In this episode, meet Kimberly Masiello, a career flipper who’s transitioned from studying art history and curating museum exhibits to teaching, becoming a principal, and now virtually teaching ESL with her own small business.
Imagine going to school for your dream career, only to have a friend's dinner conversation open your eyes to a new path you never considered. Suddenly, you want to shift your whole journey!
In this episode, meet Kimberly Masiello, a career flipper who’s transitioned from studying art history and curating museum exhibits to teaching, becoming a principal, and now virtually teaching ESL with her own small business.
In this episode, you’ll hear how Kimberly emphasizes the power of listening and problem-solving. She discusses the importance of creating stability through remote work, which also offers the flexibility to travel and explore new opportunities.
Episode Takeaways
Connect with Kim
Kim’s LinkedIn: https://www.linkedin.com/in/kimberly-masiello/
Jenny Dempsey (00:00.152)
That's a tough decision, Knowing when to cut the cord on something that you hope will improve. Welcome to The Career Flipper, a weekly podcast featuring career change stories from people around the world in a bunch of different industries about how they get from point A to point B and all the twists and turns along the way. And I'm Jenny Dempsey, your career flipping host. After more than a decade working in customer service and experience leadership in the tech industry,
as well as teaching two Udemy training courses, speaking at business conferences, and running a global mentorship program for customer service agents, I found myself laid off. Despite my experience, I couldn't land a new job in this current market, and I really started to question my worth. What am I supposed to do now? Then a friend gave me an old junkie table. I saw potential. I binged YouTube videos to learn how to fix it up and found
this new joy in giving something unwanted another chance at life. This led me to start my furniture makeover and restoration business, San Diego Furniture Flipper. Alongside that, I also speak at events, do some consulting on the side, and offer one -on -one career change coaching sessions. Despite all this wonderful stuff, I was feeling alone and honestly, kind of delusional about my new path. I mean, who really goes from the corporate tech world to covered in paint and sawdust in their garage?
So I started reaching out to just a few people that I knew who have also flipped their careers and hearing their stories really motivated me. And it made me realize that it's okay to change direction at any point in life. And I suddenly realized there are way more people out there who flipped their careers, honestly, more than I'd ever imagined. So that's why I started this podcast. It came to me in a dream and I wanted a way to share these incredible journeys and offer support to anyone considering or having already been through or
currently going through a career flip of their own. So I hope that you'll find something in each episode that helps you on your path. Now, let's get into today's episode. Imagine going to school for your dream career, only to have a friend's dinner conversation open your eyes to an entirely different path, one that you've never even considered before until now. Just something they said really clicked with you. And suddenly, you want to shift your entire career. So you do
Jenny Dempsey (02:23.234)
I'm chatting with my neighbor and friend, Kimberly Maisiello. She's had many career flips and is now balancing her career with a flexible remote lifestyle, doing work that she loves as a teacher. Let's dive into the episode. I can't wait for you to hear her story.
Hi Kim. Hi. Thank you for joining me today. We are in person at my studio. Dwightie, come here. Dwight is Dwight the Doodle. Rescue Doodle is here as well welcoming you in. Hi Dwight. Thank you for having me Dwight. He really, really is the host of this show. my gosh. So Kim is my neighbor. And what's so funny is
We lived next to each other for about a year and never met until we were both volunteering at a local dog rescue and I was doing the volunteer intake and I looked at the address and was like, wait a second, that is oddly close to where I live. And then we met from there. So, so funny how that happens. So what I want to chat about today is something that we've chatted about as I've gotten to know you over the last year and half.
learning about your career choices and how, you your focus on like living a life that's not necessarily so focused around work and doing more of the like personal work and you've made it your own. Like you took what you were doing and you created your own structure. And I would love to hear about your career flip journey. So I'm just gonna let you take it from here. Okay. Well, I started
living in New York City and I went to grad school in New York City for education. Well, originally I was going be a museum curator and I studied art history, interned at the Brooklyn Museum in Manhattan, worked on this really wonderful permanent exhibit by Judy Chicago called The Dinner Party, which is still there at the Brooklyn Museum. You can see it. And I was so sure that was my path, museum curation. Then after graduation, I ended up also interning at a different museum in Manhattan, the Children's Museum of Manhattan, where
Jenny Dempsey (04:33.538)
more exposure to education and at that same time I had dinner with a friend who's like, I'm gonna be a teacher. Wow, that's really interesting and it just sort of blew my mind. I was so set on this one path. I had myself working at either the MoMA or the Met and following a completely different career trajectory. Having dinner with this friend and this experience at the Children's Museum really started to shift my perspective in terms of what I saw myself doing.
And so I applied to Columbia and got in and went through their teacher education program and started working in New York City at a middle school teaching English. And it was, it was really great. I really loved the experience. Eventually though, we always knew we were San Diego bound. we, my husband and I left our career, left our careers there, which looking back, you, it's difficult moving to San Diego when you're very career minded. You move to San Diego and
It's almost like committing career suicide. That sunshine and the beach will get you. It will. Not for everyone, but for certain industries like education. It's harder out here, but we moved out here and we're really happy. was interesting though. thought moving here, I was going to be in the classroom my entire life, but things took a different turn and I ended up directing a school in Southeast San Diego. was a principal.
And I attribute a lot of that success to being in New York. I think moving out to a different spot, people see, experience in New York. Like, you're probably going to be a good employee. And I think that holds true in a lot of cities. But I never saw myself directing a school. That was another career shift. It was very scary. Sounds like it was a K to eighth grade school. Very difficult. The kids came from difficult environments.
difficult family situations, no food on the table. There were gangs, just really hard and it took a toll. And I think this is the part in the story where the shift that you were talking about creating your own story, this is where it was very cut and dry up until then. I followed the education career path. But I came from working as the director of the school.
Jenny Dempsey (06:54.414)
almost every day. I came home, I was miserable. It was sad, it was long, was frustrating, I was angry. It was the kids, not only their education, but their lives too, we really, especially for this population, you really are responsible for breakfast, lunch, and sometimes dinner, in addition to their education. Yeah, it was a lot of tears. A lot of nothing outside of work.
Heavy. How long did you do that? So at that school, first I was a literacy instructional coach. So I worked primarily with teachers and that was great. And then I was director for approximately two years leading up to, yeah, two years, like 2018 I left. Okay. That, so two years of that and...
I kept thinking it would get better. know, those situations where it's going to get better. It's going to be fine. Yeah. It never did. You'd be optimistic for only so long. Yeah. It just got worse. That's a tough decision, right? Knowing when to cut the cord on something that you hope will improve. Yeah. I think there are some people that stay in that spot.
for their entire careers or lives with relationships, whatever it is, thinking, it's gonna get better, it's gonna get better. And it never does. And then 10 years, 20 years have passed and what have you been miserable? Right, right. So that was finally, I was at the point where I think no more. And luckily a friend that I'd worked at with the school, she's like, come work with me at this homeschool charter. And it was hybrid and that was my first foray into.
hybrid work. It was so good. It was like a breath of fresh air, but it also fed this desire to I'm like, wait, yeah, this is hybrid, but I prefer remote. whole new level unlocked. Since the start since graduating from grad school, you know, I worked like 10.
Jenny Dempsey (09:02.478)
11 hours a day and I only knew going to work, coming home, going to the gym, cooking dinner at like 9 p going to sleep, turning around, doing it over. That's all I knew. And I got into this routine and then I'm like, my gosh, there's something else. There's something else, yeah. And it just fed this desire to find something that was completely remote and through all of this hybrid work at the homeschool charter, I started
Two small businesses. The first was a web design development SEO business with a friend. We saw clients and the other one was an ESL English school. So I had these two small businesses going on the side of working for the charter. And that was my first true look at completely for myself in a remote setting while doing this hybrid traditional work. That was an interesting.
shift out of education, but also working completely remote, which you must know about working for yourself. Right. You just kind of get, it's not even about comfort, because I think a lot of people think, it's just comfortable. It's efficient. It's more productive. You're more creative. You have the space to not necessarily always do more, but think clearer. And if you
work through the distractions. think that's another thing. And I don't know if you ran into that too, but when I started first and I've worked remote since, gosh, early 2010s, I did a hybrid part in my career then, and then it was pretty much just remote or hybrid up to the point of, gosh, 2017 when then I was working for the most part remote. So it's just like the distractions at home can kind of get in the way, but once you work through that.
It's just, it's a complete game changer for productivity. Absolutely. You can, you don't have anything bogging you down outside influences. Yeah. A lot more efficient. think I was thinking actually when you first, when we first talked about me coming on, I thought a lot about my journey as a whole. And so it was really nice to be able to reflect on everything I've done and leading up to what I'm doing today.
Jenny Dempsey (11:23.83)
And those different shifts in working in person to then finding hybrid work, to then finding remote work. I think that for me, what I ultimately found working, having my own two small businesses is that I don't have that entrepreneurial spirit. It is just not, not in me. And I'm so glad that I had those two experiences that for SEO, web design development that we.
For two years, we had that small business and we were doing well. We were gaining traction. We had employees and we were gaining traction, but it was to the point where we're like, okay, we have to, I think we have to start scaling or doing something to make this a lot easier because we were doing the bulk of the work in addition to managing the employees and the finance and the projects. And I had a talk with my friend and I was like, I don't have the drive.
to be an entrepreneur. crave, while I want to work remotely, I crave stability and I crave not having to look for clients and I hate doing payroll. Yeah, lot of the sales and the administration stuff it sounds like that comes with entrepreneurship. I wonder, I'm just going to question this because I feel the same way. I despise that type of stuff.
I'm not a salesperson. am just like the person with an open heart was like, let's do this. And I'm not going to like sell it and say it's wonderful. I'm like, this is just how it is. But like, I wonder if how many entrepreneurs actually enjoy that stuff when it comes to the drive. I think some people are willing to do it. It sounds like you were willing to do it, but you didn't like it. And there was a point where you're like, I am not doing this anymore.
But the other thing that I want to call it that you brought up that is super interesting is the stability part. Because I think when you go from working for someone else, there's like this mindset, at least like early on, I don't know if you experienced this in your career, but like early on where it's like, this is my stable paycheck, this is what I get. And I know for myself, I had those feelings as well. And then I got laid off and was like, my gosh, they could just let me go whenever. This isn't actually stable. It's all kind of in our minds.
Jenny Dempsey (13:43.488)
It feels like at this point I'm like, whether it's entrepreneurship or you're working for someone, it is the stability we kind of define for ourselves, right? So I'd be curious, I don't know if that resonates at all, but I'm curious to hear a bit more about that. Yeah, it is an internal stability. It's interesting you bring up being laid off, being a teacher in public schools, you're probably not going to get laid off. You have union protection, so it came from that mindset of being very protected. Yeah.
Even in charter schools, a of charter schools are unionizing now, but there's a high degree of stability in education. And then coming from this big city where you must have stability otherwise. Yeah. Big expected city. Right. So while you do, I feel, create stability for yourself, there's something
Stability is a very internal feeling, I think, but at the same time, having the stability of being able to do what I want, when I want, because I have the means. Because I don't have to go out looking for clients, because I know my paycheck is coming, I can go out to do whatever I want. And so I think that external stability is really, provides me that internal stability.
That's a great, great way to explain it. Yeah, and that's different for everybody. I have friends that don't do different jobs and they don't need to go from job to job to job and they don't need that. They're happy, but for it's different. then after my friend and I stopped, I ended up...
going to another small business and opening an ESL school. I'm like, look at you. You're like, well, actually I can't get in. So there must have been something inside me. It's like, okay, maybe I'll try again. Maybe I have a little delusional here. Yeah. So I did that. And while still working at the hybrid charter school. So I did that and I was starting to get a lot of students, the same issues arose as with the other business. Just, it was,
Jenny Dempsey (15:58.282)
a grind finding students and then though then having too many students. So I did well enough to have too many students and then considering what to do next. But it also lit the fire of wanting to work remotely. Tell me even more so than before. So then what did you do next to make that happen? Hundreds and hundreds of applications and to remote work.
especially in education, it's hard. It is hard to find. They want to pay pennies to teachers for tutoring jobs, or there are a lot of online schools now that want to pay teachers $10 an hour. That's not even minimum wage in California. They don't have to abide by minimum. They don't know how it works, to be honest,
Somehow they don't have to abide by laws like that. So it was hundreds and hundreds and hundreds of applications. I can't stress how many applications and people come to me, other teachers come to me and ask, how'd you do it? How did you get to where you are now? Share about that. But really it came down to hard work. There isn't a secret. But hundreds and hundreds of applications and I ended up getting five different positions.
Five. Okay. That's incredible. So how did you even sift through those five? Like how do you pick? I took them all. How did I know you were going to say that? my gosh. Okay. Now tell more. So they're all independent contractor roles. So I'm like, okay, I can finagle my schedule and I can do them all and see what sticks. Yeah. So that's what I did.
and it was messy and difficult and probably working more hours than when I was in public school. But it was all with the mindset of I'm going to narrow it down. And now starting next school year in September, I have narrowed it to one. Yeah. I feel like we can have a whole other episode on how you narrowed this down. That's impressive. Yeah. But I feel like you just have to take.
Jenny Dempsey (18:24.908)
what is given to you, right? Just say, yes, you put in all this work to apply, but you don't owe those businesses, those companies anything. You just take it all and then it might be a lot of work upfront for you, but it's in your best interest to figure out what suits you and you don't owe them anything, especially as a contractor. For a couple of them, just naturally it wasn't a good fit, I thought, so that narrowed it down.
one or two. One of them I really liked, but I wasn't getting enough students from them. And the one that I'm at now is a private school based in Oregon. We have students all over the United States, sometimes the world, and they're here to home school for one reason or another. And it's great because everyone is everywhere in the world and it provides the ability to travel with your work and it provides that stability
I crave, it's not stable in the sense I know what paycheck, it's dependent on how many students that you have at any given time, but it provides a lot of stability. And I don't have to look for students, don't have to, I sit back, I do my work. And it provides space for me to do the other things that I really like. Gosh, it like provides, you've created this.
the structure for yourself that gives you the best of all the worlds that you have wanted, where it's like you're doing work that you want to do. You're not having to deal with the, you know, kind of busy work of entrepreneurial stuff. They're finding you, like the students are coming to you and you get to go travel and do all the things that you enjoy outside of work. Yeah. Been very lucky and all within. I graduated from grad school. was 25. I'm 38 now. So all of this within a span.
13 years and I feel really lucky to have gotten through the pinnacle of an education careers becoming if a person wants that directing a school. So I feel very lucky to have gotten that when I was like 34 years old, 33 years old. So I feel like things were a bit accelerated for some reason. And I think that's interesting too, because I think about careers and moving up and I'm not an extrovert.
Jenny Dempsey (20:46.22)
And I think that's fascinating to be offered promotions when you're a person that listens. You're not the loudest person in the room. You're not, for me, I'm not the one that will be the biggest personality in the room. But I think it says a lot when you listen to people, like you do really well. Thank you. I think that's so, I don't know, that's so important to know because I feel like, especially entrepreneurship sometimes,
And especially with like social media, people are putting themselves out there like, look at me, look at me, I'm sitting on a table and I'm yelling at everybody because you got to look and you don't have to be that way. No. And I love how you said you can the person that listens because we need more listeners. I'm that weird person at the party that's going
someone interesting and ask them the non -surface questions, the questions that make them think, and then they're going to leave you like, that girl was kind of weird. That's me. I just love picking people's brains and that's kind of why I started this because I just like, I feel like I'm delusional and I feel like I, know, hundreds of applications as well and keep getting no and in the tech space, there's not that stability. And so I feel like with teaching, like, kind of like, it sounds like that's very,
They can't let you go because there's a shortage of good teachers. And then tech space, there is an excessive amount of amazingly intelligent, talented people. So the competition is so high and I like I was just like, well, hearing these stories of other people who have done things different, carved their paths, whether it's taken years and years or a few years, whatever that looks like, it gave me like a little pep of like...
inspiration and I was like, okay, I can still be that weird girl. You know, I can do that and that's perfectly fine and kind of carve this path out and listen. Going back to what you said, listen and ask questions, be curious. That's what it's all about, about listening to others. And you bring up a good point about social media needing to be the loudest one in the room. And that's just not necessary. I find that people notice you.
Jenny Dempsey (22:57.194)
when you listen to others and you problem solve through listening. And you've been a customer service consultant and you know the power of listening, I'm sure. Right, right. People want to be heard. And if you can actually listen to them and give them the space to be heard, that's a game changer. I feel like on social media too, one of the things that drives me, it's just little itty bitty things of like, you you got these big influencers out there and you
hundreds of comments on a post that's maybe a very like emotional thing and people are burying their souls on a post and sometimes like the no one replies to them and I feel like it's these little things of like make them feel heard hire someone to just reply to the comments and like form a connection and make sure that they know that they're important and they're a part of this community and I feel like that is one of those things from like I really do work hard to do that but like without that and
having that listening, the availability for listening, I think they're missing out on an opportunity and it just goes back to the me, me. Which is fine for some people, whatever. that's important in entrepreneurship. Yeah. In small businesses and creating your own path, it has to be somewhat about you and you have to be somewhat selfish. Totally. Yes. Yes. Yeah. In order to make it work. But also you have to have the other side of you too. And then things will come to you. Yeah.
Throughout my whole journey through my first job at Queens Collegiate in Jamaica, Queens, I moved up pretty quickly to run as a team, as part of a team, the ESL English as a Second Language Department. And it's just through taking the opportunities that come to you, just saying, saying yes as well. And then seeing if it works out. Right. Cause you never know unless you try. never know. And it sounds like you saying yes to those things.
Like when you took on those five opportunities, they're like, yeah, I'm going to try this out. And then kind of chiseled away of like, what works, what doesn't, you learned and you moved forward. And hearing you say all of this, I know you mentioned you don't have that kind entrepreneur entrepreneurial spirit, but I am hearing everything about it. I mean, it's just, it's your definition of it. It's not like a textbook definition, which whatever, that's probably not the same for anybody, but it does sound like you have that spirit in you.
Jenny Dempsey (25:18.284)
and you're able to really create what you want based around the life that you wanna live and how you wanna show up in your career. And you're remote and you made it happen and you're here. And if that changes one day, that changes. it sounds like you're thriving right now. Yeah, yeah, right now it's great and I'm super happy because I get to go home from this. get to see.
a student from our conversation, I get to see a student and then I get to go to the gym for a little bit. Nice. Nice. And then come home, do a little more work. So it's really, really good. And I think though, to make this work, you do have to have that intrinsic motivation to, like you were saying before, it can be very efficient, but there's a lot of distractions too that you have to manage and manage your time. That is difficult.
Yeah, it's difficult when you are the boss of you and you have to manage that. No one's going to tell you sit at the computer until this time and then clock out. You got to do that. It's all about the Pomodoro time. yeah. Solid, solid app right there. In fact, today are they want to sponsor the podcast? Yeah. Helping things up. Amazing. Well, Kim, I feel like we could.
talk for hours about this and I would love to at some point have you back to talk more. For now, how can people find you? I'm pretty difficult to find. I'm pretty thrive on social media, but I am on LinkedIn. Certainly connect with me on LinkedIn. I'm always there and I'm starting if anyone's into languages, I'm starting a language accountability study group that will be posted on my LinkedIn. So if you find me on LinkedIn, you'll find that. love that. I love it. Thank you so much for coming over today and hanging out with me and Dwight and chatting. This was great.
Thank you so much for having me.
Jenny Dempsey (27:32.876)
If you ever need a Career Flippin' speaker for your event, want to sponsor the podcast, or just want to say hi and share your story, pop over to thecareerflipper .com. I'd love to hear from you. Keep on your path, my friend. What's the best that could happen? Talk to you next week.