Chloe is an 18-year old in a 12-year old’s body.  She’s already thinking about college.  The other night, she candidly warned us that we shouldn’t count on her to get a sports scholarship.  That didn’t come as a surprise.

I told her that she would need to find a way to differentiate herself from the rest of the college-bound pack.  She looked at me and asked, with a mischievous little grin, what I had done to differentiate myself when I applied to schools (the implication in that grin being that I, too, couldn’t count on sports).

So I recounted to her the genesis of my college essay. It was a true coming of age story about the time, in the mid-1980s, when I took the train into the city with a group of friends and persuaded one of them to part with 50 of her hard-earned TCBY dollars so that I could teach a con man a lesson and win at three-card monte.  Needless to say, I lost her money quicker than you could shout TCBY.  And I realized that – as I smart as I thought I was – I was really pretty stupid.

I didn’t tell my parents what happened and I begged my friend to keep it a secret from her parents.  For some reason, she agreed despite my treachery.  It took me months to repay her, but I did.  And my essay described in gory detail what I had done and what I had learned from the experience.  And although I still like to gamble, I now only do it with my own money (although technically after next week any gambling I do will be with my husband’s money).

At the end of the day, those $50 turned out to be well spent.  Who knows if Tufts would have accepted me had I written about something else.  I’d like to think that those lost $50 turned out to be the best $50 of someone else’s money I ever lost.  I could go on and on about the consequences of that fateful decision on Fifth Avenue in the 1980s – but I like to think that essay led to Tufts, which led to my junior year abroad in France, which led to my future husband, which led to my two beautiful girls.  Now that I think about it, I really should thank my friend again for putting her misguided trust in me.

But back to my dear Chloe. She is entrepreneurial and she fancies herself a writer (see here for one of her first pieces).  She is convinced she will be an incredibly rich businesswoman one day.  Maybe she’ll actually get her literary blog off the ground (if she ever thinks of a name for it).

In the meantime, she has about six years to find her way into college, preferably with a sizable scholarship.  And I have no doubt she’ll succeed.