“If You Don’t Know the Rules, You Could Miss Out on Tens of Thousands of Points”

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Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!

Miles & Points Interview:   Upon Arriving

Daniel writes Upon Arriving to cover the latest developments in travel credit card rewards, airline and hotel loyalty programs, and many other travel topics.  Follow him on Facebook, Twitter, or Instagram!

Upon Arriving

Brad and Me After Getting Scuba Certified in Belize, January 2017

How and when did you start collecting miles and points?

I’d been casually collecting miles and points for a while.  But it really kicked off a couple of years ago when my partner and I were living in the UK and flew back to reunite with our families (and the sun).  We received unexpected upgrades on British Airways from premium economy to Business Class and I got an eye-opening taste of the “lie-flat experience” for the first time.

Upon Arriving

My Miles and Points Journey Began With an Unexpected Upgrade on a Visit From the UK

From that point, I made my mind up to do whatever it would take to avoid economy as much as possible!  And within a few months, we’d both tapped Chase for the Chase Sapphire Preferred and United MileagePlus Explorer cards and were off to the races.

Why did you start your blog?  What’s special about it?

I actually first started writing about travel related to US national parks and focused on publishing my first guidebook, Hidden Gems of the Western United States.  But after moving to the UK, I needed to fill that writing void so I started Upon Arriving to focus on our international travels.

Upon Arriving

Blogging All Started With Visits to National Parks Like Yosemite in California

I think the visuals I offer on Upon Arriving help it to stand out.  I get a lot of feedback about my photos, which I sometimes need to motivate me to stop being lazy by taking photos with my phone.

Upon Arriving

We Celebrated Brad’s Birthday in 2015 at Niagara Falls, Canada

What’s the one single thing people can do to get more miles?

Knowing how to navigate the credit card application rules landscape is crucial to maximizing earnings.  If you’re a beginner and don’t know about restrictions like Chase’s “5/24 rule” or AMEX’s 1 bonus per lifetime rule, you could miss out on tens of thousands of points by unknowingly excluding yourself from eligibility for some of the best sign-up bonuses.

What’s your most memorable travel experience?

We went Northern Lights hunting in Tromsø, Norway, and caught a solar storm on one of those rare clear nights (which happened to also fall on Christmas).  It was an absolutely magical night and we spent hours watching streaks of green and purple light dance across the night sky.  Aside from me breaking one of my camera lenses, I couldn’t have drawn up a more perfect trip.

Upon Arriving

The Northern Lights Over a Fjord in Norway on Christmas Day, 2016

I’d also have to say that I’m still coming down off the high of doing an around-the-world trip where we flew on Singapore Suites, the Etihad Apartment, and, of course, got to experience amazing destinations like Tokyo and Cape Town.  The airfare and hotels for the trip would have cost around $52,000 but we only paid about $400 out-of-pocket due to booking everything with miles and points!

Upon Arriving

Flying From Tokyo to Singapore on Board Singapore Suites

What do your family and friends think of your miles & points hobby?

Initially, there was a lot of skepticism and we raised a lot of eyebrows.  But now, after many of our family and friends have seen what we’ve been able to do, I’m regularly giving friends and family advice on travel and all things credit-related.

Is there any tool or trick which you’ve found especially useful in this hobby?

I love tools like flightconnections.com, award-o-matic, AwardHacker, and Rome2Rio to assist with planning, especially in the beginning stages.

Upon Arriving

Catching the Sunset Over Chicago From a Doors-Off Helicopter Ride in the Summer of 2016

As far as tricks, one generic “trick” I use often is HUCA (“hang up, call again”).  I can barely count how many points I’ve earned just by not giving up on the phone.  Sometimes it really pays to be relentless… and maybe a tad bit melodramatic.

What was the least expected way you’ve earned miles or points?

I’m always surprised to find I’ve earned bonus category spend on random excursions.  I’ve had a few scuba dives code as “travel” on my Chase Sapphire Preferred so that’s always a nice surprise.

Upon Arriving

Scuba Diving in the Dubai Mall

What do you now know about collecting miles and points which you wish you knew when you started out?

I wish I would’ve known how key organization was from the very beginning.

Now, I always recommend people to document everything related to their offers.  Keep detailed spreadsheets, take screenshots, make copies, and when on phone calls take notes of everything: what department you’re speaking with, what they say, who you spoke with, what you’re wearing that day, take it all down!

Sometimes I’ve had to assemble mini “case files” to claim disputed promotions and having all of those records has been vital to my success.

What would your readers be surprised to know about you?

Probably how boring my life is outside of travel.  It’s funny because when traveling I’m always going 100 miles per hour and seeking out the next thrill like swimming with sharks, skydiving, etc., but when I’m at home I’m about as ordinary as it gets.  8:00 pm is bedtime.

Upon Arriving

Cage Diving With Great White Sharks in South Africa in September of 2016

Any parting words?

There’s no denying that miles and points is a true game-changer.

But if you really want to see more of the world and your wanderlust can’t be contained with 10 days off a calendar year, then you may have to step out of your comfort zone and make some big changes in your life.

I’m not saying you have to quit your job and go open up a gelato stand on the street somewhere overseas just to travel more.  Maybe stepping out of your comfort zone means something more practical like taking a new position or negotiating more time off with a slightly lower pay.  Or maybe it means sacrificing that fancy car and wardrobe and shifting some priorities around.

Upon Arriving

Swimming With Whale Sharks Off the Coast of Holbox Island, Mexico

The right steps are different for everyone.  But if you can combine the value afforded by miles and points with a flexible schedule and outlook that prioritizes travel as much as possible, travel can take on a whole new role in your life.

For me, travel became a vessel for living out my passions on a regular basis and the result of that has been a beautiful thing.

Daniel – Thanks for sharing your thoughts on having Big Travel with Small Money!

If you’d like to be considered for our interview series, please send me a note!

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