Last month, my wife and I flew to New York for a wedding up in the Hudson River Valley. Neither of us had been to New York in quite some time. The last time I was in New York was for callback interviews in the summer between my first and second year of law school […]
Travel Hacking
Southwest Companion Pass – How To Fly For Free For Two Years
Ever since I started travel hacking, I’ve kept hearing about the Southwest Companion Pass and how beneficial it is to have. Many people consider it one of the best travel hacking perks you can earn, allowing you and a partner to travel for free for as long as two years. If Southwest flies out of […]
What You Need To Know About The Chase One Sapphire Card Per Person Rule
It’s been a while since I wrote about credit cards, but I thought now would be a good time to talk about them because of a recent rule change that Chase made that’ll likely change up your travel hacking strategy. For sure, it’ll change up the Chase 5/24 Strategy that I laid out in a […]
Chase 5/24 Rule – Maximize Your Travel Hacking
I’ve been getting really into the world of credit cards and travel hacking over the past few months. For people like me, opening up new cards is an easy way to optimize my spending and snag some free flights in the process. If you’ve got a good handle on your finances, adding even just a little bit of travel hacking into the equation is a nice way to get a little bit of return on your spend. Once you get into this world, it’s easy to see why so many people write about this stuff. It’s stupidly addictive!
For years, I’ve resisted travel hacking because I was too scared to do it. At first, I just thought it was just too good to be true. I’m definitely not skeptical by nature, but the logistics of traveling around the world for free by opening up new cards didn’t make much sense to me. It seemed like there must be a catch. Even when I figured out that travel hacking was a legit thing, I was still too scared to do it. The entire process was overwhelming and I had no idea where to start. There’s definitely a lot of information out there for anyone who wants to start travel hacking. It’s just often hard to synthesize everything you’ve read into useful and coherent information, especially when you’re a newbie.
An Amateur Travel Hacker’s First Experience With Travel Hacking
I’ve always been wary when it comes to credit cards. Even though I’ve never been shy about trying out new fintech apps or opening up new bank accounts, for some reason, credit cards have always scared me. Maybe it’s the fact that a credit card goes on your credit report. Signing up for a new card just seems so … permanent.
My fear of opening up new credit cards probably comes from the fact that my history with credit cards isn’t very robust. I got my first card back in 2006 during my sophomore year of college – a Citi mtvU Visa Card which gave me extra points when I used it at bars and restaurants. The card seemed pretty good and it served as my daily use card throughout my 20s. In 2012, Citi changed the card over to a Citi Forward Card, which was the card that I was using all the way through the beginning of this year. The only other card I’ve gotten during that time is a Target Red Card that I accidentally got when I was actually trying to get the Target Debit Card.
Because of this fear of credit cards, I’ve pretty much missed out on the whole travel hacking craze…