Why I’m Always Planning the Next Vacation

On anticipation, priorities, and always having something to look forward to

Beautiful Puerto Rico for my 40th Birthday

On Substack, I’m known for Zero F’s energy. In my personal life, I’m known for the same… and for taking a lot of vacations.

Not an excessive amount (I don’t think). But enough that I’ve developed a bit of a reputation.

The thing is, I really love to travel. And I really, really love to plan travel. I’m almost always planning the next trip — often while I’m still on the current one.

My husband worries this means I’m enjoying the current vacation less. I promise you, it doesn’t. I just really like planning.

Maybe it’s just me, but the end of a vacation stings a little less when I know there’s another one already on the calendar — even if it’s still a few months away.

Travel represents a lot of my favorite things and personality traits. I’m a planner. I like to explore. I like to relax. I like to treat myself (and my family) to new experiences.

I’m also mildly obsessed with the points-and-miles game, which is how I can afford to go on as many trips as I do. Tracking airline miles, figuring out which credit card points transfer where, hunting for the right hotel redemption — this is all part of the planning fun for me.

Which helps tremendously when your spouse doesn’t love travel quite as much as you do.

If given the choice between taking a vacation and almost anything else, I’d probably choose the trip.

Of course, I’m married. And apparently, marriage is about compromise. So I don’t always choose the trip. I promise.

Confession: travel is one of the few things that makes me go green with envy.

Nice car? Good for you.

Designer purse? I love that for you.

A 14-day trip to Tuscany? I’ll wish you well… but I’m secretly dying inside.

Travel is important to me, so I make sure it’s a regular part of my life.

I usually have a handful of family vacations each year. My husband and I plan at least one trip just the two of us. I have one annual girls trip (this will be year four!) and a few other ideas floating around. Earlier this year we went skiing with friends — although I don’t really ski, but I loved the Airbnb. I even have a solo trip planned for the fall.

I’m not made of money, and I don’t have infinite vacation days, so I take my trips in smaller, bite-sized pieces. A week here. A long weekend there. Tagging a few extra days onto a work trip when I can.

It matters to me, so I’m happy to get creative to fit it all in.

The smaller, shorter vacations also mean I don’t have to wait as long between trips. I know a lot of people take one or two big vacations a year. I’m spreading mine throughout the year on purpose.

It’s rare for us to go away for more than a week at a time. Maybe that means we’re missing out on fully immersing ourselves somewhere or truly unplugging. But if it means I get to do it again sooner, I’ll take that tradeoff.

I just really like having something to look forward to.

Girls’ trip to Spain. Drinking wine in a 10th-century winery. Exactly the kind of thing I like having to look forward to.

I also don’t hold every trip to some high, luxurious standard. I love crossing an ocean and exploring a foreign city.

But I also love spending a week with friends at a beach that’s a five-hour drive from our house. Or a long weekend in a cabin in the mountains two hours away.

Does the cabin have a hot tub? I’m there.

I love to explore. I love waking up in an unfamiliar city and finding my way around, discovering the best place to get a cup of coffee. I love watching the sunset over the ocean.

I’d say I love the sunrise too, but let’s be honest — I’m not waking up that early on vacation.

If something is this fun and meaningful to me, why wouldn’t I try to do it as much as I can?

And honestly, the planning is just as enjoyable. Researching hotels is practically a hobby. Figuring out which airline miles to transfer to get the best flight deals is an art form. Building an itinerary for a new place is a fantastic way to spend an afternoon.

And half the time, when we’re actually on the trip, we throw the whole itinerary out the window anyway — because it’s much easier to be spontaneous when you’re on vacation.

Travel may not be your thing.

But what is the thing you love so much that you just want more of it in your life? And how can you make that happen?

Which brings us back to my reputation for taking a lot of vacations.

Most of the time, when people mention it, it’s said kindly — maybe with a little well-intentioned jealousy. But every once in a while, someone has less generous thoughts about how much I travel. I’ve been accused of being “excessive,” “too much,” or “having the wrong priorities.”

If that makes my priorities questionable, I guess I’ll just have to think about it on my next vacation.