A Classic Dilemma: "Should I Leave Sarasota or Should I Stay?"

Veronica Pastore, Matt Orr and Tatyana Sharoubim weigh in on the young Sarasotan's ultimate question: Should I stay or should I go?

By Beau Denton January 2, 2014

A three-way call about the young Sarasota professional's classic dilemma.

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Matt Orr, 37, now a Los Angeles resident, is a former Sarasota realtor, the founder of This Week in Sarasota and co-founder of the Sarasota Young Professionals Group and the HuB.




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Veronica Pastore, 29, is a social media consultant, PR professional, blogger and columnist. She writes “Party Girl” for Sarasota Magazine.




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Tatyana Sharoubim, 27, is the owner of T. Georgiano’s Shoe Salon in downtown Sarasota.





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Moderator: Beau Denton, 26, is associate editor for Sarasota and Biz(941) magazines.




Beau: How did you first come to Sarasota?

Veronica: I’m from Kansas, but I used to visit family here and then moved down in 2006. I was tired of winter.

Tatyana: I moved here in 2006 as well. I grew up in New York City and moved here with a now ex-boyfriend, whose dad was here. We had an e-commerce concept, which spiraled into the retail store.

Matt: I didn’t like Sarasota when I first visited. Then I got lost on the way back to the airport. I ended up in Burns Court, which is a really cute neighborhood. I flew back to Charlotte and moved within the next 30 days. That was 2002.

Veronica: The first year it was hard to meet people, and it seemed like everything closed at 8. But I had bought a house already and I ended up getting a job at Creative Loafing Sarasota, and the rest was history.

Tatyana: I love everything about this community. I paddleboard all the time, I run, I think our bridge is beautiful, I go out to eat with friends. The people who move here choose to move here, and they are happier.

Veronica: But how can you compete with the diversity of a big city? The values here are limited, too. I’m looking for a more progressive community. Where’s the passion for the environment? And vegetarian restaurants! I want more than one.

Tatyana: Well, I grew up in a big city, and—maybe I’m selling myself short, but making all the mistakes I did with my business, learning everything as I went, I don’t think I would have been able to do that in New York or L.A.

Matt: Sarasota is a magical place, and I don’t have anything bad to say about it. But I had my boyfriend here in Los Angeles and decided to move here last year. Plus, there is a cap to the opportunity in Sarasota, so I figured it’s best to live in a big city for now. I kick myself for not relying on my own strengths earlier. I should have been doing this when I was 25. I didn’t realize that I could do something in a bigger city. I always felt the big fish syndrome in Sarasota. I was afraid that if I made a move, I wouldn’t succeed.

Veronica: I experience both sides. I’ve had a lot of opportunity here because I’m young, outgoing and energetic, and there’s not as much competition. On the other hand, if I don’t live in a big city before I die, or before I get too bogged down, I’m going to regret it. I have to go.

Beau: You sound pretty definite about that.

Veronica: Yes. I’m determined.

Matt: I’m 37 now, so I’m aging out of a lot of things. Tonight in L.A. when I go out, there will probably be like 5,000 people under 30 out on the streets, all doing their thing. I wish I had moved at that age and then gone to Sarasota. I did it backwards.

Veronica: That’s one of the best things about visiting L.A. There are young people everywhere!

Tatyana: It’s happening more and more here, but it’s—

Veronica: It’s not the same.

Matt: Unless you’re in a tourist-related business or a nonprofit, there’s just not a lot of money dispersed in Sarasota. Tatyana’s in a good position for the tourist industry, but Veronica, I’d imagine you would make more money if you had clients outside of Sarasota.

Veronica: That’s what I hear. I just had a meeting with a woman who is 20 years older than I am and also has a PR company. She’s living paycheck to paycheck. She has a great name in town, but she says I have to start looking for work outside Sarasota, because not enough people here are willing to pay for my services.

Matt: The conversations in Sarasota never change. That’s a shitty part. I read about the latest debacle about noise downtown in fascination, because we tried tackling that in 2003. There were new players this time around, but the sound bites were the same.

Beau: But do you think that happens only in Sarasota?

Matt: Probably not. People don’t like change. I went to a planning meeting here and the issues are different, but the arguments are the same. You should surround yourself with the environment that feels best for you—just know that it’s probably not going to change when you get there.

Tatyana: It’s definitely changing here. I like to say we’re a micro metropolis. There are a lot of new restaurants, lounges, bars, events that are more controlled by people our age. Influential people in the retirement community come to me all the time and say, “I’m throwing this gala, and we want young people there.” They need us as much as we need them. It’s very symbiotic.

Matt: I don’t think it’s symbiotic, that’s the problem. They say they need to get young people, but—

Tatyana: So you think they take advantage of us?

Matt: I totally do. I don’t think they do it to be mean, I just don’t see them hiring me.

Tatyana: Customers who are throwing an event and want me to bring young people will come and drop like eight grand in my store. I wouldn’t do it if it wasn’t beneficial, because it is very time consuming.

Veronica: But if we don’t have a physical product that somebody can buy, people have to commit to hiring us to do marketing or PR. And that’s not something everybody needs.

Matt: Listen, I’ve changed my mind so many times about Sarasota. I was so connected to it, then I became so bitter towards it. I think what I have concluded—today—is that it’s such a beautiful place, the people are exceptional, there’s nothing like it. My boyfriend and I have talked about how, if it’s not under water by the time we retire, we’ll definitely be there.

Click here to read four other young people's experiences about living and working in Sarasota. >>

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This article appears in the January 2014 issue of Sarasota Magazine. Like what you read? Click here to subscribe. >>