I got to thinking recently about vacations—their actual purpose, and what they will look like once retirement finally arrives.

Back in the fall, I took a 10-day adventure of fun and frivolity to the tropical Caribbean island of Grenada. It was meant to be 10 days of just sitting back and letting life flow. Vader on a beach—what could go wrong?

With virtually no agenda to follow, it turned out to be an excellent test of what it means to stop working with no responsibilities. As I watched the days unfold, I walked away with a mix of unexpected insights.

The Default Mode Test

With so much unstructured time, it was fascinating to act like a fly on the wall, watching my family and our closest friends to see what “vacation” actually meant to different people when all obligations were stripped away. In a weird way, it felt like a sneak peek at retirement.

On the days we just stayed around our Airbnb, everyone naturally settled into a routine. We had a pool, games, and plenty of options for group activities, but for the most part, we all just did our own thing. We defaulted to exactly what we would do at home on a completely free day. For me, that meant diving down internet rabbit holes, listening to my usual podcasts, and reading a book. For about four to five hours a day, I did exactly what I would do on a rainy Sunday at home.

And I wasn’t alone. The other adults and the kids did the exact same thing.

Now, some might say, “Vader, it sounds like you wasted prime Caribbean time when you should have been doing typical vacation things.”

I don’t think so. We did what centers us—whatever gets us into our calm zone. We still did the classic beach days, the hiking, and the snorkeling. But on the off days, we gravitated toward our natural baselines.

That realization provided an insight to unplanned retirement days. It proved I don’t need an external, packed itinerary to occupy my mind. Relaxation is a state of being, not a geographic location.

It made me realize that vacations don’t need to be the high-priced, fly-somewhere-to-sit-on-a-beach affairs that they are today. A great, relaxing day can happen anywhere if you gravitate toward the same internal state of rest. Moving forward, expensive travel should probably be reserved for deliberate, event-driven experiences that genuinely spark my curiosity—not just an escape. I don’t need to buy a plane ticket just to relax.

When I was stressed working a thousand miles a minute a beach vacation is perfect. When there is no or low stress they no longer work.

The Anti-Instagram Vacation

I also noticed I wasn’t pulled to “check the boxes” the way I was when I was younger.

Take snorkeling, for example. There were sea turtles right off our beach. A few years ago, I would have spent hours hovering over them just because you’re “supposed to.” This time? I felt zero pull to do it again just to say I did it. I have no need to show or tell people about the “cool” thing I saw. In an Instagram world fueled by humblebrags I am no longer pulled.

Instead, I had a much better time reading my book on the sand and people-watching. Reading a book might not sound as flashy or adventurous, but it was exactly what I wanted in that moment. I am more comfortable today doing my own thing than I have ever been, a shift I wouldn’t have predicted five years ago.

The Art of Just “Being”

The trip also brought a surprise on the social front. We traveled with our closest couple friends, shared a house for half the trip, and spent almost every day together. Yet, we weren’t as “social” as I expected.

nothing better then vacation with friends and family

On down days, we simply kicked back with our respective hobbies. We didn’t feel a sudden urge to break out board games or plumb the depths of human existence with deep conversations. We were just entirely comfortable being ourselves in parallel.

At first, it felt a bit strange. I caught myself thinking, We’ve been hanging out for 10 days, shouldn’t we be doing more together?

But the issue was likely where I had set my expectations. I assumed that having time on my hands would draw me into hyper-social interactions. It didn’t. Just being in their presence was social enough. “Doing” wasn’t a requirement for enjoyment. Ultimately, that’s a massive positive; it means we share a level of rare comfort where silence doesn’t need to be filled.

The Monkey Mind and the Shift to Abundance

If there was one area where the vacation fell short, it was this: I thought being in an exotic place would finally quiet my monkey mind regarding my retirement and goal-line stress.

It didn’t. The anxiety tagged along for the trip. Padme and I had a few conversations about it, but nothing was set in stone. Instead, I found myself sitting on a tropical beach, tuning into my usual FIRE podcasts, focusing heavily on content about how to know when you’re truly ready to make the leap. In the moment, while listening, the anxiety quieted down. But an hour later? I was right back where I started.

As the saying goes: “Wherever you go, there you are.” A tropical breeze cannot blow away 30 years of corporate conditioning and deep-seated habits.

But one concept from a podcast, featuring Diana Merriam, really hit home. She noted that the drive toward FIRE is entirely about Scarcity. We spend decades working, saving, and training our minds to focus on scarcity to reach the goal line.

However, the decision to actually retire is about Abundance.

To successfully cross over, a total cognitive rewiring has to happen. We have to train ourselves to see that we finally have enough, and trust that the financial structure we built is solid enough to hold us up while we build a life of our own choosing.

Scarcity was the requirement for the 30 years of work in the past. Abundance is the requirement for the 30 years that will happen next. I’ve been trained to look backward and react to the world. Now, it’s time to learn how to look forward, turn off the defensive programming, and create the life of my choosing.

That is not an easy switch to make. But a necessary one to be successful in retirement.

Here’s to looking forward.

Combing the beach for Abundance