How to Travel Hack a $6,000 Vacation for Free

We do a fair amount of traveling. Travel costs were our second highest expense last year – at over $7,000, it was 18% of our $38k spending in 2016. This year, we mean to put a serious dent in those numbers through more extensive travel hacking. So far, we’re off to a good start. We booked a 9 day all-inclusive vacation to Jamaica – and we didn’t pay a dime for it.

A prior trip to Jamaica.

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The Cost of Living Well – 2016 Expenses

There were a lot of changes for us in 2016. Half way through the year, I quit my job, drastically cutting our income. At the time, we decided we were financially independent if we could spend less than $40k a year. But then we started to travel a lot more, spending over 2 months on the road exploring Colorado, New Mexico, Nova Scotia, Maine, and Costa Rica. I was also in a wedding and went to Montreal for a bachelor party while Mrs. CK enjoyed a weekend at the spa. We went sailing, fishing, hiking, biking, and ate and drank like kings. Overall, I think we have been living pretty damn well, but what did it cost us?

We did a good bit of traveling in 2016.

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What It’s Like 6 Months After Quitting My Job

In the days leading up to my last day at work, I felt a sense of excitement that I hadn’t experienced since middle school. I started working when I was 14, and since then have rarely had more than a week off from one job or another. But I do have memories of being in middle school and anticipating the summer. The weather would start to warm, and in the last few days of school, our excitement grew and the teachers became more relaxed. Summer break seemed like an infinite amount of time off as a kid. This past May, I felt like that kid again. It was getting nice outside, I was getting more excited, and work was getting more relaxed.

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How to Make Crazy Deals on Craigslist

If there’s one place I get the best deals, it’s Craigslist. When I’m looking for new toy, I always check there first. In most cases, you can get stuff for half of what they cost new. Not only that, it’s also a great place to get rid of your junk. After creating an ultra efficient fridge to house my beer, I was able to unload my old kegerators for $1000 – pretty close to what I paid for them. These were just a couple of the items I’ve sold. Over the past few months, I’ve made over $2000 selling stuff I wasn’t using anymore.

Inefficient kegerators. Sold for $1000.

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Don’t Get Mad, Get Even

My gym contract expires around this time every year. As a subtle reminder, the gym will automatically start charging me higher rates. This irks the crap out of me, but like a jackass standing under a windmill, I keep getting smacked upside the head. Each time, I curse the stupid contraption then go on standing around until it happens again. The other day, I felt the familiar whack! as I checked my credit card statement – once again I was hit with higher dues.


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What I Would Do With Your Money

One of my best friends and I met when we were both interns at the same company. I ended up spending over a decade of my life there, while he moved on to bigger and better things. Much like the relationship I have with my wife, nothing is a secret between us, and no punches are held. Over beers, I will lecture him about his finances, in turn he will forcibly treat me to overpriced tacos that have been handcrafted by some tatted up kid with a man bun.


My good friend Lorenzo de’ Medici with a piece from his collection.

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The Scariest Purchase We Almost Made


On a nice summer day a few years ago, I was working on our yard and needed a truckload of dirt to fill a few spots in the lawn. After inquiring at a few places, one guy suggested trying a contractor working on a new development surrounding a historic mansion down the street. Developers sometimes sell dirt as they clear lots, so I went down to see if we could work out a deal. I didn’t know at the time, but I was about to face one of the scariest encounters on our journey to FI. Continue reading