Sometimes the creative dreams people set out to accomplish in their lifetimes don’t quite pan out as expected. But those with perseverance find other outlets, and sometimes it takes until retirement for one of those endeavors to find the right audience. 

Pensacola’s Glenn Simmons tried his hand at songwriting, creating and selling Native American wares, and then photography, which led to the start of a Facebook page called Pensacola Postcards. The last one is probably the least likely of the three undertakings that he thought would reach a wider clientele, but thanks to a post about the mechanical shark used in Jaws 2 in 2023, his page went from a couple of thousand followers to over five thousand nearly overnight. Now his page has nearly 17,000 followers, and that Jaws 2 post has nearly 3,000 shares. 

These numbers may not seem like a lot when compared to the millions of shares viral videos or memes get, but Pensacola Postcards is doing something unique, achieving success through authenticity and civil online conversations about Pensacola’s past, neither are easy to accomplish in a world that seems to favor AI content and vitriolic trolling. 

Glenn Simmons has built an online community that shares a love for a nostalgic era of Pensacola while still championing the ever-changing present. 

Glenn Simmons’s nostalgic love of Pensacola started at an early age when his father moved the family to Saratoga, NY. Thirteen-year-old Simmons was ripped from his idealistic youth in the then-new neighborhood of Crescent Lake and the white sand beaches of Pensacola Beach.  

“Being away from Pensacola made me long for it,” Simmons said. Luckily, his grandparents remained, and Simmons spent his summers back in Pensacola. 

Simmons native heritage comes from his father’s maternal side of the family; he was always told it was Catawba. Identifying exact tribal ancestry is a difficult task, if not impossible, for some families that have lost the paper trail. These visits with his grandparents continued Simmons' longing for his hometown and the stories that surrounded it.

Simmons said he doesn’t remember a very close relationship with his father, as his father was a quiet man, but his father’s stories about Pensacola seemed to be what united them. When they drove by buildings, his father would tell him about the businesses that used to be there or the families that used to live in certain houses. As Simmons got older, he would ask his father to talk about Pensacola, and finally his dad said, “You need to contact Norm Simons down there. He can answer all your questions.” 

When Simmons turned nineteen, he moved back to Pensacola and looked up Norm Simons. Simons was working at the Old Christ Church at the time, was a member of the Pensacola Historic Society, and helped establish the Wentworth Museum, now called the Pensacola History Museum. Not knowing this love of Pensacola stories would one day, 40 years in the future, serve Simmons’s artistic passion. 

Around the time that Simmons moved to Pensacola, or a few years earlier, he listened to Stevie Wonder’s album Songs in the Key of Life and began secretly writing poetry. When he later heard Willie Nelson, he decided it was songwriting that he was really after. 

The next twenty years went quickly for Simmons—marriage, kids, odd jobs, Record Bar clerk, roadie and merch man for William Lee Golden of Oak Ridge Boys fame, gym manager, sales rep for Russell Stover Candies, and stay-at-home dad.

At the time, Simmons lived by the words of his friend Paul Bryan, “I wouldn’t mind having some of those toys that the wealthy guys have; I just don’t wanna do what you gotta do to get it.”

But out of all the different jobs, the one as a stay-at-home dad is the one Simmons would never trade. His young boys, Paden and Dylan, were aged two and five at the time, and Simmons feels like the Creator knew he was headed for a divorce and gave him as much time with the kids as possible before the inevitable occurred. Looking back, Simmons credits those early days for helping create a lifelong bond that he treasures to this day. 

His family moved often between Pensacola, Atlanta, and Orlando, but always seemed to end up back in Pensacola. Some Pensacola locals may claim that Gernomio’s Curse is at play. The local legend claims that while being held captive at Fort Pickens, he attempted to escape by boat and was quickly captured and brought back. Upon his return, he cursed the land, saying that anyone who leaves Pensacola will be drawn back no matter how hard they try to escape it. 

After the divorce, Simmons moved to Nashville in 1999 to pursue songwriting full time. He landed a job at the Levi store, and a co-worker introduced him to another songwriter, Milan Miller. They collaborated on many songs together over the years, having eight of them cut by recording artists. The most success came from a song called “In a Perfect World” that was recorded by Jon Byrd. 

During that time, Simmons managed a furniture store, Merridian Home Furnishings, where he worked until he retired in 2026. Also during his nearly thirty-year stint in Nashville, Simmons began exploring more of his native ancestry and began attending Powwows, where he continued branching out into new creative outlets by making and selling Native American wares like dream catchers, dance sticks, and medicine wheels. Carpal tunnel let him know when it was time to move on from that endeavor. 

The other blessing in Nashville came when he met Tamra. They married in 2003. Not only did he gain a wonderful wife, but two more children came along with her, Taylor and Evan.

Although Nashville was where he lived and made a living, Pensacola was always home. He returned several times a year on visits and in 2017 started an Instagram page, Postcards from the Road, to document his travels. But Pensacola always seemed to be the focus, eventually changing the page to Pensacola Postcards. When he created a Facebook account, though, was when he really started to see the engagement with fellow Pensacolians. He seemed to have found kindred spirits among those who longed for the nostalgic past. 

Now retired, Simmons enjoys more time in Pensacola and has taken his stories and photos from Pensacola Postcards to dive into his next creative outlet, publishing a book. He recently released Pensacola Postcards, a coffee table book, and is already looking forward to his next one. Simmons feels like he is at the age where he would like to leave something behind for his grandchildren.

“If I could know what my great-great-grandfather felt about certain things. How he felt in the world. How he saw the world. How he saw human beings. Spiritually. Everything. And even more, especially, how his life evolved.” Hopefully, the culmination of creativity will help answer those questions that those in the future might have about Simmons. 

You can order Pensacola Postcards at Amazon, or visit Pensacola Postcards on Facebook