For the record, I hate the term “travel hacking”, but what else am I supposed to use?!

As is the case with many of my posts, the inspiration for this post comes from my own life. My dad travels frequently for work and has accumulated roughly 350,000 American Airlines miles and 1.5 million Hilton points — but literally never does anything with them, or when he does, he redeems them for horrible value.

Maybe this is just me being a bad son, but whatever you classify it as, I want to help you help your family and friends see amazing places.

Matera, Italy

Explain the value proposition

One thing that was key for me in getting my dad on board with points and miles was explaining to him the value of collecting/redeeming points and how much money it could save him. I like to use Ramit Sethi’s briefcase technique for this. Figure out where your loved one is dreaming of visiting and do all of the legwork for them — behind the scenes.

Plan out every detail — business class/first class, hotels, activities, out-of-pocket cost. Write this all down and present it to your family member or friend in an exciting way.

Something like this…

“You could fly to amazing Tokyo in First Class in a lie-flat bed seat for under $100 using your miles! Once you’re there can stay at the opulent Andaz Tokyo and experience the delights of Japan all for less than $50! You can get the freshest sushi in the world and live in the lap of luxury for a small fraction of the typical cost!”

You get the idea.

What this will do is create a value that is seemingly too good to pass up. Your loved one will think they just hit the lottery, and they’ll have you to thank.

Kyoto, Japan (by: Sorasak)

Explain that you’re there to help

The first thing my dad said when I told him about travel hacking was something along the lines of it can’t be that great if everyone is doing it.

Truth is, while the field of people involved in points and miles is sky high, this has not made experiencing beautiful places at a low cost impossible.

Sure, airlines and hotels have been tightening up a bit and making things more complicated, but this is why it’s important to sell yourself as the expert who is there to be the guiding light. If you can show them that you can make it easy for them, they will be more willing to jump in.

Surprise them with a trip

You’d have to really love the person to do this, but I wouldn’t hesitate to put my parents on a plane using my own stash of points and miles. In fact, I’m planning to take my dad to Dubai for a father/son trip. Shhhh…

People can be afraid to take action. This is no secret. In fact, my mom is such a creature of habit that she will pay full price for a hotel in Aruba even though there is a Hilton next door that she could get for free using points. Call it stubbornness or call it doing whatever you want…some people just need a little kick in the arse.

If this sounds like someone you know and you’re feeling extra generous, go ahead and book them a trip. Send them on their merry way and show them how healthy spontaneity can be. Once they experience luxury, they won’t want to go back. I promise.

Final word

Look, this post comes from the heart. I wish my parents would be as into points and miles as I am, because this game has truly taken me to many beautiful places and has afforded me countless lasting memories. I want them to take part in it, too, especially since they haven’t been back to Europe since the 70s (and my dad was born there!).

What are your thoughts? How do you convince your family and friends to get started collecting points and miles?


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