Freedom Isn’t “Time Off” — It’s Choosing Where You Work On Your Dream

Right now, I’m half in the water at Hideaway Beach on CocoCay — Royal Caribbean’s private island. There’s a massive Vegas-style pool behind me that’s mostly empty. They cleared it out earlier, and most people went back to the ship. I didn’t. My towel’s spread across a bar top at the swim-up bar, my laptop’s open, pop music is echoing from the DJ’s speakers, and I’ve been toggling between our Go-To-Market strategy, setting up transactional emails for our CTO, and a half-finished SEO brief.

I’m working. I’m building. And I’m not at home.

This wasn’t a vacation. It was never supposed to be. 

I Didn’t Come Out Here to Escape — I Came to Build

This month-long trip was planned from the start as a working retreat.
Not a getaway. Not a digital nomad fantasy. Just a different setting with the same mission: build Haulvana with as much intensity and vision as I would from home, maybe more.

I’ve got about 6 more days left on Freedom of the Seas, then I switch over to Oasis of the Seas for another 6 days. There’s a short 2-day stop in Miami between the two. That’s my window. That’s the calendar I carved out. I thought I’d be insanely productive with that kind of structure, new scenery, and separation from the usual noise.

But here's the truth: I haven’t been as productive as I thought I’d be.

The Reality Hits Harder Than the View

When I imagined this trip, I pictured 8-hour focused sprints. Daily strategy sessions. Deep work on product, pipeline, and planning. I figured I’d finish entire sprints poolside with a cocktail and still have time for a swim.

Reality? Much messier.

I have gotten real things done — mapped out our Go-To-Market campaign, kicked off targeted prospecting, set up transactional emails, worked through sales tooling, and put together an SEO brief with our analyst.

But I’ve also hit walls. Been distracted. Fought spotty Wi-Fi. Lost momentum for no good reason. The kind of friction that makes you check the date and ask, “Wait, what did I even accomplish today?”

And when the goal was clarity and productivity, falling short hits different. Especially when you're staring at clear blue water and realizing you’re still carrying the same mental load you brought on board.

I Thought This Would Be a Sprint — It’s Turning Into a Reset

What I’m learning is that travel doesn’t magically fix your output. It can reset your perspective, but only if you allow it to.

You can’t just change the view and expect your brain to do more. Sometimes, it does less. And sometimes that’s okay.

What this month has turned into is less about sheer volume and more about zooming out. Out here, I’ve been better at planning. Strategizing. Getting back in touch with the why behind the build — and the how behind the next phase. That part’s been invaluable. You don’t get that kind of space when you’re drowning in Slack notifications and meetings.

Freedom Means Ownership — Not Always Productivity

I used to think I’d “earn” rest when we hit certain metrics. That I’d be able to chill once Haulvana crossed some imaginary threshold of traction. But the bar always moves. I still feel guilty when I don’t get enough done. I’m wired that way.

The irony is that I finally gave myself permission to work from paradise — and I’ve spent half the time frustrated that I wasn’t moving faster.

That’s the trap. We chase freedom, but we don’t always give ourselves permission to feel it.

What I’m starting to internalize is this: freedom isn’t the absence of responsibility. It’s the ability to move at the pace that fits the moment — without justifying it to anyone.

Out here, I’ve taken meetings in flip-flops, fought for decent internet with a Wi-Fi repeater I smuggled onto the ship, and kept working while everyone else was heading to the hot tub. It doesn’t always feel efficient. But it feels real.

To Other Founders Feeling Stuck or Fried

If you’re reading this feeling overwhelmed, stuck, or totally burnt out — this part’s for you:

You don’t need to shut everything down to find clarity. You don’t need to go off-grid. You don’t even need to stop building. Sometimes, you just need a different kind of motion. A different backdrop. A short circuit in the loop you’ve been stuck in.

Don’t let hustle culture make you feel guilty for needing a break. Or worse — for taking one and not maximizing it.

If I Could Bottle This

If I could bottle the feeling of building my dream from the water — the clarity, the chaos, the half-wins and half-finished drafts, the pull between ambition and acceptance — it would taste like a Goombay Smash - Malibu coconut rum. Kraken dark rum. Orange and pineapple juice.

Sweet. Refreshing. A little reckless. Exactly like the kind of clarity that hits you when you stop expecting everything to go according to plan.

This trip reminded me that I don’t need a perfect routine to make real progress.
I just need to stay close to the mission. Stay flexible. And keep building — wherever I am.

Let’s build this.