Three Entitled Women

Category: Weekly Columns

spoiled kids cartoon

One of my enjoyments in life is getting to know all sorts of people, from all walks of life, places, and all ages. My boys often get embarrassed when I strike up conversations with strangers but I love what I learn from people. And, often, these encounters lead to cool opportunities and opened doors. My second career is thriving largely due to this outgoing side of my personality for which I’m very grateful.

Political cartoon about entitlement

Lately, I’ve been on a tear about the demographic crisis the world is facing regarding making babies. Many countries are heading toward a demographic apocalypse. Japan now sells more adult diapers than baby ones. Europe is not reproducing, except among their immigrant populations. The United States is not far behind Europe.

So, I reach out often to young men and women in their twenties to try and understand their mind-set about having children and life/society, in general. In the past couple of years, I met three young women in their early-to-mid twenties. For the sake of this column, I will change any identifying characteristics while relaying the essence of what I learned from them.


I will reveal that one or more of them are part of an ethnic community from which one could draw some general stereotypes, but that is not what I choose to conclude from my limited sample of these young women. Their backgrounds, as far as family structures and societal opportunities, did stimulate some conclusions to me.

Each of these young women is seeking to become entrepreneurs in the food, fashion, and/or entertainment businesses. Each has great ideas and each has great native intelligence. One had a child when she was 16 being largely raised by her aunt in Atlanta while mom pursues opportunities in New York.


None of these women have a father in their life. One never met her father, the other two have negligible relationships with their biological father and all their mothers had several other children, from several other men, and the make-ups of their families would take a spreadsheet to begin to follow.

None of these women finished college but each swears they will. Each is addicted to their smart-phones to a degree that is pathological and without ANY concern for those around them – aka ME. Each has no compunction about taking/getting anything they can get for free from the government or hitting up any person they know for money. None feel any obligation to pay anyone back but swear they will.

Millenial Generation

Yes, I’ve been a sap on occasion and loaned – aka given (I knew I’d never get a cent back) – them money. The money I’ve given is small and in some ways, I look at it as part of my learning experience. I’ve always preferred doing my “giving back” in the form of individuals and/or direct mentorship. I’ve been a Big Brother twice and currently mentor a young man who has a fatal genetic illness, which has left him with the mind of a 12-year-old in the body of a 26-year-old man — and the sweetness of an angel. I treasure all these relationships.

So, when “friends” hit me up for money, I gauge the “value” of giving it under the guise of a loan, and occasionally do. Or, I give a gift that has the same impact without any expectation of getting paid back. They are one and the same, as experience has taught me.

Obamacare cartoon

These three women have a sense of entitlement that I’ve never experienced directly. I’ve read about this among the millennial generation but had never confronted it as directly as with these three women. Not only do they feel entitled, they feel this entitlement with a level of anger that defies (my) imagination.

With two of these women, I found myself truly believing in their ideas and aspirations. I found myself almost wanting to fully fund their endeavors since I honestly believed they had moneymaking potential. But, I needed to see more evidence of follow-through and commitment before I’d go that route. I never did.

The ME Generation

There was always some excuse for one thing or another – on their aspiration list – not getting done. There was always someone to blame or someone who screwed them. Sometimes it was a specific person while other times it was “the man” or society or some big bad general problem they perceived.

Given I am more than twice their ages and older than any of their parents, these women did look to me for advice. And, given that I work in the world of Social Media and technology, I actually understand and know much about what they’re trying to accomplish. Yet, my advice would rarely get taken to any degree. Like a diet, they might start one of my suggestions but go “off the wagon” sooner than later.

Jefferson quote

I worry for this generation. Will they ultimately take responsibility for their futures, their actions? Will they own up to their part in their own lives? Will they marry and have children? I can’t believe how old-fashioned that last sentence reads but it’s still true. Will they make a family? Will they make the world a better place? I really don’t know…

Entitlement Card