The Biggest Points/Miles Mistake I’ve Ever Made – Hear from Each Member of the 10xT Staff

By: Bryce Conway, Founding Editor of

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Hi Travel Junkies,

It’s easy to view the 10xTravel staff as points/miles professionals who never make mistakes. If we are being honest, we do our best to perpetuate this belief. Nobody wants to take advice from amateurs.

But, the truth is that all of us were beginners at one point. We forgot to sign up for frequent flyer accounts, we used terrible credit cards, and we made some pretty big booking mistakes.

So, today I asked the staff to share some of their biggest points and miles mistakes to show you that we are indeed human.

Let’s start with me.

Bryce Conway – Founder of

I made my biggest mistake in 2012, my first year in this hobby. I had just heard of this amazing thing called the Southwest Companion Pass and was determined to earn one to be able to fly around the country with my then girlfriend (now wife).

My head was swimming with possibilities. Weekends in Vegas, winter trips to Florida, visiting friends in New York City, I was going to do it all and not pay a dime for any of it.

I quickly skimmed a couple of articles about how the Companion Pass worked (there were significantly less points and miles resources available in 2012) but thought I understood the basics.

Accrue 110,000 Southwest Rapid Rewards points in a single calendar year = get a Southwest Companion Pass. Seemed simple enough.

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So, I opened a Chase Southwest credit card in January and earned a 50,000-point sign-up bonus one month later. I then transferred 60,000 Chase Ultimate Rewards points earned from my Chase Sapphire Preferred Card to Southwest to complete the required 110,000 points in a year.

Ta dah! It was only a matter of time until my Companion Pass would show up in the mail. I checked my mailbox everyday with the enthusiasm of Ralphie waiting for his Ovaltine decoder ring.

A couple weeks passed with no sign of the Companion Pass so I decided to call Southwest to see what was up. Certainly there had been some sort of mistake.

Turns out there had been. The mistake was mine for thinking that transfers from Chase Ultimate Rewards counted toward earning the Southwest Companion Pass. Turns out they didn’t (and still don’t), so I was still 60,000 points short of earning one.

Thankfully, this occurred before the days of the Chase 5/24 rule. I simply opened a different Chase Southwest card and put some spend on it to earn the remaining 60,000 Rapid Rewards points and my Companion Pass.

Crisis averted.

Bonus Mistake: On a recent trip home from Europe I was delayed overnight on the east coast due to weather. Which I am usually fine with thanks to trip interruption insurance offered by many credit cards that I use to purchase my travel. But of course on this trip I forgot to use one of them.

It’s cool, I didn’t want $500 to cover my hotel, meals, and incidentals…..

Spencer Howard – Editor in Chief –

Only a month before I started learning about how to travel the world with points and miles, I opened a Delta Gold SkyMiles Card from American Express. Yep, first credit card that earned miles or points. Great job, Spencer. Pure brilliance.

Now, this was before the Chase 5/24 was in full swing but come on! If you thought that was the worst of it, you’d be wrong. Sure, the bonus for this card is often 50,000 or 60,000 or even 75,000 SkyMiles. Did I know that? Nope. 30,000 SkyMiles.

What would possess me to make such a foolish decision? Well, I did little to no research. I just knew I grew up flying Delta and my dad flew with Delta on tons of work trips (nearly 2.8 million butt in seat miles). Delta was pretty much all I knew and I didn’t know squat.

Luke Sims – Staff Writer –

When I first got into this game I was rapidly moving through cards and I had not taken the time to set up a system for organizing and keeping track of everything. That’s when I missed the minimum spend requirement for a new card because I had forgotten how much I needed to spend! Don’t be me, it’s never too early to get things organized… 10xT even has a sweet spreadsheet that makes it easy!

Travis Cormier – Staff Writer –

When I started in the points/mile world I was following a guide specifically for the Maldives. The trip guide I was following used AAdvantage miles to get there, so I decided I would do the same.

My first card for both my fiancée and myself was the Citi AAdvantage Platinum Select credit card. This was only about 4 months after getting a Discover It card.

We had no idea how the Chase 5/24 rule worked and before I knew it I was at 2/24 and she was at 1/24. (If you also don’t know about this rule you’re going to want to read this right now)

We didn’t even know about the Southwest Companion Pass, and before we knew it we were both past 5/24. We will likely never have the Companion Pass. Since we live in Texas, it would have been a great option for many low-cost trips throughout the Caribbean.

(P.S. I wrote a post about how to get to the Maldives using points and miles to make it easy for everyone else in my situation)

Julie Szpira – Staff Writer –

A couple…

I didn’t sign up for every frequent flyer program/promotion because “it’s not like I use them all the time.” Then when I started accruing more points/miles, I was mad I didn’t have all my previous flights/nights credit.

I used to use miles only for domestic economy flights.

I tried to credit a Singapore Airlines flight to United MileagePlus. Turns out it was a fare class that didn’t earn any United miles, so instead of creating a Singapore KrisFlyer account and crediting the miles to Singapore Airlines, I didn’t claim anything.

This is probably my worst travel story ever…

I assumed that missing a flight in Europe would be like in the U.S., where you go “Whoops…can you put me on standby for the next flight?”

I was in Frankfurt and horribly misjudged the amount of time it would take to walk to the gate, and instead of sprinting, I figured “I’ll just get on the next flight in an hour.”

Turns out that my Scandinavian Airlines (SAS) ticket for a flight operated by Lufthansa was completely non-transferable and I was going to have to buy a new one-way ticket from Frankfurt (FRA) to Copenhagen (CPH) for 300 Euro all for a 90-minute flight.

After some begging and pleading and talking to multiple different agents, one agent was willing to charge me a 65 Euro “change fee” and put me on the next flight.

Oh… and one more. Booking round-trip tickets instead of two one-way tickets. When flights cost the same booking round-trip or as two one-ways, I used to book round-trip because “then it’s all one reservation.”

Which was fine, until I wanted to change my first leg, and there was a $150 change fee plus the fare difference. It would have cost me $275 to switch that leg, so I could keep my return flight. The one-way ticket I was looking to book was $125.

If I had booked two one-ways, I could have just skipped my first one-way flight, flown the $125 ticket and flown home on the other one-way flight. I ended up just keeping the original itinerary, but still. Annoying.

John Tunningley – Staff Writer –

Biggest mistake I have made was spending my first few years with a Chase Freedom and redeeming all my points for cash back. I had no idea that I could transfer those same points to another Chase Ultimate Rewards earning card where they would be worth more toward travel or be able to be transferred to Chase’s many travel partners.

Happy Travels,


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