Diane Sembrot has many centuries of roots in Westport through her Wakeman ancestors. Today she is the editor of Westport Magazine, which shares all aspects of town life, from arts and culture to business and more.

“Over the years, I’ve worked in academic books, medical journals, children’s book packaging, health and business newsletters and, now, magazines and digital content. I got into this during college—I was looking for an internship, and I wanted only Westport. I had spent a lot of time in town as a teen. At that time, summer internships were hard to come by, so I just started introducing myself to local publishing and marketing companies—just walked in the front door and asked. Then, downtown, I ran into a paper sales rep who told me to go Greenwood Publishing Company, just a short walk up the hill. I did. They were a bit surprised, but said yes. I was their first intern. I stayed, doing freelance work at school, and, after graduation, went fulltime. I stayed for years because they were wonderful—and I enjoyed every minute in Westport.

I’ve worked in Westport since back when since Klein’s [Department Store] was here.  I did laps in what is now Anthropologie when it was the YMCA. I’ve worked here since Ship’s was a popular Chinese restaurant [located at 23 Jesup Rd opposite the library]. I was living here when I met my husband. We were rowers at Saugatuck Rowing Club, and I met him at the Commadore’s Ball. Actually, I saw him across the room. Sounds romantic, but he’s six-foot, three, so it’s hard to miss him. We had our wedding reception in Westport to celebrate where we met.

I’ve worked at three Westport companies: one on the Post Road, one on Riverside and one on Main Street.  The Post Road one felt like I was in a neighborhood, because I often ran a quiet loop on the backroads. Riverside was all about creative daydreaming because I had a river view (yes, I was very lucky). Main Street is about people-watching and trying to keep up with the comings and goings of downtown—it’s always changing. There are big stores and small ones, but you can always find a bit of the history if you look. Literally, look up at the top of the buildings—you’ll see some history. I enjoy the mix of current life and the long view of the town’s story. In a way, my industry and Westport changed alongside each other.

With COVID we were hit with a shock, like everyone. I certainly was. It felt like one day we were steaming along and the next I’m packing up my desk and throwing my computer in the back of my car. The team realized and accepted quickly that we would have to change how we were doing things. We knew it was a crisis—our ability to produce pages depends on the health of the town and its restaurants, shops and service businesses. We also knew the people who live here were in shock, just like us.

When the town closed down in March, the more practical matter for the creative team was what to do about the next upcoming issue. Would we publish it? We talked and agreed to go forward— we wanted to act as a connection point for our readers and we wanted to support our advertisers, who are mostly small businesses like us.

The entire staff started working remotely with no notice but set up remarkably fast. Part of the reason it worked is because we’ve worked together for so many years—we know what needs to get done. We picked up the pieces and just figured things out. Everyone was proactive and focused.

I had to alter some of the content to make sense for COVID-19 and for the general mind-set of a pandemic. What do you tell people when their whole world has changed? I tried to be authentic. We published our story on women who took the risk of becoming fulltime bloggers—and what they learned from it. That seemed helpful, because we were all connecting digitally now. The story made sense. And we tried to produce a cover that felt authentic to the time. We chose an iconic image of the town. We thought it would be reassuring, anchoring, a comfort, in a time when the way we saw the world was just spinning.

Anyway, our team found new ways of working…and we owe a lot to Zoom and Slack.

As for re-opening, we’re not in any great rush to open the offices. We want it to be safe and for everyone to feel comfortable. Because we’re not a store or a restaurant, we’ve learned that we can do business remotely. We can call and email people or set up small meetings when needed.

Next to getting out our next issues, the first question we asked ourselves was: How can we be useful? We knew we wanted to help connect people and to tell stories. We also wanted the magazines to be a break from the alarming news hitting everyone’s newsfeeds constantly. We aren’t trying to be a newspaper. We take a longer view. Being a local magazine means knowing our readers and honestly caring about them. That’s why we try to do a mix of issue pieces and celebratory stories. Of course, a big part of it is photography and design—the way the pages are presented is part of the pleasure. Of course, we had to halt photo shoots. We’re just starting to do very small ones. And our staff is doing more writing, though I hope to make assignments again.

Also, we are more than a magazine. We also run events and digital properties. We postponed big events, including a new Women in Business forum, which I had helped re-launch. I was deep into it and very excited about what it meant for us. We had great speakers and workshops lined up; I hope it comes back. And we’re postponing our Best of the Gold Coast party, which we’ve always had. That, too, was getting a fresh re-boot when COVID-19 took us all by surprise. We’re hoping to do them; we’re creative, we’ll work with the times.

As for our digital properties, I started immediately posting more web articles and collected and shared Instagram posts about local businesses that were trying to get the word out about their curbside or delivery options. This for everyone, not just our partners, to send the message that we understood, as a small, local business. We face challenges, too, and we know we are a community and need one another. Now, more than ever, we celebrate every win that comes our way, and we hit the jackpot when the talented Dave Briggs stepped up to do an Instagram Live series for us—it’s been amazing.

In general, I find that Westporters want to be engaged. They are politically and culturally aware and enjoy a good debate or cause—they will show up, they will speak out. I think it comes from being well educated and affluent, generally, but also from an arts identity or history or mind-set to think and express. Also, they can and do use their connections and privilege. Personally, I think Westport looks its best when it uses its strengths and advantages to address issues, especially complicated, painful ones like racial justice. My roots go back to Samuel Wakeman and other local families, and I am digging into what that means—their stories. And I want the real stories. Direct. That’s how you start to learn.

I like people who face challenges, and you don’t have to be loud about it; it can be behind the scenes or creative. Time and time again I’ve seen people here do extraordinary things for others facing crises, including homelessness, poverty, health, and the environment—just amazing dedication and generosity to help move obstacles, provide for immediate needs or talk about things. For me, Paul Newman and Joanne Woodward are role models for this way of living—honest goodness. This needs to get done, let’s do it. I see it in the people making the farmers’ market run, Wakeman Town Farm, Aspetuck Land Trust, our beautiful Westport Country Playhouse, the library, the Levitt, this museum, town events and on and on. Look at this year’s outdoor movies.

Westport likes to look quiet, but it attracts people with an inner fire to get things done. They don’t call it power, but it is. Maybe they don’t even see it that way—they just see a way to help and do. I have seen too many examples of the heart behind that strength to not believe in it.

When someone tells me about discrimination or feeling excluded or even threatened, I believe that, too. It’s painful, because I have to reconcile that with my own lifetime of experiences here. Westporters have always, and literally, thrown their arms around me, and I want that for everyone.

As for Covid, the town did what it does—it got to work, as realists will do. We wore masks. We stopped the parties. The roads emptied out. I know Westport hit the national news, but I’m grateful to see a great deal of sensible people acting responsibly for one another.

I think talking is important. We don’t all come to every issue with the same knowledge and experiences. Allowing for an open discussion is hard, but I think in that space is where we grow. I hope Westport Magazine serves as a space to do that.