From Misfit to This Fits: My Entrepreneurial Journey
Written for EO by Kate Holden, an entrepreneur, philanthropist and business leader behind De Luca Fine Wines, a fast-growing retail and e-commerce wine business. Kate is president of the EO Winnipeg chapter and serves on the EO Canada Board as Canada’s MPD (Member Products Director).
As a kid, I grew up feeling different than everybody else.
Some of my most vivid childhood memories consist of a constant stream of questions, asking me “why” I was the way I was. My mother would get calls from the principal because I was secretly wearing makeup in grade 4. “Why do you have to be … different?” she would ask me.
Later in my youth and into adulthood, questions around why I was the way I was continued to follow me:
- Why do you wear so much makeup?
- Why are you always in heels?
- Why is your hair always done?
I was the friend, the co-worker, the acquaintance who put a puzzled, vexed look on faces everywhere I went. I noticed my expectations were higher than others’. My career ambitions were different, too: I had dreams of owning my own business and building something of my own. More questions came.
I spent years feeling misplaced, uncomfortable with many people, and not fitting in many environments. I started to question myself, wondering why my views, feelings and standards were so different.
Then, I became an entrepreneur.
In my company’s early years, I was immersed in the “bubble” of my business. As time passed and the business grew, I began to meet other entrepreneurs, and that’s how I discovered EO. For the first time, suddenly, I found myself fitting in. There were others just like me!
Contributed by Chris Kirksey, an EO member in Washington, DC, and the CEO of 
Contributed by Dr. Gleb Tsipursky, CEO of 
Contributed by Daisy Dowling, an executive coach and full-time working parent to two young children who helps working parents lead more successful and satisfying lives. She is the author of 
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