Advertiser Disclosure: The Rewards Mom has partnered with CardRatings for our coverage of credit card products. The Rewards Mom and CardRatings may receive a commission from card issuers.

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.

If you’re trying to make the leap into points and miles but feel a little scattered, my beginner guide is the best place to start. It breaks it down into clear steps, even if your brain is juggling a million tabs

1. A Paper Planner Saved My Sanity

I’ve tried to live in Google Calendar like everyone else. And don’t get me wrong—we do use it as a family. It’s great for syncing sports schedules, school days off, work travel, and everything else.

But it also gets… crowded.

What changed everything for me was finding a paper planner that actually worked. Not a million prompts or fancy systems—just a clear, non-digital space where I could write down what mattered most.

To-do lists. What’s coming up. The stuff that I need in front of me, not buried under four layers of shared events.

And here’s the kicker: I spent years buying expensive planners. Like, the really pretty ones. But this Amazon planner ended up being my favorite—above all of them. It’s simple, durable, and doesn’t make me feel like I’m failing if I miss a day.

2. I Use Travel Freely to Track Our Credit Cards

This is one of my most recommended tools, and it’s the reason I don’t have a spreadsheet for card tracking.

Travel Freely lets me see:

• Which cards we have
• When annual fees are due
• How much time is left to hit a welcome bonus
• Our 5/24 status (for timing new applications)

It doesn’t link to your bank accounts, so it’s low pressure and easy to use. I check it once a week—usually right after I pay off our cards.

3. Monarch Money for Weekly Financial Check-Ins

Speaking of paying off cards—Monarch Money is the app that helps us stay organized as a couple.

It pulls all our accounts into one dashboard, so I can:

• See what we’ve spent across all our cards
• Track our budget by category
• Keep my husband looped in (without him needing to log into 12 different apps)

I block off 30 minutes once a week to check in, pay off balances, and make sure we’re on track for any big spending goals. It’s become a part of my routine—and it helps prevent things from getting out of control.

4. Travel Planning: Block First, Then Build

One of the best things I do to stay organized with travel is to start with our school calendar.

At the beginning of the year, I block off:

• School breaks
• Teacher in-service days
• Holidays
• Work travel or busy seasons

Then I plan trips around what’s actually doable—not just what’s on sale or what looks good on Instagram.

From there, I start using points to fill in the flights and hotels. If you want the full breakdown, I walk through it all in this post about how we plan travel around real life.

5. I Don’t Chase Perfection (or Max Value Every Time)

Here’s something I don’t think enough people say: you don’t have to optimize everything to win with points.

There are times I book through a portal at 1 cent per point because the timing is right, the hotel is available, and it just makes sense.

There are days I use a card that earns fewer points because it’s the one I have with me in the checkout line.

And there are plenty of weeks when I don’t touch our points at all because we’re just in survival mode.

Consistency over perfection. That’s what’s made this sustainable for us.

Final Thoughts

I’m not naturally Type A. I forget things. I miss stuff. But these little habits—writing things down, using the right tools, checking in weekly—have helped me stay organized enough to manage points, plan trips, and keep our family running.

If you’re just starting out, you don’t have to figure it all out today. Start with one habit. One tool. One step.

And if you’re ready to take that first step into points? Here’s the list of cards I recommend for families.

Editorial Disclosure: Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
Advertiser Disclosure: The Rewards Mom has partnered with CardRatings for our coverage of credit card products. The Rewards Mom and CardRatings may receive a commission from card issuers.