Creative Entrepreneurs

As a self-employed consultant in 2003, Day found working at home isolating and sensed that other women likely felt the same way too. So she started Company of Women as a way to meet and connect with other women business owners. When 165 women showed up for Company of Women’s first event, Day knew she was on to something. But it was more than this initial success that prompted Day to wrap up her highly successful consulting business in 2005 to concentrate on growing Company of Women.

A cancer diagnosis – her second – led Day to reflect on what was important in her life and Company of Women proved to be near the top of the list.

“My passion has always been to see women realize their potential - be it in their career or their business. But making a difference became even more important to me. It became by legacy,” Day explains.

Since she stood at that crossroads, Company of Women has grown to influence the lives of hundreds of female entrepreneurs, hosting over 100 events a year through its nine chapters and 350 members across the GTA.  “I feel so lucky as I love what I do and get to meet some amazing women who inspire me with their courage and determination to succeed,” says Day.

Through her writing, she has shared the stories of many female business owners, as well as her own insights about fear and self-doubt.  A regular contributor to the Huffington Post, Day has written/edited three books on women and entrepreneurship and is currently working on her fourth.

The next chapter of her life will see Day concentrate on developing her company, Full Circle Publishing, which has published her most recent books, One Red Lipstick which she edited, and The Good Enough Project which she co-wrote.

“I have often compared entrepreneurship to motherhood – no matter how many books you read or people you talk to, nothing really prepares you for what it is like.”

– Anne Day

Confidence remains a key issue holding back female business owners, says Day, who remembers feeling insecure while growing Company of Women. But winning the Oakville Entrepreneur of the Year Award in 2009 was a turning point for her. “While I felt like a bit of an imposter at the time, the fact that my peers thought I was a successful businesswoman gave me the confidence to become one.”

Day’s career focus has been on women and children since she graduated from Sheridan’s Family Day Care program in 1980. She has taken on leadership roles in the non-profit sector, been the Editor of Today’s Parent magazine, and worked in government on women’s issues before opening her own consulting practice to develop services for children and families. Volunteer work has long been a common thread in her life and Day has received local and international recognition for her work with non-profit organizations.

But it is perhaps her immigrant roots that offered a sign of her future as a business owner, says Day, who emigrated to Canada from England with her husband 35 years ago. “We arrived with no jobs. But we were positive it would all work out well. And it did. It was also our first clue that entrepreneurship was our destiny because we were accustomed to ambiguity and taking risks.”