Interview with Barbara Massury, Executive Advisor – Part 1: The Challenge of Being an Elite Performer

Mary Elizabeth: Barbara, for a while now, you and I have been talking about the business coaching you do for executives and how that work applies to singers. Can you talk more about how you first came to realize the connection between these two worlds?

Barbara: I spend a lot of time with singers socially and have worked with top leaders in the corporate world for the past 25+ years. Over time, I noticed something: mid-career singers and top managers actually face similar challenges. Both are elite performers! Both work in environments where the pressure is constant and the stakes are extremely high. Singers and executives both have to make big decisions about which project to focus on, how to prioritize, and how to interact in difficult environments. Both groups have stressors around managing the trajectory of their careers in an ever-changing environment.

But here’s the thing: there’s a big difference in the kind of support these two types of elite performers get. In the business world, nowadays, it’s standard industry practice that leaders and high achievers get structured support—executive coaches, mentors, or advisors. These managers have advisors who understand their patterns, and help them think strategically, navigate challenges, and keep a long-term perspective. In fact, around 50 to 70% of CEOs have worked with a coach at some point in their careers.

Singers, on the other hand? Sure, they have managers and agents, and those roles are super important. But that kind of support is very different from having someone who helps you step back and really think about who you are and what you need. I’m talking about someone who focuses on the bigger picture: a neutral sounding board who helps you navigate transitions, manage difficult dynamics or develop new approaches to stay the course. An advisor is someone who supports you in times of crisis, and helps you to be resilient under pressure. They provide you with guidance tailored to you as a person and your desire to build a sustainable personal and professional path for the future.

Mary Elizabeth: And managers and agents are looking at our crises from a much different perspective than coaches like you, since they are dependent on our success! So, a manager can’t exactly offer objective help, even if they are well-meaning. A manager has skin in the game in a way that you don’t. They feel the same pressures and anxieties we do!

Barbara: There is a web of anxiety all around you singers, all the time! Artists are expected to perform in a deficit-oriented environment; the focus is less on the enormous abilities and resources you have and more on what abilities and resources are missing. What needs to be different, what needs to be better. 

Mary Elizabeth: And how little money and time there is to do all that needs to be done…and here I’m talking about both singers and theaters!

Barbara: That is the nature of the beast, I guess. As an elite performer, you are expected to do better, be better, get better in a time crunch, with very little support. At the same time, working under this mindset can become a curse. It is so easy to lose track of our strengths, our incredible know-how, and everything we have already accomplished. I have spoken to many singers that seem to have internalized the belief that these constant feelings of dissatisfaction and instability are part and parcel of an artist’s life and synonymous with the business model!

Mary Elizabeth: I was taught from early on that a singing career equaled suffering and sacrifice. In school, they said to me that if I could be happy doing anything else, that I should do it. My voice teacher said I should think of myself as a nun. One of my early mentors told me that she had declared bankruptcy—twice!—to keep going. This career has constantly been sold to me as something that will torture me, isolate me, and keep me poor, but I have always resisted that portrayal. I believe that having a varied life, other interests and passions and financial stability  are integral to my being a good artist. I want to sing, but I want to enjoy my life, too. I want to have something to sing about, and I want to have fulfillment at home when I’m not singing.

Barbara: Yes, exactly. And honestly, the idea that you have to suffer is a) not a good soundtrack for a professional career and b) it’s just not true. In the business world, very few elite performers would accept “constant dissatisfaction” as the price for doing meaningful work. Yet in the arts, you singers seem to be told—even taught—the opposite: that struggle, loneliness, instability, insecurity and the constant feeling of “not being enough” are somehow part of the deal. 

Mary Elizabeth: When we were together in Santa Fe, I absolutely felt that what I was doing was not enough. I was constantly thinking about what was next, how to keep the work coming…and then when it came, the victory was hollow and short-lived. I started to resent having to be away from home, but when I was home I was restless and yearned for a project. Looking back now, I realize that I had been suffocating or ignoring the interests that weren’t aligned with singing for years. And that muted part of me was getting really annoyed at being ignored. Basically, I was in conflict with myself.

Barbara: When outside definition determines your perspective, this is a difficult, and I would even say, dangerous place to be. The constant need to adapt according to other people’s definitions can really mess with our sense of who we are, not just as artists, but as people. It’s so easy to end up chasing what everyone else wants from you, and you lose track of your own voice in the process. That’s where it can get existential.  

Mary Elizabeth: Existential is the perfect word. Even after a singer is already established, and has a proven track record on stage, the anxiety, the discomfort, persists below the surface, at least, it did for me. I would be alone in my temporary apartment in a new city, or sitting cross-legged on the floor of the airport at an ungodly hour, asking myself: Is this it? Now that I’m here, what’s next? How can I keep the work flowing in, but have more control over the pace and quality of that work? At what point do I get to make decisions that aren’t just about the next gig, but about where I want to be in five or ten years and beyond? And, the scary question I asked myself was always: what is the point of all this?

Barbara: If you’re not prepared for those questions, or haven’t developed healthy ways to deal with them, navigate them and understand your own enormous resources and strengths, you can lose your sense of direction. This is about knowing yourself, building clarity, and shaping a path that truly fits you.