Planning at 60 Feet Below the Surface
- AJ Shepard

- Dec 15, 2025
- 2 min read
OP Owners Log - 12/13/2025
Some companies book conference rooms.
We booked a 65-foot sailboat, cut the Wi-Fi, and took our planning summit underwater.
Last week, the team at Offsite Professionals wrapped up a 7-day planning offsite aboard the Sea Explorer, a Blackbeard’s liveaboard dive boat cruising the Bahamas. No boardroom. No PowerPoint marathons. Just salt air, hard conversations, clear goals—and 17 dives spread across some of the most alive water I’ve ever been in.
Why a dive boat?
Because clarity comes faster when distractions disappear.
When you’re living on a boat, diving multiple times a day, eating together, laughing together, and decompressing at 60 feet below the surface, hierarchy fades and real thinking shows up. This wasn’t a vacation disguised as work—it was work disguised as an adventure.
The work we did
Between dives, we spent hours planning the next phase of the company. Big-picture stuff and uncomfortable stuff—the kind you don’t rush.
A major focus of the summit was how we integrate AI into our services in a way that actually adds value for our clients, not just checks a trend box. We mapped out how AI can:
Increase productivity without burning out teams
Improve accuracy and consistency
Allow our professionals to focus on higher-level thinking
Keep our clients relevant as the world accelerates
AI isn’t replacing people—it’s sharpening them. And if we’re going to stay valuable long-term, we have to lead that conversation, not chase it.
We left the boat with clear goals, defined initiatives, and a roadmap that feels both aggressive and realistic. The kind of plan you’re excited to execute.
The diving (because yes, it was unreal)
Seventeen dives in seven days is a special kind of exhaustion—and the good kind.
We saw:
Loggerhead sea turtles cruising like they owned the place
Hundreds of Caribbean reef sharks gliding past us daily
Nurse sharks stacked like firewood
Barracuda hovering just out of reach
Octopus, squid, nudibranchs (the weird little gems), shrimp, jacks, remora
Stingrays and sand rays lifting off the bottom like UFOs
We even did a shark feed, which resets your perspective on fear pretty quickly.
But my favorite dive—by far—was the Bahamas Blue Hole.
Dropping into that dark circle felt like entering another world. Nurse sharks everywhere. Reef sharks circling. Lobster tucked into cracks. Rays drifting through the sand. Jacks flashing silver. Remoras doing remora things. Controlled chaos. Perfect balance. It was humbling and energizing all at once.
What I took away
There’s something about diving that mirrors business perfectly:
Panic makes everything worse
Calm breathing solves most problems
You don’t fight the current—you work with it
The best results come when everyone knows their role
This trip reminded me why we build companies the way we do—not just to grow, but to build something resilient, adaptive, and human.
We came back tired, sunburned, and incredibly focused.
And if this is what planning looks like, I think we’re doing it right.
- Dustin Sauer



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