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

Cancelling A Lifemiles Award Ticket Was Surprisingly Easy

One thing that I’ve heard over and over about Lifemiles award redemptions was to make sure you’ve made up your mind before booking, since it’s a huge pain in the butt to cancel them. Well the time finally came that I need to make a cancellation, so I blocked off several hours of my day and prepared for the worst. The reality of the experience was anything but a nightmare.

2017 Open Enrollment: Which Medical Plan Maximizes Ability to Earn Points?

Early November means that it is the middle of open enrollment season for those who receive health insurance through an employer. As you sort through the various health insurance options available to you for 2017, the easy choice is to simply keep what you have today. However, if you have ever wondered if there is a better choice that will allow you to maximize points earning, here are a few things to consider.

Foreign Exchange Deeper Dive

Myths around credit card foreign transactions have mostly focused on exchange rates on a given day, but how much does VISA vs. MasterCard’s processing speed affect our financial end result? Turns out that this issue is far more complex, and the officially published rates are by no means a useful predictive tool.