Why We Go To St. Barths Twice A Year (And It's Not What You Think)
My husband and I just got back from St. Barths.
Two weeks. No distractions. Just us, the ocean, and the most important conversations we'll have all year.
People ask me: "Why do you go away for two weeks just to plan?"
Because you can't do this work at home.
You can't telescope out and see your life clearly when you're standing in the middle of it. When emails are pinging and your multiple business ventures are all demanding your attention at once.
Why St. Barths?
Most people think of St. Barths this time of year for the celebrity influence; the glitz, the luxury, the scene.
That's the superficial surface.
The true magic of the island is what you find when you step away from all that: the turquoise waters that make you think bigger. The authentic French culture that slows you down. The warm locals who remind you what actually matters. The striking mountainous terrain leading to the ocean - a physical reminder that clarity requires elevation.
It's a magical oasis to do deep reflective work. And that's exactly why we keep coming back.
How This Started
We've been doing this twice a year since 2017. December and May. Always out of the country. Always in a beautiful natural setting.
That was the year I committed to my own development in a serious way. I spent years studying Tony Robbins, attending his events, and eventually getting certified as a life coach. As I combined that training with my own business and life experiences - building multiple ventures with my husband, navigating the complexity of running businesses together while staying connected - this process emerged.
And it's the single most important thing we do for our business, our marriage, and our life.
The Process
We assess our vision from the past 3-5 years across five core areas:
Professional - Are our businesses aligned with who we're becoming?
Financial - Are we building the wealth and freedom we actually want?
Relationship - Is our marriage thriving or just surviving?
Health - Physical, mental, emotional, spiritual. Where are we really?
Contribution/Philanthropy - How are we showing up beyond ourselves?
For each area, we spend 1-2 hours assessing:
Did we hit the targets we set? Why or why not?
We celebrate the wins
We review the misses without judgment, just curiosity
Then we build the new strategy. Not just WHAT we want to achieve, but:
WHO we need to talk to (and we set actual meetings)
HOW we need to spend our time differently
WHAT we'll do to hold each other accountable
After each conversation, we do something physical. A hike. A swim. A long walk on the beach. We don't think about it. We just move.
Then we sleep on it.
The next morning, we refine what emerged the day before and move to the next area.
Why Movement Matters
Movement while deciding is a metaphor for movement on the action.
When we hike after talking about business goals, we're training our mind and body that these decisions are already in motion. We're not just thinking about change; we're embodying it.
And there's something about being in nature, in a beautiful place, that makes you willing to shed what's not working and embrace what could be.
You can't get that sitting at your desk at home.
The Final Days: Synthesize and Commit
The last few days, we don't introduce new topics. We synthesize everything.
We create the action plan. The people we're committing to talk to. The accountability structures.
And here's the most important part: we commit to taking immediate action on at least 2 big decisions and 2 little decisions as soon as we get home.
Not "eventually." Not "when things calm down."
Immediately.
Because if you don't act on clarity when you have it, it disappears the moment you step back into daily life.
Why This Changed Everything
Before we started this in 2017, we were reactive.
We'd set goals in January like everyone else. We'd lose track of them by March. We'd get to December and realize we'd spent the whole year in the weeds without ever stepping back to see if we were even heading in the right direction.
Our businesses were growing, but were we? Our marriage was fine, but was it thriving?
This process changed that.
Now, twice a year, we force ourselves to telescope out. To see the whole landscape. To assess what's actually working and what's not.
And to make decisions from clarity instead of crisis.
This Is Not Goal-Setting
This is so much deeper than New Year's resolutions or annual planning.
This is vision assessment and strategic realignment.
We're not just asking "what do we want?" We're asking:
Who do we need to become to get there?
What do we need to let go of?
Who do we need to bring into our life?
How do we need to spend our time differently?
What accountability do we need that we don't currently have?
And we're doing it together. As partners running multiple businesses and building a life.
That integration - the refusal to separate professional goals from relationship goals from health goals - that's what makes this work.
Because you can't optimize one area and ignore the others. They're all connected.
Why I Now Do This With Clients
This process has been so game-changing for us that I started offering private strategic planning VIP days and multi-day private retreats for my clients and their partners.
Because I've seen what happens when leaders try to make high-stakes decisions from the middle of their daily chaos. They can't see clearly. They optimize for urgency instead of importance. They make reactive decisions instead of strategic ones.
But when you remove them from their environment, give them structured time to assess all areas of their life, and help them build concrete action plans with accountability, everything shifts.
They gain clarity on decisions they've been avoiding for months or years.
They see patterns they couldn't see when they were too close.
They leave with a roadmap that integrates business AND life, not just one or the other.
The Question
When's the last time you actually stepped back and assessed whether you're building the life you want, or just reacting to the life you have?
Not for an afternoon. Not for a weekend workshop.
For real, uninterrupted, deep time where you can telescope out and see the whole landscape?
If the answer is "never" or "not in years," that's your sign.
You can't see your life clearly when you're standing in the middle of it.
You have to step out. Physically. Mentally. Emotionally.
And give yourself the gift of clarity before you make your next big decision.
If this resonated, share it with another leader who needs permission to step back and assess.
Kasey
P.S. If you're navigating high-stakes decisions in your business or life and need dedicated time to telescope out and gain clarity, I offer private strategic planning VIP days and multi-day retreats. We do the deep work of assessing where you are, where you want to go, and building the concrete action plan to get there—with accountability built in. Reply to this email if you want to talk about what this could look like for you.