Living Vicky Blog

The Makings of a Confident Risk-taker

photo 1March is a month dedicated to women who had enough gumption to take risks and change the course of “history” to “herstory.” Recently, seventy women of all ages and backgrounds came together to discuss women as risk-takers in business.


The Morgan Stanley-sponsored workshop “Are you ready to be an Entrepreneur?” featured thirteen local female entrepreneurs who served as mentors to attendees. From consulting start-ups to organic farming, these business owners provided their own unique perspectives with ladies wondering if or when to build their own business.


Co-hosts Living Vicky’s Sheila Berry and Women’s Alliance for Financial Education’s Jamila Braithwaite kicked off the event with the rules of engagement — rules that successful entrepreneurs use:

  • Listen as intently as you speak,
  • Be open to new ideas, and most importantly,
  • activate your sense of adventure, collaboration and humor.

The interactive workshop opened with a surprising boost of confidence in the small business world. Attendees were surprised to hear that while corporate America has been downsizing, the rate of small-biz startups has climbed. According to the Small Business Administration, big business eliminated 4 million jobs, while small businesses have added 8 million new jobs since 1990.


The conversation pivoted to self-confidence, and the ideas needed to fortify your entrepreneurial  esteem.

First and foremost, ladies, don’t quit your day job! Leonardo Da Vinci was a glowing example: he often served as a party planner for the patrons who sponsored him. If one of history’s greatest artists was able to keep his patience to pursue his passion, so can you.

Attendees shared their own thoughts on the importance of staying employed while planning a future company, and all answers came back to financial confidence. Sheila Berry shared data on how men are actually more prone to quit their current job and go full-force into their business endeavor, while women are more careful in their business planning.


Timing was the next discussion thread in the workshop, which turned the adage “timing is everything” on its head. Many attendees shared their personal struggles with finding the “perfect time” to open shop. The entrepreneurial mentors nodded with understanding, but reassured attendees that there will never be a perfect time.

The solution is time integration, rather than time “management.” Integrating your time must be the mental model new business owners adopt because life simply cannot be managed. When feeling overwhelmed with the balancing act of your new business and life’s demands, follow the Marine Corps motto: “Improvise, adapt and overcome.”

Lastly, the biggest hurdle for female entrepreneurs can be themselves. Self-assessment is difficult, so we often reach out to our own friends and family for feedback and encouragement. In your personal life, this method is probably beneficial, but in the business world, you’ll need direction from people who will give you an honest, unbiased answers.  This could be your best friend that is never shy about telling you like it is.


Do your own research, and seek out to other female business professionals in your field for guidance.  To help you get started with your research, start thinking through these 10 steps and setting SMART goals for your business. As emphasized in the workshop, successful entrepreneurs are planners.

At the end of the day, after you’ve completed these steps towards confidence in your business plan and capability, you have to face your fears. As Eleanor Roosevelt, Living Vicky’s self-proclaimed patron saint, once said, “You must do the things you cannot do.” Entrepreneurs are seen as the ultimate risk-takers, and the best risk you can take is on your future success. 

Jackie MoreauJackie Moreau is a member of Living Vicky’s Curriculum Committee in addition to being the Managing Editor of, a citizen watchdog news site covering state and local issues. She is a huge fan of early American Literature, history, and never forgets her country girl roots.

This entry was published on March 28, 2014 at 11:41 pm. It’s filed under Vicky Courses, VickyEntrepreneurship, VickyInspiration and tagged , , , . Bookmark the permalink. Follow any comments here with the RSS feed for this post.

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