Finding The Wind In Your Sails While Sailing Uncharted Waters - South Shore Moms
Creative confidence coach (The Creative Confidant) with a Fortune 500 background, focuses on helping clients build their best personal brand

Louisa May Alcott writes in her classic Little Women, “I’m not afraid of storms, for I’m learning how to sail my ship.”

Sailing is a team effort. My cousin sailed on the Freedom yacht for America’s Cup. Despite a winning season, they did not win. But they did not lose alone. As we navigate through tumultuous pandemic waters, keep in mind that we’re sailing together toward a common goal.

In 2018, an all-women’s sailing team won a race to Alaska. This talented group of women figured out how to work together — using yoga breathing and individual talents to take them triumphantly to their finish. They made most of their voyage in the dark.

It’s not merely strength that makes a team — it’s having different traits, different strengths, that make a team outstanding — strengths that complement one another. When we’re playing on a sports team, we bring individual characteristics— a trademark cross-court volley, a steady three-pointer or a signature line drive. Now, in this period of uncertainty, we can discover how our unique talents can add to a strong team.

I choose to surround myself with the wisdom of inspiring women.

Take Dolly Parton, for example. While I’m not a big fan of country music, I’ve always loved the legends like Willie Nelson, Kris Kristofferson and Johnny Cash. Dolly had so many records, so many hits, including my favorite title for these times, “When Life is Good Again.” She grew up in rural Appalachia — in a one-room cabin, with 12 siblings.

Dolly’s mom stitched her a coat using scraps, appropriately titled “Coat of Many Colors.” They didn’t have money for new clothes, obviously, but this colorful frock of rags made her feel invincible. If we put on a magical coat or touch a favorite rock or shell, would that give us power? Perhaps we could do anything.

Gladys Burrill wore her colorful coat on the inside. This woman didn’t make records, she broke records. She’s literally in the Guinness Book of World Records for being the oldest person to run a marathon (Honolulu at age 92.) And while that’s an absolutely remarkable accomplishment at any age, she’s run more than one. In fact, she had seven marathon attempts in total. It’s no wonder her nickname was “The Glady-ator.”

Gladys died a few weeks before her 101st birthday, and if it weren’t for her obituary, I wouldn’t have known that she actually did way more than run marathons. Gladys grew up with extreme poverty during the Great Depression, overcame polio and went on to pilot multi-engine planes. It defies our imagination to add that she also hiked through deserts in Arizona and climbed Mt. Hood all before running that first marathon at — wait for it — age 86. Her son described his mom as “relentlessly positive.” I admire her so much that I’d engrave it on my headstone.

There’s never any shortage of women to admire.

The bigger the obstacle, the greater the story. Jesmyn Ward grew up poor in rural Mississippi and recalls how her grandmother studied in a one-room schoolhouse that her great-grandfather built so that Black children would have a place to be educated. Though her grandmother ended her schooling at age 13, Jesmyn was determined to go further. Unlike them, she didn’t have to choose between education and getting food on the table. Jesmyn earned a BA and MA at Stanford, later following up with an MFA from the University of Michigan.

These esteemed degrees do not come close to telling her story; her writing does, for she weaves a colorful coat of words.

Jesmyn continued writing when her family moved to Louisiana and were unfortunate victims of Hurricane Katrina. With risk comes the possibility of failure. It is the steps and missteps that ultimately propel us forward. During a 2018 graduation speech at Tulane, Jesmyn described how success isn’t based on one step alone, but a series of steps, and not one good choice, but a series of choices.

I took a journalism class at Georgetown where the professor asked us to write our own eulogy. With many of my life’s decisions, I wonder, Would this be something worth mentioning in my eulogy? Because interestingly enough, a eulogy doesn’t necessarily cite all life’s successes, our degrees, our accomplishments… it often references qualities we admire in a person. “Sally was a generous soul; her kindness knew no limits.” “Robert had the best sense of humor; he could make even the most morose friend belly-laugh.”

I don’t have aspirations for platinum-selling records; or to run a marathon at 32, 52 or 92; or to give a commencement speech (while all would be incredible goals to have). Perhaps my simple goal, my legacy, is to leave people feeling happier than they were before they had a conversation with me.

And here’s where Vince Vaughn’s character in the movie Dodgeballmakes an appearance. Peter LaFleur says: “I found that if you have a goal, that you might not reach it. But if you don’t have one, then you are never disappointed. And I gotta tell ya, it feels phenomenal!” By keeping the bar low, we’re bound to reach our goals. Pretty funny way of coaching, especially since I consider myself addicted to goal-setting. It’s equally important to have reachable goals as it is to have goals themselves.

Life has slowed in many ways, but it may have sped up our goals.

Think of it as a spotlight on your life, and we decide what is worth highlighting. Like a chameleon, we can shed our skin, even change colors, one layer at a time. We are still ourselves, but better, improved, raw.

We’re sailing through uncharted waters; all the good metaphors have already been taken. Succeed together or lose alone.



After spending 20 years in brand marketing for Fortune 500 companies and enjoying her two young children, Joanna felt a pull to return to the work force under her own terms. She designed The Creative Confidant to give clients tools to activate talents, identify leadership styles, and forge a brand which align with their sensibilities.

With an awareness that people aren’t products, she uses her marketing expertise to help individual experts and organizational leaders build their best brands. A self-professed “Performance Junkie,” Joanna also has a broad musical and theater background. She plays the piano and violin, loves to sing and has done stand-up comedy. Whether it’s making presentations or making people laugh, Joanna loves to perform. She strongly believes confidence is contagious, it’s just a matter of finding the right view of yourself.

Joanna holds a BA in English and Fine Arts with emphasis on Performance from Georgetown University and an MBA in Marketing with a focus on Organizational Behavior from Boston University.

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