My grandfather was the VP of a bank in Chicago in the early part of the last century, and he was also a real estate developer. Third generation ended with my dad, and I have seen ALL the mistakes a family can make. We never had money, but there was a trust in place that took care of my grandmother and her spinster sister for their entire lives. For all intents and purposes, that's gone.
My grandfather owned a construction business (which was sold off after he killed himself). An uncle owned his own trucking company and retired from it. A couple of my cousins started their own.
One of my relatives founded The Frank Cotterman Ladder Company--if you work in a warehouse and have climbed portable steps, or have been in a book store and saw the ladders on rollers along the shelves, that's him. He was a distant relative that I never met, but I have many incredibly fond memories of his widow--"Aunt Do-Do," my grandmother's aunt.
My parents were always dead set against being self-employed. I remember my dad wanting to be... both my dad and my mother have told me my mom didn't want him owing his own business, she wanted the security of a steady paycheck, predictability, etc. etc.
My brother started a limo service in Ohio with a friend, and quickly grew it to the point where they had a full-time secretary, another driver, and he had to make the decision to either be full-time self-employed with his partner, or sell his half. My parents and his wife convinced him to sell. He's had a good career in mass transit, has been VP at a couple of metropolitan mass trans companies, so he's certainly successful. His friend's limo service now has several full-time mechanics, an over-the-road bus, several huge party-busses, a fleet of town cars and SUVs, etc. etc.
My son has grown up watching me build the swap meets while working other jobs, and has been a part of it. Eight years ago I quit my full-time job to become a full-time freelance writer, and run the swap meet. Did that for 5 years, and three years ago left writing and have been doing the swap meet full-time since.
When I was in 5th grade, I remember telling my dad "I don't know what I want to do for a living, but I don't want to wear a tie to work every day, and punch a clock for someone." He was an engineer for American Motors at the time, and nearly came unglued.
Later, when I launched the swap meet, his words of advice were "If it was such a great idea, someone else would already be doing it."
My son is 19, doesn't know what he wants to do for a living, but knows he will be self-employed. He's working his way through college, and taking business classes. He's struggling with life, like all teenagers/20-somethings are. He's trying to figure out what he can do now, and make his own money, while working for someone else and going to school.
Over Easter, my mom was visiting and we were talking about what he wants to do for a living, and he said he didn't know, but whatever it was, he'd be self-employed. She started telling him about all he advantages of working for someone else: regular hours, not having to worry about every little thing, a steady paycheck, you know how much you're going to make..."
He cut her off and said "and you know how much you AREN'T going to make."
The whole subject of family businesses, self-employment, etc. is very dear to me. I'm 44, and wish I'd have come to it much, much earlier, and I wish I'd have had encouragement from my family. Self-employment was NEVER something encouraged while I was growing up--in fact, just the opposite was always touted. I had no idea it could be done. I not only had to come to the realization of it on my own, I had to put up with constant discouragement for it.
Boy Wonder is going to do it on his own too... but instead of a family road-block, I'll be his cheer-leading section.
-Brad
