Points and miles regrets: 5 things I wish I’d done as a newbie

Most people have things they regret doing (or not doing) in life. I don’t have any regrets about life decisions, but I do have plenty when it comes to this hobby. I’ve been doing this for almost six years and during that time, lots of deals have come and gone. This hobby requires boldness. You don’t have to go all out, but it does take some guts to jump in on a crazy point-generating deal.

While I may seem carefree about manufactured spending and other point-earning schemes now, there were times I played it safe when I shouldn’t have. Especially as an anxious newbie. Here are some of my biggest regrets when it comes to this hobby:

#5 using Walmart Bill Pay to pay off my Barclay credit cards

This one isn’t so much about what I wish I’d done, but what I wish I hadn’t done. I’ve warned you all about the dangers of using Walmart Bill Pay to pay off credit cards. Chase has been known to shut people down for doing this and so has Barclay. But in November, I was churning gift cards pretty furiously to cover an upcoming trip and went a little overboard.

So I did something I shouldn’t have done: I began using Walmart Bill Pay to liquidate gift cards and pay off my Barclay account balances. Of course, it backfired and Barclay shut down my credit cards in December.

The Barclay Arrival Plus card was one of my favorites. Up until that point, I had no problems using it to generate thousands of dollars in travel credits every year. Live and learn, right? Wrong! The thing that bugs me is that I knew better. I warned others about it but got reckless and ended up losing my most lucrative point-generating tool. But all good things must come to an end, right? Maybe, but it could have gone on a lot longer if I’d just refrained from using Walmart Bill Pay…

#4 Not churning Chase and Amex cards when I had the chance

I’ve never been much of a regular credit card churner. In the beginning it was because I was averse to risk. Later, I mainly churned Bank of America and Citi cards, picking up an Amex bonus when it was high enough. But I always tried to stay on Chase’s good side by mixing in tons of regular spending alongside ms on my credit cards.

Now that Chase has implemented the 5/24 rule and Amex has a once-per-lifetime limit on sign-up bonuses, churning these cards is pretty much out of the question for me. Yes, I’ll survive without churning Chase credit cards but I should have taken advantage of it back in the day, when it was so easy.

#3 Not buying $500 worth of merchandise to earn 25,000 SkyMiles

In 2011 Delta offered a pretty incredible deal: Earn 25,000 miles for every $500 spent at SkyMall. They were practically giving points away. I considered buying $2,000 worth of merchandise and reselling it at a small loss to earn 100,000 Skymiles.

I didn’t go through with it because of all of the totally legitimate concerns most people would have about stuff like this: Would purchases be properly tracked and points awarded? What sort of merchandise would resell well? What if I ended up with $2,000 worth of stuff I couldn’t get rid of or return?

Nowadays, I know people who spend tens of thousands of dollars buying and reselling popular merchandise on Amazon. I haven’t gone this route, but I did churn ~$23,000 worth of merchandise gift cards via The Plastic Merchant last year. But at the time, reselling $2,000 worth of SkyMall merchandise seemed really daunting.

I do wish I had done it, because the following year I redeemed my Skymiles for a business class ticket to Europe. It was bittersweet and I wondered, “Will I ever have this many SkyMiles in my account again?”

Yeah, we all know how that turned out…

#2 Cancelling my Chase Ink Bold Card

When the Chase Ink Plus card came out in 2012, I was ecstatic. Not only did this mean another 50,000 bonus points from Chase, but I could easily generate 250,000 points every year through the card’s 5x category bonuses.

Things were slow for me on the manufactured spending front. I had trouble finding an ms-friendly Walmart store. At the time, I also commuted to a  full time job in Oakland. Manufactured spending wasn’t something I had a ton of time for.

The annual fees on my rewards credit cards were stacking up, so I put several cards on the chopping block…including the Chase Ink Bold. At the time, I thought I didn’t need two of the same cards because 1.) I wasn’t ms’ing much and 2.) both my dad and brother had their own Ink cards I could utilize for the 5x bonus.

So why do I regret cancelling the Ink Bold? Because I gave up at least $2,500 worth of easy points in order to save $95. Now that I have a great relationship with the staff at my local Walmart, liquidating $50,000 worth of $300 gift cards is a piece of cake. Thinking about those 250,000 points I gave up to save $95 haunts me every day…

#1 Not mileage running for Executive Platinum status (i.e. flying to Chicago nine times)

Let’s admit it: A lot of what we do to earn points and miles is weird to outsiders. When I explain how I spent ~$900 on a 12 night mattress run at a hotel I didn’t even stay at for 600,000 Club Carlson points, or how I mailed out 470 index cards to earn 243,000 IHG Rewards Club points, people look at me funny. That’s followed by questions and the eventual conclusion that yes, it does make sense to do something like that if the points out-value the cash spent.

But when I was new to this hobby, it all sounded way too ridiculous. So when an opportunity arose to earn top-tier American Executive Platinum status by flying roundtrip between San Francisco and Chicago nine times, I couldn’t go through with it.

The ~$1800 cost didn’t bother me. I knew I’d get that value back in redeemable miles and elite benefits. It wasn’t even a lack of time. In fact, I had worked out a perfect itinerary over the course of several weekends. Ultimately, I couldn’t pull the trigger because of how insane it sounded: Flying back and forth to Chicago nine times?!?! Just hop on a plane, hop off, turn around and do it all over again?!?!

But a lot of stuff in this hobby sounds insane to the average person. We do it anyway and we benefit from it. Today I would jump at an opportunity like this. Even though I can earn miles in lots of other ways at a cheaper rate; even though I don’t even need the benefits of American Airlines Executive Platinum status right now. I would do it for the fun of it alone.

One of the longest flight itineraries I ever put together was San Francisco to Sydney via Honolulu, Tokyo, and Bangkok. That involved over 36 hours of flying and it took me three days to arrive in Sydney. It was totally insane! My family in Australia (who had been following along on social media) kept messaging me, wondering if I was really coming to visit or if this was all an elaborate ruse.

It was an adventure and I look back on it with fond memories. Everyday life is pretty mundane and risk-free. I would love to do something impulsive and adventurous like fly back and forth to Chicago nine times if the opportunity presented itself.

All of these regrets center around a single theme: Not taking risks. Whether you’re a newbie or have been at this for years, don’t get complacent. Look for the fun in this hobby, even if it’s flying around aimlessly or doing something mundane like mailing out 470 index cards for IHG points. When all the miles have been redeemed, it’s the memory of those trips that stay with you. And if you have fun in the process, you’ll even think back fondly at the crazy things you did to earn those miles.

Do you have any regrets in regards from your early days? Which crazy deals have you participated in to earn points and miles?

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