How Did You Get Started With This Hobby?

a group of ancient buildings in a field

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!


  1. I would probably disclude your “$35000 For $1000” comment. Kind of tacky without substance. Not being a troll 🙂

  2. When I first got into this miles/points hobby I was afraid I was too late and EVERYONE was surely already traveling the world for nearly free, since I’m always the last person to hear about the great deals. This couldn’t last much longer if I was just now jumping on this bandwagon. But after years of doing this, and realizing I was practically having to twist the arms of family and friends trying to convince them how very easy this sort of relatively free travel is, I’m now wondering how there are as many doing this as there are.
    I guess all my family and friends were more staunch in the same belief I always had that “there’s no such thing as a free lunch” or “if it’s too good to be true…” …etc. I didn’t believe it could be this easy either until I finally threw caution to the wind and snatched up my first 50,000 mile credit card bonus and used them for a $25 flight to Europe and was pleasantly surprised that there were no hidden strings attached or my credit wasn’t ruined for my next 3 lifetimes or no one came to claim my soul…etc. It all worked without a hitch. After that, I was hooked and have been willingly addicted to this miles/points hobby ever since. My family thinks I’m crazy. I think they’re crazy. So we’re even.

  3. Started with the 40,000 pt bonus on a Hilton credit card and spent (wasted) points on stays that didn’t have enough value. I then started reading blogs and purchased points from the good old US Airways point sales, enough that it equated to buying 1 biz class ticket, getting 3 free and flew 4 of us biz SFO-NRT. I still shelled out money, but definately a jumping off point. From then on, I really started reading the blogs and fine tuning a strategy. I have still have a lot to learn, but our family has taken trips we would have never taken otherwise.

  4. We were planning a trip to Peru and I wanted to see just how many points we already had with no knowledge of travel hacking. I Googled “how to get more points” or something like that and found Boarding Area and a few other bloggers posting how they were going about credit card sign ups. I went in, slowly at first, I managed to get 1 then 2 then 4 cards. The scary part was when I applied for the Citi Exec AA card twice and got both of them at the same time. How would I possibly ‘spend’ $20k! But I managed and we got to Peru for about $150 in Biz Class. My partner wasn’t sure this was legit but sees the light and now we’re enjoying(not with a few hiccups at times) traveling in the front of the plan on international flights.

Leave a Reply

Your email address will not be published. Required fields are marked *