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Do Hard Things Because They Are Hard

Last week I went to Utah to run an unusual marathon. My time was well over two hours slower than any marathon I've done, but that was by design—I was running with someone who was doing a series of extreme events back-to-back, every day for 100 days in a row.

The pace, therefore, was slow.

His name is James Lawrence, more popularly known as the Iron Cowboy. I'd heard of James a year or two ago after watching a documentary of his previous quest where he attempted (and accomplished, with a few small variations along the way) 50 Ironman-distance triathlons in 50 states in 50 days.

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Travel Hacking Opportunity: Easy Way for Small Business Owners to Earn 110,000 Points

Link: 110,000 Point Bonus Offer (Must have an LLC or S-Corp)


I haven't been writing much about travel recently, for reasons that are probably obvious. Travel doesn't exist at the moment! At least not in the same way it used to.

But it will again, especially with all that we've learned in the past year and vaccination well underway. I'm convinced that when it does, there will be some amazing deals and opportunities.

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Do This When You Visit a New Place

ender-vatan-2_wSj_4osX0-unsplash Pandemic life has taught many of us to appreciate moments in life that might otherwise pass us by. I've been trying to pause and take note of how I feel at the end of the day, often as I walk in the park or one of my nearby neighborhoods.

With that in mind, here's a tip inspired by The Art of Stopping Time, a book by Pedram Shojai: whenever you visit a place that's new to you, consider the sense that you might never be there again.

Just imagine: this might be it! Your only opportunity in one lifetime to visit this particular place. How might this make you feel?

What, you say you aren't traveling much now? That's okay.

This "new place" could be anywhere: a part of the woods you've never seen on your next nature hike, for example, or even a street in your neighborhood you've never driven before. The point is to create awareness and appreciation.

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Under the Unseen Blue Sky in Sydney, Australia

If you’re going through a dark night of the soul, you might as well pass the time in a beautiful place.

That’s what I was thinking as my hour-long Qantas flight from Melbourne began its descent to Sydney. Australia has long been a place of joy and peace for me, and Sydney in particular. Ever since I first stumbled into town five years ago, when I was denied boarding on a flight from Brisbane to Nauru (long story), I’ve been coming back every chance I get.

This time felt different because, well, I’m different. I’ve been judging the days on a 1-10 scale, and I get excited—at least moderately so—when I feel higher than a 3.

And so as the flight lands in Sydney and I take the airport train to the city, bracing myself against an onset of anxiety, I begin my self-talk.

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New Travel Hacking Offers: Earn 100,000 Hilton Honors Points & More


Greetings from paradise, also known as Australia.

I started writing this post from one of my favorite places in the world: the balcony of my room at Park Hyatt Sydney (check out this photo of the sunrise!). I’m staying here with points earned from the Chase Sapphire Preferred, my #1 recommendation for travel rewards cards.

Normally the room would cost $900 a night (!), but naturally my cost is ... $0. I’ve been here over and over, usually at least once a year, and every stay has been “funded” through my points from this card.

And it’s not just here. All over the world, I’ve been able to fly and stay for nearly free, all thanks to the wonders of travel hacking.

All of this is possible for you, too! Or at least it is for many of our readers, who regularly write in to tell me about how they used their points for amazing experiences of their own.

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5 First Steps for Travel Hacking

If you’re new to this blog, one of the things I write about is travel hacking—the art of having incredible experiences that would otherwise be unobtainable for most people.

It’s a bit different from budget travel, which tends to focus on staying on hostels, flying on low-cost carriers (LCCs), etc. Travel hacking can not only help you travel, it can help you travel better.

I stumbled on this world by accident. I just wanted to learn to travel for less, and then I got upgraded on a transatlantic flight. When it happened again a year later, I was hooked. Then a couple years later, I began my quest to visit every country in the world.

Travel hacking allowed this experience to be much, much cheaper. I can say with confidence that a full third of the 11-year project was either free or nearly free thanks to miles and points.

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Buy One Wedding, Get a Honeymoon Free

One time I went to Dubai for my honeymoon, except it wasn’t really my honeymoon. I was traveling with Stephanie, my longtime friend, travel hacking colleague, and frequent travel companion. Even though she is basically a member of my family, Stephanie and I aren’t partners in the romantic sense—which occasionally leads to humorous encounters when we travel.

For some reason, our hotel in Dubai had gotten the idea that it was our honeymoon. When they assigned us a luxury three-bedroom apartment as our room, we may have failed to correct their impression. We did, however, express our gratitude for the free champagne they also gave us.

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“Everything Is Figoureoutable:” Notes from Paris to Doha

On a recent trip, I had to get back to Doha from Paris, a 5 1/2 hour flight. I was transferring via an initial connection from Zurich, and I booked the Zurich flight to arrive less than an hour before the Qatar Airways flight departed.

You might think that’s cutting it close, and it was. In the worst of times, Charles de Gaulle airport can be an absolute nightmare to navigate for transit. It’s not unreasonable to walk more than a kilometer between terminals, and some terminals are reachable only by an extended bus ride. Add long security lines (no PreCheck!) to that equation, and it’s not unreasonable to allow 2-3 hours for a connection.

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Couple Uses Southwest Companion Pass to Save $3,800 and Take 14 Free Flights

Link: Southwest Rapid Rewards® Plus Credit Card

I’ve mentioned the Southwest Airlines Companion Pass a couple times over the years. In short, if you’re able to get it—by earning 110,000 qualifying points in a year—a companion of your choice can fly with you for nearly free (just pay the taxes on their ticket) for an entire year.

Here’s a fun story from Annabelle and Christian, two students from last year's Dream Trip course, that have used their Companion Pass to take more than a dozen free flights so far.

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Brand New: Get 50,000 Southwest Airlines Points with the Just-Announced “Plus” Card

Link: 50,000 Rapid Rewards Points (Brand New Offer)

Out of the blue—we just heard yesterday—Southwest Airlines has introduced an all-new awards card, the Southwest Airlines Plus.

This card offers a a 50,000 point bonus after a low $2,000 minimum spend. Southwest also promises that these points will count toward Southwest's always-popular Companion Pass, where you can take the companion of your choice with you on every trip for an entire year.

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“If you’re going to spend the money anyway, you might as well get something out of it.”

Ediza Ferris is serious about travel hacking, and it pays off. A recent trip took her and her husband from the States through Sydney to Dubai—where they were whisked from the presidential hotel suite to the First Class lounge via private chauffeur. Ediza is truly hacking her way to incredible experiences thanks to the world of miles and points.

I started traveling when I was young, around age 5 or 6. My parents immigrated to the States from the Philippines and we've always made steady trips back and forth to go back and see family.

I took the opportunity when I was 16 to study abroad for the summer in a theater program. It wasn't until then where I realized the world was so much bigger than myself, and so much older than how it's described in the history books.

Since then, I've wanted to see more, eat differently, and discover anything new so that I can piece together for myself what this world is actually made of.

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Midnight Sky Notes from Jakarta to Tokyo

Sometimes it’s good to live for the moment. Case in point: you’re flying JAL from Jakarta to Tokyo. It’s an overnight flight, but a short one. When a flight like this is blocked for 7 hrs, you know it’s probably more like 6. Then when you factor in takeoff and getting settled and at least having a snack before sleeping and a cup of coffee before landing, you’re looking at a 5-hour maximum sleep window.

But then the friendly flight attendant offers another glass of Syrah. This being a Japanese airline, she's already apologized four times for asking you to change your seat upon boarding.

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How to Travel to Random Places and Work on a Project

Greetings from the sky, on board Cathay Pacific’s longest flight. There are 16 hours scheduled for my “air world” time today, although it looks like we may arrive one hour early.

I love flights like these. I’ve already taken a three-hour nap (hey, I was tired) and am now up to work for several hours while I drink espresso and Perrier. It’s dark outside now, but eventually the sun will come up in-flight. A few more hours later I’ll land in Hong Kong, a full 12-hour time difference from where I left. Travel is life.

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Get 175,000 Points + $500 in Travel Rewards from Business Cards

Link: Enhanced Business Platinum Card

Link: Platinum Delta SkyMiles Business Card

Link: SimplyCash Plus Business Card ($500 Credit)

Once again, it’s raining points and miles—a bunch of new travel hacking offers have hit the market all at once, offering you the chance to earn up to 175,000 miles (or more depending on how you count it) and an additional $500.

There's been some confusion about all these AmEx offers, so I thought I’d break down the most attractive ones and also clarify something. Let’s start with the clarification: these are marketed as business card offers, but if you’re eligible for U.S. credit cards, you’re probably eligible to get at least one of these.

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