The Art of Being Able to Stay… and Knowing When to Go

The best trips are the ones you don’t over-plan. Here’s how to build flexibility into your travels—so you can stay longer (or leave when it’s time).

I meant to be gone for a week. Just a little break, a quick escape from the endless gray skies and the relentless snowfall back home. And then… I extended my trip. Once. Then again. Because every time I checked the weather forecast, I saw another blizzard, another storm warning, another school cancellation.

Today marks the 19th snow day of the season for my kids. Nineteen. Our poor Japanese exchange student, who arrived wide-eyed and enchanted by the first snowfall, has had his Instagram-worthy winter wonderland turned into a never-ending, soul-crushing freeze.

But it’s not just the snow. Everything feels heavy right now. And not just in the “metric tons of frozen slush” kind of way.

Democracy is cracking at the edges. My workload is intense (largely self-imposed, but it is what it is). The weight of my health issues being exacerbated by frigid weather and the immobility it brings... heavy. Some seasons just feel like a constant weight pressing down on you.

Sometimes, you just need to hit the Easy Button.

For me, that meant going back to a place where life felt simple for a little while. Where I could step outside without bracing myself or worrying about breaking a bone in a fall. Where I could move my body, breathe a little deeper, and let some of that weight go.

But making that decision—to stay longer, to shift plans, to choose ease—wasn’t just about impulse. It was possible because I built my trip with flexibility in mind. And that might be one of the most important travel skills I’ve learned.