Black Tie and Tales: A Black Tie Goodbye

“My newspaper wants to hire someone who’s good at talking to people. Are you interested?”

My former editor sprung that question on me a month into my post-graduate life in Palm Beach. I had already gotten into a fight and started sleeping in my car in that short time, so I figured a change would be good for me. 

Plus, I was a terrified early 20-something who needed a job. You remember that feeling, right?

That was my introduction to the Observer Media Group and the Black Tie beat. 

When you do the math (something I try to avoid), I’ve been working in Observer offices for close to seven years. I’ve met amazing people, documented the ins and outs of the philanthropy scene and only picked up one visible scar along the way.

That’s all come to an end. I’m writing this on my last day at the Observer.

And really, what a ride. I’m a mix of emotions — mostly good, some melancholy — but I’m feeling ready for what’s next. 

The Black Tie beat has been a good fit for me, it demands an energy I’ll admit I have in spades. I felt comfortable in the hum of philanthropic activity at the Winter Park/Maitland Observer newspaper in Central Florida. 

The Winter Park office was the Little Engine That Could, but Ultimately Couldn’t. We shuttered close to two years after I started. 

But things were moving at the Sarasota office — the resident BT reporter left early — and I was offered the Black Tie position here.

I didn’t know a thing about Sarasota, I was South Florida-born and raised. Why drive across the state when we had beaches at home?

But after a few years in Central Florida, I missed the sea breeze. I took the Black Tie job, adopted a cat and moved into a beach shack in the Siesta Key Village

I learned a lot from the sun-fried retirees who lived there and drunkenly yelled deep into the night, fumbling for something they’d never have again.

At the same time, I was dressing up in suits and mixing and mingling with Sarasota’s upper class, the fashionistas and fixtures who serve as the philanthropic support network for this nonprofit-heavy town. 

Photo by Harry Sayer

The Black Tie beat is unique. It’s all just people, right? That’s true of most facets of journalism, but that’s especially true in this little bubble world we’ve carved out in SRQ. There are longtime donors and figures who make up the scene year in and year out. Learning how to connect with the various personalities was a fun part of the job, it certainly kept things interesting. 

The Black Tie community, fortunately, was welcoming at my arrival. It helped that I look like everyone’s Republican grandson, I’m sure that endeared me. 

There have been countless people — too many to mention in this column, really — who have provided me with advice and direction when working with local nonprofits. I think that was my favorite part of the job — seeing the good people doing good deeds. 

I’ve had many Observer colleagues and local creatives who’ve helped me along the way as well. Niki Kottmann, Troy Herring, Cliff Roles — they all helped me figure out my creative voice and style as best I have it. 

People in the BT scene have said I made my mark, which is kind. I’m not sure if that’s true, but what do you want from me? I was raised Catholic, we’re not bred to feel good about ourselves. 

Journalism is a weird industry. It pays terribly, the hours are miserable and a third of the country wants to kill you. You feel compelled to stay of course, the act of creating being too special to give up.

But feeding an inflated ego rarely pays the bills. Plus, I’m tired of working weekends. The Black Tie beat is a wheel and I’m getting off for now. 

Courtesy photo

I think I’m stopping at a good point and I’m thankful for the Observer Media Group for taking a chance on me. The opportunities the company has given me to push myself and grow have been priceless, and I’m pleased to see my work improve year after year. 

What’s next for me? My fiancee and I are moving to Wilmington, North Carolina, for the summer. I’m told it’s a big little town on the beach that brings in plenty of tourists. I think I'll handle that just fine.

I’m grateful to OMG for helping me figure out my voice. I’m happy to be leaving for something new. And I’m rooting for whoever the Observer finds next to cover this fun little beat.

My advice for them? Drink water and have a good time. 

Editor’s Note: Until our new Black Tie reporter begins, contact Observer Executive Editor Kat Wingert at [email protected] with your Black Tie questions/comments/concerns.