I had dinner a few months ago with a girlfriend from college. She had been asking about my startup and recent jump from steady employment to the always-volatile world of entrepreneurship when she noted that I have a history of taking some pretty big risks and yet I “always land on my feet.”

She was both proud and a touch wistful as she made that observation, going on to note that she was in a comfortable job (at which she was quite successful), with a loving husband, and had just purchased a beautiful home, all by age 27.  In contrast, I was single, had quit my job, moved into a tiny place in upper Manhattan (where I rented a couch in the middle of the living room), and poured my measly savings into a high-risk venture while deferring 6-figure student loan debt.  She was living the life she wanted – 10 years from now.  I was making the risky choices, which may or may not ever pay off, but are certainly anything but comfortable.  Who exactly should be envious of whom here?

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