When summer rolled around, my dream as a kid of eight or nine was to join some pals on a lake somewhere in Wisconsin or Indiana to see how the rustic half lived and played. I spent my formative years in an urban neighborhood of crammed apartment buildings on the north side of Chicago. A time away in an overnight camp for a few weeks seemed like an idyllic interruption. But being the only child of a Jewish mother whose hobby was planting and nurturing fears, I was lucky if I was allowed to cross our street by myself.

I found myself knocking on an unlikely door recently. I’m not a religious person, but I arrived at the door of St. Augustine’s church to light a candle for a friend. As I struggled with the key code, a woman appeared next to me and let me in. After lighting the candle I turned around to see the late afternoon sun streaming through the stained glass windows, projecting disco-ball-like colored spots of light on the pews. Beautiful, delicate light. And I started to cry.

The first time I was told I had to play a game in order to get my Christmas presents I was annoyed. Isn’t it enough that I was good (well, mostly) for the entire year? Isn’t life the game you play to get the prize of Christmas presents? Now I had to figure out clues to determine which of the anonymously wrapped gifts under the tree was mine. How unfair.

I never set out to be a designer. A one-off stint doing album art led to more album art, then a paint scheme for Nascar, branding a law firm and marketing for non-profits. Before we knew it, my wife and I had a full-blown design business with an international client base. Our “work from anywhere” business model led to Martha’s Vineyard.

Julia Rappaport

Writing about food, which I’ve done now for just a few months shy of a decade, was never something I set out to do. And, especially at the beginning of my career, it was anything but trendy or glitzy. It was dirty, gritty, and messy – at times quite literally.

Elissa Lash

She wanted a home. He wanted her to have one. This is the kind of beautiful observation I get to make when helping people to buy or sell a house.

Moira C. Silva

It is mid-February. Winter’s sea-frosted breath is seeping through the cracks in my house and chilling the bones of everyone we left behind. I admit that it gives me the tiniest bit of guilty pleasure to imagine this as I linger over brunch with my family in historic Winter Park, Fla., 90 miles from where I attended high school. Call it Vacation schadenfreude.