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.

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.

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?”

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.

When I first started learning how to travel with points, I remember feeling completely lost. I’d heard of families flying to Hawaii for pennies and booking dreamy resorts with “just points,” but every time I looked into it, I ended up with 18 tabs open and zero clarity. I knew it was possible, I just couldn’t figure out how.