If you’ve ever thought, “There’s no way I could keep track of all this,” just know: I’ve been there.

Managing points, credit cards, school calendars, work projects, and family travel doesn’t come naturally to me—it’s something I’ve had to get better at. But over time, I’ve built a few habits and systems that make it feel less overwhelming, and more like second nature.

This post isn’t about having it all figured out (because I don’t). It’s about the simple things that have made the biggest difference—for both our travel goals and our everyday sanity.

It happens to every traveler at some point: the flight is delayed, the room isn’t ready, the weather ruins the big day you planned—or your kid gets sick the night before you’re supposed to leave.

Or in my case? Starts throwing up on the way to the airport.

Because of course.

There’s nothing like a travel day morning to test your sanity.

One kid’s missing a shoe. Someone’s crying because we didn’t bring that kind of granola bar. You’re running through the mental list of things you swore you wouldn’t forget, and your husband is calmly sipping coffee like boarding time is optional.

I’ve done this enough to know: the chaos is part of the deal. But I’ve also learned how to make travel mornings feel a lot less stressful—with a few routines and one small habit that’s made a surprisingly big difference.

This is the behind-the-scenes of how I track our points, stay on top of payments, and plan trips without losing my mind.

When we book flights and hotels with points, people usually want to know the “how.” But once we’re past the strategy part (and if you’re curious, this beginner guide is a great place to start), the next question is usually: “Okay, what do you pack?”

People assume that because I talk about points and miles a lot, I must be a spreadsheet-loving, detail-obsessed person who never gets overwhelmed. That’s… not exactly true.

The truth is, I have a love-hate relationship with travel credit cards.

I love what they’ve done for our family—I mean, we’ve stayed in five-star resorts for free, flown to Hawaii in peak season, and saved thousands of dollars on school break travel. But the mental energy it takes to keep it all running? That’s real. Especially as a mom managing a household, sports schedules, and a business.

A few years ago, if you had asked me whether it was worth traveling over school breaks, I would’ve laughed and said, “Only if we win the lottery.”

Because as someone who has worked in the travel industry for most of my adult life—first as a travel agent, then for an airline—I knew the golden rule of getting a good deal: Travel off-peak. That’s where the savings were. That’s where the wide-open seats, low hotel rates, and promo codes lived.

But when our kids got older, everything changed.