Why I’m a Travel Hacker, and You Should Be Too

I’ve read a lot of articles on a lot of travel blogs and combed over thousands of posts on flyertalk, but rarely does anyone discuss why they engage in the frequent flyer / points and miles community.

loyalty cards

Sure, we make off-the-cuff comments comparing Singapore and Cathay First Class as if they were our favorite orders at Chipotle, but I think there are less superficial reasons and some fairly fascinating lessons I’ve learned from doing it. Here’s my attempt at explaining the biggest ones for me.

I don’t like that banks and airlines take advantage of customers by writing rules that are designed to confuse and penalize

This one is fairly easy to get behind, though originally I was fairly naive about this because I rarely paid for my own flights (parents, then work), but holy cow airlines and banks have some of the most customer unfriendly policies out there.

I can’t think of too many other industries that think nothing of penalizing you for the privilege of taking your clothes on a trip with you or for storing your money with them. Even just in explaining basic air travel pro tips, I often get stopped because something I said makes no logical sense (e.g. bringing larger bags through security to get it gate checked — avoiding the bag fee).

I am only just starting my business, and to be fair I am not at the mercy of making quarterly earnings, but I will do almost anything to make sure my customers have a good time using my product and walk away happy. Full refund? No problem. Need extra help or instructions? Give me a call. It’s a damn privilege to me that you’re even considering to use my product, so I’m going to do everything in my power to help.

Call an airline or bank? Wait an hour or talk to a robot. Yay.

Banks and airlines use these complicated rules and procedures to take advantage of under informed customers, so I don’t feel bad if I’ve studied and learned all these byzantine rules and use them to my advantage. Maybe it’s a form of protest.

A customer that knows my product and how to use it better than most would be asked to help design the next iteration. But that’s where we are. There is a slight robin hood satisfaction to it and I’m willing to admit that.

I like creating material value by using my brain

There are a lot of consumptive hobbies out there. TV, fashion, food, wine (I do like wine! :D). But it’s pretty cool when I’m sitting on a flight I’d otherwise not be on, because I wouldn’t be able to afford it.

Points and miles do have monetary value (how valuable, no one will give you the same answer) and to me, collecting them feels like a real life video game with puzzles that get you powerups like upgrades and lounge access and points that unlock achievements like lie-flat seat to Thailand or a really comfy bed at a posh hotel in Tokyo. These are experiences I’d never be able to afford and likely wouldn’t pursue if I didn’t collect miles. Certainly beats Halo or Counterstrike.

It gives you a taste of luxury, and enough exposure to show you why it’s not worth pursuing.

These grandiose experiences are cool and in some ways educational (I now have opinions on caviar, top-end hotels’ approach to service and which airline has the best transpacific business class), but after a time, they become a sideshow to the real value you find in people and relationships around you. I don’t really see the point in international three cabin first class (other than ego) and now will often sleep through most of my long flights. Business class is still about getting a bed, since that sets you up so much better to feel human when you land. A ten course meal however does not make you feel human.

When you reduce the price of a first class ticket anywhere in the world to “nearly free” you stop focusing so much on the opulence or using it to show off and care more if your flight will get into Hong Kong on time so you don’t keep your friend waiting for dinner or your parents waiting at O’Hare to pick you up. Your perspective changes.

Now I save up my money to apply towards projects (like Attaché) rather than glitzy stuff that will rot in a closet or even superficial experiences like $14 drinks in a speakeasy bar. I think that’s a perspective I’ve been very fortunate to realize early on. The best things in life are free. If you have enough money for a roof over your head and food in your belly, then the rest is gravy.

It has brought me in contact with really fascinating people

I’ve sat next to sitting prime ministers and members of parliament, as well as hollywood directors and angel investors. If you fly enough, especially in premium cabins, you’ll meet a lot of fascinating folks that will challenge your worldview (or at least your perception of a lot of industries). It also breaks “the famous spell” and you start to realize all those people on TV are living breathing humans that read magazines and pick their nose. They apparently hate airline food too.

It makes for gifts of a lifetime

Sometimes, the miles are far better spent on others than yourself. Help that family member get home for the holidays. Give someone a much needed vacation. Help a friend out of a jam. These types of incidents are far more gratifying than any first class trip could ever be.

Because I can be literally anywhere in the world in under 48 hours

Sometimes when I explain what we do, people just stare back and say something to the effect of “I wish I could do that” (If you have a SSN, a credit score over 650 and about $3-5k, you absolutely can), fewer say “Show me how I can do this!” and even fewer actually follow through (I can count on one hand)

Yes, there is work involved. Yes, it requires being very organized. It requires about 6 months of lead time to build up balances. But it is very possible to do. And once you have the miles, the work that’s required is absolutely worth the freedom to be able to go to the airport, get on the plane for (nearly) free and be anywhere in the world within hours.


No planning required. No saving up. Just get on the plane and be in Shanghai tomorrow. People used to take years doing this and half your crew would die along the way!

That is unparalleled freedom, and it changes a lot about how you view the world. From San Francisco, I now see it as no bigger chore to go to South Africa or the Maldives as to drive to Tahoe or LA. I watched an interview on Pando Monthly where Brian Chesky outlines his vision for a world where one year leases are no longer the norm and people are just perpetually mobile. Right now, the transaction costs (the cost of an air ticket) are too high, but what if that was brought down to the price of a Big Mac? How many amazing things could happen if we could bring down the transactions costs of finding housing or a job? How fortunate that we live in an age RIGHT NOW where transactions costs are being hammered into the ground at lightning speed?

Because it has freed me from pursuing a lot of the things that “we’re supposed to”

In some ways, this freedom was a driving factor in “breaking the spell” of the corporate ladder climb I was on. I was doing well and I wasn’t unhappy, but I saw increasingly around me managers and executives that were depressed and losing their families, even as their paycheck rose. Once eager excited coworkers in my start class have the optimism beaten out of them. Sitting in the Lufthansa First Class Terminal happy as a clam, noticing all the gruff German businessmen barking orders to the staff and generally being grumpy and rude to each other. Then there’s this guy on Reddit. Everyone was slowly dying.

This was not the worldview I wanted to have and these are not the people I wanted to be, even if they were the picture of success on paper.

Becoming nomadic caused me to get rid of my stuff, which ended up being very freeing because I soon realized I didn’t miss it. I was briefly stung by two robberies this year, losing intangible assets (photos, business materials), but I’ve bounced back pretty quickly from that even. Maybe it’s called finding yourself, but I still have plenty of unanswered questions. I’m just glad to have experienced so much that I’m starting to understand what I truly value and that’s given me drive to do the things I’m doing now (and before I’ve had to make the livelihood vs. kid decision). And read this brilliant article from Nomadic Matt, because he sums it up beautifully.

I’m now way more comfortable with uncertainty, and when you can go literally anywhere, then you’re less afraid of where life may take you.

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