Maria Darby Talks Uncertainty, Failure … and What She Learned from Talking to Chevy Chase

I have come to know Maria Darby through her many years of service to the Junior League of Baltimore.

Once you know Maria though, you start to see her name everywhere you turn—and for good reason!

Maria looks out for people and she has always done so for me. If I were facing uncertainty, I would want Maria there with me to formulate a plan … likely in cute fashion and with high-end snacks. 

With that, meet Maria–

Anne Hilb: Maria, tell us about yourself as a person and your current work.

Maria Darby: At this age, I can truly say that I am living my BEST life – personally and professionally.

Maria and her husband.

At Keswick, I’m doing work that brings me joy and I am blessed to have a team that is passionate and committed to our mission of helping people live well, age well and be well. I’m married to a man who loves me for who I am, supports my dreams and gives me the space I need to be me. And, I have a tribe of family and friends that encourage me and push me to embrace the known and the unknown with equal vigor. Life’s not picture-perfect, but it’s mine, and I’m determined to make the most of it.

AH: In your own words, why is uncertainty so scary for people?

MD: I think uncertainty can be scary because the word—by definition—denotes a lack of power over a situation or an outcome and that can make us feel uneasy. 

I, on the other hand, like to think that uncertainty or being uncomfortable is the first step in personal and/or professional growth. Uncertainty is in many ways about living in “the grey area” and/or facing “the fork in the road,” which for me translates into unexplored possibility.

To be honest, I am often at my best when I lean into the sense of “uncertainty,” because fully embracing it opens up the world of opportunity and innovation – a path that is yet to be defined. When you think of it that way: What could be more exciting!?

Offering welcoming remarks at The Daily Record’s Women’s Leadership Conference, Maria had the honor of sharing Keswick’s story—amplifying the power of women as leaders and as change agents. 

“Keswick is proud of the role that women had in creating our history – identifying an unmet community need, and then engaging and leveraging their network to create a healthcare solution for the benefit of the underserved,” Maria told us. “I believe that in uncertain or challenging times, often it is women who propel communities, issues and ideas forward, and ensure ideas translate into action.” 

AH: What’s the best advice you have ever received?

MD: I have been extremely lucky to have had a cadre of fabulous formal and informal mentors over the years and have received so much great, useful, practical (and not-so-practical) advice that has facilitated my growth as a leader and as a person making it hard to choose just one. BUT…there are two that have continued to resonate with me:

  1. Don’t wait for consensus, create it. And when it’s your decision to make, make it; and
  2. You are stronger than you think.

These two statements are always running through my mind—especially in times of uncertainty. 

AH: How do you acknowledge uncertainty when you cannot yet share the details of a pending change? 

MD: I think some of our discomfort with uncertainty stems from a lack of access to information or feeling “in the dark” about situation or change of some kind.

To combat this in situations when I cannot share details of future plans, I double-down on sharing the vision that is guiding the change and/or the outcomes that will result from the change. I also am as transparent as possible about the timeline for the dissemination of information regarding the change—to lessen as much anxiety as possible in those that will or think they will be impacted.

I acknowledge the uncertainty, even if I can’t alleviate it.

AH: What is something most people don’t know about you?

MD: Years ago, I had an opportunity to attend a party at Russell Simmons house in the Hamptons where I met him and his then wife, Kimora Lee Simmons, his brother Rev Run of Run-DMC, Chevy Chase and Martha Stewart among others. I was star struck across the board—but what I most remember is how “normal” they all were. My conversation with Chevy Chase was truly memorable, not because of what he said but because of how he made me, and the others at the table, feel. He was so personable, interesting and outwardly focused, traits that makes others feel at ease. I reflect on that often and incorporate it into my own behavior when interacting with others.

AH: What is one piece of advice you give to those you mentor or to those looking to grow in their careers? 

MD: I always share two things…

  • If you aren’t making mistakes, then you aren’t trying hard enough. We all love to do things well and be successful on the first try; yet, we learn so much more useful information from our mistakes than our successes. It is not the failure, but how you handle the failure, that defines you.
  • Pursue excellence always. Never settle for the status quo at work, in the community or in the world.  There is no excuse for mediocrity and no reward for just showing up. 


Still confused? Or want to talk this through a bit more? I’d love to; this stuff is my specialty. 

As you think about your plans — both at work and at home — for this year, I invite you to learn more about Graymake, LLC and the opportunities we have available for you and your employees.  To set up a 30-minute phone chat with a member of our team, sign up here or email


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