My father was one of ten kids and grew up poor my most standards, but not hungry thanks to my grandfather who sometimes worked 3 jobs. My father was the first to go to college, initially against his parents’ wishes. They wanted him to work full time to help support the family.
My mother’s background was a little different. Born in the south, her family was about as WASP as you can get. Family stories include nannies and the governor coming over for my great grandmother’s infamous Sunday suppers. Girls were supposed to marry into proper families with the “right” last name. My grandfather had his own plane as a teenager in an era where most teens didn’t have their own cars.
But after being drafted and serving in combat, he became an alcoholic after he returned home. A brilliant man, he would start businesses that became very successful, and then start drinking again when they did and threw it all away. There was much more of a stigma attached to being an alcoholic at the time, so each time after they lost everything, he’d pack the family up and move to a new town to start over. My mother says her best memories were when they had nothing because he wasn’t drinking.
My mother was disowned for marrying my father who was Spanish (as in Spain Spanish), Catholic, and poor. When he was drafted into the military after he graduated, she converted to Catholicism, got on a train with one suitcase to meet him where he was stationed, and they married with a priest and 2 witnesses. No family and no wedding gifts. They literally started with nothing. But my father worked hard and became more successful than any of his (or my mother’s 3) siblings.
By my junior year in HS, between clubs, sports and an active social life, I was rarely home anymore and my mother went back to work, but realizing no one was going to take her seriously with nothing but “housewife and mother” on her resume since she got married, she took out a loan on the house and started her own business. Everyone thought she’d fail including their CPA who called my father to warn him they could lose everything, but we believed in her and within 5 years she not only paid off the loan, but paid off the mortgage, doubled her office space, hired more employees, and walked into a dealership and bought her dream car off the showroom floor. I have SO much respect for her for what she achieved. Such an amazing woman.
I went to what is considered a top college here on CC, but I didn’t look at college as a means of getting a job or how much money I could make. For me, it was all about gaining as much knowledge about anything and everything, and I assumed the rest would take care of itself. I did go on to law school, but only because I still didn’t know what I wanted to do by the time to apply early in my senior year, and it’s what adults had been telling me they thought I should do by the time I was in 8th grade because of the way thought, spoke, and reasoned. I knew before the end of my first year that I didn’t want to make a living arguing and fighting, but I stuck with it and graduated - for reasons I still question.
There was a recent post here about what qualified as “Hispanic” for college applications. With my father being Spanish, I could have checked that box, but I remember thinking about it and deciding that whatever advantages it might afford me, those advantages weren’t intended for people like me. With my father always gone working, I was raised mostly by my southern WASP mother, more affluent than even most of my classmates, never feeling disadvantaged or discriminated against, and had zero association with Hispanic culture, so I checked the “white” box and it was somewhat of a defining moment for me.
Many people assumed things were handed to me on a silver platter, but this was not the case. I worked in a factory during summers earning 3 times what typical retail jobs earned, and worked 6 to 7 days a week 10 to 12 hours a day earning 1.5 to 2X normal (union) wage for anything over 8 hours. All that money went toward my education to lift as much burden off my parents as possible. During law school, I worked as a live-in prefect at a college prep school where I was given free room and board and took out max loans to help pay for tuition.
After graduating, I decided I wanted to be a land developer and talked (begged) a developer into giving me a job, but after being tasked with attending $1K a plate dinners for politicians and kissing their behinds to get zoning approvals, I decided it wasn’t for me and ended up going into the IB/ VC business with my best friend from college. His father had been a Wall Street mogul who 60 Minutes had done a segment on, and he served as our figurehead giving us credibility at a young age. It afforded me a comfortable life where I was able to buy a house, drive a nice car, a membership to the yacht club, etc.
But we were killing ourselves. It was a pressure cooker, and I was constantly flying to NY and back within 24 hours. Most people I was dealing with were twice my age and after meeting many, they’d often say they were expecting someone much older. It was a constant battle to prove myself.
When my best friend was diagnosed with a rare form of cancer and lost the battle, it changed my life and perspective on everything. I had developed stress related auto-immune disorders and had zero social life. A funny thing happens when you always say no to invitations because you are too busy. The phone stops ringing and the invites stop. Outside of my work, I didn’t know who I was anymore. Toward the end of his life, he begged me to get out and save myself, so I did, but now I was alone, and as happens so often with men, I had allowed myself to be defined by what I did for a living and my success.
None of that mattered anymore, though, and I had to figure out who I was and what I wanted independent of that. So I gave it all up. I sold the house and moved to a much smaller condo in the heart of the city. I re-invented myself and figured out how I could make a living working for myself from the computer. No more travel. Been there, done that, and over it. All meetings were net meetings now.
When one client decided they wanted to hire me, I kept saying no until they made me an offer I couldn’t refuse and I accepted. Big mistake. They assumed they owned me after that and there were weeks when I didn’t step outside from Sunday night until the next Saturday morning, working until 3, 4, or 5 in the morning and waking up with the “dry heaves” from the stress. Always in great shape, I had suddenly gained a lot of weight. One day, I looked in the mirror and didn’t even recognize the person I was looking at, and said . . . enough, and quit.
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