“If You’re a Skeptic Like I Was, You’ll Change Your Mind When You Book Your 1st Award Trip”

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Welcome to the next installment of our interview series where travel bloggers share their insights on having Big Travel with Small Money!

Miles & Points Interview:   Out and Out

Harlan writes Out and Out to share his thoughts on miles and points, personal finance, financial independence, and more.

You can connect with him on Facebook, Twitter, and Instagram.

Out And Out - Interview With Harlan

Harlan Pretending to Be a Moai on Easter Island!  He Flew Down in LAN Business Class!

How and when did you start collecting miles and points?

I started collecting miles and points in 2013.  Up ’til then, I didn’t know anything about how to redeem for award flights and hotel stays.

I thought credit cards were a terrible idea, and my personal credit was very poor.  Once I cleaned it up, I became eligible for premium co-branded credit cards.  Chase offered me the Chase Sapphire Preferred card.

A few quick Google searches led me to Million Mile Secrets, and I signed-up for it after reading about the amazing trips you can take for nearly nothing!

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

Soon after I began learning about miles and points, I became overwhelmed with the amount of information that was available.

I started Out and Out as a place where I could record what interested me most, sort of like my own miles and points journal (which of course added to the amount of information available!).

Out And Out - Interview With Harlan

I Loved Exploring the Mountains of Alaska! I Stayed in Anchorage With Hotel Points

At the time, I wasn’t seeing much about how folks actually redeem their miles and points, or earn them.  I knew all the ways I could redeem them, but the information was mostly theoretical.

I try to explain how I earn and redeem my points.  I’m also interested in personal finance and financial independence.  Credit cards are powerful financial tools, and I love how miles and points fits in with my financial and life goals.

In addition to miles, points, and finance, I’m also interested in the power of positive thinking, and how to create real change with kindness and awareness.  So I approach my blog with a sense of gratitude, and really hope that’s reflected no matter which topic I’m writing about that day.

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

The obvious answer is to sign-up for a new credit card.  That’s by far the fastest way to accumulate more miles.

But I also like the idea of forming a habit loop based on the cards you have.

For example, every time I make a purchase, I think, “What category is this?”  Because certain cards offer bonus miles or points for things like dining out, airfare, grocery stores, or drugstores.

By paying with the right card, I always earn the most points possible, usually an extra 10,000 points a month, which adds up to well over 100,000 points per year.  That’s more than enough for an award flight or free nights at a top hotel!

Out And Out - Interview With Harlan

Hanging Out at Hyde Park in London. I Took a Weekend Trip With Miles Just for Fun!

What’s your most memorable travel experience?

There are so many.  As cheesy as it sounds, I had a really memorable time in Hawaii.

The weather was perfect, in the 80s each day, and very sunny.  It was the middle of January, so a nice break from the gray Northeastern winter.  I stayed at the Hilton Hawaiian Village and flew to Honolulu on a cheap Delta fare (I believe it was about $400 round-trip!).

There was a moment where it all came together, and the whole thing was all worth it.  The early morning flights, signing-up for all the credit cards, the drive to the hotel, and all the planning.  It was such a moment of peace and beauty.  That’s really what makes it all worth doing, moments like that.

Out And Out - Interview With Harlan

The Atrium at the Grand Hyatt Santiago Is Lovely Around the Holidays!  And It Was in the Middle of Their Summer, So It Was Hot Every Day!

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

My Mom has no idea how I keep track of it all (I’ll get to that next!).

And my partner thought it was an exercise in futility, until we took our 1st trip paid for with miles and points, of course!

I understand the sentiment!  I was very skeptical about how I could use miles and points for a fantastic vacation worth thousands of dollars.  There must be some catch, right?  It sounds too good to be true!

Lots of my friends were also skeptics.  But now they’re signing-up for credit cards, and I’m helping them plan their own vacations!

Out And Out - Interview With Harlan

The Sunsets in California Are Incomparable!  I Stayed at the Manchester Grand Hyatt Santiago, and This Was the View From My Room!

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

I love shopping portals.  I’m obsessed with them.

I’ll even go to a brick-and-mortar store to try on clothes, and then order the same items online just to earn more miles!

With that thought, Cashback Monitor is my favorite place to check which shopping portal offers the most miles or points for a purchase.  If you buy most things after clicking through a shopping portal, you will be able to take an extra award flight, or earn more free nights in hotels each year.  Without a doubt.

I use Evernote to keep track of my travel plans.  The offline function lets you access all your information without an internet connection.  It has saved me so many times.

I add directions, maps, booking confirmations, tickets, emails – anything related to my trip goes in there.

When I get to where I’m going, I use the app to take tons of pictures that I don’t necessarily want on my phone.  When I get home, I can look over the trip in its entirety: how I booked it, where I went, what I saw and ate, and then pass those tips on to others!  An indispensable tool that I use constantly, every day.  It’s perfect for travelers!

Out And Out - Interview With Harlan

I Loved Fiji and Can’t Wait to Go Back! The Radisson Blu Resort Fiji Denarau Island Was Incredible! I Stayed Here for Free With Club Carlson Points!

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

Promotions I forgot I’d signed up for.

Sign-up for every promotion you find!  You never know where your travel plans will take you, and it only takes a few seconds to sign-up.  I once found I’d earned ~50,000 Club Carlson points on a short stay from an email promotion I didn’t remember.

I’ve had a similar experience with IHG.  And sometimes airlines give you bonus miles for flying during certain times, or routes.  You never know when you’ll be re-routed, or need to buy a last-minute ticket!

It may not be so fun in the moment when unexpected things pop up, but weeks later when you find thousands of bonus miles or points, you’ll be glad you spent a those few extra seconds signing-up for promotions!

Out And Out - Interview With Harlan

This Little Guy in Sydney, Australia, Was Very Curious About My Phone Camera!

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

I wish I’d known to take advantage of good deals while they’re still available.

When I started out, I assumed every good deal would be around forever.  I had no idea how quickly things can (and do!) move in the miles and points world.  So if you see something you’re interested in, be prepared to jump on it!

To that end, I wish someone had told me not to think of my loyalty accounts as a savings account toward that trip I’d take “some day.”  Devaluations are happening more all the time, so it’s best to use your miles for trips sooner rather than later.

For example, the American Airlines award chart is changing in March 2016.  I plan on using a lot of my American Airlines miles before then!

Earn the miles, and use them!  It helps to take time to think about your travel goals.

Out And Out - Interview With Harlan

Exploring the World-Famous Canals of Venice!

What would your readers be surprised to know about you?

I’m an artist at heart.  My degree is in painting, and I have many works of my own art at home.  I look forward to creating more work in the coming year!

I also recently began reading tarot cards, and have always been fascinated with supernatural matters.  There’s a lot of energy in the world, and it’s amazing what you can accomplish when you begin to focus your own.  I suppose it ties into the power of thinking positively!

Also, I’m from a tiny town in rural Mississippi.  That’s where I was born and raised!  I’ve lived in New York City for about 11 years now.  My accent has faded a lot, so some folks are still surprised when they find out I’m really a small-town Southern boy. 🙂

Any parting words?

I’ve known a lot of folks that have gotten discouraged about collecting miles and points.  They’ve said things like, “I’ll never earn that many miles,” or, “There’s no way I can meet the minimum spending requirement on that card.”

Out And Out - Interview With Harlan

Having Fun at the Ruin Bars of Budapest!

It’s simply not true.  Baby steps!  Every mile is another 1 toward your dream trip.  And there are many powerful ways to meet your minimum spending requirements.

I’ve also heard from friends that credit cards are bad to have because they can ruin your credit.  Understand that credit cards are powerful financial tools, and that using them responsibly actually improves your credit.

I told 1 of my friends, “Treat your credit card like a debit card.  And pay it off each week.”  She got a Chase Freedom card, and is beginning to see the points add up, and is pretending like it’s a debit card.

That works for her.  Find out what works for you and start earning miles and points.  The sooner you begin, the better.  Start today (because tomorrow is always the busiest day of the week)!

If you’re a skeptic like I was, you’ll change your mind when you book your 1st award trip, and experience a moment that will become 1 of your favorite travel memories!

Harlan – 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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4 responses to ““If You’re a Skeptic Like I Was, You’ll Change Your Mind When You Book Your 1st Award Trip”

  1. Awesome advice Harlan! My wife was a little skeptical about my obsession with collecting miles and points 2 months ago, but after taking our first trip last week to Oahu for 4 awesome nights, she’s now fully on board. We are trying to get our Companion Pass soon and hope to travel around the US this year, and we want to start traveling overseas next year!

    Also, I’m setting up a WordPress blog for my wife so she can document all of our travels 🙂

  2. I always love to see travelers advise not to hoard miles and points! My husband and I are not at a time in our lives where we can take 2-3 weeks off to travel around Europe. But we can spend 4 nights in New Orleans, 6 nights in Aruba, a 3 day weekend visiting dear friends in Fl, a 7 night cruise to the carribean and we have!! All paid for with points/miles and every trip special and enjoyed. Whatever your travel desire is go for it. Tomorrow may never come.

  3. Thank you, Jad! 🙂

    Isn’t it awesome getting someone else “on board” with points and miles? A 4-night trip to Oahu is awfully convincing!

    Good luck with the Companion Pass and your upcoming international travels. I am totally sure you will make it happen and have so many amazing trips ahead. 🙂

    When you get your blog set up, let me know! There’s more than enough room for everyone and I love hearing about peeps use their points.

    Thanks again for reading!

  4. Leslie, I say seize the day! I’m in the same boat – have had lots of short trips all over, but dream about long-term travel.

    It sounds like you’ve had lots of amazing experience with miles and points. The memories are what’s most important – life’s too short!

    Getting your trips for nearly free is pretty great too. 🙂

    Thanks for the reminder to go for your goals, and for reading!