Looking back: How my points and miles strategy has changed over the years

I started in the points and miles world as a college freshman in 2014. I had long wanted to go on a solo adventure through Europe but couldn’t afford the $1,000-plus round-trip ticket over winter break and pay for other expenses that would inevitably come up on the trip. So, I turned to the internet for help.

Lo and behold, I found The Points Guy’s YouTube channel, which at the time was TPG founder Brian Kelly dishing out points and miles and credit card advice to a camera. Needless to say, I was amazed at what I was hearing. I could fly to Europe for less than $100? Round-trip? All I have to do is open a credit card and put my living expenses on it? Consider me sold.

Shortly after finding this channel, I opened a United℠ Explorer Card and put my rent payments and other expenses on the card. Once the 60,000 United miles were in my account, I quickly booked a two-week trip from Chicago to New York City, London, Paris, Prague and Berlin. The miles covered most of these flights, and budget carriers handled the rest. I slept in hostels, met other travelers and had a great time.

By the end of the trip, there was one noticeable side effect: I was addicted to points and miles.

I’ve spent the last couple of weeks looking back on my points and miles journey and how I’ve transitioned from a beginner student traveler to a frequent business and leisure traveler. Throughout the years, I’ve changed how I look at the value of my travel rewards and how I’ve chosen to earn them.

The early days: Chasing welcome bonuses, booking economy

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Ah, the early days. I look back on them fondly.

As a college freshman with a part-time job, I had little income. However, being an authorized user of my parents’ credit card helped me build credit early, so I was approved for several cards. Namely, I opened a United℠ Explorer Card and Chase Sapphire Preferred® Card relatively early in my points and miles game. Then, I moved on to other cards throughout college, getting several airline cobranded credit cards and transferable points cards.

I would apply for cards a few times per year and pay my rent (paying a 3% fee) to meet welcome bonuses. I’d redeem the points for trips on school breaks or at off-peak times when I had remote classes. I would also load my classes early in the week, so I could travel from Thursday to Sunday to visit friends from high school, see new cities and explore the world.

At the time, I didn’t have enough daily expenses to focus my spending on the best categories. Instead, I always chased the next bonus. I also focused on redeeming points and miles for economy flights while staying in hostels or cheap hotels. However, I did have a handful of great luxury experiences. Most of my travel was to Central and Eastern Europe, Asia and around the U.S. This helped me stretch the points I earned and travel extensively.

To stretch points further, I would also book cheap long-haul airfare. My first trip to Asia was on a $450 Air Canada ticket between Chicago and Hong Kong. It was also the ticket that helped me earn United Premier Gold elite status for the first time, getting me officially hooked on the elite status hamster wheel.

In short? I wanted to earn as many points as I could while spending as little as possible — and I was willing to sacrifice comfort to do it.

Post-college: Focusing my spending, redeeming for luxury

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A month after graduating from college, I moved from Chicago to New York City.

This increased my expenses, but I had a stable income for the first time in my adult life. However, at the same time, it was my first “real” job with a limited income, and I lived in the most expensive city in the country. This made me think hard about maximizing every dollar I spent to fuel my desire to travel the world.

During this time, I started paying more attention to the cards I used for everyday purchases. The American Express® Gold Card and The Blue Business® Plus Credit Card from American Express became the two most-used cards in my wallet, and I started leveraging shopping portals and airline dining programs to earn the most points on my daily purchases.

When I traveled, I started redeeming for business- and first-class tickets. I was lucky enough to have a fully remote job (even pre-pandemic) at that point in my life, so I was still on the road frequently. As a result of my maximized spending, I could fly amazing products like Lufthansa first class, Austrian business class and JAL business class. Not bad for 22.

Oddly enough, however, I still didn’t value hotels at this time. I would occasionally redeem points for the cheapest Hilton or Hyatt property in town, but the bulk of my stays were in cheap hotels or hostels. This was nice at the time — it helped me meet more travelers and save my points for more flights. However, it was still an extra expense and often meant I sacrificed my comfort.

Today: Value and comfort

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Nowadays, I’m in a more comfortable living situation, and I travel frequently for work.

That said, I’m still focused on saving money. I would like to buy a condo sometime soon, marriage is on the horizon, and I want to eventually retire (crazy, right?). Still, the constant desire to travel has stuck with me — I just want to do it comfortably without breaking the bank.

I still maximize my earnings and always do my best to earn more than 1 point per dollar on all purchases. Sometimes, I make exceptions to this rule, though.

I’m back on the elite status hamster wheel, so I put some of my annual spending on my Delta SkyMiles® Reserve American Express Card to earn Medallion Qualification Mile bonuses that help me maintain Delta Diamond elite status. This makes my frequent travel more comfortable and can help me out of a sticky situation when irregular operations happen.

My redemption strategy has shifted more drastically. These days, I’m still traveling abroad frequently, but not as much as in years past. On those trips, I do my best to redeem for business- and first-class tickets. I’m also traveling domestically more. So, I use Delta SkyMiles and Avianca LifeMiles to book cheap tickets back home to Chicago and to visit friends around the country.

I also have a renewed interest in hotel points, specifically IHG One Rewards and World of Hyatt points. I find that I can book reasonably priced award stays in most major cities with these currencies, saving me thousands of dollars a year. I’m not staying at Park Hyatts every month (as much as I love them), but a Hyatt Place is much more comfortable than a hostel bed at this time in my life.

The key to all of this is traveling in comfort without breaking the bank. I love traveling frequently, but I wouldn’t be able to save money while taking at least one weekend trip per month if it wasn’t for points and miles.

I love maximizing every point and mile I earn, but I’m not afraid to use the Chase Ultimate Rewards travel portal to save $250 on a flight. This would have disgusted me in years past — oh, how times change.

At the same time, I want to stay and fly in comfort. Elite status and premium credit cards make the travel experience more enjoyable on work and personal trips, and I’m willing to pay a little more to maintain them every year.

I’m also willing to dish out more points to book a business-class ticket outright, even if it’s not the best deal. Sure, I could book a $20-a-night hostel, but I’ll pay 12,000 World of Hyatt points for a hotel room instead.

Looking ahead

The takeaway here is that — like anything in life — priorities change.

Initially, I was hungry to earn as many points as possible and redeem them largely for economy flights so I could take as many trips as possible. I would stay in hostels, and that was fine when I was in my early 20s.

However, as I approach 30, I value comfort and saving money for life goals. I still want to explore the world, but sometimes that means staying closer to home or burning extra miles for a better flight or a nicer hotel room I can comfortably work from.

It will be interesting to see where things go from here. Marriage and eventually having children will, someday, mean I probably have to take fewer personal trips. So, I’ll have to make the ones I take more meaningful.

This could mean spending too many SkyMiles on a ticket to Mexico during spring break, or maybe I’ll join the Southwest family travel bandwagon and use a Companion Pass to jet around the country.

Only time will tell, but I’m excited about the future. There’s so much left to explore.