Why Rich People Love To Say- “Pull Yourself Up By Your Bootstraps”

4 min readJan 21
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My great-grandfather Chas lived high on a hill, overlooking acres of land. He also sat high on a pile of money. He was born in 1893 and lived to a rip old age of 101.

We all knew he had money but pretended like we didn’t. But it became a cruel game when he would not help family members who needed help.

No, none of us were entitled to his money. We just felt like family helps family. But he didn’t see it that way. He thought everyone should pull themselves up by their bootstraps. He had run a dairy and worked hard. He looked at the world through ancient glasses.

The 1980’s and 1990’s were nothing like the century he grew up in. Born in 1893, he had seen so much happening throughout the century. He saw opportunity, he saw ways to make money.

So he expected the rest of us to be able to make money too. Meanwhile, my parents got divorced and my mom had trouble keeping a job. My father was also not paying child support. She would go visit her grandfather and ask for money for food or new tires for the car.

She was ashamed to have to ask for help. But she didn’t have a choice. He would ask why she wasn’t working. She had been jumping from job to job. She always had a problem with someone at her job.


On this particular day, I was 15 years old and the sun was shining hot inside the log cabin-like interior. It seemed musty, like the old house it was. There was no air conditioning. Great-Grandpa sat in the chair and stared out the window. My mom brought him a cup of coffee and hoped for once he would change his mind.

“I’m sorry,” he told her, “you need to go work”. She looked down at her hands and then asked if she could just have a loan. He declined that too.

I saw the shame on my mother’s face that day, trying to get some grocery money and I’ll never forget it. She resolved never to ask him again. And she never did. My great-grandfather cared more about money than people. He died alone in that lonely old house.


When the well-off say the cliche bootstrap comment, my theory is they want to absolve themselves of any…


New England born- now living in the Midwest. Blogger, author, influencer, history addict and genealogist in training