Is Travel Hacking Basically Prepaid Discount Travel?

Earlier this year, I had a dream about being in an apocalypse world.  Above the heavily torn urban landscape, flying demons lurked about in the sky and occasionally dived down hunting for human flesh.  Streets were filled with dead people scattering in concrete rubble.  Back “home” in a barely standing walk-up, my landlord was making a fellow tenant cut off his finger for being three days late on rent payment.  I was unfazed.  Strolling past countless destruction, I entered a Fidelity branch in an unmarked building and asked about depositing $50,000 in exchange for 25,000 United or American miles.  As I debated between the choices, the representative handed me a duct-taped plastic bomb set to detonate at the deadline for my deposit. It’s all about priorities. I woke up to the realization that none of it was real, except my plan to deposit $50k with Fidelity for miles.  Then it dawned on me that points & miles were no longer just a hobby… it had become a serious obsession.  Moving large sums of money around for airline miles, paying credit card fees, and hoarding gift cards are all convoluted activities that come with a cost.  I could not have imagined myself doing any of this before starting to play this points & miles game, . I figured I needed to take a holistic view of this game.  How much am I spending on points & miles?  Is it worth it?  It’s time for a cost-benefit analysis.   COST During the… read more

Alaska Airlines Fall Sale: Last Day to Check Bookings for Lower Prices

Just a friendly reminder that today’s the final day of the Alaska Airlines Annual Fall Sale, which features flights starting at $64 across their entire route network. Each city has their own set of deals, but at least from rhe San Francisco Bay Area, there doesn’t appear to be any amazing deals to traditional vacation destinations like Mexico and Hawaii. However, there are pretty good deals to various West Coast cities, including Salt Lake City, Portland, and a couple southern CA cities.

Do Your Taxes Now

Consider paying your taxes with a points-earning credit card, and don’t wait till the last minute! With one month to go, this is a great time to start thinking about how to maximize your benefits in the process, and hopefully lessen the pain of paying taxes a little.

How Did You Get Started With This Hobby?

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.