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

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

Low 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 surprised by what I heard. 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 one 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 travel and as I transitioned from a novice student traveler to a frequent business and leisure traveler. Over the years, this has also changed how I view the value of my travel rewards and how I’ve chosen to earn them.

The first days: Hunting for welcome bonuses, booking economy

Ah, the first days. I look back on them with pleasure.

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

I would apply for the card a couple of times a year and pay the rent (paying a 3% fee) to meet welcome bonuses. I would redeem the points for trips during school breaks or off-peak hours when I had distance learning. I also loaded my classes early in the week so I could travel Thursday through Sunday to visit friends from high school, see new cities, and explore the world.

Related: Should I pay with a rewards credit card even if there are fees?

At the time, I didn’t have enough daily spending to focus my spending on the best categories. Instead, I was always chasing 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 US. This helped me stretch the points I earned and travel a lot.

To stretch points further, I would also book cheap long-haul flights. 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 achieve United Premier Gold elite status for the first time, officially getting me hooked on the hamster wheel of elite status.

The short one? 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.

Related: 9 trips TPG employees booked with points and miles for 2023 travel

Post-college: Focusing my spending, cashing in on luxuries

A month after I graduated 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. But at the same time, it was my first “real” job with limited income, and I lived in the most expensive city in the country. This made me think hard about maximizing every penny 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 began 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 completely remote job (even pre-pandemic) at that point in my life, so I was still often on the road. As a result of my maximum spending, I was able to fly amazing products such as Lufthansa first class, Austrian business class and JAL business class. Not bad for 22.

Oddly enough, I still didn’t value hotels at this point. I would occasionally redeem points for the cheapest Hilton or Hyatt property in town, but the bulk of my stays were at 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 added expense and often meant sacrificing my comfort.

Related: Sweet Spot Sunday: How to fly round-trip to Europe in business class for 88,000 miles

Today: Value and comfort

Nowadays I am in a more comfortable life situation and I often travel for work.

That said, I’m still focused on saving money. I’d like to buy a condo sometime soon, marriage is on the horizon, and I’ll eventually retire (crazy, right?). Still, the constant wanderlust 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.

I’m back on the elite status hamster wheel, so I’m putting some of my annual spend on mine Delta SkyMiles® Reserve American Express Card to earn MQM bonuses that help me maintain Delta Diamond elite status. This makes my frequent travel more comfortable and can help me out of a difficult situation when irregular operations (IROPs) happen.

My redemption strategy has changed more drastically. These days I still travel abroad often, but not as much as before. On these trips I do my best to redeem for business and first class tickets. I also travel more domestically. So I use Delta SkyMiles and Avianca LifeMiles to book cheap tickets home to Chicago and visit friends around the country.

I also have a renewed interest in hotel points, especially IHG One Rewards and World of Hyatt points. I find that I can book award stays at reasonable prices in most major cities with these currencies, saving me thousands of dollars a year. I don’t stay 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 point in my life.

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

I love to maximize 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 comfortably. Elite status and premium credit cards make the travel experience more pleasant for work and personal travel, and I’m willing to pay a little more to maintain them each year.

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

Related: Benefits galore: Why the Delta Reserve Amex is my favorite cobranded credit card

Looking forward

The takeaway here is that – like everything else in life – priorities change.

At first 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 wanted to stay in hostels and that was fine when I was in my early 20s.

But as I approach 30, I value comfort and saving money for life’s 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 that I can comfortably work from.

It will be interesting to see where it goes from here. Marriage and eventually having children will one day mean that I will probably have to take fewer personal trips. So I have to make the ones I take more meaningful.

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

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

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