Ever Leave Home

Those Instagram status updates can sometimes serve a purpose.

In case you missed it, we had a little merch launch last week—two posters and two shirts. Thank You to everyone who has checked it out and of course a special thanks to those who have ordered. Posters are in motion—only 50 of each—and I’ll be sending t-shirt numbers to the printer tomorrow, so it’s best to order soon to guarantee you get what you want.

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After a birthday trip to see my sister Emily in Los Angeles back in January, my counselor encouraged me to keep making travel a priority. Because that LA trip left me feeling more alive than I had in a long time, to the point I thought seriously about moving. Beyond the time with my sister, the days were filled with friends and fun. My counselor helped me see that it was deeper than travel. The heart of the matter was of course connection but also wonder—putting myself in places where I can be inspired and surprised.

I went to North Carolina at the end of March—just before the launch of this Substack—to spend a day in Emerald Isle with Eric Brown, who is a dear friend and an incredible photographer. Emerald Isle is where I lived my first five years. There was a lot wrapped up in going back and having Eric there added another special layer. To come away with photos I could use for the launch of Ever Get Home, photos I now treasure, the trip was close to perfect.

I was home for all of April and May, which made sense as I committed to writing again, but also I’ve been itching for an adventure. You know how Instagram added those weird status updates that none of us asked for, the ones you see when you check direct messages? Last Sunday I noticed that my friend Jeremy Cowart’s said “en route to St. Augustine.” I messaged him to ask how long he would be in Florida.

JC: “I’m there all week! You around? Man I’d love to see you.”

JT: “Let’s make it happen! I’ll stay in touch and we’ll come up with a plan.”

JC: “Sounds good!”

Jeremy went on to say that while he was coming with his family, he could definitely sneak away to get together. I could pick whatever day worked best for me.

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My last trip to St. Augustine was just over a year ago, with my sister Emily to see Phoebe Bridgers at the ampitheatre. I booked us a room at a cheap-but-decent hotel near the beach. We parked by the lighthouse and a shuttle bus took us to the concert. We met two awesome humans, Nicole and Kelsi, on the ride over. We liked them right away. When we ran into these shuttle-bus friends at a fantastic grilled cheese spot after the concert, it felt like we needed to officially be friends. We joined them for a late dinner and then joined them at the beach until 4 in the morning. I felt like I was 20 years old again.

Last Thursday was Emily’s birthday and I decided that if I couldn’t be with her in Los Angeles, perhaps it was the perfect day to go to St. Augustine. The cheap-but-decent hotel was available again and so I booked a room to double-down on the nostalgia.

I had been wanting to launch Ever Get Home merch for weeks but it kept getting pushed back. I committed to Thursday and told myself this would only take a couple hours. Of course it ended up taking most of the day, which meant I didn’t leave town until nearly 5pm. Which was okay because the merch launch was important to me—this was Gracie’s merch debut after all.

I drove straight to the Historic Downtown, where I had not been in years. During my sales rep days before TWLOHA, I used to visit a store called Surf Culture on St. George Street. Years before that, I have memories of being there as a kid, both on family vacations and with my dad as he sold t-shirts to a few different shops around town. (I’m the son of a sales rep who sold and still sells t-shirts. I went on to be a sales rep, selling t-shirts before starting a non-profit that was initially funded by t-shirts.)

I had dinner at The Floridian on Spanish Street. The food and vibe were great. I knew the owner Jeff a million years ago when we were kids hanging around Surf Station, a shop my friend Tory owns across the bridge—near the lighthouse actually. I asked the waitress if Jeff was around. She said he was away on vacation with his family, a 40th birthday celebration. This made me smile because, in the picture of Jeff that lives in my memory, he must have been around 15 years old. I would have been 17 or 18. When I shared this with the waitress, we both laughed. It’s true that time flies by.

Walking around Downtown St. Augustine made me smile. I’ve always loved the history and character of the place. It’s only a couple hours north of where I live but this part of town is very different from anything near me. After the heat and busyness of a day this time of year, the Downtown streets empty out at night. You feel like you’re in Charleston or New Orleans or a movie. Someone mentioned Key West so I may have to head there soon.

My sister Emily can be elusive and I was still yet to talk to her on her birthday. She texted during dinner and so I called her when I finished and we reminisced about our trip the year before. Em and I share a love for Sugarfish, our favorite sushi in Los Angeles. She had plans to head there for birthday dinner and those plans made me happy.

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Friday was Jeremy’s last day of family vacation and so he asked if we could meet at 9am, to give him plenty of beach time with his crew after that. As someone who is typically asleep at 9am, this request required a moment of consideration on my end. I decided that because I am an adult and because I love Jeremy, and since seeing him was the reason for my trip, then yes I could meet him at the early hour.

My friend Dustin Miller lives in St. Augustine and I invited him to join us. Jeremy and Dustin have a lot in common and so I loved the idea of the two of them meeting. Both are incredibly talented in similar creative fields—Jeremy is a photographer whose work has expanded far beyond that into fine art and NFT’s. He’s always cooking up something new and there is a good chance it’s never been done before. Dustin is a brilliant cinematographer. We’ve spent a lot of time together over the years, traveling for various TWLOHA video projects. Dustin’s career has grown exponentially since I first met him and these days he travels all over for all sorts of big things, from music videos to commercials to documentaries.

Beyond the creative work, Jeremy and Dustin are both married and they both have four kids. The common ground doesn’t end there as they’ve each adopted two kids. It’s safe to say I knew they would have plenty to talk about. And to top it all off, Jeremy and Dustin are two of the kindest people I know.

I may or may not have walked across the street to Starbucks when I woke up. Because I’m a creature of habit and also because I needed some help being awake for the 9am coffee meeting. Jeremy was staying south of town and so we picked a place that worked for everyone.

The three of us met at Kookaburra. As someone who loves Australia, I was excited to try this place. I was definitely excited to be able to order an egg-and-cheese pie for breakfast. Of course the highlight was getting to see Dustin and Jeremy. They were in line when I arrived and seemed to be hitting it off. I love watching two people I know become two people who know each other. We spent the next couple hours in conversation. They talked about their families, we talked about work and other things as well—what’s been hard and what each of us is excited about. I’m good at asking questions but they made sure I answered too.

Soon it was time for Dustin to drive to Jacksonville for a meeting, and for Jeremy to get back to his family and the beach. I had secured a noon checkout at Hotel Cheap But Decent, which meant there was just enough time to shower and pack before I hit the road again.

I asked if we could take a group photo and then laughed in remembering who I was with. These two know how to take a picture. Jeremy snapped a couple from his phone. I had texted the two of them earlier and so we had a group text going. A little while later Jeremy shared the photos there. This one was my favorite.

DM: “Y’all are really cool. I needed that this morning.”

JC: “Same here.”

JT: “That was awesome. I’m so glad you guys met.”

How amazing is connection? What a gift to find a friend. What a gift to share as well.

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I decided to take the scenic route on my way home. I’ve lived in Florida for most of my life but somehow I had never driven A1A (along the ocean) from St. Augustine to Daytona. I had been on parts of it but never the whole thing straight through. I drove south past Matanzas Inlet and thought about the last time I was there with friends visiting from Atlanta. I called one of them. I passed Marineland and remembered going with my family as a kid. I drove through Flagler Beach and remembered surfing the pier for the first time with my dad. At Ormond Beach I made a right and made my way to 95. By this point I was definitely excited to pick up Gracie from Grandma’s house. (My mom. Gracie’s Grandma.)

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My counselor smiled last Wednesday when I told her about my plans to head to St. Augustine. This was not an epic trip. I didn’t need a passport or ten days off or thousands of dollars. But it was a change of scenery, the chance to reconnect with places from my past, and most of all the chance to spend time with friends I love but rarely see.

It’s fun to share our bucket-list destinations. I would love to get to Italy and Bali. My family tree goes back to Poland and Ireland—I would love to see these places too. I hope everyone gets to visit the countries that they dream about, but I know finances and responsibilities mean these trips are out of reach for many.

So where would you go if you could get away for a night or two? Is there a place that makes you smile within a few hours of driving? Is there a podcast or audiobook, new album or old playlist, that you love the thought of spending time with on the way? Do you have a favorite restaurant or store or hotel, or a new spot you might like to try? Could you use the time to think about something or not think about something? Would you go alone or invite a friend?

Maybe it’s time. Maybe you have no idea where you would go but the possibility feels exciting. Well whether it’s now or soon I hope you’ll give yourself permission to go. There may always be reasons not to. Money might always be tight. A road trip can’t change everything but a shift in perspective, or connecting with a friend—these things have value. So keep an eye on those Instagram status updates. And don’t be afraid to surprise some people the next time you post a new one.

I wonder, where is your St. Augustine? Do you have a Jeremy and Dustin you could spend time with? This may require waking up early or staying up late. You may need coffee before you meet for coffee. Regardless of the details, I’m pretty sure the whole thing will be worth it. And so I hope you hit the road soon. I hope you take the long way home as well. The journey tends to be the destination.

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Gracie wants to know if you’ve ordered a shirt yet. She’s calling it the shirt of the summer. I told her she might be a little biased.

Learn more about Jeremy Cowart.

Learn more about Dustin Miller.