Some friends and I just took a much-needed trip to San Juan.
We’ve all hit that stage in life where we can’t really “just unplug.” The news keeps coming, work texts still buzz through, and student loan payment reminders sneak into our inboxes between sips of piña coladas. At the ripe old age of 29, I can step away from the world, but I can’t fully escape it.
Still, there was one burden I consciously left behind on this trip: my obsession with meal planning and restaurant research. Call it a passion for food, call it the lingering echoes of disordered eating, but vacation usually brings a small wave of anxiety around where and what I’ll eat.
What are the top restaurants? If I say I went to XYZ, will someone nod knowingly and say, “Oh, I’ve been there!”—and I’ll feel like I’m in the know? But I also want to try something off the beaten path… something new. I want to be respectful of the local cuisine, but what if the hotel concierge points us to a tourist trap? I don’t eat meat—haven’t in years—and if I do, I’ll get sick. But should I just try a bite? What if the beans are cooked in lard? Will the most photogenic food actually taste good? Should I just pack granola bars?
It’s exhausting in this little brain of mine.
So when my friend and I boarded our flight, we both admitted: we hadn’t done much research. I’d looked at restaurants months ago when we first booked the trip, but then forgot everything. Honestly, all I do is plan—events and content for work, my half marathon training, weekly meals and groceries, even my mom’s birthday party.
Somewhere between takeoff at JFK and landing in San Juan, I realized what I truly needed a break from: planning. (Yes, I know we had to plan the trip itself, but you get the idea.)
This was a vacation from planning—and it delivered.
Not every meal was perfect. There was a regrettable encounter with some mofongo, and we learned the hard way what a rum floater can do. Breakfast was mostly Starbucks, and I drank more of their coffee in four days than I have all year—but hey, I came to really appreciate their oatmeal. The best cocktails weren’t at a trendy beach bar, but at a Mexican restaurant. And the Chase lounge.


But when you stop planning, you make room to appreciate the moments that do go well (who knew the best beers would be served on some guy’s boat after snorkeling?)—and even the ones that don’t (like laughing until we cried over the disappointing mofongo, spilling water everywhere, and our waiter trying to join in on the joke).
We live in an era where every bite and experience has to be curated. But it’s not that deep. When we spend so much energy chasing fleeting perfection, we miss what’s right in front of us.
Besides, if you blow your whole budget on a fancy meal, how will you justify buying matching $5 oversized, hideously colored gift shop t-shirts with your friends?
xx,
Vacation Mode GB