CEO of Cayton Children's Museum

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Joining MC Sungaila today is Jessica Aronoff, CEO of Cayton Children's Museum. Jessica entered law school with no intention of becoming a lawyer. Her goal? Doing impactful work in a nonprofit. As it turns out, having a law degree was indeed a valuable tool and asset for her work in the field. In this episode, Jessica shares her evolution in the nonprofit space, from Executive Director of teen dating violence organization Break the Cycle to Vice President of Philanthropy for The Wonderful Company. Jessica's career path demonstrates the different ways you can apply your law degree. Tune in to hear from an inspiring and visionary leader.

Relevant episode links:

Cayton Children's Museum  , Break The Cycle , Equal Justice Works Fellowship , The Wonderful Company  , Pacific Symphony  , The Anthropocene Reviewed 

About Jessica Aronoff:

Jessica Aronoff joined the Cayton Children’s Museum in 2019 as Chief Operating Officer and moved into the role of CEO in 2021. Jessica brings more than 25 years’ experience across the corporate, philanthropic, legal, and nonprofit sectors—guided every step of the way by an unwavering commitment to social justice and fostering purpose and potential in leaders, teams, and organizations. Prior to joining the Cayton, Jessica spent several years consulting in the areas of growth and change management, leadership development, corporate culture, and social impact, including serving as a FUSE Executive Fellow in the Los Angeles County Probation Department. Previously, she served as Vice President of Philanthropy for The Wonderful Company—where she led all philanthropic, community investment, employee giving, and corporate social responsibility programs—and as Executive Director at Break the Cycle—a national nonprofit organization working with youth to end domestic violence. A Senior Fellow at the Brittingham Social Enterprise Lab at USC Marshall School of Business, Jessica received her BA in English from Wesleyan University and a JD from UCLA School of Law.

I am pleased to have joined us, Jessica Aronoff, who is the CEO of the Cayton Children's Museum in Santa Monica. I had the pleasure of working with Jessica many years ago at Break The Cycle, where she was an Executive Director. I’m interested in hearing about her journey and her unusual path. Welcome, Jessica.  

Thanks so much. I'm excited to be here.  

Thank you so much for being here. In this show, we talk about people's career journeys and evolution. Also, I’m exemplifying, in your case, the many different things that you can do with a Law degree and how that training can be helpful in accomplishing what you want to do in life. You have certainly had some significant impact on the world in the kinds of work that you have done at the different organizations you have been at. Even though you haven't been in court and you haven't been doing any of that, but a major impact. I hope that people will read this and consider the different ways of having an impact on the law. First, start from the legal story in terms of how it is and why you decided to go to law school. 

One of these interesting, maybe bizarre people who went to law school never wanted to be a lawyer. I worked for a couple of years after I graduated from college at a nonprofit organization, and it's part ambition and part arrogance. I thought I could be doing higher-level work than what they were asking me to do. How do I jump some levels? I thought, “I could go to graduate school, but what kind of graduate school?” My mom was a lawyer. My sister was in law school or had graduated from law school at that point. I was like, “Law school sounds good.” I had taken the LSAT during college, I didn't even know why, but I decided to go to law school. 

I saw it as a means to an end that wasn't about practicing law. It was about doing more impactful work. The work I did before I went to law school was at a nonprofit children's advocacy organization. I always knew I wanted to do some public interest work. I entered law school knowing that I was on a public interest path.  

That helped me to enjoy law school more because I didn't feel like I had to get into the rat race so much. I was there to learn and to have a tool and a credential at the end of it. I'm not sure I would recommend that to most people because it's both expensive and hard. It's a big investment of both time and money that if you're not sure you're going to use it, I don't know, but it worked out for me.  

I always thought that there were some people who go to law school saying, “I can't stand the side of blood, and I need to go to graduate school. It's either business school or law school, I will do law school.” That can be tough because law school is hard unless you have some reason for being there. Most people have it for a certain practice of law they want to do. As you described it that you had a purpose in being there. That got you through the challenges, and it has happened to serve you well, but I also hear your admonition of there must be some kind of meaning.  

I appreciate you framing it that way because I hadn’t thought about it that I did have as much purpose as somebody who was sure they were going to go on the law firm track, the judicial clerkship track, or whatever it is. I was clear about why I was there, and that helped. The other thing that law school did for me was, but it wasn't until my second year. I suddenly had this epiphany. Maybe it's called growing up. I realized that I was there for me not for my parents or anybody else. I had this a-ha moment where I was like, “This is all for me and my learning opportunity.” It made the school click in a way. I had a push-pull relationship with the school prior to that.  

Even though I was a pretty good student, I was always trying to do the least amount of work possible to do well. Suddenly, it meant something different to me, especially during my second two years of law school. I enjoyed them because it was intellectually fascinating. I became a better student because of it. I wasn't resisting so much. 

The fact that I wasn't comparing myself to everybody else. I wasn't trying to hit all the measures that everybody else measured success at law school, or at least I thought they were. I don't know what was going on in their head. The funny thing is, in the end, I ended up doing so much better because of it. It has been a lot of years. I shouldn't even be mentioning this, but I graduated sixth in my law school class. Who would have thought that would have happened? It was because I was enjoying it. I doubt that many people talk about law school that way.  

Because you have a certain amount of freedom from that point, you had a purpose being there, but realizing that is your purpose and your goal in a way that you're like, “I'm feeding myself by being here in terms of growth, learning and stuff like that.” Maybe that's a good mindset to have for those who are in law school or that’s enjoyable.  

I feel like that has been a journey for me in my career too. What does success look like? I had a friend once say he works in a different industry, and he had been quite successful in his twenties. He used to worry that people would look at him and think, “You were successful before and now look at you.” Not that he was unsuccessful, but he was ordinary. He said, “I used to think about what are they thinking about me. I realized they were not thinking about me. They're thinking about themselves.” 

That has been a long process for me about what success looks like based on my definition, what is important to me, and what a fulfilling, meaningful, intellectually engaging, purposeful life looks like to me, not anybody else's measure of what I should be doing. I started to learn it in law school, but I feel like it's been a multi-decade journey of learning that.  

What success looks like is based on your definition and what's important to you. What a fulfilling, meaningful, intellectually, engaging, purposeful life looks like to you, not anybody else's measure of what you should be doing. 

That involves being comfortable in your nerve center and your own core. Whatever somebody else thinks or says about that is not relevant necessarily. I also think that what you said is that there's a certain path. That is true in law that there is an accepted war about what it means to be a successful lawyer. You get your judicial clerkship, you work for a big law firm or us attorney's office, whatever it is, and you either go to the bench or retire as a partner somewhere. That's from law school. I remember that was the path to success. 

It's easy to get like that in law school because it was certain expectations. That's good ammunition to say, “It's hard because there's this vision of success, especially in law. What is your vision of success, and what does success look like at different points in your life? What does that mean to you? Because we only have so long to be here, what can we accomplish and be proud of accomplishing?” That is what matters.  

I fell into that trap too. I don't want to pretend I have been immune to it. When I graduated from law school, I got a fellowship with an Equal Justice Works Fellowship. That is when I started working at Break The Cycle. It was a startup organization, and I launched the legal services program. I thought for a while, “I'm going to represent young victims of domestic violence in court and fight on the front lines of justice.” 

I learned pretty quickly, maybe unlike most of the people you have on your show, that I hated being in court. It was stressful and uncomfortable for me. I was worried about the tiniest little wrong thing. These were life and death things that were at risk there. It was a level of stress. I didn't feel ever in the flow when I was doing that. It didn't feel like my place.  

As our program grew and I started to supervise other people doing the work, I realized I was much better at that. I was much better at telling other people how to do the job than I was doing it myself. I learned because of happenstance and being where I was and when I was that management and ultimately organizational leadership and strategy were much more of a fit for me.  

I moved in that direction. Luckily, I had the opportunities and created the opportunities for myself to be able to move in that direction. With that said, I still all the time feel like my Law degree comes in handy, whether it's the contract that has been put in front of me that I feel like I can read with some level of competency or at least not be intimidated by the language that's in it, or honestly, some of the doors that it's opened and the respect. There are jobs that I got that I know, even though being a lawyer was irrelevant. It was a credential that impressed people and gave me an ability. I became a better writer, reader, and synthesizer of information in law school. It's all of those things. In the end, it did provide me with what I hoped it would.  

That is the reason why synthesizing and digesting a lot of information quickly. That's one of the major skills from law school that certainly, I use all the time as a health lawyer. That's what we do. We have to get up to speed on the area of the law, figure out where this case fits in, read the record, and get that quickly. That is a valuable skill in a lot of different settings where you're drinking through a fire hose, having to sort through everything and parse it out analytically.  

It's certainly one of the top three values that I most add to any room that I'm in when I'm brainstorming and having a conversation. I cut to the chase, can make quick decisions, analyze the situation, and cut to what's the critical core issue.  

Everybody is emotional thinking about various things, and you're like, “It seems to me the pivotal point is X.” 

Some of it is innate. Some of it is the people whose brains work that way, maybe getting attracted to law school. I do think it gets trained in law school. When your brain works that way, sometimes it's hard to realize that not everybody's brain works that way. One of my management challenges is and as a leader is recognizing that different people think in different ways. It was obvious. There is value to the different styles and not overpower the slower thinker or the person who needs to take time away from the conversation to process it and come. I try hard to not be a bulldozer, but I know that there are ways in which I can be that way and lawyers often can be that way, generally. There are positives and growth opportunities in that.  

It's something interesting when you said you had certain strengths, and those were in the organizational leadership arena. That is one that we think is not generally taught in law school. I remember seeing the business school people working in teams. In Anderson Business School next door, they are all working in groups. They were learning how to get along and lead others. In law school, not so much. We're up on our own, leading, doing what we're doing and not doing that. What is interesting about your story is that you have those inherent strengths in those arenas and apply the legal training to that.  

Some of it was inherent strength, and some of it was I learned the hard way. Much of the things that I have learned were from screwing up early on. I was lucky enough to start supervising people at a young age. I screwed up and learned from it. I was also open to learning from it. I had some important mentors and coaches to me early on who believed in me enough and be honest with me about the ways in which I was screwing up.

So much of the things that you learn is by screwing up early on.  

I paid a lot of attention. In the places where I interned and during law school and the summers, I had meaningful learning experiences. The biggest thing that I learned was observing the workplace and dynamics between the young, fresh out of law school employees, the senior leadership, the ways in which that worked and didn't work, and being clear.  

I remember coming across some people who were miserable at their jobs, and I thought, “That will never be me. I will never allow that to be me. Even then, I knew life was too short for that. Also, I was purpose and mission-driven in my career so it wouldn't make sense to do that and be miserable. If I'm going to be miserable, I might well be making a ton of money, but if I'm going to get paid almost nothing, I better be fulfilled.  

You said you had some opportunities, and you created some opportunities. Can you elaborate on that? 

I have always been somebody that, for better or worse, if I see a vacuum, I feel it. The opportunities may have been there, but I chose to step into them to demonstrate my value and my worth. I was at Break The Cycle for several years in a variety of roles, ultimately in the last several years as Executive Director but prior to that, in a variety of roles, helping the organization expand nationally, and all of these things. I learned a ton in that process.  

After I left there, I did some consulting for a bit of time. I ended up going and working in-house at a big corporation, The Wonderful Company running their foundation and corporate social responsibility program. There was an existing program there. There was what they called a “Charitable Giving Program.” That felt accurate to what was being done but small compared to what could be done. 

That is a privately held company. They have strong personalities in leadership. I could have walked in and continued doing what was being done before, which was writing checks to some good causes. There is nothing wrong with that, but to me, it was like, “This could be fun. We could be doing some high-impact stuff.” Early on in my getting there, I built a strong rapport. Lynda Resnick is the co-owner with her husband of the company. I said to her, “You guys are philanthropists. Let's start acting like philanthropists here. This is not charitable giving.”  

What I think I said to her was, “Charitable giving is what my grandfather used to do when Easterseals would send him something. He would send a $10 check and get the return address labels. That was great, and that was what he was capable of doing. You're capable of so much more. This company is capable of so much more. Let's do it.” She lit up and said, “Let's do it.” 

We went on a fun several-year process of exploring how we could have a greater impact, primarily in the Central Valley of California, where most of their agricultural operations are. These are small farm workers, mostly from immigrant communities, and fairly low-income. There was so much room for impact there. It was fun, innovative, and impactful.  

That is an example of what I'm talking about. I created an opportunity from within an existing framework, but where I saw that it could be so much more. I'm proud to say I have been gone from there for nine years. They have expanded even more since I left. I'm proud of that. I'm proud to see that I was part of building something. I don't think I'm a startup person. I have worked in startups, but I'm good at being the second one in. Not necessarily the first one in.  

I'm not necessarily the one who's going to get the first round of funding, but I'm good at taking what I see as the shell of an idea and figuring out how it could be even more than it was. I did that at Break The Cycle. I did that as a consultant in certain cases and certainly did that at The Wonderful. I'm doing it now. The Cayton Children's Museum is the second iteration of what was the Zimmer Children's Museum and was around for several years.  

Why did I not hear that name?  

Esther Netter is our founder, and she started Zimmer in 1991. It was this beautiful, lovely community, a mom-and-pop institution, that had an enormous impact. I have an almost seventeen-year-old son and I used to go there when he was little. It was something that I had affection for, but I came on board here just as we were opening a new iteration of the museum in a different location, a much bigger space, and it's now the Cayton Children's Museum. It’s a much bigger and higher profile location. We’re right by the Santa Monica Pier. It's beautiful. You have to come to visit. There was the opportunity to turn it into a real, meaningful community cultural institution. 

That has been fun except for a little thing called COVID, which certainly challenged things. We had only been open in our location for 8 months before our COVID shut, and then we were shut down for 17 months. Even that, there was an opportunity. The pause and the opportunity to step back and say, “What are we about? What is it we're trying to accomplish? How do we get clearer about our mission, our vision, and our values and make sure that every day we're living into that?” It has been fun and hard.  

What a time for that challenge and especially for museums. I serve on the Symphony board as well. If there was no performance, that's what we do. You can do it over Zoom or whatever, but it isn't the same as being there. That's a challenge, but using it to coalesce around what is our best and highest purpose and how we are going to show that or manifest that is good.  

I'm grateful for that opportunity. I wish we hadn't had that opportunity.  

I'm interested in what you said in the beginning. You said, “I'm not a startup founder person. That's not where my strength is. It's more in the second one.” Not only managing what's been created but expanding on it. I put it in the category of coming in and seeing the possibilities that other people might not see. It started with this idea, but there are many more possibilities germinating out of that and you are ready. The organization is ready at this point to go in those arenas. That's what I see across all the different organizations you have been at and what you are good at.  

Knowing that about yourself is important. People often think about in terms of careers, “I like doing this. I want to do this law.” What is also important are the things you have talked about in terms of, “It was a stress I didn't like going into court. That's not a good role for me. I'm better at this stage company or this stage nonprofit than at other stages of nonprofits.” Those are all crucial to selecting what it is you're going to do. I don't think that many people think about that in the same way, but you need to, in terms of figuring out how I am going to do my best work.  

This is where I get a little woo-woo. That different kinds of stress feel different in your body. There are certain kinds of stress that feel like torture to me. There are other kinds of stress that, even if I'm not loving it at the moment, afterward, I get that lit up, almost electric feeling. You're like, “I was in the zone when I was going through that.” There is a big difference between the two. One is depleting, and one is energizing, and they are both stress. I don't know enough about physiological stuff, but they both probably trigger certain things in your brain. For me, there's a big difference, and I have learned to pay attention to the difference.  

Considering that, I encountered that pretty early when I was doing tribal litigation work, and I realize that this is not for me. This is the stuff that I don't want to handle. Not only that, but I feel badly cross-examined. That is the whole core, the trial thing. I felt bad for people because I didn't want to do that to another person.  

You may not be the best at it because you don't want to hurt someone, so there is that. Recognizing in making decisions isn't where your skills are. I am a 180-degree different person, and the people who do this stuff, that's like oil and water. Whatever it is, it's not going to match. It's never going to be a natural flow out of how I operate. This clearly is not a good choice. I do something else that matches that better. That's something that people don't plan for that, you don't think about it, or you ignore it when you encounter it.  

I like to think that the younger generation is more in tune with this thing. People are talking about work-life balance in their twenties. I don't know about you, but I sure was. The furthest thing from my mind was when I certainly didn't think I was entitled to work-life balance. In my first job out of college, I was making $18,000 a year, and I was the first one in the morning and the last one to leave at the end of the day. None of this hourly overtime, none of that. It was a different time.  

I'm hopeful that there's more thinking about careers. It's a lot of time to spend of your life at work and hate what you do. I made a joke earlier about if I'm going to hate what I do, I should at least get paid a lot, but I'm joking. I don't even think all the money is worth that. I don't know. Maybe if somebody offered me all the money, I would change my tune on that. Doing work that makes me feel aligned with my integrity, my purpose, and what I'm good at feeling purposeful is important to me.  

As an employer, there is a little bit of an unrealistic expectation right now among some younger employees. This is not just in my environment. I hear it from a lot of my peers at other institutions, both nonprofit, for-profit legal, or otherwise, of an expectation of being able to pick and choose what work you do and what work you want to do. I don’t like this part of my job, so I shouldn’t have to do this part of the job. All the time, I’m like, “There are lots of parts of my job I don’t like.”  

Early in my career, if I had rejected all the aspects of my job I didn't like, I would have lost a lot of learning opportunities. As much as I think it's a great thing that young people entering the workplace are thinking more about their purpose, why, and whether this work is meaningful to them. I encourage that enormously. It is how I have made every decision in my career. I also think sometimes a little bit of paying your dues. Not only is it how it works, but it's also how you grow to learn what you like doing.  

A little bit of paying your dues is not only just how it works, but it's also how you grow to learn what you like doing.

There are things I do every day. I love budgets and Excel spreadsheets. Would I want to do that every single day, all day? No, but I love it. I wouldn't have known that necessarily early in my career if I hadn't been forced to do something that felt like something I didn't want to do. It's one example, but there are endless examples like that. It's a balance. Everything is a balance. 

I always think about it in terms of it being a great position if 75% to 80% of the time you love it and you can't wait to go to work thing. There is always that 25% that is not your favorite thing. If you minimize the amount that's there, that's doing well. I don't think of any sort. 

Don't get me wrong. On Monday mornings, I don't always feel like getting up and going to work. It's not like, “Let's be serious.” I won't allow myself to be dreading my work. That is where I draw the line.  

Sunday night is a drag, and like, “I'm going to have to go on Monday.” That's too many Sunday nights like that. In terms of the areas in which you worked and impacted domestic violence now and the children's museum are all different areas. Sometimes people go into things and say, “I'm going to help women. I'm going to help girls. That's what I'm focused on, but the areas you have impacted have varied, but what's the common thread you make the most of all of the different positions?  

Not only in the areas I have worked do they vary, but also in terms of where are my personal passions where I have volunteered my time, where I donate my money and things like that also vary. The common thread is about justice and equity and defending the rights and well-being of vulnerable people. The children's museum might not seem like that, but play is essential for children's development, and not all kids have access to safe, meaningful, purposeful, thoughtful, enriching play, and the creative arts.  

Kids are important, especially right now. The other thing is that coming out of the COVID shutdowns of schools, both in terms of social and emotional well-being, mental health, but also learning loss, and the lack of socialization. A four-year-old kid has spent 50% of their life not around other kids. We don't even know yet what that does to a generation.  

Having a place where kids can be kids and where there is thoughtful space for them to do so. They can do that at all income levels, building out our field trip programs and things like that, where we focus on title one schools coming into our museum space and all the things. We bring our museum programs out into the community as well. It's important. To circle back to your actual question, it is about a duty to protect the most vulnerable people in our society. More than protect but fight for.  

That's why I asked you because I was like, “When you look at it, it's seemingly disparate. What is the thread in your view?” There usually is one. That's why I asked. It's interesting to think about the particular role that the museum can play given the post of the jobs match for children. There are many studies coming out now, especially when you start with age. It depends on what their at as to how impacted their development has been from having remote schooling and not the socialization with adults or children over that time period. Does that cause you to think about changing your programming or what you would do as a museum at all? Are you doubling down on the things that you are already doing?  

It's primarily doubling down. Our slogan is Playing Our Way to a Better World. We never intended to be a space that was a generic play space or, as we often somewhat tongue in cheek, referred to as the play area at McDonald's. That's not us. We are purpose focused. It's about children learning to understand each other. It's about celebrating cultural diversity, collaboration, and actual creative expression. All of that and very purposefully curated and designed for that purpose.  

You are right that in this time, we are clearer that we need to double down on that and be better at articulating what that difference is and what that meaning is. We're a nonprofit organization. It is a challenging time fundraising-wise, especially for institutions like ours that get grouped into the idea. You would know this from your work with Symphony arts and culture.  

There are many other causes that appear and, in certain ways, are more urgent, homelessness, housing, crisis, hunger, traditional education, depending on your leanings on certain issues, reproductive justice, protecting our democracy, things that are important to me, and a lot of the philanthropic dollars that are out there are going to these issues that seem like emergencies. 

A children's museum or Symphony is never going to seem like an emergency. Yet, the cultural fabric of our communities, what brings people together, is urgent and critical, especially for children. This is important stuff, but it is a challenging time. Where we had to tweak what we are doing has more to do with how we communicate what we're doing, not so much changing what we're doing. We have been clear about why we're here and what our purpose is all along the way predating me coming here.  

It seems like you have landed at organizations where it's become important to refine, double down or expand on whatever their original vision was. Everything is either intentional, or it has happened. It feels like, in your case, at the children's museum now, it happened because of COVID. A lot of these things have come forth that you're able to bring new skills to bear, but it's interesting that the stages at which your skills are perfectly aligned with where the organization is going are needs.  

I always say, “I am in my sweet spot with institutions that are in their adolescent stage.” It's funny because I'm the parent of an adolescent, and I'm not sure it feels like a sweet spot in the same way, although he is wonderful. Similar challenges and similar rewards. Sometimes you feel like you are beating your head against a wall. When it works, and when it's great, it's cool. That is where I feel like my sweet spot in terms of where I add the most value and where I get the most excitement out of my work.  

I feel like I'm learning things. I saw a slice up front, and the rest, I'm like, “It's interesting to see the rest of it and how it all fits together.” Do you have any wisdom or advice for somebody who might be interested in doing this work, who's in law school, or anything from your path that if I had known this when I was in law school, I would've done something differently?  

One bit of advice that I got from someone who was in the administration at UCLA Law School when I was there was I turn my nose up at all the traditional path stuff. She said to me, “Do you want to raise money from the big law firms? I said, “Yes.” She goes, “You should know about how they do their business.” I was like, “That's an interesting point.” That young, a little bit self-righteous me wanted to be like, “That stuff is dirty. It's not my thing. I don't need to know that I'm on the righteous path.” There was a little bit of that.  

That version of me would have been shocked at the version of me that went to work for a multibillion-dollar company that is not without its controversy. The most important thing that I would tell that version of me is don't close any doors. It doesn't mean you have to keep every door wide open, but don't arbitrarily shut doors out of some self-righteousness or principled thing that you don't even know anything about.  

I'm going to go a little woo-woo on you, but every day, I say to myself, “May I be open? May I be curious?” That is how I want to walk through life. I think that is true, especially in your learning journey and your early career journey. You might think something is not for you. I'm not saying you have to explore every opportunity, but don't shut it out just out of some idea.  

There was somebody who was an advisor to me when I was at Break The Cycle who said to me, “Express curiosity.” She said, “When someone says something, you want to immediately jump down their throat and tell them there were whatever, or write them off immediately, at least to yourself go, hmm.” That hmm has been powerful to me throughout both my professional life and frankly in my personal life too. To pause and go, “Hmm,” and express that curiosity, in the end, you might still say, “I don't want to have anything to do with that world, but at least you know that it came from a place of pausing as opposed to a knee-jerk reaction.  

It wasn't just a reaction because you’re getting some time to pull back and think about it. Having that curiosity gives you an opportunity to maybe explore why somebody had said that or what’s going on. What led to that? Someone is rude to you, and you realize, “They had some terrible thing happen to them. Their God died, or something terrible happened earlier.” You’re like, “I’m going to look at that whole thing a lot differently based on where they came from. If I took offense and didn’t ask questions or wasn’t curious about it, I would see the whole thing differently because I wouldn’t find out what was underlying it.” 

You mentioned that a couple of times, which is interesting. There’s an openness to you anyway, in terms of asking for guidance and being open to input from others because I’m not sure that you mentioned earlier at the beginning of your career at Break The Cycle. Even though you had people providing productive comments, giving insights to you, some people could say, “Go fly high. Forget that. I’m not going to listen to that. I don’t need that. I’m trying to deal with my day-to-day stuff.” You were open to that too.  

It's entirely possible that lots of people gave me other advice that I ignored, but there are certain things that have stuck with me. I am an observer. I pay a lot of attention to what's going on around me. I still continue to do this. I noticed when people do certain things and how other people respond to them. Early in my career, I thought, “I don't want to do that.” I worked with people who were secretive about information. They felt that their power was in holding all of the information and not sharing it.  

This was a powerful recognition of mine, which is that I noticed early on that it diminished their power because people's assumptions were always worse than what the reality was. If you instead were transparent and vulnerable and said, “Here is what I'm struggling with. Here is what is going on.” I had a meeting with an employee. Her supervisor is leaving, and she's a little uncertain about where things are going. I said to her, “I don't know, but we're going to figure this out together. The one thing I can promise you is I have your back.” 

It is important to be able to say, “I don't know.” Admit your vulnerability, and you don't have all the answers because pretending erodes trust more than admitting you're struggling. That was something I learned by seeing people do it the opposite way. I thought, “They think they're doing it right. They think they're holding onto their power by not sharing the truth.” The opposite is happening. I think through transparency is where you build power because you humanize yourself as a leader.  

Through transparency is where you build power. 

If you're not transparent about certain things, there are all kinds of imaginings and things that it's like, “That's not the case, but you're spinning out.”  

People do it all the time, even when you do tell them the truth. You might as well at least avoid some of that.  

There is still that discussion, but at least I had my say. What you said about, “You may not know an exact path of what the next steps are, but to assure someone that whatever those next steps are, they will be considered as a person in connection with those and that your intention is to protect them in certain ways.”  

As a leader, I have found that the most powerful thing I can do, and I mean powerful in terms of how the people who report to me respond, but also the people I'm accountable to, like my board of directors or supporters of our institution, is to say, “I don't know,” but to say it with confidence. To confidently not know.  

There are lots of things I don't know. I also do believe in myself, my team, and our ability to figure it out. We're not going to get it right 100% of the time, but you know it's going to have been thoughtful. You know we're going to have to put in the work and to be able to say, “I don't know the answer to this.” Not be apologetic about that. We, as women, often don't want to admit what we don't know because it feels like admitting a vulnerability that everybody is ready to pounce on. We're not even taught how do you handle not knowing. There are some people who are going to respond in a particular way when that comes from a woman, for sure.  

I had someone, a man who is older than me and indirectly in a position of power over me, say something along the lines of, “You have a very particular point of view.” I thought to myself, “He might as well have ended that sentence with the little lady.” It was very gendered. I had an opportunity at that moment to decide how to respond. I mostly sat there and let him sit in the silence afterward.  

He said, “Which, of course, is important. The organization needs that.” I was like, “Yes, I agree with you. The organization does need that.” He caught himself, but it was a challenge to know how to respond in those moments. Going back to not knowing, admitting that I don't know has been a growth area for me. I realized if I do it with confidence, it instills trust and belief from a lot of people, at least the people I care about what their opinion is.  

That goes in the category of, do you need all twelve things that are listed on a job listing when you're applying or not? We often match all twelve in most cases.  

I still struggle with that. I want to feel like I have mastery. It's hard voluntarily putting yourself in a position where you know you don't know what you're doing.  

I have never done these things before, but that's also where your growth opportunities are. You have to pull back on that a little bit. If you keep doing the things that you're 100% qualified for and have done everything before, there's a point at which you're going to stop growing. Maybe find out new skills you didn't even know you had because they haven't been put to the desk before. I like your talking about that in terms of you can say, “If you don't know confidence, that is fine.” People who matter go, “We feel confident from your confidence that you will figure it out. We're okay. You don't need to worry about that anymore.” You have a great team and management style that you feel confident in your team to be able to say that too.  

I don't want my team to fake it with me so in order to make sure that they are being real with me, I have to be real with them.  

That's true because you're modeling that too.  

I'm creating the culture with how you are managing as well.  

There are so many different things to what you're doing, and I'm like, “I knew there were, but wow.” There are a lot of different layers going on at the same time when you're making decisions. The comment about don't close the doors too soon. There might be opportunities. I like the comment from the UCLA advisers. Those people will be on your board. Do you want to understand them or not? 

That was exactly her point. I was thinking very small. 

You were like, “There are tons of stakeholders. You need to understand all of them and have a little orchestra all working together.” That was a solid point. Are you doing this all alone? 

You never know when wise advice is going to come your way. Each of these people that I have said, anecdotally, they have said something. One of the people was a friend of mine. One was an administrator at the law school that I happened to be having a conversation with. There were other people who were in more formal mentoring or advisor roles to me, but most of the time, it's not that.  

You don't know where the wisdom is going to pop up. Listening and paying attention, and when you feel that little tingle of something, and it feels significant, write it down and make a note of it. Of course, you have to remember where you wrote it down because I have notebooks all over the place that I don't even know where all the wisdom is. I do think you never know who the mentors and the why sages in your life are going to be.  

Sometimes it is some comment that resonates that you know that it was important to me at this point. It can come from some unusual places. Sometimes in the middle of some other conversation about something else. That is important to you because people think about mentors, sponsors, and things like that.  

They think about it in terms of a set way of someone who has been your mentor for your whole career and always there giving advice in more formal roles. That can be true. There are people who show up at the right time with the right message of what you need to grow or to hear at that point in time that resonates with you. That, too, is its own form of insight, wisdom, and mentoring.   

That has certainly been my experience. Same as yours, unique circumstances. Also, people will come out to help you with a particular opportunity that you're applying for. It happens as a coalition comes together at that moment to help make this opportunity possible for you. They may never come together again just at that point they did.  

They don't have to have signed on to be your formal mentor or advisor to be of enormous insight, support, sometimes connections, and access for you.  

That story is helpful for that because people hear things. They say, “Mentor and sponsor. I'm supposed to have one of those and sign one of those up from my life.” It doesn't always look and work that way, but to be open and pay attention to things that can be pivotal for you in terms of opening your mind up to things or opening opportunities.  

Jessica, I enjoyed this. It has been interesting, and I appreciate you joining the show for this discussion. It has been a unique one, which is good. You have a unique path, so it fits. Before I close, I usually ask a few lightning-round questions. The first one would be what talent do you wish you had but don't?  

I would love more than anything to be a phenomenal singer. An effortless, beautiful angelic voice that comes out when you are walking around the house, and everybody is like, “Wow.” I love that more than anything. The fact that I don't have it doesn't stop me from singing while I'm doing stuff around the house, but I would enjoy it even more if it sounded beautiful.  

Who were your favorite writers?  

I have had a hard time with that question in part, especially these last couple of years, with the shortest attention span ever. Reading, I have been doing more of it. It feels a little too obvious and cliche to say Tony Morrison, but she is always my go-to. I wish I had read more honestly. If you have suggestions about writers, I should be reading. I used to do a lot of non-fiction reading, and I feel like now the world overwhelms me too much that I can only read things that I can get lost in. I listen to podcasts to keep me up to date on what's going on in the world. If I'm going to read, I better lose myself in a great story.  

My initial response to the question of those is overwhelming or too much reading going on with work or law school as at work. I had a pause in external reading that wasn't for class or cases in most of the law school, but I started with short stories because I thought, “I can spend twenty minutes to half an hour. I know I can do that. I may not be able to finish this, but at least, short stories.”  

My version of that, which is less intellectual, probably is that I started reading a lot of young adult fiction because they tend to have shorter chapters, and they grab you right away because they are written for an audience that has a shorter attention thing. There is some great young adult literature out there these days.  

That's a growth area in public, and they cover a lot. 

If you need a starting place, John Green is amazing. He also has a great podcast and a book called The Anthropocene Reviewed, where he reviews things in the world. He is brilliant. It's a good place to start, but his books are great.  

Who is your hero in real life?  

The word hero is challenging for me because it feels like putting people up on a pedestal that I'm not always comfortable with because it feels like you set yourself up for disappointment. In terms of hero, save the day people, there were two doctors that treated my son when he was a baby that I genuinely believe are living, breathing heroes. They're both at Children's Hospital of Philadelphia. One is a surgeon, and one is retired now but was the endocrinologist there. They are truly heroes in what they do. Some of these doctors serve and take care of young ill children, which my son, who is doing great now, was ill when he was a baby. Those are living, breathing heroes.  

They are saving young lives. This is an important impact.  

I also think Stacy Abrams is incredible. I don't know if I call her a hero, but she was pretty incredible. When I think about someone who is impressive, I can listen to her speak all day. I don't know if I would call that a hero. 

This might be to next question. They might overlap. Given anyone in the world, who would you invite to a dinner party?  

Prince.  

Tell me how that was best.  

There is no question about it. First of all, he is my favorite musical performer of all time. He is brilliant. To see him in concert multiple times was a mind-blowing experience. He is so talented.  

I have listened to it so many times. The guitar solo that he did with all of the great guitarists blew them all away. It was amazing.  

The entire lifetime of music that has been found in his vaults in terms of a prolific genius, artistic genius. I can't think of anybody who compares. I think he would've also been hilarious to talk to and quirky. I would have loved to be in his presence.  

This person, I'm like, “There is something there. Is there something growing up?” It was a pivotal song or something meant to you. You’re like, “No, he is an interesting person.”  

He was the first artist that I owned every single one of his albums.  

Last question. What is your motto if you have one?  

I mentioned earlier that I say every day, “May I be open? May I be curious?” I don't know if that is a motto, but it is something that I try to remind myself of. Similar to that is the word grace. I have it tattooed on my arm as a reminder because I realize that more than anything, I want to walk through life, giving myself and others grace. Feeling worthy of grace and feeling that others are worthy of grace. It feels like a powerful word to me that shouldn't be reserved for the dancers or the religious folks. I am neither of those two people, and still, I deserve to own, live with, and give out grace.  

That is a beautiful way to conclude our discussion. I appreciate that. I'm going to carry with me that, be open and be curious way of dealing with things and having that openness in life. You can be a little bit too certain about where we're going and what our path is. Don't be afraid to look off to the right or the left to see if there's something else of meaning that you could be doing. Thank you so much, Jessica.  

Thank you, MC. This was fun.  

I enjoyed it. Thanks for joining.  

Thank you.