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Local Women Forge Unexpected Career Paths to Success

“Women may not only off-ramp from and on-ramp back to their careers over a lifetime–they may also pivot toward a number of different careers, tapping their extensive transferable skills and building new skills and developing new interests along the way.”

A common question children are asked is “What do you want to be when you grow up?” This question implies that there should be a short and simple answer. Yet, realistically, the answer is often quite complex. Many factors impact career journeys: economic fluctuations, family needs and personal maturation are just a few. Whether stemming from a prior career or from working as a stay-at-home mom, experiences rich with growth opportunities accrue continuously throughout one’s lifetime making the answer to this question far from straightforward.

“Career paths aren’t linear. They shouldn’t be seen as a continuous assembly line leading directly from graduation to retirement.” says Mindy Berkower, a former Chappaqua resident and Chief Client Officer and General Counsel, iRelaunch LLC (irelaunch.com), a pioneering company in career reentry. “Women may not only off-ramp from and on-ramp back to their careers over a lifetime–they may also pivot toward a number of different careers, tapping their extensive transferable skills and building new skills and developing new interests along the way.”

Growth doesn’t stop at any point throughout life. It is not possible to predict where life’s twists and turns will lead; there are too many moving variables. Yet, as exemplified by the stories of five inspirational local women, unexpected detours can translate into unique and valuable opportunities.

Investing in Personal Objectives


Chappaqua resident Elise Orlando worked on a trading floor for an investment bank assisting companies through the public offering process for over ten years before she became pregnant with her son, the oldest of her three children. A year later her daughter was born and eventually her family grew to include a second daughter.

After her son’s birth, Elise went back to work full-time. As time went by she found herself becoming more and more concerned with her son’s development. Shortly after she brought her middle child home from the hospital, Elise’s son was diagnosed with autism. This became the impetus for her career change. Giving up a career in finance was easy for Elise because she had a new and important purpose that took precedence over corporate finance: to care for her son and her newborn.

Elise quickly realized there were few educational opportunities in her community for children with autism. Through research, she learned of a cutting-edge teaching model pioneered at UCLA. She set up a home program, hired a team of therapists and taught her son using this program’s “Applied Behavior Analysis.” It was during this period she realized he could learn and this teaching method would be able to reach him. She connected with other local families who were in a similar position. Together, they established a nonprofit group to raise funds for autism education. These efforts ultimately lead to the opening of the Devereux Millwood Learning Center for 5-21 year olds with autism in Millwood in 1996. “There were many challenges getting there, but my goal to have a place for my son to learn was realized.” The Devereux Learning Center has since moved and is now located in Mount Kisco.

Elise feels that her career has followed a somewhat unique path in that she didn’t have a choice about many of the decisions she made. Her family was growing; she wanted to provide opportunities for her son and to be there for her daughters. For Elise, her family’s needs provided an abundance of motivation and a clear purpose. Today, she continues to advocate for her son who is now an adult. She serves on the Board of Directors at Extraordinary Ventures New York (www.EVNY.org)  in Mount Kisco, NY, and FECA (Foundation for Empowering Citizens with Autism (www.fecainc.org) working to provide opportunities for adults with autism and other developmental disabilities within their communities.

Following Your Passion


Holly Blum was a Vice President at a healthcare public relations firm. She was successful and proud of the work she was doing; she was helping to promote medications and treatments that were saving lives. However, when Holly became a mother she found the demands of her job were not in alignment with her family’s priorities. She decided to pause her career to be with her kids. While at home in Chappaqua, Holly opined on what she enjoyed about the work she had done in public relations. She knew she loved the parts of her job that related to writing and working with patients. She especially liked learning about people’s stories as she prepared them to interact with the media.

Since she was a young girl, Holly has had a gift for expressing emotion through writing; the countless notes and cards she wrote to her family were an important part of her childhood. As she grew older it became clear that this was a natural talent and passion.

Then, one day, Holly was at a wedding listening to “the worst wedding speech she had ever heard” when she had an epiphany. Holly’s speech writing company, A Speech to Remember (www.aspeechtoremember.com), was born. The company focuses on speeches for life’s special occasions. The ideas come from her clients and each speech is unique. Holly gathers information, and drafts the speech in collaboration with them; taking great care that authenticity is preserved. Besides loving her work, Holly appreciates that her job has the flexibility to allow her to be present for her family.

Holly advises people evaluating career paths to think about their interests and skills; then ask family and friends what strengths they perceive you to have, to help pinpoint what direction to go in. It can be hard to rise to the challenge of pursuing your passions but “sometimes it takes a leap of faith and you just have to believe in yourself.”

The Birth of a New Career


Kathy Benardo of Chappaqua has a master’s degree in art history and spent five years as a product developer for the retail division of the Metropolitan Museum of Art, and then eight years at the Museum of Modern Art. In 2002 she married Sanford Benardo, an adoption lawyer who was just beginning to branch out into third party reproduction law. After having their second child in 2005, they decided to create the Northeast Assisted Fertility Group (www.assistedfertility.com), a surrogacy and egg donation program that filled a need for these services in the Northeast (most of these programs were on the West Coast). It was a natural transition for Kathy, who felt that she had gotten all she could from museum product development, whereas third-party reproduction was a growing field.

The husband and wife team avoids the expected marital conflicts through a clear division of duties. Kathy’s husband handles the surrogacy side of the business and she directs the egg donor program. As much as Kathy enjoyed being a part of the art world, owning a business allows her the flexibility to work from home and be with her kids after school.  She feels that her new career path is more stressful, but helping people build families is also more rewarding. In her second career, Kathy applies the same creativity and entrepreneurial spirit fostered in her museum work. “You are always you, no matter what job you do. You bring your strengths along with you and can apply them to whatever career path you choose to take.”

Nurturing Your Ambition


Kelly Leonard O’Keefe of Chappaqua had a long and successful career in book publishing. When a change in executive management occurred at her company, Kelly and several of her contemporaries were laid off. She used this opportunity to set up her own digital marketing consulting company that she still manages serving authors and local nonprofits. In 2016, Kelly’s beloved father passed away. She witnessed hospice for a second time in the family and it resonated with her deeply. Being with her loved ones during their last days and hours of life was a spiritual and transformative experience. In the months following her father’s passing, Kelly realized she wanted to focus on end-of-life care and hospice as a new career. With no healthcare background, she was starting from square one.

She applied to a CNA (Certified Nursing Assistant) program at Westchester Community College and was accepted. The 12-week course included over 90 hours of classroom instruction and 30 hours of hands-on clinical work in a nursing home. The direct care experience of helping non-family members convinced Kelly further that this was work she could do as a new profession.

Since completing the course and passing the New York State CNA Competency Exam, Kelly volunteers with Hospice Care in Westchester & Putnam (part of Visiting Nurse Association of Hudson Valley) and was recently hired by Home Helpers Tri-County, in-home care serving Westchester, Putnam, and Fairfield counties.

Realizing Your Dreams


Susan Draper from Armonk was a buyer at Saks Fifth Avenue before she became the Director of Women’s Planning at Barney’s New York. While working, she enjoyed spending her spare time being active in her community through her role as Commissioner of Outreach on the vestry at her church. She took some time off from work when her youngest child was born. For three years, she focused on her family and the volunteer work she found so rewarding. When she returned to the workforce, Susan decided to take a job as a part-time trainer and spinning instructor. She enjoyed exercising and staying in shape and this role allowed enough flexibility to be there for her kids. The yoga studio Susan attended was having financial troubles and was about to close. Though she was new to yoga, Susan thought the studio was “simply too pretty to close.” In a completely unexpected venture,  she became the new owner of Quest Yoga Arts in Mount Kisco.

Susan embarked on a yoga teacher training program and used the buying skills from her days at Saks to create a fitness wear boutique in the reception area of the studio. Her vision was to offer yoga classes that were accessible to everyone, not just expert yogis.

Susan loved her time at Quest. She created a community filled with warmth and found the experience of teaching and helping others feel better to be very uplifting. Yoga has brought her so much joy over the years–from an opportunity to teach side by side with her daughter to occasionally teaching yoga to her son’s college swim team.

However, in planning for the future Susan reexamined her path and decided to return to her educational roots. During her time as an undergraduate at Kenyon College, she had excelled in math and science. Back then, she had considered going to medical school but wasn’t comfortable with the debt an advanced degree would require. However, the timing was now right and she decided she was ready to pursue her interest in healthcare.

Susan completed her nursing degree with honors and was subsequently hired at Greenwich Hospital. It was daunting to start her first day in a stressful career at age fifty-five, but the caring and nurturing role of being a nurse is Susan’s clear calling.

Finding Fulfillment Through Reinvention


Self-discovery can be a lengthy excavation process and can take a lifetime to explore. Circumstances inevitably change and careers often must be modified in tandem. Adaptability, resilience and self-confidence play an important role in navigating flexuous career paths. These women stepped out of their comfort zones to embark on new experiences, finding success and fulfillment through reinvention.

The question of what one wants to be when they grow up is difficult to answer because it infers that growth stops at a certain point in adulthood. But growth doesn’t end when adulthood begins; it is ongoing, continuing throughout a lifetime. Therefore, the answer to this question is ever evolving, making the journey of a career’s path as significant as the final destination.

(L- R): Elise Orlando, Susan Draper, Kelly Leonard, Kathy Benardo and Holly Blum - PHOTOS by Carolyn Simpson, DOUBLEVISION PHOTOGRAPHERS

This article originally appeared in The Inside Press on April 18, 2019. We thank editor Grace Bennett and author Sabra Staudenmaier for allowing us to republish it here. 

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