In this episode, Ethan Orenstein takes us through his career journey from journalism to content writing and SEO to surfboard fins and coastal inspired art.
Have you ever been stuck in traffic on your long commute home, wondering if there's more to life than this?
In this episode, Ethan Orenstein takes us through his incredible journey from journalism to content writing, SEO, and digital marketing. Along the way, he discovered his passion for surfboard design and art, which led him to create Wave Arcade, a business selling bamboo surfboard fins. Despite setbacks like the COVID-19 pandemic and algorithm changes, Ethan adapted by refocusing on his art, producing stunning surf and coastal-inspired artwork. He emphasizes the importance of seeing failure and setbacks as chances for growth and reinvention.
Episode Takeaways
Connect with Ethan
Listeners can use code: FLIPPER for 15% off an order on both wavearcade.com & https://wavearcadeart.etsy.com
Jenny Dempsey (00:00.138)
I feel it has been extremely valuable to me just as a person exposing myself to failure and setbacks and I think I'm better for it. 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 in between.
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 customer service mentorship program, I found myself laid off in 2022 from my main corporate
Despite my experience, I couldn't land a new job and I really started to question my worth. What am I supposed to do now? And who am I without a job? 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 joy in giving something unwanted a brand new chance at life. And 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. If you want one, let me know. Despite all this wonderful stuff, I was feeling alone and honestly kind of delusional about this new path. I mean, who goes from corporate tech to covered in paint and sawdust in the garage? So I started reaching out to just a few people that I knew who've also flipped their careers. And wow, hearing their stories just motivated me and it made me realize that it's okay to change direction at any point in life. I realize now that there are
more people out there who flipped their careers more than I'd ever imagined. And that's why I started this podcast. It came to me in a dream to share these incredible stories and offer support to anyone considering having already been through or are currently navigating their own career flip. So I hope you'll find something in each episode to help you on your path. Okay, let's get into today's episode.
Jenny Dempsey (02:06.144)
So I have a tattoo of waves on my wrist and it's not because I'm some epic surfer though. I of course loved my surfing class at San Diego State University, but I really just prefer the baby whitewash waves and a longboard. But let's get real, I haven't been surfing in years. But anyways, I got this tattoo because I was inspired by a quote from Dr. John Cabot -Zinn, a professor of meditation. He says, you can't stop the waves, but you can learn to surf. And this quote has always resonated with me, especially as I interview career
from around the world. And today you'll meet Ethan Orenstein. He navigated his way through corporate roles and SEO and content writing and eventually leaving to carve out his own path. And this journey led him to found wave arcade where he showcases his beautiful surf and coastal inspired art. Ethan's journey is a great example of learning to surf life's waves and I can't wait for you to hear it. Let's go.
Hi, Ethan. Hi, Jenny. So excited to have you here. We've known each other for quite a while, working together, gosh, almost 10 years ago in an office in Encinitas. And then you dipped off for a while and we worked remotely together. And then there was a point in time where we just would get together as consultants and sit at Kulture Brewing on the 101 and drink beers like on a Tuesday afternoon. Yeah, that is where some of my best.
ideas and brainstorming came from. Yes, yes. Man, that mango hazy IPA. Let's yeah. Anyways, I'm getting sidetracked. Well, you have always inspired me because you have had a very unique career journey. You've really made it your own. You've not settled for just sitting in a desk and doing what you're told. I personally, which the listeners will learn more about this in a little bit, but I personally have your artwork hanging in my house.
I am obsessed with it. Actually, no one can see because there's no video with this, but I am wearing a Wave Arcade shirt right now. I'm very proud of that and just proud to know you. And I'm going to give you the floor. Tell your career flip story, Ethan. Thank you for the kind words that that really means a lot. I guess I'll start with a high level overview of my flip, if you will. The more I think about it, though, my
Jenny Dempsey (04:22.412)
I guess my entire career was, I've just been flipping and flopping the whole way through. Flipping and snapping. I studied journalism in my undergrad and with full intention of becoming a journalist after that for news or whatever it may be. So I had an internship in college, which led to a job offer,
They were going to pay me like 11 bucks an hour in San Diego. I'm like, I'm more as like a lifeguard at the community pool in high school. So, regular journalism is not the best path. And that led into me becoming a content writer where we worked in Encinitas, which led to SEO and digital marketing. I kind of found myself in this SEO digital marketing role where...
I didn't really know how I ended up there and it was never really something that I wanted to do or was all that interested in or passionate about. There I was thinking kind of, this is my career, this is what I do, this is what I'll have to do, I guess. I felt kind of stuck doing that because I grew up with, I guess, being sold that go to school, get a job.
like follow that career path and that's just the way it is, whether you like it or not. That thought kind of crept into my head at some point. Maybe it was, I think it was when I had the opportunity to work remotely in Utah, just cause not being near the ocean too, I was not able to surf. so I don't know, I had more time to kind of think about these sort of things and not being in an office with.
We had some great coworkers there, but so being isolated from the people and the things that made that place fun to work. Yeah. I started to think, what, do I really want to do and why am I doing this? And during that time is when I became interested in surfboard design and surfboard fin design specifically. So I was reading all this stuff, doing all this research into materials and things like that. And I was also getting back into art, which is something that I've always loved to do, but it's always just been a.
Jenny Dempsey (06:35.31)
creative side outlet for me. So this is all in Utah and Salt Lake City. So I'm researching the fins, I'm starting the art back up, I'm making these wetsuit koozies out of old wetsuits that I had, and then I would screen print little logos and artwork on them. So that was really fun, but still at that time I was like, okay, this is like a fun side project, just a nice little creative outlet in addition to my SEO job that I will be.
stuck in until I'm ready to retire or whatever it may be. So I moved back from Utah. As you know, I quit that job on my first day back. You came into the office and you're like, peace out. Yeah, that was a really awkward moment for me, but it's fun to hear other people's perspective. Great part of the story. We're all like, wait, should we follow him? My desk was.
decorated for my return to the office and I'm like, so I'm quitting. And I thought like, I had been there for, I think it was like five or six years at that point. So I thought, okay, maybe a new position is kind of the right move. Maybe I'll start to enjoy this role better with a change of scenery or whatever it may be. So I got another SEO job working at an agency this time. Again, it was a company that had a lot of
great people, good work environment, all that sort of stuff. And they had an office in downtown San Diego in East Village. I was able to bring my dog even, which was great. I just remember doing the commute in the morning and in the evening, stuck in traffic. And I just had these moments of like, is this like really how I want to spend the majority of my time? That finally I decided that no, it was not.
So I spoke with my partner, now the mother of my first child, Ellie, and kind of told her what I was feeling and what I wanted to do. She was fully supportive of that. And my plan was I'm going to start Wave Arcade as a business and I'm going to sell these surfboard fins that are made out of bamboo. So I quit the job. My last day was October 31st, 2018. And I was like, okay, now I'm making handmade.
Jenny Dempsey (08:58.222)
We were in a condo complex at the place. So the garage, was like a one car, small garage, close quarters to everyone else's houses. My idea was I wanted to do something that was using kind of local and eco -friendly materials. So I was going around the neighborhood on my bicycle looking for bamboo stalks I could cut down and I was collecting those and I
I would have this machete and I would use it to make these round stalks into strips and laminate those into a board essentially that I could bake and then shape things out of. And I realized I wasn't going to be able to scavenge enough bamboo to make as many things as I was planning on making. So I went over to Botanical Gardens in Antonidas, because I know they grew a lot of bamboo there. And I walk in, find someone working there. like, hey, who can I talk to about
your bamboo and they pointed me to some gentleman working the bamboo area. And I told him about my project and I told him I needed like a bamboo source. He's like, well, we, cut it a lot and there's really not much we can do with it. So there's a huge pile of it down at the bottom of the property that you're welcome to take as much bamboo as you want. I drive my 2010 Jetta down there, flip down the seats. I just started loading up all this.
As much bamboo as it's gonna fit. Take it back to the one car garage. I get to work harvesting it down and splitting it into strips. I remember I was sitting out there probably late morning, middle of the week, and one of my neighbors comes by and he's like, Ethan, what is it that you do? I was like, I'm a few banners in the driveway. He's like,
this. He's like, mean this? Like, he gives me such a weird look and walks off. So I, yeah, I just got to work. Doing that, I had some power tools. rigged up like a sanding table and a saw type thing to cut it all down and process it. And this is probably going on for like a week or two as I'm working on this throughout the day. And another neighbor comes by very
Jenny Dempsey (11:10.146)
visibly pissed off because I'm making so much noise and much dust. Little echoey condo complex. And he's like, this needs to stop. I was so excited about jumping into this new project. Like I didn't even think about stuff like that. Yeah, you're probably right. So that kind of put a pause on things.
I was like, okay, what do I do next? I found, eventually I found a, there used to be this maker space, had a wood shop, a metal shop that you pay a monthly fee and you can go there and work. It was down in Bay Park. So I started going there until I was able to finish my first production run of fins. And so I did that, tested out the fins. They were great. They were fun. They looked cool, but they were breaking. no. I was like, no. I spent all this time.
working on this first product and I'm like, my God, I'm a failure. This is not going to work. Around that time, we had moved into a house house that was a little more separated, had a larger garage. I had a space to try new things and work again. I'm like, okay, I need a reset. I jumped in headfirst. I think I'm going to make this huge production run of fins and sell them and they're going to work and that's going to be my business.
So I kind of took a step back and started working on different prototypes and figuring out what was going to work best for that sort of thing. And at the same time, I was, I think I was adding more of my like art and apparel and t -shirts and stuff to the website too. Just exploring like different things that were interesting to me. And I guess this is probably a good time to mention that as I was learning SEO, I had spun up a couple websites of my own, just to write about things I was interested in or just try out different concepts.
So I did have these, I guess content websites, you'd call them, that I would work on from time to time, but those were more just experiments for me. They weren't my main focus ever. One, I used to rebuild old motorcycles. So one was focused around motorcycle restoration and getting bikes with no titles registered and that sort of thing. That's a little caveat, but it'll come back later in the story.
Jenny Dempsey (13:33.526)
I'm in my new garage working on prototypes, kind of expanding the art series. think I launched some of my early stuff, like posters on Etsy. were the first iteration of my national park series. They were kind of more like trail maps almost. So yeah, I guess at that time I had, it probably sounds like I had a lot going on because I was just kind of throwing stuff out or like doing random things to, because at this point I was, when I quit,
I had cashed out my 401k, which had some money in it to pay the bills and keep me going while I wasn't making money. And I'm kind of keeping an eye on that as like my runway is dwindling. I'm expensing a lot, but not a lot of new income was coming in. I mean, that is unfortunately a consideration when you go into.
Right, yeah. I settled on a design I liked. People were liking them, people were buying them, people would see me with my boards or fins at the beach and ask me about them. So that was always fun. I made these hand planes, like body surfing hand planes, out of palm tree frongs, some recycled wetsuit and things like that. And that appeared in the 2019 Visla Creators
thing where people showcase their upcycled and interesting certain products. That was kind of fun. Around the same time, Culture, which we were talking about earlier, they had opened a little local marketplace type thing for artisans and local sellers to, was like a collective type marketplace. Everyone had their little table in there and they would take a cut of the sales. So Wave Arcade had
little booth in there and I made this, I made a display that looked like a retro arcade cabinet and I had my fans, had some hand planes, t -shirts, stickers and I was like, okay, this is, I'm fine. I'm like, things were connecting, things were moving in the right direction. And I'm like, okay, this is like my first in -person little setup. Like great, things are going great. And then two months later, COVID hit and all
Jenny Dempsey (15:46.602)
shutdowns. The marketplace was no more. I remember going down there early in the shutdown, the streets were very quiet. No one's out there. I'm loading up all my stuff, sadly, into my car. like, okay, that was cool. And I'm sure, yeah, like my story there is probably not unique in any way. But yeah, was just another
another setback that felt so out of control and like, damn, was felt like I was doing everything right. Things were moving along and then boom. So, yeah, it was kind of back to that feeling of, well, shit, now, now what am I going to do? Like, I'm I'll still do this. But in the early days, like the beaches were shut down. So no one was surfing. No one wanted to buy things. Yeah, no one could go. Yeah. It was another moment where I was like, OK, I really need to start.
making some sort of money to pay my folks now. So I'm kind of just sitting there thinking like, okay, what are my options? obviously I want to keep doing this because I'm passionate about it, but I also need to figure out how to start making some money. like I mentioned, I had these content websites and I had put Google AdSense display ads on them when I set them up and I didn't
touch them every every couple months, I would look at analytics and see how they're doing and that sort of thing. Maybe work on them here and there when I felt interested in doing so. But one day I look and I see that they're getting traffic and AdSense is like had made 20 bucks in the last month or something. I was like, well, these can buy me a beer now. I I know this SEO thing, I know kind of how that works. So maybe if I put some
focus into these, can grow them and that can become a thing. I guess I flipped again from film and wave arcade as my main focus to back into websites and SEO just this time for myself, not for an agency or another company. And I got to work. had, at that time, I think I started with two websites, Motorcycle Zombies, which was
Jenny Dempsey (18:02.776)
the restorations and stuff. then Guido Manehar, which was my Spanish practice driver's license practice test website. But very, I guess, inspired by a former employer of ours. So I was working on those and then I met our friend Lance at Culture and he asked what I was up to. I told him about Wave Arcade, told him about the websites and he's like, actually I'm working on a project that might fit
one of your websites and he was working on insurance advertising type of stuff with our other friend Mark at the time. And he's like, yeah, your websites sound like they could be a fit for this. So we started working together, got their ads on the websites and then those websites kind of took off and I worked on a morgue or the traffic and I was very fortunate for some time and that was really cool. That was
Okay, here I am. I'm doing something for myself and it's working out and yeah, it felt great. were thinking. Yeah, it's, motivating to have successes like that. So that, that lasted from about late 2020. I spun up new websites and that, was my main focus again, SEO and content and building these websites and then wave arcade and the artwork.
Side of Things was again, my creative outlet and I had my Etsy shop and I was selling on there. But yeah, it was back to Side Project. Fast forward to spring of 2023, there was a pretty big guru update that hurt some of my traffic. And then following that, the insurance industry took some hits. So traffic and revenue for those websites were on the downturn. August comes around. I have Leo, my son.
So I'm a new dad now. Another algorithm update comes and pretty much decimates traffic on my websites. I mean, things had been going great for three years at that point. It was back to square one again with those. And now having a newborn and being a dad, I had been in that position before, I guess, where things that did not go my way or things that were out of control kind
Jenny Dempsey (20:18.35)
had their negative effects on me, but this new kind of life change and responsibility, it like hit me very different. This took me a while to kind of work through my next move just like mentally because I'm sleep deprived. have this, your baby, we're like figuring it out. One thing I've always valued was my freedom, which was one of my, I think, main reasons for going down this path in the first place. Having a kid, it kind of made me realize how precious
and limited your time really is. So, of course, so much of my time now is focused on him. I have to be really strategic of where else I'm spending my time. Like, there's only so many hours in the day. And yeah, how do I want to be spending them? So I kind of thought about it. I'm like, okay, do I want to try to get these websites back and work on those? And for a while I was like, yeah, I probably should do that. Like, that's what was so successful for me for a good while.
And I sat there between childcare. I'm trying to think of what to do and I'm tweaking with the websites and working on stuff on them. And I'm just, I just have that kind of similar feeling that I had in my job jobs where I'm like, what am I doing? Like, this is, this is not how I want to be spending my time. Okay. What is it that I want to be doing? And it came back to Wave Arcade and artwork and creating things and kind of sharing things that way.
I mentioned I had my Etsy shop where I was primarily selling the National Park series of surf spot posters. It was doing pretty well. People loved the posters. I was getting good feedback. They were fun to make. Yeah, this is what I want to do. I want to create more art. I want to expand into new series of...
artwork that I'm interested in. And this is what I want to share with the world. So here I am again in the midst of another flip into the unknown again. What your experience is, thank you for sharing all of that, by the way. You really sum up the evolution of career flips, how it is, even a career flip is still not point A to point B.
Jenny Dempsey (22:26.722)
There is so much and there's always something, you know, one career flip leads to another idea. Or, you know, if it's not an idea of what to do next, it's an idea of how you want to live, how you want to show up, how you want to spend your time. And I'm picturing you, you know, commuting downtown San Diego and stuck in that terrible traffic, which I feel because I can't stand it. I will not drive during those hours. And like having that, you know, realization of like, is this really what I want to be doing?
but also thinking about the other people in the other cars of like, not, you know, might not even be questioning it. It's just what we're ingrained of like, this is what you do. Kind of going back to, you know, when you're in college and you know, the path that we're told to follow. And I just think it's so important to highlight the flips with an S and how that's totally okay. And there's always an evolution and one thing will lead us to another. And where you're at now creating the artwork that you do, and I hope people check it out is it is amazing. I love
the new plants and the black and white that you are bringing out and just like you're, you're not having to source things from the botanical garden and fill up your car with gosh knows how many bamboo pieces are probably still stuck somewhere. You're creating these things and if you decide to change that at some point, you can. that, the freedom that you mentioned is so important to you, especially for someone who is creative.
And even for those that work in business, like just having the opportunity to like do something that makes sense to them and align with the life that they want to live. know, have, Leo's going to look up to you and be like, I can, you know, I can do what I want and I can create things and, who knows, you know, where he'll.
go and he's growing so fast and you want to spend that time together and it's just, I don't know, I just love everything that you've shared and I think it's so important that people realize that it's okay to do the multiple things. And the other thing, wait, the other thing I wanted to bring up was that like what really resonated with me is how we get these feelings of like, have, I'm so called to, you know, X, Y, and Z and we try it and then it fails. And then it's like, my gosh, that's the stopping point for so many people of like, yeah, I'm done, I give up.
Jenny Dempsey (24:33.806)
and you just evolved. You don't have to give up. You could just like, all right, this didn't work. I'm gonna move to something else and try something else to find something that does because that calling's there for such a reason. And it's only gonna lead us into doing better down the road or different or whatever it is. I found that I think if you go down.
this path of kind of doing things on your own and figuring out there's bound to be failure and setbacks along the way. I think a lot of people who go down that route, like sometimes that's like a roadblock and it is hard to get past that. It sucks. I mean, no one likes to fail. No one likes when what they're working on or what they poured themselves into is not working out the way they envisioned it would. But I kind of, at some point I was able to shift my focus into
realizing, wow, like, I look back and I've been able to do so much, learn so many new skills and kind of ways of thinking and the failures make you, well, they've made me kind of just have this desire to adapt and kind of move forward and keep going and learn from all that. That experience is something that's less available with the traditional.
route of going the corporate route. I feel it has been extremely valuable to me just as a person exposing myself to failure and setbacks and I think I'm better for it. that's exactly better for it. think it's not like failure isn't like the end all it's just you're actually better for all of these things and it's just going to set you up to be better. I think I've learned the most with furniture flipping from all of the early days of messing up or
you know, just things I'm like, that was the wrong thing to use, or I should have sanded that way more, or that was the wrong grit, you know, and then having to go back and do it again. And suddenly this coffee table project has taken me 15 hours and it's like, should not have done that. And I'm like, but I learned, and now I'm like, all right, I got a system down. And even still with that system, I'm learning ways to be better, making mistakes, trying new things, like, ooh, this is not as good as it looks like on social media. I'm gonna do it this way instead. And also, you
Jenny Dempsey (26:46.188)
asking for help when you need it, but realizing you can create it the way you want to and change it whenever you want to. Yeah, there's no right way to live your life. You have to figure out whatever mix of things or path is gonna work for you, just mentally and physically and everything. I think we grow up, we're told, go to school, get a job, do this, do
For some people do great in that environment and are perfectly happy and perfectly successful and have happy lives and wouldn't change a thing. But for others, definitely me. I don't know. just, I felt trapped and I felt like I was like, it was an unfair trade of my time and my freedom and my.
curiosity and it did not feel like a sustainable way for me to live. When I got into that new role, I kind of sat there on these drives in the traffic and I'm like, okay, can I do this? I was late 20s at the time. Can I do this for another 30 years, 30 plus years? And yeah, did not, was a, going through that thought exercise was a depressing experience for me and I was compelled to make a change.
challenging when you're going against the grain of something that is so embedded in our culture, but also in our family systems and our friend groups. Like when you're stepping out, but you are, you and I are liking that we're the types of people that it's just not where we want to be. And I know for myself, like I didn't necessarily know that, but when I look back, I'm like, I was always doing something else in addition to work, whether it was having a blog on the side
Speaking at, you know, whether it was a business conference, I'd always infuse my own with like a guitar and a song, you know, or, you know, whatever it is, a health coach, like I was always doing something on the side. And I thought that that was just, that's what made me me. And when I got laid off and started to look for jobs and was being told that the things that you have on the side make you a flight risk, we don't want you. It opened my eyes to the fact of like, wait a second, this is such a big part of me. I'm not giving that up. I can't just be the one job type of gal.
Jenny Dempsey (28:58.606)
And then I was like, well, wait, if that's not going to be out there in the world that I can just go find and someone hire me, I'm going to make this my own thing and create my own path. And that's really kind of what led me to this is like the failure of over 350, well, maybe not 350, but 320 at this point job rejections and being told these things. And I was like, you know what? This is a sign. My stability, my corporate self that thought my worth was work was never actually
I thought that's who I had to show up to be. And it took the smack in the face of getting laid off and so many closed doors to know that screw them, I'm going to make it my own. Well, I think your story, like that story right there is such like an inspiring eye opener really, because one thing that as part of that kind of story that we're told growing up is we're kind of sold this idea that going that path comes with
certain sense of security and stability. The rug can get pulled out from under you at any time. Totally. There's so many valuable lessons that you've really shared. I think ultimately that people will be driven to you to support this fact that you are creating your own path. You're creating the art that you've always wanted to do that was just on the side and now is here and this is your next chapter. And so, Ethan, where can people find you? How can
Check out your art. They can find me at wave arcade .com. They can find me on Etsy, wave arcade art, and most of the social medias, wave underscore arcade. Love it. Well, Ethan, thank you so much. This was such a great conversation. I am always cheering you on, a big fan, and will always continue to hang your artwork in my house. So thank you so much for joining. Thanks for having me. It's been a pleasure. Thanks for riding the career flipper wave with us today.
If you enjoyed this episode, please share with a friend who could use a splash of inspiration.
Jenny Dempsey (31:00.312)
Don't forget to leave a review and hit that subscribe button for more incredible episodes every Thursday. Your support helps us reach more career flippers and those dreaming of catching their own wave. Make sure to connect with Ethan and check out his art using the links in the show notes. To connect with me, head over to thecareerflipper .com. Whether you're just paddling out in the middle of a big wave or have already made the flip, remember, you're not alone. Support is always out there. Keep surfing
path my friend? What's the best that could happen? I'll catch you next Thursday!