The Best Use Of Miles Isn’t For Yourself, It’s Giving People You Love Trips They’ll Never Forget

Give things to people you care about. Give them a momento, and give them experiences.

The most meaningful things I have from my maternal grandfather are (1) the stock ticker tape dispenser from his desk. I remember it from visiting his brokerage in the 1970s, and (2) his stamp collection. We collected stamps together when I was a pre-teen. My parents divorced when I was very young. When I moved across the country to live with my dad in high school, he ‘came out to a stamp show’ but was really checking on me.

He cut his teeth on Wall Street during the Great Depression. He was successful but modest. When my aunt and uncle moved to Australia, they visited each other regularly but eventually he got too old to travel that far (his very last flight was domestic, to my wedding). My grandmother got too old to fly… coach. I redeemed miles to give her a trip in international first class, which she’d never done. It was the difference between seeing her son and grandchildren, and not seeing them.

The fact that I was able to do that for her meant everything to me. I was just starting out in my career, but I’d learned about miles. A roundtrip in first class was only 120,000 miles. I loved spoiling my grandmother, and I loved growing more successful so that I could take both of my grandparents to lunch.

My grandfather always paid. So what I began doing was asking his permission to allow me to pick up the bill. That way I could do something nice for them without taking away from his role in the family. It felt good, both the meal and understanding the correct way to do it.

Now I spoil my kids – a little bit. But I have to take much greater care with that. That’s why this really resonates witih me:

Spoil your kids occasionally.

It feels good to give them experiences you never had.

But model a grounded day-to-day life.

That makes the little indulgences even more special. pic.twitter.com/6NwSQVefoE

— Kevin Dahlstrom (@Camp4) June 28, 2026

My daughter flies coach. She’s flown to Europe and Australia many times in business class. She’s also flown first class – at five years old she had her own Etihad First Apartment for the first time. She doesn’t really understand points and miles conceptually. She’s still quite young. But she understands that they mean sometimes she can have a bad on a long flight, and she loves changing in to pajamas and having me read her a book and tell her a story at bedtime. And she loves asking a flight attendant for juice or a snack whenever she wants!

Two times before age four she boarded a Boeing 737 and asked the flight attendant standing in the galley, “does this plane have beds?” We were flying to Vancouver and to Orlando on those trips. And on the Orlando trip we were in coach (Vancouver was the first segment of an Air Canada award to Sydney).

But it’s important that’s doesn’t learn to become entitled to these things, and I think my wife and I model that for her. We’re certainly grateful for what miles and points have allowed us to do. My wife certainly didn’t grow up flying first class. The first time she ever tried it was after we started dating – she had a work trip to San Francisco, and I upgraded her return leg without telling her. She had to decide whether that was incredibly cool – or incredibly creepy that I could alter her reservation without her knowledge. She decided on balance that it was cool.

My wife’s parents flew first class for the first time coming out to visit us when we lived in D.C. And their first time vacationing in Asia was a Cathay Pacific first class redemption.

Miles and points can show us what’s possible, we can get used to it, but I also think they’re humbling because of how much work it takes to get the most out of them and because you can’t just fly anywhere at any time the way you might with unlimited cash. Plus, sometimes you feel like you don’t quite belong. I’m not sure that I have belonged having the entire first class cabin to myself on ANA, Asiana, Korean Air, THAI, Lufthansa, Singapore and others. But I can fake it.

I think what I’ve learned most sharing points with my grandfather, my wife’s parents, and now with my kids is that how a brand treats the people you care about matters a lot more than how it treats you. It doesn’t even matter to me how much an airline abuses me (except to the extent it means delaying my getting home to my family). I don’t need a suite on a business trip. But when they’re with me, or especially when they’re traveling alone, how they are treated matters most and that’s what wins loyalty.

In fact, it manufactures both the member’s loyalty and that member’s guest’s loyalty. Hyatt has data on this from their Guest of Honor program that shows they win future business on both sides from offering it.

Air Canada has Status Pass. American offers mileage redemptions of status for a day, and that is better than nothing but has always felt too transactional to me. Also, it should be simpler to use.

But when a loyalty program lets you extend treatment to the people you care most about, that matters far more than anything else. It helps you make memories. It gives you positive reinforcement of your choices (they ‘see why you travel all the time with ____’ and they also appreciate how much better you made the trip for them). And you have something in common to talk about later.

I don’t have either of my grandparents with me anymore, but I still remember how much that last Australia trip in first class meant to my grandmother, how much my grandfather’s last time (also on points) meant to me, and how much I love that stock ticker tape dispenser in my office.

Oh, and call your parents and grandparents sometimes. You won’t have them around forever, and you’ll wish that you had.