The Tyranny of Expectations

Nothing ruins fun quite like the pressure to have fun

For a recent high summer family getaway, we rented a beach house just a couple of hours from home. Unlike the transatlantic family trip to Mallorca we took in June, this domestic trip felt low-key—not once did I scan my feelings to assess if I was having fun, if the three international flights and six months of planning were being juiced to the max, if the pictures were capturing a beauty I may or may not see again, whether enough core memories were being etched into my kids’ minds or if the promise of returning illuminated by a foreign culture was being fulfilled.

For this getaway, there was none of that. We drove. I didn’t spend hours researching restaurants in the area or filling every waking hour with fun activities. I packed my bag the morning we left with outfits I hadn’t planned a month in advance.

We played it by ear.

1. Left: linen oversized brown shirt from H&M, skirt from Becca 2. Top center: Blue Nylon shirt from Ross men’s department, 2022 black pleated shorts from COS but similar here, vintage Oroton leather belt 3. Top right: White oversized top from Zara (sold out) but I also got this one from Muji and this one in black from The Frankie Shop , skirt is from Dissh 4. Bottom center: Tibi carpenter jeans from last year but Dickies painter’s pants have the same vibe 5. Bottom right: Big white cotton button down shirt from Gap which fits me like a dress shirt in size L big, black skirt from Becca over a Johanna Ortiz high rise belted swim bottom (one left in size L.), Swim top from Amazon but anything goes.

On the first day, while we waited for check-in, we stumbled into an unpretentious Italian restaurant we didn’t previously search on Yelp where a young, enthusiastic chef from Naples (Italy, not Florida) served white wine mussels with bread he baked that morning and a beef carpaccio with the ideal lime-to-olive-oil ratio. On the second day, we took the boat from the beach house without a specific plan or destination in mind and ended up discovering a deserted island with shiny, limpid water and Caribbean-like white sand.

The whole island experience reminded me of those moments when I shut off the Net-a-Porter app, head to my closet to play dress-up, and suddenly discover a brilliant color combination or a new way to wear that skirt I had been neglecting, which magically makes me forget about whatever I almost impulse-bought on Net-a-Porter a few instants before.

Swimsuit from Hunza G, linen shirt from H&M, my favorite hat from The Free Press, and a DIY beaded necklace.

While exploring and being creative with what’s readily available may not be as sexy as hitting “order now” or sharing a photo geotagged at a Michelin start in Aix-en-Provence, it instantly alleviates the pressure for a purchase to make us extremely happy or a place to leave us forever changed. This pressure to like something I’m absolutely supposed to like, this tyranny of expectation, eventually becomes a burden too heavy to carry, a burden I did not realize I needed a vacation from. And boy, as cliche as it sounds, how I needed that break from the relentless search for extraordinary moments in distant Instagram landscapes and, instead, embrace the beauty within reach—in a place that felt comfortably familiar. Hanging out with my people. Knowing Publix and CVS were just a mile away. Where it rained every day, and I didn’t stress because time was precious but also wasn’t, as I somehow had the certainty the sun would come out again and again.

On the third day, when we all got on the boat to visit that pretty island, expecting we would find it again, the boat didn’t work. I might have been devastated in Spain, where a missed beach day or a glitch in the itinerary could feel like a major loss. But here, close to home, it was okay. It was only a Florida island after all, an accessible slice of beauty I can always come back to. Like the clothes in my closet—always there, just waiting to be rediscovered.