The 7 Most Costly Travel Hacking Mistakes I Made (So You Don’t Have To)

I signed up for my first travel rewards credit card 11 years ago... Looking back, I see how much I missed and messed up. Learn from my early errors and start earning free travel the right way. When I first started figuring out Travel Hacking, I was excited, but completely unprepared. I made some classic mistakes that cost me thousands of dollars in free travel and slowed my progress significantly.

If you’re just starting your Travel Hacking journey, this post will help you avoid the most common—and most expensive—pitfalls. These are the 7 biggest Travel Hacking mistakes I made, and what you should do instead.

1. Choosing Credit Cards Based on Ads Instead of Strategy

Like most beginners, I signed up for a travel credit card based on a flashy commercial, social media ad, or targeted website banner. The card looked impressive, but the rewards were limited, the sign-up bonus was weak, and it didn’t align with my travel goals.

What to do instead: Choose credit cards based on your long-term strategy, not marketing hype. Focus on cards with valuable welcome bonuses, flexible points, and strong transfer partners. This is exactly what I teach in my course.

2. Not Understanding the Value of Transferable Points

Early on, I didn’t understand how much more valuable transferable points are. I used my Chase & Capital One points for gift cards, cash back, or their travel portal, thinking I was getting a good deal. Later I realized I could have transferred those points to airlines and hotels and enjoyed a nicer vacation for far fewer points.

What to do instead: Learn how to transfer points to airline and hotel partners to unlock the highest possible value for your rewards.

3. Waiting Too Long to Sign Up for A Card

Once I started learning about some of the special Welcome Bonus offers that other people received on their cards (Higher Welcome Bonus, Special Category Bonuses, Extra Perks, etc), I started waiting for the "perfect" offer to sign up for a card. Oftentimes, I would wait many months with nothing ever materializing.

What to do instead: The sooner you start, the sooner you can start earning. Every month you wait is a missed opportunity to build points for your next free trip.

4. Using the Wrong Card for Everyday Purchases

For years, I was putting groceries, gas, and recurring bills on a basic 1% cash back card. I didn’t realize I could have been earning 3–5x points in those same categories with the right travel cards.

What to do instead: Use cards that offer category bonuses on your largest spending areas. This way, you earn significantly more points without spending more money.

5. Missing the Significance of the Chase 5/24 Rule

One of the most costly mistakes I made was signing up for too many cards too quickly. I didn’t know about the Chase 5/24 rule, which limits new Chase card approvals if you’ve opened 5 or more credit cards in the past 24 months. This included some non-travel store cards that I signed up for at a cash register just to save a little money on a purchase.

What to do instead: Start with Chase cards first, then think about the other non-Chase cards later. The order you apply for cards matters—a lot.

6. Redeeming Points for Low-Value Rewards

I once used 25,000 points to get a $250 cash back. At the time, it felt like a win. But now I know those same points could’ve flown me to Europe or Hawaii in economy or even business class.

What to do instead: Use your points for high-value travel redemptions, not merchandise or low-return gift cards. I teach how to calculate point value inside my course.

7. Trying to Learn It All On My Own

I thought I could figure Travel Hacking out through blog posts, podcasts, and Reddit threads. While I learned a lot, I also made expensive mistakes and spent hundreds of hours learning how to piece everything together.

What to do instead: If you want to maximize your results and avoid mistakes, learn from someone who’s already done it. My course distills everything I’ve learned into a step-by-step process that actually works.

Skip the Mistakes and Start Traveling for Free

Travel Hacking has helped me earn over 3 Million Points, just in the past two years, and take trips I never dreamed were possible. Family vacations, anniversary getaways, and last-minute emergency travel, and more - all for free or nearly free. If you're just getting started, the best thing you can do is avoid these mistakes and follow a proven system.