October is National Women’s Small Business Month, a time to celebrate the incredible contributions and the diverse tapestry of women in the world of entrepreneurship. In the United States, more than 11 million women own small businesses, and their journey is a testament to growth and opportunity. Furthermore, the landscape of women in leadership roles has evolved remarkably, with women currently holding 32.2% of corporate officer positions, a number expected to reach 50% by 2030.

The statistics are compelling. Between 2014 and 2019, women-owned businesses experienced a staggering 21% increase, surpassing the 9% growth of all businesses during the same period. Additionally, as of 2018, women-owned firms comprised nearly 20% of all firms employing individuals in the United States, with an impressive increase of 6,861 firms from the previous year. This data vividly illustrates the steadily rising trajectory of women’s entrepreneurship.

In 2008, I embarked on a journey to establish Dooley & Associates. During this pivotal time, I leaned heavily on my peers for advice and encouragement, adopting the personal motto that “Failure was not an option.” I felt like a little bird, nudged out of my comfortable nest by a multitude of mama birds, each reminding me to soar.

I can’t say my parents were necessarily thrilled when I announced my decision to start a business. After all, I was 29 years old at the time, had just built a new home, and had a great job at a wonderful company working for an exceptional family. However, it was my mother, an entrepreneur who founded and successfully operated a gardening business in Lake Geneva, and my father, the owner of a third-generation business, who set examples of what was possible for my career.

My mother was truly my greatest inspiration. Her diligence, creativity, and unwavering commitment to building her business were second to none. Coming home to work for her in the summers during college was both rewarding and grueling, lol. She epitomized the definition of a boss lady. She pushed me to my limits until I had sweat dripping down every ounce of my body, but then she’d say, ‘Jen, let’s go get a treat,’ and we’d hightail it to the ice cream shop. She was my prime example of learning to work hard while also making time to play. Her dedication to serving her clients set a high bar, as I observed her taking client calls during dinner and working on weekends to turn her dreams into reality.

Jenfam Cropped

Since founding Dooley & Associates, my journey has been enriched by a long line of remarkable female clients who are entrepreneurs or leaders within their organizations. Each female client I have engaged with since 2008, whether an entrepreneur or a business leader, has not merely been a client; they have all become sources of inspiration, embodying the essence of leadership and possibilities.

The list of these inspiring female leaders includes:

Tamarra Coleman
Tamarra Coleman

Executive Director of Shalom Center of Interfaith Network of Kenosha County, Inc.

Rita Gentile
Rita Gentile

Owner/Voice Instructor of RG Performing Arts

Sharon Hellenbrand
Sharon Hellenbrand
Sharon Lidman
Sharon Lidman

Chief Operating Officer & Co-Founder of Construct-A-Lead

Tara Panasewicz
Tara Panasewicz

Chief Executive Officer of Boys & Girls Club of Kenosha

Lora Reinders, LCSW
Lora Reinders, LCSW

Psychotherapist and Clinic Director of Pathways Consulting

Kristi L. Schaeffer Kleutsch, CSA
Kristi L. Schaeffer Kleutsch, CSA
Amy Smith and Jennifer Dooley-Hogan
Amy Smith

Co-Owner of Jerry Smith Farm

I wouldn’t be where I am today without the influence of all these amazing women and many more. We all juggle so much, know so much, and give so much to so many. It’s reassuring to witness how you balance it all, set boundaries, and lead with heart. Each of you is a woman of action who has set the bar high in my daily life. When I’m having a bad day or feeling lost, I look to you for inspiration, advice, and guidance.

I also wouldn’t be where I am today without my incredible female co-workers. Day in and day out, they challenge, inspire, and motivate me to think bigger. Dora Knuteson has been by my side since the beginning and continues to open my eyes to trends and amaze me with her ability to translate ideas into brands. Melissa Cronin was a client before she joined our team and brings a whole new dimension of creativity and flair to our team, leaving a lasting impression on everyone she interacts with. I’m forever grateful for both of your patience and support.

As we stand at this moment in history, let us raise a toast to the future with unwavering optimism, knowing that our collective potential knows no bounds. The best is indeed yet to come, and together, we shall continue to chart new horizons and inspire others along the way. Here’s to the limitless possibilities that lie ahead!