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.

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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.

So today I want to give you the real story—not the highlight reel. What it feels like behind the scenes. What overwhelms me. What makes it worth it. And how I actually keep it all going without dropping the ball (or ruining my credit).

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If you’re new to all of this, my Beginner’s Guide to Points & Miles is a great place to start—one step at a time, no overwhelm.

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When I Realized This Wasn’t Going to Be “Set It and Forget It”

When I got my first travel credit card, I genuinely thought I could just put all my spending on it and magically have enough points to take my whole family on vacation.

Reality check: that’s not how this works.

At some point, I realized that if I wanted to travel regularly with a family of six (especially over school breaks), I’d need more than one card—and a lot more strategy. But I also didn’t want this to become a full-time job.

That’s when I started looking for systems that could help me do this in a way that felt sustainable—and wouldn’t leave me staring at 12 open tabs and a meltdown waiting to happen.

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The Part That Used to Overwhelm Me

Before I really understood how points worked, I would search “how to travel with points” and end up reading blog posts that felt like I’d stepped into another language.

There were terms I didn’t understand, flight search tricks that seemed impossible to follow, and advice that made it seem like you had to be doing it all to be doing it right.

What I didn’t understand then—and what I try to tell other moms now—is that there are levels to this. It’s like going to the grocery store with one coupon vs. extreme couponing. If you just want to grab one free item and save a little, you can. That’s still a win.

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Judgment, Credit Fears, and Why I Stick With It

Do I ever feel judged for opening so many cards? Absolutely.

There’s a stigma that people who open more than one or two cards must be irresponsible or living beyond their means. And to be fair—this isn’t the right strategy for everyone. If managing a credit card is a struggle or you’re carrying balances, this isn’t the season for points.

But we pay our cards off in full every month, and I’ve created a system that actually makes our finances easier to manage, not harder.

I use Travel Freely to track due dates, annual fees, and welcome bonus deadlines without ever entering personal account info. I also use Monarch Money to keep our finances in one shared view—so my husband isn’t out of the loop, even though we now have 17 cards between us.

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The Mental Load Is Real—But Here’s How I Handle It

Earning points is the easy part. It’s redeeming them—especially for international flights or transfer partners—that sometimes makes me want to throw my laptop across the room.

I’ve learned to recognize when it’s not the day to book that tricky redemption. And I’ve learned that it’s okay to walk away, close the computer, and come back with a clearer mind.

I also give myself permission to prioritize our family’s schedule and sanity over squeezing every last cent out of a redemption. That means sometimes I book through a portal. Sometimes I redeem at one cent per point. And I’m okay with that.

If you’re wondering when the effort feels worth it—it’s not when I hit “confirm” on a booking. It’s when my kids walk into a resort lobby with hot chocolate dispensers, water slides, and beds that light up from underneath. Or when we realize we’re the only family on the plane who paid $0 for flights. That moment in Mexico? I’ll never forget it.

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My Rules for Keeping It Manageable

Here’s what I don’t do:

• I don’t try to optimize every single redemption
• I don’t open cards just for the sake of it
• I don’t use jargon or complicated spreadsheets
• And I definitely don’t do this if it’s going to cause stress in my marriage

I do:

• Spend about 30 minutes a week reviewing our finances and point strategies
• Use apps like Travel Freely and Monarch
• Take it one card, one bonus, one goal at a time
• Keep our travel goals front and center

If you want to travel more but this all feels intimidating, just start small. This guide will help you do that in a way that fits your life.

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Why I’ll Keep Doing This (Even If It’s Not Perfect)

This isn’t a system I follow because I love financial tools or collecting credit cards. I do it because the return is so high for our family.

We’ve had stays we never could have afforded. Trips we would have put off “until someday.” And moments I’ll never forget—watching my kids sip hot chocolate at a luxury resort I booked entirely with points.

If it ever stops being worth the effort, I’ll stop. But for now, this is one of the best strategies I’ve found for turning everyday spending into extraordinary memories.

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Want to see the cards I use most often for flexible travel rewards? Here’s the list.

Or if you just want a simple place to start, grab my beginner guide—it’s designed to walk you through exactly what I’d do if I were starting today.

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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.