But his desire to keep up with his peers led him, on his $40,000 salary, to buy a new car and a three-bedroom house, which turned his previous bike ride to work into a 40-minute commute. The added debt got him to focus on his finances, so he began making models of how he could pay it off, mapped out his trajectory to retirement at 65 and began investing. He then used credit card checks charging 0% interest for 12 months to pay big chunks of his mortgage, his student loan and car loan.
When he started working at Microsoft MSFT +0.21% and moved from Chicago to Seattle, getting a salary bump up to $85,000, he made many of the same decisions (which he now calls mistakes) again: buying a house, having a long commute, and not taking a vacation. Three years in, a girlfriend convinced him to take his first real, multi-week vacation — to the Philippines. He spent the first week thinking about work, checking email. But the scuba diving, ma
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