At age 28, I hit my financial limit. I was fired from my job boxing pizzas, and I was $14,000 in credit card debt. At that point, the $12-an-hour gig was all I was living on. I went from bread crumbs to salt grains. Not long after losing my job that spring, I found myself standing in line at Arlington County Courthouse paying for a speeding ticket. I had to split the payment between my debit card and a credit card. It cleaned out my bank account and left me a hundred dollars shy of maxing out my credit cards.

Somehow, that same year, I managed to fly to Las Vegas for a bachelorette party. One of my best girl friends was getting married. I dropped $307 on the flight, and birthday cash I’d received from friends covered spending. On our last night there, I played roulette at the Cosmopolitan Hotel until the sun rose. It was NBA All-Star Weekend and Michael Jordan’s birthday. We bet on 23 all night, and it hit five times. The trip paid for itself.

So how did my life get to that point: nearly 30 with degrees galore and somehow boxing pizzas, spending weekends in Vegas and broker than broke?