✈️ WINNERS WEEK TRIP - Behind the Scenes at Our Jamaica Retreat!

This past week was what we call Winners Week — our annual trip with the top attorneys at the firm. Every year, we set specific fee targets, and the attorneys who meet those targets get invited to join Holly, me, Andrew, and his fiancée on a special trip as a thank-you and celebration of their hard work. It’s one of my favorite traditions we’ve created at the firm because it gives us a chance to not only reward great performance but also spend real, quality time with the people who are grinding it out every day.

The destination changes each year. How we decide where to go is a process in itself. First, we set the qualification targets — that part doesn’t change. But then when it comes to picking the location, we put together a list of options. Usually, we narrow it down to two or three places, get the pricing and details for each, and then we let the attorneys vote on where they’d like to go. The twist is that if you qualified the previous year, you get two votes instead of one. The thinking behind that is pretty straightforward — if you’ve already been and are likely to qualify again, we want to make sure it’s somewhere you’re excited to go back to. If you didn’t qualify yet, you still get a say with one vote, but the extra vote is our way of giving a little nod to those who’ve made the trip before.

This year, the winning vote was for Sandals Resort in Jamaica — and I have to say, it was a fantastic choice.

We always allow each qualifying attorney to bring a plus one. I think that’s really important. These trips aren’t just about work — they’re about the people behind the work, the families, the support systems. So, we want folks to be able to share the experience with someone special. And the trip itself is designed to be equal parts relaxing and relationship-building. There’s no rigid schedule, no mandatory meetings or lectures. Instead, it’s about connecting in a more casual, natural way. You might meet up with somebody for lunch or dinner, or just bump into each other during an activity and hang out. Some of the best conversations I’ve had with our team have happened sitting by the pool or sharing a meal in these kinds of settings.

That said, we do always make sure to plan one big dinner where everyone gathers together. It’s the one “required” event of the trip, but even then, it’s low pressure — just an opportunity to get everyone in the same place, share a good meal, enjoy each other’s company, and celebrate the hard work that got us there.

Holly and I try not to work too much while we’re away on these trips — at least that’s the goal. But I’ll admit, I had my iPad with me and stayed in touch with the team back home on a few matters that needed attention. It’s tough to fully unplug when you care about what you’re building. I also used some of the flight time to knock out a few emails, which actually felt pretty productive.

But for the most part, I really did take time to relax. I even read a book just for pleasure — not for work, not for business strategy, just because I wanted to. And honestly, I hadn’t done that in a long time, so it felt good to slow down and enjoy it.

Holly and I only did one excursion on this trip, but it was a memorable one. We went to visit a bioluminescent bay — one of the few places in the world where the water literally glows when you move through it because of the algae. There are only about four places globally where this phenomenon occurs, so we figured while we were there, we couldn’t miss it. We got in the water and watched as every splash and movement lit up around us. It was incredible — one of those experiences that really sticks with you.

The rest of the time, we just hung out, enjoyed the sunshine, and spent time with the team. It’s always great to be reminded that behind all the hard work and courtroom battles, we’re just people. And sometimes, the best thing you can do for your team — and for yourself — is to slow down for a minute and appreciate that.

While we were away, Teddy stayed with my parents. They’ve got two dogs, younger ones, probably three and four years old. Teddy’s eight or nine now, so he still has the energy to keep up with them for a little while, but I could tell he was worn out when we picked him up. He always has a great time over there, but I think playing with the “young crowd” takes it out of him these days.

We got back on Saturday and jumped straight back into work mode. Sunday was Easter, so we spent the day with my family. Had the traditional Easter dinner — ham, potato salad, stuffed eggs, and all the good stuff. One of my favorite parts of the day is always seeing my nieces and nephews with their Easter baskets, hearing about what the Easter Bunny brought them, and just sitting around, catching up with everyone. It’s those little family moments that make the craziness of life feel balanced.

Here’s a fun side note — included is a picture of me rocking my Stitch flip-flops. Holly bought them for me a few years ago because she knows I’m a big Stitch fan (yes, I fully admit that). I’m pretty pumped about the upcoming live-action Stitch movie, and my niece has already claimed me as her movie buddy when it comes out. She specifically said, “You’re going with me,” and I wouldn’t miss it for the world.

One random thing from the trip that stuck with me — the resort had a bunch of cats roaming around. They seemed well-fed and super friendly. I didn’t pet any of them, but they were always lurking nearby. Funny enough, no resort dogs, but the cats were definitely a presence. Snapped a couple pictures of them, so I’ll share those, too.

It was a great trip. Grateful for the team, grateful for the time, and grateful for the chance to step away for a moment and just breathe.

And of course, as always — if you are in pain, call Shane!