Leaving Teaching and Becoming Your Own Boss with Joanne Homestead

Joanne Homestead is an email-copywriter, strategist and former-educator. She is on a mission to help passionate female entrepreneurs and coaches who are growing businesses in the wellness, well-being and mindset space. With her expertise, tools and creativity, Joanne breathes new life into businesses via copywriting. She loves helping create unique voices ands storyline that are relatable and personal.

Her journey into copywriting evolved from a 15 year career in teaching. As an educator she held multiple roles over the years — from a primary school teacher to a literacy interventionist as well as an instructional coach for teachers. The pandemic made Joanne take the final leap out of that profession and into her current work

She is now the proud founder of Desk Plant Creatives, where she offers email-copywriting, courses, programs and a variety of service-packages to female led businesses. 


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In this episode you’ll learn:

  • What Joanne does
  • How did the pandemic affect her career
  • How she got into teaching
  • Why was it hard to leave teaching
  • Lessons from the first time she decided to resign
  • What she found out in her career transition workshop
  • Her second job as a reading specialist
  • What made Joanne finally switch her career
  • The impact of attending a Virtual Summit
  • Listening to interviews of former-teachers and their shared experiences
  • Joanne’s final leap from her teaching career
  • Storytelling — the connection between teaching and copywriting
  • Identifying the parts of teaching that she’s been passionate about
  • The numerous transferable skills of teachers
  • “What’s your dream job?”
  • Advantages of being your own boss
  • Words of encouragement from Joanne

Resources Mentioned:

Joanne’s Free Guide to Writing Emails that Sell: https://www.subscribepage.com/3_simple_steps_to_irresistibly_entertaining_emails_that_sell

Joanne’s Instagram

Joanne’s Linkdin

Software Generated Transcription:

Dan

Joanne, thank you so much for joining me. Welcome to the Meaning Movement podcast.

Joanne

Hi, Dan. Thanks for having me on. I’m excited to be here.

Dan

It’s so fun having you on. The question I like to start with is how do you begin to talk about what you do?

Joanne

Well, I’ve had a very large transition in the last two years. I was a teacher for 15 years, and I taught in elementary schools in different grades, different districts, all the way around the world for 15 years. And two years ago during the pandemic, I made a very big switch. And now I am an email copywriter and strategist for women entrepreneurs online. And I work with clients who are in wellness and well being and mindset. So I basically write words and craft my clients stories for their email sequences and newsletters. And I help them stand out, build relationships, nurture, and help them sell their courses, programs, and services. A lot of kindness and integrity.

Dan

I love that. Teaching for 15 years, teaching around the world, and then a pandemic and a career change. I want to dig into each piece of that. How much of the career change was motivated by the pandemic and did that present an opportunity? Was that just the needle that broke the camel’s back or just maybe near that transition for us?

Joanne

Yeah, that was definitely the needle that broke the camel’s back. I actually tried to leave teaching two times during those 15 years, and finally when the pandemic hit, it kind of pushed me over. And it was that moment where I said, okay, it’s time to really leave teaching at this point. I also at the time had my son, who was two years old at the time, and he was at that age where I really wanted to spend more time with him. So I wanted the flexibility of my schedule to just have lunch with him or get home before it was got dark, things like that just before he goes to bed. And so that was also a factor in helping me to finally leave teaching.

Dan

Yeah, I love that. So 15 years in teaching. Was teaching always just the career path that you were going to be on or how big of a deal was it for you to leave teaching?

Joanne

It was huge because from College on, it was always teaching. I got my undergraduate in elementary education. I got my teaching degree. I got my license so I could teach in public schools. And then I taught for a few years in Shanghai at an international school, which I really loved. I could be as creative as I wanted, but there was definitely a lack of resources in the school and then came back to the States, and I actually got my master’s degree in curriculum and instruction in literacy. So also education based. It was for kindergarten through 12th grade, and it was to become a reading specialist in a school I could be a reading interventionist or be a reading coach for teachers. So all teaching all the time, breathing, living teaching.

Dan

And did that career path emerge early for you? I mean, you studied it in College, but did you always want to be a teacher?

Joanne

I thought maybe I did always want to be a teacher. But I looked back and I found this old printout that I had written in middle school for computer class. In it, I said I wanted to perform as a flautist, I think a flautist.

Dan

Yeah, I’m not sure.

Joanne

So I don’t remember that. But I mean, I definitely feel like growing up, I have a younger sister and I would always create all these activities for her. Like I was her teacher. I would read her a lot of books and we just do a lot of things together. And I’d make up these I just make these worksheets for her, like riddles, math problems. I just make little things for her to solve. And I always enjoy doing that. And I feel like that was a big part of teaching for me. It’s just like creating these educational experiences where the kids can interact with whatever the experience is and learn something from it. So yeah, I would say yeah, it’s kind of always been there. So yes, it was a very big deal when I left teaching.

Dan

Yeah. So you tried to leave a couple of times. You said what happened to the other times you tried to leave? And I think this is super relevant because I think a lot of people end up listening to the show because they’re thinking about making a change, and change is hard. And so just to hear stories of something like this where you’ve thought about it for a long time and then finally we’re able to take the leap or whatever metaphor we want to use there, it’s very relevant to people’s lives because I imagine there’s a lot of other people listening who are in similar places where they’ve maybe flirted with an idea and maybe even dipped their toe in the water here and there, but haven’t gone in all the way. So, yeah, tell me about some of those. What do you mean by that? I guess about trying to leave teachers?

Joanne

Yeah, it was very hard because I feel like especially for teachers, our identities become our job. It’s all mixed together and it’s hard to lead because it’s part of our identity at that point. And we also have that guilt because we love the children and we want what’s best for them. And so it’s hard to leave the children because you feel like you have a responsibility for them to learn and teachers, you can train for it. Those were definitely things for me that made it hard, but also because I think as a teacher and a lot of teachers think this is that they don’t have any other thing they can do if they leave teaching because you are a teacher, what else can you do? We don’t even know. And that was where I was. I tried leaving, but I just had no idea what I would do besides teaching in a school. That’s all I knew. So the first time I tried to leave, I had taught for seven years, and I was just so burnt out to a point where just my mental well being, my emotional well being, my physical well being, I wasn’t sleeping well.

Joanne

I just felt like my body physically couldn’t even handle it anymore because I think I was just so passionate about teaching, and I work overtime, and I just work all the time. And things in schools are always changing. They don’t really give you any training, so you’re constantly trying to keep up with whatever they’re mandating in schools for you to do. And so there was so much expectations and pressure, and it was just too much. So I resigned, and it was big because I was, at the time, the sole income maker for our household. Well, so it’s kind of crazy just to resign and not have a job lined up. So I was the sole income maker for our household, and I did not have another job lined up. And I actually had no clue what job I was even going to get. But I was done. I couldn’t handle anymore. And I thought, okay, maybe I’ll be a Secretary or something. It just sounded like something very simple to me. Sorry, I’m not offending any secretaries out there. It just sounded so much more manageable. I imagine myself sitting at a desk. I could answer the phone.

Dan

We call them administrative assistance. That’s probably more a term people will be less offended by.

Joanne

Exactly. That’s what I realized when I started applying secretaries.

Dan

It can be quite complex. I know a couple of that are all stars.

Joanne

Oh, yes, I know. After I left the teaching, but I did become a virtual assistant, and I do know there is a lot of I met at the time, I just had no idea. I’d only been in teaching. And so I realized, yes, secretaries are called administrative assistance. That was something I learned.

Dan

But I get the sentiment, like, you just want something where you can just show up, be at your desk, not have to be stressed, and then go home. Right. Wouldn’t that be nice? Just have a job that’s just a little square box that you could sit in and then leave.

Joanne

I totally was probably getting that from media. It’s just in my mind that was something that sounded so simple to me.

Dan

Totally.

Joanne

I started applying and kind of asking some friends and seeing if there was anything in the corporate world. I had no experience in the corporate world at all. I actually tend to cringe when I say the word corporate, but I was so desperate and just really wanted out so I had applied for a few things, and I got a couple of interviews. I wanted to be like a call assistant for a company that provided all the logistics for CEOs for their transportation when they are out of state having meetings or retreats or something. And I remember in this interview, the vice President had interviewed me. And the first question she asked and I had kind of prepared for this interview, ready to answer questions. But her first question she asked totally just threw me off. She asked me, what is your dream job? And I had to think for a while because I was not prepared for that question. I didn’t know how to answer it. I said, what is my dream job? I don’t even know. I don’t know what I said. And then she followed up by saying, I see that you’ve taught for so long.

Joanne

Why are you making this big switch to something that has really nothing to do with what it looks like you’re passionate about? And that really struck me right there because I realized, yes, that’s true. My passion is teaching. Why am I trying to do this? And so I told her, I said, well, I really like to help people. It did help me think about I do like to serve and help. And so I tried to make it sound like I really wanted to help these people, like these CEOs with their transportation.

Dan

They’re stuck. Otherwise, we have to help them.

Joanne

We got to help these CEOs, these really successful multimillionaires.

Dan

If we don’t, you will.

Joanne

Exactly. Okay. That interview told me that obviously I needed to stop and think for a minute what I was doing here, because she really brought up a good point.

Dan

Yeah.

Joanne

I went to a career transition workshop at my alumni Cu Boulder, where I got my master’s degree. And it was this actually this really interesting thing where the career counselor had this ten page workbook you had to fill out beforehand. It was all about, what are your top three movies or your top three favorite books? Who do you admire? And I thought it was a load of just fluff. Again, no offense. Anyone out there? I just didn’t know.

Dan

Yup, Yup.

Joanne

So I didn’t even fill it out. What does this have to do? I just need another job. What does this have to do with anything? And so I went to the workshop and that just blew my mind. It really connected things for me because I ended up one of my friends that I knew in the area also went to it. We didn’t know we were going to be at the same thing. So it was great to have her there to discuss and talk things through with her and just like, make connections with what I was passionate about, what’s meaningful to me in work. And the books and the movies really created a theme that I didn’t even see for wanting to like, there was a theme of an underdog who really wanted to fight for justice and wanting to help people who are struggling. That was just an interesting theme there. And so I went to see the counselor afterwards on a 101, and he basically told me, he said, yeah, it really sounds like teaching is your career. And I said, oh, that’s not what I wanted to hear. I can’t. I just can’t.

Joanne

And so it was just another experience where I was just realizing things about myself that I hadn’t ever thought about because I’ve always just been in teaching. And so that was another piece of it. So make a long story short, I ended up not finding my desk job, and so I applied to be a substitute teacher because the next school year was starting in the meantime. And in that process, I ended up finding a reading specialist job in a school, which was kind of my dream job at the time, but thought I could never get because of funding and budget cuts all the time. That position is very rare. And I found it. And so I applied and I got it. So I did that. I actually did that for five years. So that’s why my teaching career went up to 15 years in the end.

Dan

Yeah. Super interesting story. It feels like this has kind of been bubbling up, emerging in you this kind of. Yeah, maybe a personal journey, personal development journey along the way of questioning. Is this really what I want to do? And finding some resolution in that maybe just to narrate the true transition. Right. That was your attempted transition. How did you go from doing that to saying, I’m going to start this thing, I’m going to start doing freelancing and starting my own business. Can you write some of that transition for me?

Joanne

That started in February of exactly two years ago in February and actually started with an email that you sent. I’m a part of your email newsletter. And so, yes, you started it.

Dan

I’m so happy that I get to play a part of this.

Joanne

Yeah, great. I remember the subject line had something to do with I think you said something about teachers in there, and that absolutely piqued my interest there. So in the email, you said you were going to be a part of Virtual Summit with Brittany Long, who was a former teacher, and she was going to be doing, I think it was a two or three week Virtual Summit interviewing former teachers who left teaching and are now working online. And so she interviewed lots of different people and what kind of roles they ended up in online, like maybe a copywriter or became a business coach and started doing graphic design. And so I signed up for that Virtual Summit. And you were also part of the Virtual Summit. And so I signed up and I could listen to the interview every day, and then it would expire. I wouldn’t be able to hear it. So every day I drove to school for work. I would listen to the interview in the morning when I was driving there. And on the way back, I think I would listen to it again. And it was three weeks of this every day.

Joanne

I mean, I listen to probably 15 interviews. So great of all these teachers who left and said the message was, you can do it. If you want to leave teaching, you can do it. It’s possible you can make a living doing something online. And this whole online business world I just didn’t know about, and I didn’t understand. And suddenly I had this hope, like, oh, look at all these people who were teachers, and they left. And it was just interesting listening to their stories. And it really resonated with me because a lot of them were very similar, like burnout just too much pressure or wanting to have flexibility with their family. So within that virtual summit, I learned about the Esther Inman who does the 90 day VA course where you sign up for her course online. And in 90 days, she’s trained you to become a virtual assistant online. So that was the route I decided to take because out of all of the different online roles, I didn’t know enough to know what I wanted. So I took that route, and I took the course. And so that summer, I started my business and became a virtual assistant and started taking on some clients.

Joanne

And I was still planning to go back to teaching the next school year, but I really didn’t know what was going to happen because the pandemic had just started already. And so I took on just one client just so that if I need to go back, I could do it as a side hustle. So I was thinking maybe this could just be a side hustle. I could do a gradual transition out that will really help with the finances, because, again, I was the sole income earner. Yeah. And what ended up happening was not gradual at all. The school year began. They were going to switch my role from reading interventionist. They wanted to put me back in the classroom, which was giving me flashbacks, not great flashbacks for me. And they wanted me to just do it online. And they were going to mix thirty-five first graders from different schools for me to have. And I just said, no, I can’t. I just can’t. And that was the push that pushed me out. I just said, for my own health, I just can’t do that.

Wow.

Joanne

And so I did the leap, no gradual transition. And I resigned, and I started looking for more clients as a virtual assistant.

Awesome.

Joanne

So, yes, I do have a lot of respect for administrative assistance.

Great.

Joanne

The first task I had to do for a client was cancel their Comcast business account, which, if you Google, is the hardest thing to do. And my client cancelled. She kept apologizing. She said, I’m sorry I’m making you do this. I said, no, don’t apologize for my job. I can do whatever you need. And so that was my first task. After I did that, I said, I can do anything now.

Dan

Yes. After you’ve done that, if you’ve dealt with Comcast, you’ve done it all. You can do anything on this side of your transition. How do you think about, like, a couple of times you said that you are passionate about teaching. How do you think about that passion.

Joanne

So as I did all these tasks as a virtual assistant, I realized what I loved best, which is why I got into the VA world was I wanted to figure out what tasks I liked doing was the writing. And not just the writing, but the storytelling involved in writing, which is how I ended up now Niching as an email copywriter, because there’s so much storytelling involved. And I realized when I was teaching, that is something that I absolutely loved doing when I was teaching was basically connecting learning to stories that resonate with the students or give them an experience that wanted them to own whatever it was I wanted them to own and really connected with them. And you could just see, like, instead of just teaching a lesson, which for most students will just go over their head and they’re not going to listen. They’ll just hear me as the Charlie Brown adult. If I tell a story, it could be a story about me and I connect it or a story about a previous student, or I could just make up a story. They are just totally like, their whole bodies are listening and watching and they’re almost not breathing because they’re just so wrapped up in this story, and then it connects, and then they just get super excited.

Joanne

So I realized that same passion is what I get to do now as an email Copyright is I take my client stories and I craft them so that readers want to read it and they want to take action, and they know that’s going to help them with the next step they need. And so that was the connection to teaching for me.

Dan

I love it. Yeah. It sounds like you’re just to kind of make this little more practical for people who might be in a similar spot where there’s something that they’re passionate about, but for some reason, it’s not working, maybe even to drill down a little bit more. What’s beneath that passion? Why, instead of just saying I’m passionate about teaching, like, parts of teaching, what specific activities do you do that you love? Because that’s where more of a crossover energy, I think, can be found. Do you feel like that’s accurate?

Joanne

Yeah, definitely realizing that. Okay. I needed to look beyond the teaching part. What exactly in teaching did I love doing, and that was one of the things. And the other one was collaborating. Last five years as a reading interventionist, I did a lot of coaching for teachers to help them coach them in their literacy lessons. And so I loved collaborating with teachers and working with them and together brainstorming and figuring out what’s the best way we can develop this curriculum for these particular students. And so I’ve been able to take that as well into what I’m doing now and realizing I miss interacting with people. Like the writing part I love, but I also love working with people, too. And so I do consulting where I can really collaborate with my clients and help them figure out their email marketing. And so that’s also lighted me up a lot.

Dan

I love it. I love it. How do you talk about your experience as a teacher in a way that shows the relevance to what you’re doing now when you’re talking to potential clients?

Joanne

Well, definitely, as a teacher, you do everything. And so you have so many transferable skills. It’s insane how many transferable skills teachers have because they don’t just teach. They have to do counseling, emotional counseling. They need to collaborate. They need to be their own assistant and figure out all the logistics of field trips and lessons and scheduling. They have to manage parents. They have to manage students. They’re a manager. Honestly, like, all the levels they have to do so much, which is a reason why a lot of teachers burnt out is a lot to handle. And so when I work with clients, I feel like a lot of those. There’s so many transferable skills. It just has a different name when you’re in business and learning, like project management. Yes, I actually did a ton of project managing as a teacher. It just wasn’t called that. Developing curriculum for my clients is. Okay, we need to do backward design. What is your end goal? What’s your end goal for? Maybe like an email sequence. Okay, now we’re going to work backwards on how we can help with the messaging to get your lead to take that buyer’s journey with you.

Joanne

It’s just the same thing. It just has a different language. And I’ve just had to learn a lot of business language, like ROI. When I had first tried to leave teaching, I had interviewed somewhere else for educational Business, and they asked about ROI, and I had to. I was so embarrassed, I asked them, I said, what is ROI? I don’t know what that is.

Dan

It’s not a part of your world. How would you know?

Joanne

It’s not a part of my world now? I talk about it all the time. It’s funny. Just a few years ago, I would have no idea. Now I’m like, oh, yes, we talk about all the time. It’s just a different language. And I’m doing the same things that I was doing as a teacher.

Dan

Yeah, that’s so fantastic. I love just that idea of, like, what’s another name for it that’s I think a simple place to start. Think about all the things that you do in your job that might be, quote, unquote, soft skills or might not translate to wherever you’re going and think about what are the other names for similar activities in the direction that you’re headed. I think that’s a really helpful framework for people that they’re thinking about this. I want to just kind of circle back to the interview you had where you were asking, what is your dream job? How do you answer that today?

Joanne

Yeah, I think of it very differently now, or I feel like it’s so much more tangible now. Before it was so abstract, I just didn’t know. And so I would say now my dream job is where I can work for myself and create my own schedule and decide my pricing for my services that make sense for how I feel. It’s valued for my clients. And yeah, there’s a lot of back end work with running your own business, but I love it. I never would have ever thought of myself as an entrepreneur or someone who could be in business, never in my life. And now I’m just loving it. I just could not even believe how it’s just changed the way I think of business now and marketing and sales. It doesn’t make me cringe anymore because it’s just about connecting with people and helping them, you know, it’s the same thing. It’s just in a different world. So definitely as a dream job, working for myself and realizing I don’t work well in systems like school, like systems where there are these parameters and you have to do this in order to do your job, because I don’t feel like I’m being trusted for my expertise because they’re telling me, you have to do it this way.

Joanne

And I’m thinking, no, actually, I have a better way to do it, but I don’t have the flexibility to do that. So as a boss for myself, I can kind of decide, like, okay, what services do I want to provide that makes sense for me, that I really like, that I know I can do really well, and I have the creative flexibility to be able to act on it, love it, and know that it’ll work. So I think a big part of that dream job for me was getting out of a system, working for myself. And I think also working with people who are more mission driven or have a sense of wanting to help other people. My clients are all in wellness and well being and mindset. So really, I think that’s a big drive for me too, because as a teacher, I felt like advocating for people, helping people live a better life was a big part of it. And so now I feel like I still get to be filled with that because I know my clients, that’s what they’re doing for other people. They want people to live like a purposeful, meaningful life.

Joanne

And to me, that fills me. Whereas I was going to try and work with clients who are in, I don’t know, like finance or law justice stuff. And I realized that is not my realm that doesn’t like me up. It just wasn’t for me.

Dan

That’s great. I love it your transition. I love just thinking about your whole transition. You’ve just come so far, and I wonder if you have any words of encouragement or wisdom for someone who might be in a place like you were years ago feeling burnt out but not sure what to do because there’s so much of self education, personal development that you’ve been through to go from, like, I really want out to where you are now. And it’s really hard to think about making that transition when you’re on the other side of it. And I’m curious if you have any words of encouragement, words of wisdom to share to the Joanne of a few years back.

Joanne

Yes, the Joanne of pre-pandemic past.

Dan

Yes.

Joanne

I think definitely like, something you’re doing with your podcast is awesome because you get to interview all these people and their stories. And I think really hearing other people, like, real people, their stories and how they’re struggling or trying to transition was huge for me. So I would definitely say just hearing other people’s stories, find a podcast, find a virtual summit, whatever it is, and specifically in your career, I think, also really helps because then it really resonates. And I feel like it just gives you a lot of hope and courage to say, okay, all these people can do it. I can do it, too. I think that’s definitely one thing, like listening to other people’s stories, and the other is breaking through, like, limiting beliefs about yourself, which can be very difficult to do on your own, because sometimes you just don’t know or you don’t see it. So finding someone you can talk to, like that career workshop I went to was really enlightening for me, finding a coach, doing some kind of self discovery process. I know that’s, like, what you do.

Dan

The calling course is all about that.

Joanne

There we go. Perfect. I think that was also a huge thing. It’s like figuring out what were my limiting beliefs. I didn’t think I was a writer. I mean, I wrote a lot since I was a kid, but I never saw myself as a writer. That just wasn’t an identity for me. And now it is. Now I can go back and kind of piece it together and go, oh, yes, I have been a writer. I just never thought of myself as a writer. Things like that.

Dan

Yeah, those are great recommendations. Yeah, really great. Well, we’re coming up on our time here, Joanne, for people who are really enjoying your story and want to follow along with your work or maybe they’re looking for some help with some emails. How can they connect with you? Is there anything you’d like to invite them to?

Joanne

Yes, for all the listeners out there, you can connect with me on Instagram and my business name is Desk-Plant Creatives, desk plant like a little succulent desk plant. I love it and LinkedIn my name is Joanne Homestead copywriter so you can find me there. I am currently on maternity leave but I’m hoping to get back to work in March and we’ll be posting a lot of content on Instagram and LinkedIn on copy hacks and email marketing. Storytelling is a huge part of it. So how to build that trust with your audience and create stories that are really engaging. I also have a free guide that you can sign up for and it’s how to harness the power of storytelling for your business. If you are an entrepreneur listening or you’re a small business owner and I teach you how to turn your leads into rating fans of your work, they will just want to buy up everything that you want.

Dan

I love it. I love it. We’ll make sure to put links to your Instagram, your LinkedIn as well as your guide in the show notes so people can just click on through and follow along there. Joanne, thank you so much for coming on the show. It’s just been so fun to connect with you and really appreciate it.

Joanne

Yeah, thanks for having me on.

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