My Story (part 1): Jumping without a parachute

This time last year our financial situation was pretty bleak. My income had completely dried up. Our savings were exhausted and our expenses exceeded our income by about 50%. How on earth did we get here? In this 7-part series I’m going to explore that very question.

Writing my story was more difficult than I imagined it would be. It reads like a trainwreck! Gah! But this is my story. If I can’t take an honest look at the decisions that led me to a financial meltdown, meaningful change is not likely to come.

So let’s get to it.

In March 2005 I purchased a house for $629,000. I financed it 100% with an 80/20 split loan. To accompany my spiffy new house at the lake I purchase a $50K wakeboard boat and a $30K SUV to tow it. Such a Yuppy! Could I afford the payments on my salary? Yes. Was I living on the edge? Absolutely.

Meanwhile, I was getting burnt out from years of working 70-80 hour weeks in a thankless, yet lucrative job. I had lost all passion for my work. Working conditions had me stressed to the point that it was actually affecting my health. I needed a change, but I had just taken on over $700K in debt.

As I contemplated leaving my job I decided to sell the income property I owned in San Francisco. The proceeds from the sale would allow me to pay off my $125K second mortgage and also leave me enough to cover my living expenses for a year.

So in March 2006 I left my six-figure income job to take some time off to use that awesome new boat refresh and pursue a new career. I naively thought that I could transition into self-employment and within a year make the same amount that I was bringing in at my six-figure job. I owned a house, SUV and a boat, all of which were financed…but I had no credit card debt. I was in good shape, right? Hmmm…..

It probably would have smart to have a contingency plan in case my plan to replace my income did not pan out. But I didn’t.

“By three methods we may learn wisdom: First, by reflection, which is noblest; Second, by imitation, which is easiest; and third by experience, which is the bitterest.” ~ Hugh White

My Story (part 2): Hoping for the best

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