I’m constantly talking to friends, family, and even strangers about the points and miles hobby. I do understand that it can be a bit intimidating to get started, so I’ve even tried to boil it down into a “how to get started” presentation that I’ve given a few times. But even after spelling things out for people, I’ve noticed that the uptake rate has still been pretty low in terms of those that dive head first into it like I had.
I’ve often wondered why that was the case – everyone seems to marvel at the idea of traveling for “free”, so why aren’t they actually doing anything about it? Perhaps it comes down to the need for some sort of catalyst.
I hadn’t really sat down to think about articulating how it all started for me until my interview with Million Mile Secrets, and it was fun reminiscing about how much I’ve learned since the beginning, including all the painfully dumb mistakes I’ve made along the way.
Here’s a little more detail on my origin story, which all began with a girl. What’s yours?
As is the case with many stories, it all started with a girl. In 2010, my girlfriend at the time decided to move from the Bay Area to Chicago for business school, and I started making monthly trips out there to visit for the next 2 years.
When I know that I’m going to be doing something regularly, I’m the type of person that’s going to find the best way to do it.
In this case it meant tracking airfare prices to find the ideal day and time to buy tickets, discovering the fastest way to get through security in San Francisco and Chicago airports, boarding before everyone else so I wouldn’t have to check my bag, and even finding my way to the premium seats at the front of the plane.
This quickly became a hobby, bordering on an obsession. And through countless hours on FlyerTalk, I learned how to get the most out of elite status to achieve many of those goals. Earning miles for these trips was actually a secondary benefit at 1st, until I realized how incredibly valuable they could be.
And as a fitting end to that story, my now wife and I cashed in all those hard-earned miles for our round-the-world honeymoon to Australia, Maldives, Sri Lanka, and Dubai a year after she graduated. We were able to use those miles and points to book over $35,000 worth of travel for less than $1,000!