From Cash-Back to Travel Rewards: My Credit Card Journey

My wallet has undergone a significant transformation over the years, evolving from a simple cash-back setup to a sophisticated strategy for maximizing points and miles. For anyone looking to optimize their credit card rewards, understanding this journey can provide valuable insights.

Initially, I viewed credit cards as a means to spend wisely and earn rewards. However, when I first entered the world of credit, I wasn’t ready for high-end cards like The Platinum Card® from American Express. Instead, I started with a cash-back card, which was more suited for beginners.

At 18, my mother added me as an authorized user on her Disney® Visa® Card. While I didn’t have a particular affinity for Disney rewards, this experience taught me the fundamentals of responsible spending. I learned to treat credit cards as tools for budgeting rather than free money, adhering to essential principles like avoiding expired rewards.

Once I grasped the basics, I was eager to explore the full potential of credit card rewards—cash-back, transferable points, and premium benefits. However, I approached this new landscape cautiously, taking one step at a time.

In my early 20s, I found points and miles to be somewhat intimidating. With a busy schedule filled with internships, job applications, and college projects, I preferred a straightforward rewards structure. This led me to the Discover it® Cash Back Credit Card, which offers 5% cash back on select rotating categories (up to $1,500 per quarter) and has no annual fee.

The Discover it card encouraged me to think critically about my spending habits. Although it lacked a traditional welcome offer, Discover matched all cash back earned in the first year, effectively doubling my rewards. This made my first-year earnings at least 2% back, with the rotating categories yielding 10% when considering the match.

The Discover it Cash Back card was an ideal starting point for me, allowing me to earn rewards without overwhelming complexity. I typically redeemed my cash-back rewards as statement credits, keeping things simple.

As my lifestyle evolved, so did my priorities regarding rewards. I became more interested in travel and began exploring different credit cards to enhance my earning potential. My first travel-focused card was the Chase Sapphire Preferred® Card, which offers valuable Chase Ultimate Rewards points.

Chase Ultimate Rewards are highly regarded, valued at approximately 2.05 cents per point, according to The Points Guy’s September 2025 valuations. The Sapphire Preferred’s elevated earning rates—3 points per dollar on dining and 2 points on travel—made it an attractive option. With a $50 annual hotel credit for bookings through Chase Travel℠, the $95 annual fee felt justified.

I enjoyed transferring my Chase points to World of Hyatt for spontaneous weekend getaways and exploring redemption options through the Chase Travel portal. New applicants can earn 75,000 bonus points after spending $5,000 in the first three months, making it an excellent choice for those new to travel rewards.

Next, I sought a card to maximize my largest monthly expense: rent. This led me to apply for the Bilt Mastercard®, which allows users to earn 1 point per dollar spent on rent payments without transaction fees. While the card doesn’t offer a traditional welcome bonus, I appreciated the opportunity to earn double points on the first day of each month through Bilt’s Rent Day promotion.

Bilt Rewards Points are valued at approximately 2.2 cents each, and I often transfer them to Atmos Rewards for booking American Airlines flights, where I’ve found some great deals.

With a solid foundation in Chase and Bilt rewards, I aimed to diversify my points further. Noticing a gap in grocery rewards, I applied for the American Express® Gold Card, which offers 4 points per dollar at U.S. supermarkets (up to $25,000 annually, then 1 point per dollar).

The Amex Gold card was a significant upgrade for me, as I frequently cook at home and wanted to maximize my grocery spending. I redeem Membership Rewards points for various travel expenses, including flights and hotel stays, with TPG valuing Amex points at 2 cents each. Given my grocery habits, the $325 annual fee felt reasonable.

At this point, my wallet was well-rounded, but I still lacked a premium travel card. The Capital One Venture X Rewards Credit Card caught my eye with its access to Capital One Lounges and a Priority Pass membership. The $395 annual fee is offset by a $300 annual travel credit, effectively lowering it to $95, making it a worthwhile investment.

I’ve enjoyed the benefits of lounge access, especially at my home airport, Greenville-Spartanburg International Airport (GSP). With Capital One miles valued at 1.85 cents each and transferable to over 15 partners, I have greater flexibility in planning my travel.

My latest addition is the Hilton Honors American Express Surpass® Card. Initially hesitant about hotel-specific cards, I was drawn to its perks, including Hilton Honors Gold status, gas bonuses, and a solid welcome bonus. The $150 annual fee was a small price to pay for the benefits, including daily food-and-beverage credits and room upgrades.

Throughout this journey, I’ve focused on collecting diverse currencies, optimizing my rewards, and managing annual fees. While I’m satisfied with my current lineup, I’m considering adding a Citi card soon, especially since Citi ThankYou Rewards has recently partnered with American Airlines AAdvantage.

Every traveler’s needs are unique. To make the most of your credit cards, take the time to assess your spending habits and what you value most in rewards. By doing so, you can create a tailored strategy that works for you.

The Points Guy aims to empower individuals to leverage their everyday spending for cash back or travel experiences that might otherwise be out of reach. We publish various editorial content and card comparisons to help you find the best card for your goals. When you apply for a new credit card through our site and are approved, we may receive compensation from our partners, which can influence how products appear. However, our editorial team maintains independence and integrity in our content. For more information, please review our advertising policy and product review methodology.