right now you have a steady amount from certain clients. You can probably anticipate you’re going to make X amount of income because this is how much work you get on a monthly basis. 

That’s something that you’ve established with not just me, but probably multiple other clients. And you have a rapport where if I knew that I needed to not use you for a couple of months, I would reach out to you. And I’m sure that that’s how other relationships have started to form as well. I would be able to tell you just anticipate having fewer projects during certain times of the year. 

The Importance Of Client Relationships. 

Sarah: Yeah, and I think that brings up an important point about the relationship you have with your clients as a copywriter or any type of freelancer. You’re working for yourself, but you have all of these little partnerships. The better you can build those relationships and the more open you can keep the communication, the better off you’re going to be. 

As you said, we have that open line of communication, and it makes the risk on both of our ends feel a little less severe. You don’t have to feel as bad because you know that you would give me a heads up, I don’t have to worry as much knowing that I would get that heads up. 

One of my clients actually decided to go with a full-time copywriter, which meant that my freelancing services were no longer going to be needed. Not that everyone does this, but I got a two-week notice, which was great. Because now I can start to figure out what I need to do next. The thing with freelancing is that if you need extra income, and no one’s biting at the bait that you’re putting out there in your proposals, there are plenty of other little things you can do. I’ve done tutoring before to supplement my income so I didn’t have to worry. 

Freelancing gives you that flexibility where if you need to dip into another skill set of yours for additional income, you can. I’m a little bit of a go-getter, so that was never an issue because I knew I would get it done however I had to. 

The Freedom And Flexibility Of Freelancing. 

Daphne: Yeah, I love that you mentioned being able to look for other sources of income. You and I have the exact same kind of experience coming out of the classroom. I came into an independent contractor position as an educational consultant, which is what I’m actually doing right now full-time in addition to all the Teacher Career Coach projects, but that made me really nervous. It was the first big leap. 

But the more you get into this world, the more you learn about it, the more data you’re able to watch, the more confidence you have. I am a completely different person than I was five years ago, when I came out of the classroom. Right now, if I lost that full-time salaried position, I know that I’d be able to quickly figure out the next thing.

I’ve even gone on Upwork myself just to look around. There was a position where they were just looking for someone to make PowerPoint presentations and it was $60 an hour. They said that it was going to take something like 20 hours, and I don’t have the bandwidth to take that on right now, but I could easily do that if I needed to.

There are just all these different types of things that I’m more confident with now that I’ve immersed myself in that world. They’re things that I never would have thought of or a competence that I never thought that I would have had, had I not really been in this world. Do you feel the same way?

Sarah: Yeah. And I mean, I think back to teaching. The benefit is you can look ahead at your district step plan and know how much money you’ll be making in 5 years or 10 years, and so on. And there’s definitely security to that. But to your point, the other side of that is yes, there are risks in freelancing, but there’s so much opportunity.

Maybe you couldn’t take on that 20 hour a week project, but you could easily find something you could do if you really wanted to. There are so many things on those freelancing sites. You could easily find a one-off five-hour project. There are so many opportunities, and you don’t feel locked in.

With teaching, if you want to make more money, you’re like, do I want to be an administrator? For me, it was like, Gosh, no. Or do I need to now transition to a whole new district and have to wait until a certain time of year to apply? Whereas in freelancing, you can just kind of do what you want to do when you want to do it. And yes, there’s more risk in that, but there’s also a big freedom. For my lifestyle anyway, with the moving around often, it’s great. I almost can’t imagine not having that, you know?

Daphne: The freedom that I’ve experienced over the last five years is incredible. I took on a full-time position as an instructional designer at a company, and I realized quickly that even though it was the coolest office and was a great company that I loved working for, that wasn’t what I wanted anymore. 

Even if I saw myself on a salary schedule and I could stay there for the rest of my life because I love the company so much and I liked their mission so much. And I had great potential there. But I had to leave and go back into educational consulting because of that freedom.

Sarah: Yeah, and, you know, I think there’s that whole idea of how stability seems great. But like, what is stability? When I first left the classroom, everyone was like, “How can you leave your stable career?” And then, within the first two years of being out of the classroom, I watched so many people lose these “stable” jobs, even before the pandemic. 

So, it’s just, it’s funny what we think to be true, and what we kind of lock ourselves into based on those assumptions or societal standards or whatever. Versus what feels right for us. 

The Biggest Lesson’s Sarah’s Learned Since Leaving The Classroom. 

Daphne: I completely agree. Is there anything else that you like about freelancing that we did not touch upon in today’s episode?

Sarah: Oh my gosh, yes. So many. I’ll just try to keep it short here. I knew I didn’t want to go into admin or anything like that. And you know, I could record a whole other episode about what my qualms were that led me to leave, but for me, I feel like that ceiling that was once existent is no longer. I don’t have to change a district to make more money. I can charge more or I can get new clients. There are so many ways to achieve different goals I have whether it’s financially or seeking out professional opportunities that I really vibe with.  

I know we already mentioned freedom, but I love that opportunity to really go wild and do what you want to do. And go where your heart takes you. I mean, you really are in the driver’s seat with freelancing. And that can be scary. But it can also be really beautiful and really rewarding. There have been some clients where I was doing it just for the money and it didn’t feel right. My fiance was like, “So like, give them your notice that you’re not going to continue your services.” I had flashbacks to teaching and how heavy it was to make that decision to leave. But I realized I didn’t have to worry like that anymore. 

So, you know, I definitely think that there’s just power and beauty and being able to do what feels aligned. Because again, for me, when it came to leaving the classroom, there was a lot that didn’t feel aligned. I wanted to be a teacher since I was teeny tiny, but I think we all have this vision of what it’s going to be like. And while I loved so many aspects of it, at the end of the day, this system that I was working in just didn’t allow me to really live out my values about holding kids accountable and preparing them for the world beyond the classroom. And that was crushing to me. It was emotionally exhausting. The advice I got most often was basically to compromise certain values to get by. I mean it was said more politely than that, but I was like, No, thank you. 

And so with freelancing, I don’t have to compromise those values, because I’m in charge in a way. You obviously have to work with other people, but those pain points that I experienced with teaching, if they start coming up with a client, I have the power to take action on that. And that’s really, really amazing. And I think it’s so important to be in alignment with what you’re doing. I don’t want to be cheesy but it’s been life-changing in many ways. So that’s probably been the best part of this whole journey for me so far. 

Daphne: I couldn’t agree more. I mean, I’m not in that traditional freelancing role,  but I have the freedom to make my own schedule and work on other projects in the same way. And I know that this is coming from a place of privilege because I am able to track my data and see financially that I’m stable enough to do whatever I want at this point. But having the ability to look at the upcoming months and saying, I do have infinite possibility of how much money I want to make right now? Do I want to create something that’s going to make money? Or do I want to take the next three months and just go hiking a lot and work on myself and, you know, focus on my relationship with my fiance? 

All of that feels so strange to say that I do have the ability to do that and do that comfortably. But that’s part of it. Once you are in this world, once you have created a solid foundation for freelancing—because I don’t want to say that’s going to happen in your first month of work. You have to work to get to that point and do so smartly. 

But yeah, I know that it is coming from a place of privilege. Like, I know that I am lucky to be here. And I know that it may not last forever. And someday I may have to make a change. And I may have to pivot and go back more into a traditional career. But I would not give up the last few years for anything. And this has been something that has been truly life-changing for me. And I feel like we are sharing that same experience and many people who start freelancing feel the same way.

Sarah: I think a lot of teachers go into teaching expecting it to be their forever career. After leaving, there was a piece of me that felt like I was losing this part of my identity. But again, as a freelancer, I was able to find clients that helped me keep up that teacher spirit, like you and those clients that I break down big concepts for. I’m still feeding that educator inside of me. 

But it’s been the biggest experience for personal growth. I mean, my fiance has said multiple times, “It’s been amazing watching you grow over these past two years.” Again, you learn so much about yourself, and with teaching, you kind of get so caught up in the system, because you have to make it work and a lot of cases. With freelancing, yes, there are ups and downs, but none of it’s been wasted. I’ve learned something from every single one. 

I truly think that not only am I better for it, but I also think I’m more aligned with myself and my soul or spirit or whatever you want to call it. And you know, it took some flubs to get there, but I feel like I know more about myself now than I ever did before. And again, that’s coming from someone who wanted to be a teacher since I was like five years old. 

I think I was so caught up in always having that next step planned that I never really stopped to think about what I want, or how I felt. You just kind of keep going because life is busy and it’s easy to do that, right? And get caught up in it. So, it’s just been an incredible employment opportunity, but also a journey of self, if that makes sense. And so like you said, I wouldn’t change it for anything.

Daphne: I know that the listeners can’t see me, but I got emotional with your response right now. I teared up. I feel very similar. But I’m also just so happy for you and I’m so happy that I’ve met you and have been able to work with you. 

I don’t think I could have ended this on a better sound bite than what you just said right now. I mean, that was so beautiful. And I’m just so grateful that you came on to share your story.

Sarah: Oh, thank you so much for having me. It’s been a secret thing that I’ve wanted to do ever since I started doing work with you on your podcast. So dreams come true.

Daphne: Thank you so much for being here.

Thank you to our podcast sponsor, Forever My Always by Eevi Jones. This book is a beautifully written and illustrated keepsake perfect for recent grads about to venture out of the nest for the first time. Gift a copy today!

Where to go next

If you’re just beginning to think about leaving teaching, brainstorming other options is a great place to start. But if you’re like many others, teaching was your only plan—there never was a Plan B. You might feel at a loss when it comes to figuring out what alternatives are out there.

Start with our free quiz, below, to get alternative job options for careers that really do hire teachers!

What career outside the classroom is right for YOU? Free Quiz

Taking the First Steps to a New Career

If you’ve already taken our quiz, it may be time for the next steps. I want to help you get some clarity in the options available to you. To know EXACTLY what you need to do (and not do) in order to get your foot in the door.

One of the biggest mistakes that I see teachers make is that they try to navigate this process alone. Often, they put off “researching” until the very last minute. Which sets them up for a very stressful application season—trying to juggle teaching, figuring out a resume, researching jobs, and hoping to nail down some interviews before signing next year’s contract.

You don’t have to do this on your own.

If you are considering a career change from teaching, I have a resource that can help you today. With the help of an HR expert with over 10 years of experience, I’ve created a guide to support you in the early stages of your transition out of the classroom.

In the Career Transition Guide, I’ll walk you through the factors to consider and answer those first-step planning questions including:

Career Transition Guide
  • A compiled list of over 40 careers that teachers can transition into
  • An overview of how to read job descriptions
  • How to evaluate the risk of leaving a full-time teaching job for the unknown
  • Example translations from classroom-to-corporate resumes
  • A checklist of everything you’ll need to do for your career transition (so you know you aren’t missing anything!)
  • and more…

Take the first steps on your path to a new career now for only $19 $9!


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Step out of the classroom and into a new career, The Teacher Career Coach Course