From corporate marketing & advertising to Caribbean bartender, meet career flipper Matthew Smith
Welcome to the first episode of Season 2 of The Career Flipper Podcast!
Host Jenny Dempsey kicks things off with career flipper Matthew Smith.
Matthew went from working in corporate advertising in New York City to bartending in the Caribbean. Yep, you read that right! After losing his job right before COVID, struggling to find a new one, and going through a tough breakup, Matthew ended up moving back home and living in his parents’ basement. But then, a “temporary” job in St. John, U.S. Virgin Islands, came up to help cover his NYC rent. Well, four years later, he’s still in the Caribbean, finding happiness and community he never expected.
In this episode, Matthew shares how he made that huge leap, what it was like to leave the city life behind, and how he found a community that helped him grow. He talks about the challenges, the surprises, and why taking risks—despite the fear—can lead to some pretty amazing opportunities.
Takeaways:
Connect with Matthew
Instagram: https://www.instagram.com/matthewhs7
This episode is all about taking a leap, embracing change, and finding unexpected happiness. It’s a great listen if you’re thinking about making your own career flip or just need a bit of inspiration to get started. Grab a drink, get comfy, and enjoy!
Jenny Dempsey (00:00.108)
your life kind of deals you a hand or you make a decision to leave and you don't know what happened. I go back to the basics. What makes you happy? What feeds your soul and not to sound overly cliche. Do what you always said you were going to do, be it owning a restaurant, painting or pottery or whatever it is that you really, really love.
Jenny Dempsey (00:25.663)
to first episode of season two of the Career Flipper podcast. I never imagined I'd even do a season one, but
It's done and dusted and to say that I'm on season 2 is pretty amazing and I am just so grateful and happy to have you here with me. So thank you for making this possible and tuning in. You know, every week I sit down with people from all over the world in any and all kinds of industries to explore just how they flipped their careers and moved from point A to point B and C and D and everything in between. I love to dig into the twists, the turns,
the winds, and the occasional faceplants along the way. I really think we have a lot we can learn from one another when it comes to changing our careers. And I'm your host, Jenny Dempsey. After a shift on my own career path, I couldn't stop wondering, how do people actually make this work? Why do they choose to pivot? How do they pay for things? And honestly, this curiosity turned into the podcast.
Today I'm chatting with Matthew Smith, who went from starting his career fresh out of college in corporate advertising in New York City to bartending in the Caribbean. After losing his job right before COVID, then not being able to find a new job during the onset of COVID, then going through a tough breakup, Matthew moved back home and was living in his parents' basement. He then had the opportunity to take on a temporary job with a friend's business in St. John in the U.S. Virgin Islands, simply just to
cover his New York City rent. Four years and many drinks served later, he is still there, finding happiness that he never thought existed within a strong community of people. In this conversation, Matthew shares the details of how he made that huge jump, what it was really like to move from the city to a Caribbean island, and how he found a supportive community that helped him grow. He talks about the struggles, the surprises, and why he believes taking risks is worth it.
Jenny Dempsey (02:31.472)
when it feels scary. Matthew's story shows that sometimes life's biggest challenges can lead to the best opportunities. So whether you're thinking about making your own career change or just need a little inspiration, this episode is for you. Grab your favorite drink, get comfy, and let's dive into this chat with Matthew. That surfboard behind you, I know listeners can't see this, but there's a surfboard behind you. Do you actually surf? So.
Surf, that's a stretch. I have tried to surf. And once I found out that I was not going to be the next Kelly Slater, my girlfriend and I turned into a house decoration. Nice. I love it. I took surfing in college and that was pretty much the extent of my surfing abilities. it was a class in college. They make it look so easy, but no, that stuff is challenging. Yeah, it is challenging.
Well, it's so great to have you here, Matthew. Just for everyone, for some context, I was on LinkedIn and you know how it like brings up referrals of people to like connect with. You were one of those people. When I read your tagline, I was like, I need to talk to this guy. So I'm so glad you're here. Tell everybody a little bit about who you are, what you do, where you are in the world, and then we'll dive into your career flow.
Absolutely. So, hey guys, my name is Matthew Smith and I am currently a first mate slash bartender living in St. John and the US Virgin Islands. So my day to day is all customer service, service industry stuff. But yeah, I moved from New York City to the Caribbean and here we are four and a half years later after the move. That's amazing. And so how you got to this point?
living the life that so many people sitting at their desk dream about. How did you get to this point? Okay. Just like go into it. Where did it start? You were in New York city. Are you from there originally? No, I'm actually from Atlanta. Okay. And or a smaller town outside of Atlanta, but nobody knows where it is. But no. I actually, in order to tell the story, I have to go back to college. Okay.
Jenny Dempsey (04:52.686)
So I went to college at the University of Colorado and I was from 2015 to 2019. And so I got my degree in advertising, which then led me to New York City after graduating. And so I moved to New York, had this new gig in the ad world, which I was super excited about. And in more details, I was an assistant account director.
So I pretty much managed the relationship between the client and the agency. So it was a lot of back and forth emails, a lot of managing expectations. And I was essentially being trained up to eventually lead teams and be the head person that would manage these relationships. But I was so new to that world right after graduation. I was at the bottom rung of where I would go. And so I got into my job and
I loved my coworkers, but the transition college to the professional world was a challenging one for me. And I kind had the shell shock of is this the next 30 years of my life in that world? And I didn't love it. It was full and I got to work on some cool projects. But honestly, I mean, it sounds kind of cheesy. It didn't fire me up.
make me happy. And I thought that I guess I kind of self into thinking that that was normal. Like, okay, I guess body probably feels this way. Yeah. And so it was this weird, I don't know, limbo, if you will, of I didn't really know what to do. And so I did that. Granted, it wasn't much time when I was going to motions right into moving to New York and starting the job. It was about a
eight month period or so. Okay. So this was before COVID. This was in probably February when COVID was, but the restrictions weren't there. Yeah. I guess what happened was I walked down on a Monday morning after a great weekend and I was pulled into the CFO office and essentially the agency I was working for was going through some issues.
Jenny Dempsey (07:15.63)
And so unfortunately, a lot of members of the company had to be either put on leave or laid off. And unfortunately, since I was so new, I got laid off. And I remember walking out of the agency after just thinking I was getting used to my job, that middle change that I had to make. Right. I was like, whoa, now I'm 23, unemployed in New York City. What do I do?
Yeah. And it's kind of that shell shocking moment. And I remember just thinking I worked hard to get here and now it kind of within 30 minutes ago it was gone. Yeah. So I spent the next two weeks interviewing, trying to find another gig and that is when COVID hit.
So right when I had a couple interviews lined up, I'll never forget it. They all emailed me and said, hey, we'll circle back in like two weeks once this all settles down. Right. All right. More vacation. And we all know what happened. the pandemic essentially destroyed a lot of what was New York City. And so, I then left New York, went back to Georgia.
and was quarantining with parents, still unemployed, still trying to figure it all out. But you couldn't get a job. My industry was shut down completely. And just to add to all the fun, during quarantine and COVID, I went through a pretty big breakup. So now I was heartbroken, unemployed, and in basement.
At the time, I remember just thinking, all right, life, what else you got right now? But it was kind of that trifecta. Losing the job, granted, it was kind of a blessing because I wasn't in love with it. And then when COVID and the breakup, it just put me in a mental space of, I'm going to go do whatever I want to do.
Jenny Dempsey (09:35.52)
After the breakup, a couple of weeks later, I'm still nursing a broken heart and doing all that fun stuff. Then I was talking a buddy from college who actually up in St. John and the US Virgin Islands. His family had a business down there that they needed help with running during COVID. The USVI didn't have as tight restrictions as other places. Essentially, I was doing is I was going to go down there for a couple of months.
help his family run their business, make enough money to pay the rent that I left in New York because I still was unemployed to try to navigate all of this. Yeah. And I packed up my bags, got a one-way plane ticket and left and went down to St. John on June 28th of 2020. Wow. So you land there and it, I mean,
What was going through your mind when you got off that plane? mean, this is like a whole new chapter in a way. And there had been so many things leading up to this point. And you mentioned, you know, it's even was a blessing in disguise that you lost a job because you didn't love it. Did you think what you were going into was something that was going to be temporary? Or did you think at that point, oh no, maybe I'll be here a while. What was kind of going through your mind at that point? I didn't really know what to think.
because I had never been there before. And we were in such unprecedented times that I didn't know what was going to happen in the future, the world or anything. I did know that I was really happy to be out of my parents' house somewhere else so I could stop dwelling on the past and do something different. But I was the same. The USVI is a territory and so it's so different from the continental United States.
And so I just remember getting there and just thinking I was open to any opportunity. Yeah. was an experience. I did. I got there and my first job that was set up for me by my buddy, it was his godmother who owns the business. Okay. I was managing a tourism company and working and doing their marketing and ad for them as well as guiding snorkel trips. And so on the side, I would help guide.
Jenny Dempsey (11:57.314)
but mainly I was the manager and managing all the employees and doing the marketing. So it was kind of a lot thrown into to show up to this place I've never been, be told you're in charge of all of these people and to run the marketing and out of this company. And I'm thinking, sweet. But it ended up being an amazing experience. And after my two months stint, I went back to New York for a
two weeks to pack up all of my things. Okay. so still have the apartment. This whole time I still have my New York apartment. wow. Yeah. And that New York rent. But I did it when I, the entire goal of going to islands was to make enough money to subsidize that rent. And I did. And so that felt good. And then I remember thinking that that was supposed to be the end of it.
And then I was going to either move to LA or back to New York because of my original dream in life was that I wanted to do marketing and advertising specifically for movies and TV shows. And so I was always kind of still like, all right, I'm going to do this. But when it kind of came down to leaving, I didn't want to. Loved the person I was becoming doing what I was doing and being in such a unique place.
And so I didn't want to leave. I did not know it would be four and a half years later, but I just knew something in my heart that this was the place I needed to be. And so I went back to New York, packed up my thing, said goodbye to my roommates and friends and came back to the island. And this time it was for an indeterminate amount of time. And then after that, I long sport, got tired of working for my first company. Wanted to change it up.
And it was always kind of a bucket list thing for me to be a bartender. Kind of like Tom Cruise in the movie Cocktail. I met a woman who owned a bar down here. It's called a drink St. John is the bar I worked at, but I met her on the beach from my old job and she, and I just went in to grab a drink one night and I told her, was like looking to change jobs here and she, and it's hired me on the spot.
Jenny Dempsey (14:26.882)
And that started the, bar for two and a half, three years or so. Wow. And had you had any bartending experience? Did you know how to mix drinks or did you literally write that in there? I learned it right then and there. And it was, I think I, love doing it. And so I love and they gave me a shot. I had no experience, but I knew I was good at people. And so that's kind of what they were banking on and ended up being a great relationship. And the two awesome girls that
are like my big sisters. Even though I don't work for them anymore, they're still family. And anytime they need me to step in and help out, always do it. But it was cool. And I think that where I live in St. John, they call it Love City. And that's because everyone here is such a tight-knit community of people. And everyone kind of takes care of one another. After, I guess, everything that had happened in my life up until that
point, this was a place I need to be. answer of why I'm staying is the people. It's beautiful. mean, it's an island. It's a very touristy place, but the people and the culture and the community is why I'm here. Yeah. Wow. And I mean, from New York, it's a very different vibe, it sounds like, and especially
with the kind of this, what I'm hearing throughout your whole story is this golden thread of people. even mentioned it your first, that, that ad job before you got laid off, like there were people that you liked working with and there were people that you like, you know, your roommates and there were, there's a golden thread of your ability to be a connector and build relationships throughout no matter where you are. And so it makes sense hearing this story. And I know obviously all the pieces and everything now put together like
But hearing this, just makes sense that this is where you landed to be in such a close knit, like strong community. But there was something that you said, Matthew, and I'm going to jump around a bit because I got a bunch of questions for you. But something that you said was, know, when you were going back to New York and you were like getting ready to like, you know, your apartment and you were like figuring things out with that, you had paid the rent. But you mentioned something about
Jenny Dempsey (16:48.406)
You really liked who you were becoming after having these experiences. Can you tell me a little bit more about who were you becoming? What changed for you? Who were you at that point that you weren't before? I was becoming a version of myself that I hadn't seen in a long time. I think, you know, when we're kids, we have this kind of endless optimism about life.
and there are so many directions you can take and through elementary, middle, high school, college and work and so on and so forth, all of those possibilities that where you see your life go and kind of start to narrow. And when I got to this place, I kind of saw that revert back to, my gosh, I don't know what life could be. This is awesome. Because I didn't know what was going to happen. And I was okay with that. Yeah. And I will
stuck in this line or this timeline, so to speak, of a direction I wasn't sure I wanted to go or didn't knew I didn't want to go but couldn't get out of. It was the first time in a long time there were so many possibilities of how it could end up. And I was excited. I was really, really excited. And I think that's what I was holding on to. And I was taking care of myself more, you know, like staying physically fit, like mentally training myself and
really reflecting on my inner thought past and really kind of using that as fuel for what's next. And I think I kind of gained a level of clarity and appreciation that I think I had lost. That's really powerful. that, I don't know, I feel like that resonates. then it leads me to ask you, do you think, and this is obviously hearsay, but like,
If you would not have gotten laid off, do you think you would have made the decision to leave or would you have stayed even though you knew that it wasn't a job that was going to light you up? That's a question I've thought about a lot because honestly, I don't know. Going back to in my life, even though so many crazy things happened, it was a blessing.
Jenny Dempsey (19:12.384)
because it kind of gave me that out. Life forced me to leave. It wasn't my decision. I think it would be a lot harder if life was normal. Look, my parents in the US say, I'm leaving this job in New York and I'm moving to an island and this is what's going to happen. I think it would be like, what are you doing? And so I don't think my story could be without COVID. Going back to your question,
I would like to think one day I would have, or maybe staying in that world, I would have found my niche in it. I I wasn't in it for long. And so it's hard to say initial reactions and looking from example, the position I was in and then X amount of years later, the position I could be in, I knew from a very early stage in that job, did not make me excited. And so I would like to think,
I would have left and I hope I would have done it earlier than sooner. But you know, you don't know. What was that quote? Forgive me. I don't remember who said it, but was how much did they first pay you to give up on your dreams? And I think it's really easy to stay in something comfortable. And maybe if I had gotten comfortable and got a couple of promotions, I never would have ended up.
doing something that genuinely makes me happy. Right. Right. I hope that answers your question. I kind of around it a little bit. No, that totally does answer it. And I think that resonates for a lot of people because it is harder to make the big leap when it's kind of on ourselves versus life throws a data. I think sometimes when there is more of like circumstance happening, it is easier because you're kind of like,
Well, this already happened. What else could happen? But like when we're actually making that pivot and you brought up the thing like, what will our parents think? What will our friends think? What will I be able to pay my bills? Like there's so many other things when it's the choice on us. It doesn't make it wrong either way, but it's, just hear so many different things, whether someone makes the choice and leaves kind of this stability. And I say that in air quotes, but like stability and comfort of a company versus, you know, it's thrown at you.
Jenny Dempsey (21:37.565)
Kind of in the tech world right now, so many people are getting laid off. Like it is just the nature of kind of the industry. And I'm curious if you have any like advice for people who may have gotten, you know, let's say they just got laid off and there's a lot of unknowns and you know, they, what is something that someone in their shoes like could do? Like what advice would you give someone who might
have just gotten the news and is like, you know, what do we do at this point? And how do we kind of move forward without knowing what's coming up next? That's a very, very good question. I think, and this is just my personal opinion, you can always make money. You can find a way to make money. I think if I was in that position,
your life kind of deals you a hand or you make a decision to leave and you don't know what happened. I go back to the basics. What makes you happy? What what what feeds your soul and not to sound overly cliche, but do what you always said you were going to do. Be it owning a restaurant, painting or pottery or whatever it is that you really, really love. For me, mine was traveling and I found a way to do it and what I'm doing now.
And that's what made me happy. And so I think just go back to the basics. And like when you're a kid, what'd like to do? And don't put too much pressure on yourself. I think that's some of common misconception. I'm the first one to do it. I will put so much pressure on myself. Same, Yep. Give yourself some grace. The world's not ending. You're going to be okay. And it's okay to take a chance and it's okay to not know.
It's okay not to have it all planned out. And I'm going to phrase it. love quotes, by the way. I love that. of from Steve Jobs. He was giving a conference years ago, but the gist of it was you can only connect the dots when you look backwards on this decision got you here, this got you here, got you here. You can't do it moving forwards. And so give life a chance to be spontaneous. And then from there,
Jenny Dempsey (24:06.469)
I think you just, like I said, just don't put too much pressure on yourself and do what makes you happy. Yeah. I love that. And I think that resonates so much with so many people because yeah, you can't figure out where you're going to go until you start looking back. And even when those folks that just got laid off, sometimes when we look back, just like what you said, what makes us happy? Like keep it simple. Like what are the things we enjoyed doing as a kid?
These little things that sounds kind of silly are really like a big deal when we're trying to figure out that next step. And it makes me think of what you mentioned earlier was, you know, your dream was to be in advertising for TV and movies and how that dream has kind of evolved in a way to where you are now that has given you an opportunity to do so much more than maybe you ever could have dreamed about and found things that
really made you, like let you up in a way that you're like, if I just would have stuck to this one idea that I had, which was a wonderful dream, there's nothing wrong with that. But sometimes I think, and I know for myself too, we get so caught up in the plan or the idea of the thing, and then we're not looking outside of it. And it kind of limits us in a way that there's might be so much more out there than
we've really thought about. if we just kind of like, you know, as in your story, life circumstances just happened. There was a lot of heartbreak. There was a lot of, you know, changes in the world. And you're like, well, what else have I got to lose at this point? Sometimes when things like that happen, we're able to like look in every nook and cranny for these things. And so it just kind of like hearing you say that it just really, it just makes sense. And I hope that
people listening. even for myself, as I say this out loud, I'm like, I don't want to be in a situation again, where I'm limiting myself or I'm sticking to some plan that I think is going to provide me, I don't know, some stability or something, but it's not going to actually be what lights, what lights me up. And I don't know. I love that your story really highlights taking that. I don't even, you know,
Jenny Dempsey (26:28.381)
I don't want to call it a risk because it just feels like the right choice. it doesn't even, I don't know. Like I think a lot of people listening like, wait, whoa, that's such a big risk. It doesn't even, it just literally sounds like the best choice for you in that moment. And what if everyone took a look at what we are calling risks and just looked at them? It's just a choice. It doesn't have to have this as you know, any stigma attached to it because it could lead to who knows what as it did for you.
And you're living it every day. And you said, you've been there, is it four years? Yes, it's a little over four years now. And as of now, I always tell myself, as long as I'm happy and healthy and feel like it's what's best for me, I'll be here. Have your parents come to visit you? Yes, they have. have. They come down, I'd say, two or three times a year, but they're so supportive of the thing. They...
could not be happier with the way life's going. And that was one of the hard things was I didn't know, I guess, how they were going to react in the sense of you have to agree. You have this whole plan. And when you totally 86 it, wouldn't blame them. They were kind of thinking like, what are you thinking? Yeah. But they didn't. They were fully supportive the whole time. And to this day, my mom and dad both say I'm, it's their whole point is
They were really, really happy that I was doing what I wanted to do in life, not what anybody was telling me to do or what life was telling me to do. You can't go wrong with that. I mean, that's a gift to have that and to know that they're cheering you on and to have that community of people around you, whether they're in the States, you know, cheering you on from abroad or they're there in your tight knit community. You're seeing them every day and they're wanting to hear your story. Just like you were telling me before, like people want to know how you got there.
And it's incredibly inspiring. And Matthew, thank you so much for sharing this. Thank you so much for having me. It was really an honor to speak with you today. And guys, if anyone wants to get in touch with me, the best way to do it will usually be through Instagram. And so Matthew HS7 is where you can contact me. And if you want to shoot me videos or want to chat about anything, I'm here. But again, Jenny.
Jenny Dempsey (28:56.273)
Thank you so much for having me on and I really, really appreciate it. Awesome. Thank you so much, Matthew. Thanks for listening to this episode of The Career Flipper.
If you enjoyed today's combo, share it with a friend who might need a little inspiration on their own career path. Don't forget to subscribe so you don't miss any future episodes. And if you have a minute, leaving a review or rating the show really helps it reach more career flippers around the world. If you have a career flip story of your own, I'd love to hear it. Visit thecareerflipper.com to learn more about how to submit your story for a future episode. And if you're looking for someone to speak at your next event about career changes
making that leap? Think of me! I love sharing these stories and giving others the courage to take their own first steps. Drop me an email to hello at thecareerflipper.com. Keep going my friend. You never know where that next step might take you. What's the best that could happen?