The Character You Want to Be: An Interview with Jen Waldman
Have you ever had someone in your life that you’ve never met but so immediately becomes a major influence? Like a mentor but not? That’s Jen Waldman in my life. I’m regularly shouting with joy while listening to “The Long and the Short of It”, her weekly podcast with co-conspirator Peter Shepherd.
And then there was that time I had zero chill and asked her and Pete if we could be friends by email. I tell the whole story on instagram. Shockingly, it seems to be working out!
Jen Waldman is described by her closest friends as “a human stethoscope”, cutting through the noise and getting to the heart of the matter. After listening to her own heart, Jen happily walked away from a career as an actor on Broadway so that she could have a bigger impact offstage. She now devotes everything she's got to helping other people tap into their creativity and express themselves. You can find the latest opportunities at Jen Waldman Studio Online. She is also a longtime speaker and facilitator with Simon Sinek.
Learning from Jen has been a huge affirmation to me that I’m not totally off the rails in how I’ve been building and leading in my business. I’m so grateful for her work that I was uncharacteristically brain-frozen during our conversation (and therefore more wordy). I’m so grateful for her patience and professionalism with me. She’s a practiced leader and knows how to say exactly what she believes.
This interview has been edited and condensed for readability.
Dana Ray: You are someone I admire in their ability to define the ideas you're communicating. You just did that so beautifully in how you describe your work. Can we start by talking about your definition for your work? What’s it for and who’s it for?
Jen Waldman: My Why is to help people better know themselves so that they can better express themselves. I work with artists who are members of the Broadway community and in COVID times the global theatrical community. I help them to get really specific with their technical approach to their art. And at the same time, I help them get very specific about their humanitarian approach to their art and how they can actually use art as a change making device as opposed to the means to an end. The art really serves as a catalyst for change.
I also work with business owners, leaders, people in the nonprofit sector, fields that wouldn't necessarily fall under the artistic umbrella but who need more art in their organizations. I step in to help with crafting great stories, creating narratives, bringing more humanity and empathy and creativity to the work so that the work that they are doing can have more impact.
To summarize: I help people build their character both on and off the stage. And by people I really mean humans who stand for something.
Dana Ray: How have you practiced and developed the skill of creating definition? And what role does this play in your work?
Jen Waldman: It plays a huge role in my work and it comes from my theatrical training! In the world of theater, at least in the world of the American Theatre, the playwright is the be-all-end-all. And what we try to do as theater artists is elevate their words and honor the writing. A lot of improving and paraphrasing happens in the world of TV and film, which in my world of theater is sacrilegious. You would never paraphrase a playwright's words! It's so disrespectful because you know the craftsmanship and the wordsmithing that went into choosing each and every single word. And so theater is a very disciplined practice of getting every single word right.
An example of this is what it takes to perform Shakespeare. We excavate a Shakespeare text by going to what they call “the lexicon.” Shakespeare used the same words in many plays but almost always with a different meaning. When you’re speaking Shakespeare's text, you have to get your mouth around what he actually intended with that particular word in that particular context.
In my non-theatrical work, definition in relationship to context serves me well because I'm always questioning what does something actually mean? And am I working with the same definition that someone else is working with? Because if we are, that's great, but very often we're not. And it isn't until we actually say what we think we're talking about that we can find the common ground and have the aha moment. So I'm a big fan of defining the words you use to know exactly what you mean so that you can articulate it to someone else really clearly.
Dana Ray: I love how the process for precision honors that words are not single items. Even with Shakespeare, a word is not just one thing because it depends on the space in which it appears and the intention behind its use. And so by asking someone what they meant by this word and offering your own definition, you're acknowledging that there's not a right meaning. Instead, there's the meaning that creates understanding and that we can take action on the word.
Jen Waldman: I teach a class called “Shift” which is a mindset class. And for every exercise, we start by defining the word. I'll have twenty people in the class and twenty definitions will come up. Everybody’s got their own worldview of what they think things mean which is a product of experience. And we've all had different experiences.
This is why I tend not to use my Why Statement--helping people better know themselves so that they can better express themselves--in conversation. If I were to say someone to someone, “In this conversation, I'm going to help you get to know yourself better,” they’d say, “What are you talking about?” And if I were to say, “I feel like there's something under the surface that needs to be expressed. Let's see if we can find it,” they’re more likely to engage with me because that's about them!
Dana Ray: There’s a translation step between the internal language that makes sense to us, and the words that are going to connect us to another person and allow us to work together. Those aren't the same set of words.
Jen Waldman: Agreed.
Dana Ray: I’ve had this experience with the word “compassion” which doesn’t have a lot of depth for me. But when you change it to self-trust, or dignity, or respecting needs, my brain gets all of that. Changing the vocabulary has enabled me to build an experiential definition of the word.
Jen Waldman: I too would find trouble resonating with “compassion” as a standalone word because there's nothing active about it, it's something you have. But if you were to add an active word like “practice” in front of it, then it starts to have some meaning for me. How do you practice compassion? I can actively pursue that question.
Dana Ray: Verbs vs nouns!
Jen Waldman: What a difference a verb makes!
Dana Ray: In the spirit of verbs, I love your language of “bringing humanity to the work.” What does that look like in your work?
Jen Waldman: I think humanity is the holistic sense of self, that your humanity is derived from so many different places and our contemporary society has a very unfortunate habit of trying to limit people's humanity and fit it nicely into a box that's perhaps very easy to check off or easy to understand.
Dana Ray: Commodification.
Jen Waldman: Yes. There are the technical definitions of what it takes to be human as opposed to some other mammal and then there are the things that make up our human experience and those qualities we have that make those experiences. Seth Godin would call them our real skills. It’s all of those things that allow us to be complete, the kind of people who have purpose and integrity and drive and vision. I think all of that is wrapped up in our humanity. So much of it is just about our ability to see other people as fully human. I guess that's really what I mean--the ability to see other people as fully human.
Dana Ray: There’s something in the word complete, too, that feels very alive.
Jen Waldman: I think there's a really important distinction: there's a difference between being complete and being finished. And our humanity is never finished, but we can be complete. We are complete and yet can still be learning and still be growing and still adding new ideas and new skills.
Dana: You also used the word “character building.” And I also love this use of the word character because knowing that you're in theater, it takes on multiple layers of meaning.
Jen Waldman: I think there's so much crossover between the work I do with actors and the work I do with non actors. We're taking existing stories and trying to understand all of the specific “given-circumstances” that make up the world that that play or that musical or that story exists in. And then after we've established the world, we can look at the characters for how they move through that world and seek to understand why they're behaving the way they're behaving. It's all dictated by circumstance. So when you dig into what it's like to create a character that's going to be on stage in an existing story, you have so much information to work with.
And you can take all of those building blocks and bring it over to the “real life side of things.” We can look at the stories we're engaged in right now and treat them the same way. What is the world of this play? What are these circumstances? And how are these circumstances dictating how I or the other characters in my life are moving through them?
The work that I do with the actors is basically an empathy tool that I can teach to people who are not actors so they can see a story for what it is, see the world for what it is, and understand that everybody's actions are motivated by something that has to do with the circumstance. When I think about character building, I want to help people make decisions that are more in alignment, or have more integrity in relationship to the character they want to be in their own life. To get them closer to taking actions are thinking thoughts that will help them become the person they mean to be.
“I want to help people make decisions that are in alignment with the character they want to be in their own life.”
Dana Ray: Which for your people who are taking a stand for something, that looks like acknowledging the full humanity of other people and are acting in accordance to that?
Jen Waldman: Right before the shut down, I was supposed to be doing this character building workshop for physicians and physiatrists at a major New York hospital. The point of the workshop was to work on building the character of a doctor who has the ultimate empathetic bedside manner. And in building that work, what I found is that many people believe that you have to show up as the person you feel like you are in that moment to be genuine. That if I'm irritated, I have to show up as this irritated person because that is authentic to me. But when you actually can craft the character, even if you show up at work and you're irritated and you're short-tempered, you can still step into the character of an empathetic doctor with an ideal bedside manner. Playing that “role” is fully in integrity with who you intend to be in that moment. It doesn't make you less authentic. In fact, I believe it might make you more authentic and full of integrity. And then when you close the door, you can deal with life's irritation. It’s identifying how your character moves through the different circumstances of life in a way that makes you feel proud of who you are.
Dana Ray: I just read this line: “Authenticity is not disclosure.” So I’m hearing you say that authenticity is not to disclose your current state, but to act in service of your work; in your example, it is to be a doctor with a good bedside manner.
Jen Waldman: That's exactly right. I love how you just articulated that.
Dana Ray: What experiences have informed how you work with people and how you work with language?
Jen Waldman: Pivotal moments I've witnessed in people's growth where the way they're, they're talking about themselves or their work, or the way they are allowing themselves or their work to be spoken of is like a very critical element. So many clients are coming into my mind right now. It’s hard to pick just one instance.
One story is when I had a client who was about to star in a Broadway show and her casting really represented a major historical event for the New York stage. But she had never personally starred in a Broadway show before so she was seeing this event as a personal milestone. We were talking about what she was going to do and I said, “This is going to change the world” or something to that effect. And she looked at me like, “What are you talking about?” And I expressed that “...this was a milestone but ultimately, this milestone has nothing to do with you. It has to do with the people who are going to see it happen.” And that was a big transformation of being able to get outside of yourself and see the impact that your work is having.
It’s so easy for us to insulate and isolate ourselves from the larger impact because when we do things that are scary, or we do something for the first time, it feels like it's all about us because it requires our courage to actually get out in front and do the thing. Ultimately, being able to turn the language from all about you to all about the impact can be so transformational and give people inspiration to follow through with the task at hand.
Dana Ray: Ooh, inspiration to follow through. When I think about my own experiences, when someone opened the aperture for me, I can imagine myself having two experiences simultaneously. The first is gratitude. I can't believe I get to do this. I’m drawn into continuing with this bigger picture. And the second is feeling overwhelming responsibility and fear. How do you help your people negotiate those things once they get that bigger picture of what their work is about the change they are actually causing in the world?
Jen Waldman: Oh, it's such a good question. And honestly, it's something I personally struggle with too. I want to have a legacy but don’t want to have to do anything that would cause one. (laughs)
For me a very useful tool is having a clear picture in my mind of the client I have best served, who has been most transformed by changing their mindset and approaching their work in a purpose driven way. And when I feel stuck, I imagine myself talking to her. But when a client is feeling stuck, she serves as inspiration for me to remind myself of like, it is possible to cross that bridge. So I will often use this idea of past self and future self as a tool with clients to help them get out of the present moment and actually see what is possible. I am a big fan of, you know, “stay present to what is going on.” And I also recognize that that can be a trap, where if you're so present you can't imagine a positive impact that your work is going to have five minutes from now. Five days, five months, five years.
When I see a client who is struggling with that, we will do something like a Dear Future Self moment. How might your future self thank you for the work you are about to do? How might that person who is out there right now believe that there is no place for them in this industry? How might you show them that there is a place that changes the future? Using a little future focused language can go a long way.
Dana Ray: I tend to write letters from a person when I call Elder Dana. She's at least 90. She is over people’s shenanigans. She's just very clear eyed about who we are.
Jen Waldman: Elder Dana. I love that.
Dana Ray: I think she's made most of the important decisions in my life.
Jen Waldman: Peter Shepherd and I recently did an episode on The Long and the Short of It on this idea. It was really funny because I come at it from one direction and he comes in from the other direction, which is always how it goes with us. I Just thought that was so funny that that played out in that one as well.
Dana Ray: In another episode I loved, you and Pete talked about qualities of leadership and defined what you think is required to be a leader. How would you define leadership as an artist?
Jen Waldman: Leadership is a skillset. It is a practice or skill that allows someone to paint a clear picture of something better and help other people follow them there or help other people believe in that thing. One of the defining features of a leader is that they have followers. So there's an ability to galvanize people around an idea or a vision, and sometimes leadership looks like a title. But not everyone who holds a title is a leader. And sometimes leadership looks like being an active member of your community, and not necessarily the event organizer, but being the one who energizes the group. Leadership takes a lot of different forms, but ultimately requires skill. And the good news about skill is that it can always be taught and cultivated.
Dana Ray: You just took the word “leadership” and did what you did earlier with the word compassion, which is we put the word practice in front of it. So I'm going to re-ask the question: what are the practices in leading?
Jen Waldman: Let go of your ego. I'm saying this with such a contorted face because it's so hard to let go of your ego in favor of service. Part of what gets cloudy in being in a leadership role is that because people are looking to you, it's easy to let that get you off course. So I think it's practicing letting go of ego.
Stay in-tune to what the people who are following you care about and need. Practice empathy; Pete defines it as asking questions and holding space and I love that definition. As a theatre practitioner, I can pull any number of tools from my theater toolbox in order to practice empathy and imagine what it might be like to be someone else. And explore their given circumstances and see where they're coming from. Leadership is understanding where people are coming from, what they care about, what their hopes/dreams/fears are.
Another leadership practice is the willingness to envision things that are unreasonable. Where you've got to be able to get beyond the scope of the here and now and imagine things that are outside of this current moment. Having the audacity to envision something idealized. So I do think that visioning is a big part of leadership. But it's not just having the vision. It's being able to clearly articulate what you see to other people who might not be able to see it yet.
Dana Ray: How does a leader find followers for their vision?
Jen Waldman: I think a lot of it is wrapped up in empathy: I see your hope, I see your fear, I see your pain. I'm going through this very weird transition right now, which I spoke to you about a little bit offline, where the community I lead is an absolute disarray. You asked me if the theater world was on fire and I said it was already burned down. And I'm looking at the ways in which I have served my people for 15 years. And what I could offer them a month ago, they don't need it anymore. They need something else. I've been grappling with the fact that I see a future for theater artists. I see a future for the theatre industry. But today, they are in so much pain and so much despair and so much terror that just getting tomorrow to tomorrow feels like a huge accomplishment. So when I look at them now, I'm asking myself questions like if I put aside everything I've ever given them and I started from scratch. How would I show up in service? If I was meeting them for the first time in this moment? How would I show up in service?
I just had a team meeting with all the people who work with me at the studio. And we were talking about what if we completely transform what we're offering right now? What if we make this moment solely about what people need in this moment? Because continuing to keep leading towards a future that doesn't exist anymore feels… well first of all, it feels tone deaf, and second, pointless.
In response, I'm challenging my own sense of leadership right now. I’m asking myself, “Can I get my ego out of my own way?” To not say “But for 15 years, I've been teaching this!” Well, now I need to look at these people I love and care about who are suffering, I have ways I can help and I will. But discerning how to show up in service right now is tricky.
Dana Ray: And you went through this question process in March at the start of the pandemic.
Jen Waldman: And very successfully! Coming out of March into April, I was like, I am so energized. I know exactly how to help these people. And we did it. I mean, for the first four months, it was off to the races! And quite frankly, a safe haven amidst all of the chaos.
But the circumstances of the people in the theatre industry and so many people in this country are changing this weekend with the unemployment benefits being terminated. It’s just a totally different scenario, a totally different world. People are really in survival mode; scarcity-mindset is real right now. And so just how do you help people feel safe? First of all, that's like the primary concern is how you help people feel safe. But I'm dealing with an artist community. So how do you help people feel safe and remain artists? So that's been an interesting thing to have to try to figure out. How do I show up in a leadership role with that? on the table?
Dana Ray: This is a question that I've been asking. I'm seeing more and more how trauma within Creative Industries can make an artist leave their field. Trauma often caused by abusive cultures and people. I get really fired up about when I see people have to leave the work that they've loved. What does it look like to stay safe and get to keep this art form that you have studied and loved? What does that mean?
Jen Waldman: My industry is in a pivotal moment. In the last couple of years, there have been some changes made in the right direction to protect, to protect people in their work environment. For example, hiring intimacy directors, who would be the ones choreographing the love scenes. And of course, for as long as I've been an actor, we've had fight directors choreographing the violence. But what is now demanded of the theatre industry and rightly so because oh my gosh, we are so behind where we need to be.
We need anti-racism training as a requirement and to actually have an anti-racism consultant present in the rehearsal and audition room. This is what is being demanded--whether or not the people responsible will follow through is a whole other story.
But the other element is preventative mental health care. Many of our stories contain characters experiencing trauma of some sort. And if there was a fight that led up to, let's say, like the murder of a character in a play, we would have a fight director there to make sure that the stages violence is safe. But for the person who has to play, let's say, the husband of a wife who has been murdered, that person receives no training, no help, no processing, nothing. But we're asking them to take on the trauma of witnessing your spouse being murdered!
Dana Ray: In one of your Facebook Lives, you said if we were to put actors in an fMRI machine and see them performing, we would have new understanding of how certain acting techniques actively cause trauma.
Jen Waldman: Yeah, it's really problematic. And like you, I've seen people leave the field for these reasons. But what's happening in the COVID moment is that actors who are open to possibility are seeing that these specific skills that they've developed can actually be repurposed and adjusted or adapted for other environments. Actors are highly trained in creativity and empathy. These are two skills that are needed in nearly every single industry. So my hope is that the people leaving the theater industry right now because of the trauma of COVID will find a way to keep expressing their creativity and their empathy just in a different way, wherever they do land.
Dana Ray: Jen, I cannot thank you enough for this generous conversation. Getting to know you and your work this year has been an affirmation of the work I'm doing and the way I'm seeking to do it. THANK YOU.
The Jen Waldman Studio (JWS) opens enrollment at the beginning of every month. In September, there will be tracks devoted to performing artists transitioning into building their own businesses or seeking employment for the duration of Covid19 and the shut down of theaters. You can subscribe for updates at the website and follow latest developments on instagram.