From high school English teacher to professional writing trainer & coach meet Leslie O’Flahavan from Silver Spring, Maryland
Have you ever been asked by your boss to take on something totally outside your job description, and then suddenly, you’re discovering a whole new skill or side of yourself? It’s funny how these little pivots can change everything about how we see our potential.
Meet Leslie O’Flahavan! She’s someone who didn’t make a huge leap, but instead slid her career forward, moving from nine amazing years as a high school English teacher to becoming the owner of E-WRITE Online, a training consultancy where she speaks and teaches writing workshops for Fortune 500 companies, government agencies, and nonprofits around the world. She’s even a LinkedIn Learning instructor with six courses and created the “Bite, Snack, and Meal” approach to web content writing (she’s got a Wikipedia page to prove it!).
In this episode, Leslie shows us that a career shift isn’t about ditching everything you know—it’s about putting your skills to use in new ways. She shares how going into new roles with an open mind (and asking for help when you need it!) can make all the difference. You might find that you already have all the courage you need to pivot, whether it’s a small tweak or a big change.
Connect with Leslie
Jenny Dempsey (00:00.088)
So if I were to encourage anyone who's thinking about flipping a career and kind of inventorying whether they have the courage, I would ask them, well, think about what you've been called to do in your actual real job now. Your boss flipped your career on you. Your boss changed your responsibilities and you had a stark choice there. Quit or stay? did you stay? Yeah, I stayed.
then you've already kind of experienced what it feels like to have the flip imposed on you. Why would you be less able to flip when you seek it for yourself? Welcome to the Career Flipper, a weekly podcast featuring career change stories from people all around the world in all kinds of industries. We talk about how they get from point A to point B and all the twists and turns in between. If you've been thinking about switching careers, consider this your permission slip.
And I'm your host and fellow career flipper, Jenny Dempsey. After many years working in customer service and customer experience in the tech startup world, I got laid off and I stumbled into furniture flipping, taking pieces, headed for the trash, and giving them a second chance. If you're into that sort of thing, check out my furniture makeovers over on Instagram and TikTok under San Diego Furniture Flipper.
But I started this podcast because I felt really weird and honestly kind of alone when I switched from tech to furniture restoration. But as I've been flipping my own career, I've discovered that I'm not the only one making big changes. So I figured why not talk to others and share their stories? We all can learn a lot from one another. I hope that this episode gives you a little actionable boost of inspiration on your own career journey. Okay.
Have you ever been asked by your boss to take on something totally outside your job description and then suddenly you're discovering a whole new skill or side of yourself? It's funny how these little pivots can change everything about how we see our potential. In this episode, you'll meet Leslie O'Flahaven.
Jenny Dempsey (02:11.424)
She's someone who slid or glided her career forward, moving from nine happy years as a high school English teacher to becoming the owner of eWrite Online, a training consultancy where she speaks and teaches writing workshops for Fortune 500 companies, government agencies, and nonprofits around the world. She's even a LinkedIn learning instructor with six courses. I've personally taken a few and highly recommend them.
as well as created the bite, snack, and kneel approach to web content writing, and there's a Wikipedia page to prove it. In this episode, Leslie shows us that a career shift isn't just about ditching everything you know, it's about putting your skills to use in new ways. She shares how going into new roles with an open mind and asking for help when you need it can really make a big difference. You might find that you already have the courage you need to pivot, whether it's a small tweak or a big change.
And maybe this episode opens your eyes to really redefining what it means to flip a career. Let's get into the conversation now.
Well, hello, Leslie. thank you so much. Hello. Me on the career. Hey, hey, Jenny D. It's so good to have you here. We go way back. go way back. I don't even know what year, but it's at least 10 years, I'd say. We've known each other for about 10 years. Yeah. The customer service, customer experience space through writing.
through different projects that we've worked on, you have really been someone that I have looked up to, over the years for just guidance on life, but also you're just a vibrant, wonderful human and I love being in your presence. So, having you here. Well, we feel that is a mutual admiration society right there because you have always spurred my own creativity and we've had
Jenny Dempsey (04:17.322)
everything from the girlfriend giggles to the tycoon planning together and I love it. love it. Well, tell everybody a little bit about you, where you are and what you do now before we dive into all the clips. Okay, here we go. This is the status of me right now. So I'm the owner of eWrite, which is a writing
training consultancy. So my company's mission is to help people learn to write well at work. That is my mission. And I provide training and consulting services to support that mission. I'm the owner of this company and it was, it's 29 years and three months old. So I founded the company in 1996. I had a business partner. She retired in 2011 and I've been the sole owner since then. Wow.
29 years and three months. Congratulations. So let's just get into it. How did you even get to this point? Tell about all your curve flips. How did you start this, I will absolutely tell you this story. And I hope my story really includes flips. In fact, that's the question we'll answer together when we're done. Because I don't know if I flipped or if I
slip, slide it, or if I turned right or turned left along the way. So here is my quick story. I'm going to tell it to you in a nutshell. I have been a writing teacher all my professional life. I spent nine years as a high school English teacher, and it was nine years of joy and thriving. I loved being a high school English teacher. When my first child was born, I held her in my arms and I was like, well, this isn't going to work.
I can't be a teacher all day and then, as was my habit, come home and work the whole rest of the day, you know, work from 7 a.m. to 3 30 p.m. at school and then work from 5 30 p.m. to 10 30 p.m. at home. I thought, how in the world can I be a parent and a teacher of the caliber I want to be? This seemed unsolvable. And Jenny, I am sure the parents
Jenny Dempsey (06:39.178)
who are listening to us are actually rolling on the floor laughing because I didn't have the vision to understand that everyone who has a family at home is as torn as I couldn't conceive of being. I just didn't imagine it was possible. So I started to think at that time, what other work can I do where I won't be so torn, where I will have enough energy to do a great job
in my job and also enough energy and time to do a great job in my life as a parent. And I had the naive notion that I would go into business for myself and that I would start a writing training consultancy. And again, everyone is now rolling on the floor laughing even harder because you don't get more free time when you're self-employed. That's ridiculous.
That's ridiculous. I had less free time. You're not really in charge of your free time in any meaningful way when you're self-employed. Yes, you can go to the dentist and you don't need to tell anyone that you're not available from 10 a.m. to 1130. That's true. But you have to be developing your business, marketing it and available in ways that are all around the clock.
So that was also funny. So I flipped my career or I tilted it or I moved it from being employed by a school district or a university as a writing teacher to becoming a business owner. And I'm so happy I did, but not because I needed to burn down my identity as a high school teacher. I wasn't burnt out.
I didn't hate teenagers. That wasn't it at all. It was a decision I made with goofy optimism and that worked out great. So like when you start it, like it is really hard. You're a new mom and you were juggling that. How did you learn early on to kind of manage juggle your time? Like how did you do all the things? Well, well, you know, I didn't. I didn't do all the things, you know.
Jenny Dempsey (08:59.52)
When I became a parent and I was experiencing that torn feeling, I used to describe it as follows. It's like you're a piece of paper and you can tear the piece of paper in half, but the half is never enough for the task at hand. Like half of you isn't good enough for your family and half of you isn't good enough for your work. So both need more than half of you.
It's not deprivation, it's joy. I felt joy and I do feel joy now. And the reason was good fortune. I was fortunate enough that my business didn't need to make a whole lot of money in that first year. My husband and I talked about it and I did not make a whole lot of money. Here at Full Four Disclosure, I made $3,000.
No, that is not a lot of money. No, it's my income has grown and grown and grown and grown and I make good money now and I've been making good, good, good money for years, but I didn't make a lot of money that first year. And, you know, my choice to leave my school district, my teaching job was naively informed. Like I said, I was being kind of.
I don't know. I wouldn't say childish, but I didn't really know what would happen. And everything worked out fine. That's kind of how I would describe those early times. Yeah. Yeah. So you made that choice and you're at this place now where you can look back and be like, you can see the growth. But in the beginning, that kind of like, I mean, I love how it like it was a very optimistic choice.
made it for the right reasons. You followed your intuition in a way and you, it sounds like there really wasn't any second guessing or wondering if it was going to work out. You just kind of knew. You're right. There wasn't. Now you and I have talked about these kinds of feelings before about how to make a decision. And I just want to list the numerous supports I had that gave me this feeling of wellbeing.
Jenny Dempsey (11:23.562)
Okay, number one, as I said, my husband and had discussed this and we agreed that if I didn't make a lot of money the first year that was okay. Number two, I had credentials in the field I could go back to. know, teaching would always be there. I could go back there. Number three, I had a business partner and my gosh, this was
I often, I am so fond of her to this day. And I think about this as like one of the love relationships of my life, even though we were business partners, that we made something together, that we enjoyed our collaboration, our creativity, that we, know, the business was kind of like carrying a sofa bed to a second floor apartment, you know.
And she carried a corner and I carried a corner. We carried it really well. So there was that, you know, I was fascinated by how she thought and we worked well together. And that was really great. And, you know, I had financial backstops in my life. If everything went to shit, I would still be OK. My dad was a great support. He was proud of me. He was happy for me. And all of that gave me a feeling of well-being, plus just a basic
feeling of well-being, which I had then and I have now. That's incredible because listening to the ways that we're able to be supported just continues to lift us up as we move forward. Like I wouldn't, hey, I mean, just with friends and my boyfriend and his family and just the level of support of just being able to even like reach out to you and like, Leslie, this is going on. you know, like little.
little things that really add up to supporting, you know, what we what we're going to do. And so as time went on and you're, you know, building this business and then in 2011, you know, your partner retires. So did that change anything for you? Because, you know, what what happened at that point? Jenny, I was so happy to have the business for myself.
Jenny Dempsey (13:34.28)
I was ready and I was happy. My partner was chronologically ready to retire. She's older than me and she wanted to retire. We had set up the business in a way that favored both of our strengths and both of our interests. So even though it was many, it was a consultancy and we could each bring in and do projects separately or together that we liked.
I knew what I wanted to do and where I wanted to grow. wanted to do bigger and bigger training projects. I wanted to be a prominent voice. I wanted to be an expert and be seen as an expert. And we were doing different kinds of work. And when she said that she was ready to retire, I was ready to take over and to move forward. And, you know,
No small, no small thing. She retired happily. I went on without her happily. We remained friends and we respect each other and enjoy each other to this day. I love that. It's just such a, it's the partnership everyone dreams of having. I know, I know.
I know I would only wish this wonderful thing that you could all have your own Marilyn Rudick. But I have mine. She's mine. You know, so you knew, I mean, you both knew the you were in, you know, in English and you knew the writing and you knew how to teach that so well. Where did the business knowledge come from? Because now you're running this. Was it mostly her or like how? No. How did you learn it?
we we learned it on the go and we made a few mistakes some funny and some not so funny so Marilyn my partner was a novelist she she wrote she wrote it to harlequin romances. She was she was a freelance creative writer and we did not know what we're doing but we knew when we needed to hire advice and higher help so from the start we had an account.
Jenny Dempsey (15:52.762)
We didn't know anything about accounting or keeping business records at all. So we had the world's most patient accountant, you know? And when that woman left and went back to her home in Germany, we had the world's also most patient accountant. So we had to hire help. We hired accounting help. We hired graphic design help. We hired legal help.
for a little bit to set up contracts and that kind of thing for us that we could reuse. As we went at one project, a curriculum project we were building, we hired a lawyer to advise us about copyright issues because we were teaching about web writing. We wanted to use online examples and we needed to know whether we were blundering into a copyright concern. So along the way we did hire help. We needed to hire
web design help, needed help occasionally with web maintenance issues. We needed, we need a lot of help and we, we, collaborated well in hiring that help. were such a small company that at the start, especially that, you know, if our efforts together, marketing efforts yielded a small number of contracts, that was what we had the bandwidth to do. So it was kind of like our, our, our naive marketing.
gave us enough work that we weren't overtaxed. And I see you nodding, people listening can't see you nodding, but as a self-employed person now, you know this is a dance we're doing between bringing in enough work to little work, and it's also not great to bring in too much work. So that was something that we did. we were offering training on topics
At just the right time, that was another gift of history, I guess you'd say, that we were good at explaining and helping people do new kinds of writing, web writing, email writing, e-newsletter writing, those kinds of things. They needed the help. So we didn't have to do a super hard, hard, hard sell and haven't. I have never had to do a hard sell. I've never bought a mailing list, not in 29 years, never.
Jenny Dempsey (18:16.45)
when you're starting out on this journey, whether you have a partner or not, I don't know. Like for myself, I was like, I got to figure this out. I, know, coming from this kind of corporate background that I had, like, you didn't really get the opportunity. You could ask for like collaboration on different projects, but you were hired as the expert and you had to figure it out. So I went into this kind of solopreneur journey with like the podcast and furniture flipping really just like.
I have to figure this out for myself. And if I can't, then that means, and I hate to admit this, that I feel like I can't do it because as a result felt like too much. I don't want to bug anybody. I don't have the money to hire. I feel like the opportunity is there to ask just as you laid that out. You both knew that you needed the most patient accountant.
and you needed that, know, whatever it was, but it's sometimes really hard to ask for that. I don't know. Well, this isn't about flipping your career so much. Right now, you and I are talking about setting up a new business. And Marilyn and I made sure that if we needed to in the business, if we needed to put money in the business or forgo paying ourselves,
so that we could buy expertise that we did it. Because yes, we figured out software, that kind of thing, or we sent out a newsletter that looked kind of janky because we didn't want to pay the graphic designer to do the masthead for that. But we often did pay for help. But I want to go back to something you said, because in advance of our conversation today, I was really focusing on, I flip my career?
because I know who you've been talking to, you know, it's the person who was a waitress and then became a lion tamer as I said or something like that, you know, and I didn't flip it so much as I moved my skill set into a different lane and I thought about this before talking and I wanted to go back to something you just said about the kinds of learning or the kinds of
Jenny Dempsey (20:34.134)
responsibility creep that happens when we're working for someone else. And I've seen this in all my friends work lives and especially in my elder daughter's work life. It's like, you may show up to work every day and your title says project manager, it says e-learning developer, whatever. But if your boss thinks that you should also add this other task and if your boss thinks you
You should also go to that one day training on that really complicated software package so you can learn it and then do it all the time. You do this. And that's more like what my career change was. It wasn't my boss directing it. I directed it. But it is not that different from the way our bosses add and change our responsibilities.
sometimes when we're willing and sometimes without our willingness. So if I were to encourage anyone who's thinking about flipping a career and kind of inventorying whether they have the courage, I would ask them, well, think about what you've been called to do in your actual real job now. Your boss flipped your career on you. Your boss changed your responsibilities and you had a stark choice there. Quit or stay.
Did you stay? Yeah, I stayed. Then you've already kind of experienced what it feels like to have the flip imposed on you. Why would you be less able to flip when you stick it for yourself? I mean, that is a great perspective with that because it's true. Like, and I think a lot of us now, especially in the startup world, you are the what is that the multi hats, you know, they'll throw a new hat at you every day. you that's right.
figure it out. And it is that feeling of like, can I do this? I'm scared. Do I want to do this? I don't want to do this. I have to work extra. All the things you just mentioned, you're absolutely right. Like that nails it right there that yeah, that's what it feels like. And I really wanted like the podcast. are, you know, some of the guests, yeah, big flips. Some are
Jenny Dempsey (22:48.364)
more of like a shift or a pivot. And the reason why I love having kind of everyone on there from the lion tamers to, the beat keepers to all the things is simply because I'm thinking of who I was when I was, you know, 10 years ago, sitting at my desk, burnt out thinking I want to do something different and I don't know and I'm scared. And if I were to heard these stories from the, you know, small scale to big scale jumps, I would have maybe
thought a little differently and thought, you know, just as you mentioned, like looking at my own role and the things that I'm doing and how I did that, I was able to flip it away and it was a little more confidence. And I hope that someone listening, you know, maybe on their work break right now, and they're like so stressed out and like, just, know I'm, I want to do something different and they don't know yet. And even though they have this skillset, just as you did, Leslie, you had the skillset and you just kind of like,
lighted into creating your own thing and it has been successful and it's yes really motivating yeah I hope so I hope so and I this sense that a flip means erasing the work you did and in some ways the person you used to be I don't think that's necessary at all not whatsoever and you know when
continuing with the theme that I was on before is like when your boss tells you, I need you to add this new responsibility that's kind of out of your range, you know, some and you do it, you accomplish it, you figure it out with help without help, you figure it out. Sometimes you kind of stoke yourself with
righteous indignation or resentment. You know, you're like, well, this isn't fair and it helps you bear the stress of having to do this new thing that you didn't include in your skill set yet. When you flip your career, that's never there. You can't say, well, they're making me do it and this isn't fair, but I want to keep my job. You have to figure out how to use QuickBooks.
Jenny Dempsey (25:04.908)
because you need to do your, you you can't pay the accountant for every entry. So you got to figure out how to use QuickBooks. And it can be scarier when you don't have that righteous indignation, you know, where you can't kind of blame somebody else for having put this on you. You have to absorb it. But, you know, the strength to do it is forged in the same place. Can I do this hard thing? Can I add this new skill that I'll need?
in this new role, yes, I can. I did it in an old role. I can do it here. I mean, I have not heard it put that way before. And it just it resonates so much because we really are all doing the things already. And that's right. What is, you know, one one more thing that is maybe the thing we want to try. And if we don't like it, we can go back because we've done it. And putting that perspective on flip.
I think really captures it. Maybe it needs to be the career slipper. Done. All right. Season two, we're changing. it's a career slipper. All right. Lastly, this has been an absolute joy. Thank you for sharing your journey, your wisdom, your laughs. How can people find you and also connect with you?
I can't wait for that. And you can find me online at my website, which is eriteonline.com. You can find me on LinkedIn for sure. I like LinkedIn. I like business Facebook. I like LinkedIn. And I will definitely connect with you, with anyone there and converse with anyone there. Every month, I do a LinkedIn live broadcast with another dear
partner. She's not my business partner, but she's my brain partner. We do a LinkedIn live broadcast called Fix This Writing. Two experts show you how to make bad writing better. And my partner is named Professor Kim Sido Campbell. And if you follow me on LinkedIn, you'll know when we're doing those. And you can always watch them recorded. And I guess those are the best ways for now. Thank you so much, Thank you. I appreciate you.
Jenny Dempsey (27:26.538)
And I appreciate you too. And I want you to start a new podcast in the new year so I can be a guest on that on all the podcasts. Dancing shoes on. All right. Great. Thanks for tuning in to this episode of the Career Flipper. Be sure to connect with Leslie using the links in the show notes. If you enjoyed this episode, I hope you'll share it with a friend who could use a little boost of inspiration.
Make sure to subscribe for more flippin' episodes like Leslie's every week. And if you get the chance to leave a review, that would mean so much to me. It really helps the show reach more career flippers around the world. What I love most about doing this podcast is the likely chance, the small chance, that these stories might be the spark that someone needs to break free from feeling stuck and finally take that first step toward their dreams. I know it's tough and crazy and scary and all the things, but...
It's so worth it. Whether it helps you grow or opens doors to something you never imagined, it's a step that can change everything. So keep on your path, my friend. What's the best that could happen?