Ask Jack: Trading in Your (Chance at a) Chevy for a Cadillac-ack-ack?
Way before the book Rich Dad, Poor Dad existed, I had my own financial angel and devil on my shoulders in the form of my grandfather and mother, respectively. Granddad retired at 54 and lived more than four decades in perfect comfort based on the investment decisions he’d made prior to retirement. My mom is… well, let’s just say she didn’t retire at 54.
Mom always had champagne taste and a debutante’s contempt for anybody who did not. When my grandfather decided to buy himself a Cadillac shortly after retiring, my mother told me, in quite snippy fashion, that it was “a used Cadillac, like what a loan shark would drive.” I don’t know what I thought I was going to find in Granddad’s garage when I got there, but the six-month-old ice-blue Eldorado Biarritz that he’d actually bought wasn’t it. He took me to the grocery store in it. When we went to the register, he took out a coupon book.
“Granddad,” I asked, “why do you use coupons if you have a Eldorado with a stainless steel roof?”
“Johnny,” he winked at me, “that’s why I have one.”
Shortly afterwards, my father bought a Town Car. It was brand new, which pleased my mother. But in my heart of hearts I always liked Granddad’s Eldorado better, all the more so because I knew he got it cheap. Every time I manage to buy something outrageous at a steep discount, I think of my sharp-dealing grandfather and his delight at never paying retail for anything. Which brings us to today’s questioner, who is considering following in the old man’s footsteps, after a fashion.