27d • General discussion
The year I fell in love with being self-employed
In 1997, I was 27 years old.
I was hanging out in Chicago, going to all the hottest clubs, and enjoying life. There was a man I would see often who would always say to me, “I own a mortgage company. You should come work for me.”
At the time, I had just been laid off and I was a single mother. Eventually, I said, “Okay, sure.”
When I stopped by his office, he explained that the position was commission-based. My first thought was, “There is no way I can live off commission. I need the security of a regular paycheck.”
But something changed.
I had to change my mindset.
I took the chance in 1997, and now, in 2026, I am still self-employed.
I will be 56 in August, and when I look back, I realize that one decision changed the direction of my life.
So my question for you is:
What year was it for you?
When did you realize you wanted more?
What is your story?
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The year I fell in love with being self-employed
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