Cyndee Woolley and daughter
Cyndee Woolley is everywhere! She has spent her life and career in Naples and her love for our community overflows into all aspects of her life. Cyndee’s heavy involvement with local small businesses and nonprofit organizations is an outflow of her passion for Southwest Florida. She lives to make our community great. Born and raised in Naples, Cyndee attended what was then Edison Community College, as well as the University of West Florida. She has spent her career in marketing and communications and, after working in this capacity for a variety of organizations, Cyndee started her own firm, C2 Communications. This successful venture, coupled with the publication of her book, Building Brand You, display her desire to help businesses succeed through the power of story.
But Cyndee doesn’t stop there. Most notably, she recently started The League of Courageous Women, a nonprofit organization dedicated to encouraging young women in middle school, high school, and beyond to dream big dreams, set high goals, and actively pursue leadership opportunities.
Cyndee is a mom to an 11-year-old daughter, Bridget, an aspiring dancer who loves to travel and excels in school. She and her daughter spend lots of time together; I especially enjoyed hearing Cyndee’s perspective on family time, motherhood, and the idea of balance.
College? I was born and raised in Naples. I got my associate’s degree from what used to be Edison Community College (now Florida SouthWestern State College). I went on to University of West Florida, where I received my bachelor’s degree in management and marketing. I decided to gain some work experience before pursuing a master’s degree. I am currently working towards a master’s in business administration from Hodges University.
Career Path? I have always wanted to be a small business owner. Before starting a business, I knew I needed experience in different sectors. I’ve been involved in sales and marketing since 2000 in various capacities: hospitality, construction, public relations, and communications. Throughout my career, my real passion has been the ability to share someone’s story as a way to compel others to get engaged in the community and take action. I love to hone in – to share others’ stories. I built my business (C2 Communications) as a way to pursue this passion.
Tell us about your book. I wrote Building Brand You in a time when social media was just emerging and the economy was flailing. It’s a tool book designed to help business owners answer the question “How do I market myself?”
What motivates you in your career? C2 Communications is nine years old, and it has been so rewarding on a professional level for me. I’m really interested in making the community a better place for my daughter, especially as I see her grow and change. And as a single mom, the business has allowed me to create a better life for us.
Tell us about your daughter. Bridget is 11 years old, going on 30. She’s smart and compassionate. She’s an aspiring dancer. Bridget sets really big goals for herself, and she puts her heart and soul into achieving these goals. Nothing can deter her when she sets her mind on something. Bridget attends Gulfview Middle School.
What has been your greatest accomplishment? There’s a group of my daughter’s friends I’ve been able to inspire. I’ve connected with them, and I’ve been able to connect them with other leaders in the community. Inspiring the next generation of women leaders has given me a lot of hope. I’ve loved being a part of shaping this group of girls as they set big goals.
What has been your biggest regret? I had the opportunity to backpack across Europe after I graduated from college. I should have taken that opportunity to travel before I had to start making payments on my student loans. I wish I had traveled before becoming a mom – before work.
Tell us about your volunteer positions and community involvement. I’m a member of the Northside Naples Kiwanis Club, and am on the board of Keep Collier Beautiful, a nonprofit dedicated to improving waste handling practices in Collier County. I’m also heavily involved with the Leadership Collier Foundation and a member of the Public Relations Society of America. In addition, I’m executive director of the Farm City BBQ of Collier County. I’ve been on the Farm City BBQ committee for 16 years, but formally took over the organization around 10 years ago and filed for nonprofit status in 2011. We’ve donated about half-a-million dollars back into youth leadership programs.
What’s next for you? Research shows that about 44% of girls in 4th and 5th grade desire to be a leader. In middle school, there is a point at which that number drops dramatically. About 36% of girls in 6th grade want to be leaders. Within a relatively short period of time, they are losing momentum to be engaged as leaders in their schools and within their family units. A new non-profit organization I’ve started seeks to raise up the next generation of women leaders. The League of Courageous Women is dedicated to inspiring young women to make bigger goals. Through various events and programs, we are connecting middle school, high school, and adult women with one another to inspire future leaders.
Our goal is to raise awareness about the need for cultivating women leaders and elevate the conversation about women in leadership. On September 29, we are hosting a Leadership Summit; we’re partnering with various agencies and organizations, including Hodges University, to present topics related to women in leadership. We’re planning to continue hosting networking events, connecting women of various ages. Additionally, we are planning to add on a formalized mentorship program and implement a “Courageous Cash Kickstarter Program.” The fund will support girls who have ideas on ways to improve their schools and home.
How do you balance motherhood, your career, and your burgeoning nonprofit? I don’t think balance is the answer. I think presence is the answer. We get off-balance when we’re at home, and all we’re thinking about is being at work. Or when we’re at work, and all we think about is being at home. True fulfillment and balance happen when we shut our phones off, talk with one another, and genuinely listen.
Best parenting advice you’ve ever received and from whom? When I was starting my business, I was crazed and stressed. I worked long hours, and I stayed up so late. Sometimes, I would drive home and tell my daughter, “Mommy’s computer is at the office tonight,” or “Mommy shut her phone off for the day.” I would see her face light up with excitement. I remember my grandmother telling me that her biggest regret is that she spent too much time cleaning and not enough time playing when her kids were little. I really internalized that. I want to be the example of that for my daughter. And now that she’s 11 and has her own phone, she says to me quite often, “I’m shutting my phone off to be with you.”
What does a typical weeknight look like for you? Every night is different; our schedule is a mix of ballet, board meetings, and many other activities. However, I believe in making time for family meals. We always sit down to dinner together. I also make breakfast every morning before school.
What do you do for fun on the weekends? My daughter is very active in ballet, and so I often do pilates on the weekends at her dance studio. We enjoy walking the Gordon River Greenway. My daughter and I enjoy traveling to explore various places and go to concerts – it’s something meaningful we pursue together.
What do you love about Naples? I love that we have a quieter pace of life here. We have the ability to slow down and enjoy each other. We have great schools, and it’s safe to send our kids to school here. Naples is a great place to have a family and spend quality time with your family. I love visiting Miami, New York City, and Los Angeles, but I come back to Naples because it’s a great quality of life for my daughter.
Click here to find a copy of Building Brand You by Cyndee Woolley.