Analiza: Welcome to the Women of Color Rise Podcast. I'm Analiza Quiroz Wolf, proud, Filipina American mom of two, and former CEO of a nonprofit and Captain in the US Air Force. I'm on a mission to support having more diverse leaders at the table. We'll be talking with successful CEOs and C-suite women leaders of color and learning about their leadership journeys. If you're a woman or woman of color, who wants a seat at the table, you're in the right place. Now let's get into today's show.

I'm really excited to be talking with Melissa Wu today. Melissa is Taiwanese American. She's also the CEO of education pioneers called Ed Pioneers. And before Ed Pioneers, she worked as a partner at TNTP. She was a consultant for the Boston Consulting Group and she spent a lot of her career on issues of teacher retention, school and system improvement as well as performance management. She has an MBA from Harvard Business School, and she has a bachelor's from Princeton. She's also a University Trustee there. Finally, she's a mom to two kids who are six and eight. I'm really excited to talk with you, Melissa, thank you for being here.

Melissa: Thank you so much for having me.

Analiza: So Melissa, we're gonna learn all about you. And the question that I always like to start with is the journey of your life starting from upbringing to how did you get to this big job that you have now?

Melissa: So that's a big question. And one that can be answered in so many different ways. But I grew up in Massachusetts, where I continue to live now. And I grew up in a community that had really amazing public schools and was also predominantly white. My mother is white, my father is Taiwanese. And I think I start with that, because it was really a big part of my experience as a kid being one of the only families being part of one of the only families of color being one of the only, you know, multiracial families in the community. And I didn't experience overt racial oppression through that, but I did often feel marginalized, I often felt other and it's very clear to me that I was different, how it was different. And that experience of sort of being on the outside on the periphery, I saw the ways in which I think structural and systemic racism were playing out in communities in culture. And I think I can access that because I had a lot of access to any space I really wanted, but still have kind of the position to be an outsider within that. And so I had kind of an interest in issues of social justice issues of education. I come from a big extended family, my dad's one of seven kids, my mom's one of three, there's, you know, my mom's side of the family, there wasn't a super strong college going culture, my dad's side with him, and there wasn't really strong culture and culture. And so across 21 first cousins across this big family, there was a real diversity of experiences. And even within just my dad's part of the family, there was still real differences between, you know, my cousins whose parents worked in a laundromat in Jackson Heights, Queens and my cousins whose parents were chemical engineers, you know, 30 miles away in Brunswick, New Jersey, and just seeing the ways in which all of that played out in their life experiences in their opportunities meant that when I went to college, I carried with me a real sense of understanding that I had of my own privilege, actually, that I had gone to this really strong public high school that prepared me well for a top college where it wasn't unusual for most of my classmates to be going on to four year colleges and many of us to be going to elite universities, because I went to Princeton undergrad.

There were a few important experiences there. I actually participated in a fellowship program as a sophomore, I had had jobs growing up, but they were, you know, at the summer camp that I had gone to as a kid, and that was what I usually did during the summer and somewhere I was like, Okay, I guess I can't be a summer camp counselor anymore. I need to actually go and like get an internship. But I didn't really know how to do that.

My RA from freshman year was helping lead a program called Princeton Project 55. That was before the days of the Internet and job boards before the days of even idealist.org. There were not really clear pathways for students at places like Princeton to enter the nonprofit sector. And this program, Princeton project 55 was doing just that, matching current undergrad with summer internships and recent graduates with your own fellowships in the nonprofit sector, and now select seven cities.

So I did through that program, a summer internship in Boston with Oxfam America and just had my kind of world blown open because I didn't really know that you could get paid to fight global hunger, poverty and inequity and I sort of felt like I had really won something big and realizing that because I had grown up in a family where service was a big part of how my mom raised us. It wasn't a big showy thing. I didn't have a lot of community service hours, it wasn't always really formal. But we were always going to church, we were always going to the local LDH home and just chatting with residents or doing projects. And my mom ran a 4H club, I started before 4H club as a high school student.

So this just kind of this being in community and an orientation towards like, hey, if there's stuff that's wrong in the world, you should try to fix it was something that I was really raised with from a young age. And so it was so exciting to realize, like I could do that work, which felt really important and really fulfilling. And I just didn't really realize you can do it outside of volunteering. So that was one kind of big pivot point.

I ended up pursuing that after graduating as well and got a year long fellowships through that same program. And the year-long fellowship was, I think, really important, because it gave me an opportunity to see through my peers as part of a cohort in a way that was more defined than in my summer experience. And I got to see New York City where I did my fellowship placement at a startup called the TEAK fellowship. We got to see all sorts of issues, you know, housing, legal, criminal justice, you know, like all aspects of the city, I was working in education that a college access program at that point, but it was an exciting moment to like, look at all the issues that I was interested in as measuring in sociology.

So I was really interested in all of these issues. And what were the root causes, the injustices that we saw and what we now call the opportunity gap in one language at the time, but I was really interested in where those things came from. And they came from places like housing, they came from economic inequality. But it was such a great laboratory to get to see that and to also play out some of my own thinking of what were some of the actionable levers. So I went from that experience, I stayed with the TEAK Fellowship, which was a brand new organization, I was the first full time employee as like an assistant to the founding executive director. I stayed there for six years kind of growing with the organization taking on different roles, year over year, ultimately serving as the deputy director and managing all of our staffing programs. I supported fundraising at various points throughout my trajectory there. But after six years, found myself really proud of the organization we had built and the lives of the students that we were touching and the families, but also recognizing that the work that we were doing as an academic enrichment program, we were helping talented kids from low income families get into and succeed at top high school, so they be prepared for success when they went on to top colleges,

I found myself working on a program that was an intervention, you know, really still concerned about what were the systemic issues? And what why, you know, if we were touching 150 Kids in New York City, what about the million students that weren't in our program? And what were the options for them? And why? How are we getting underneath the problems there, but this is where I maybe was thinking about going and getting a master's in social work or a public policy degree, because that's where my interest had interests were. And I got a lot of advice from a lot of different people that I should really go and think about getting an MBA.

I took this advice and went to Harvard Business School to kind of sharpen a set of managerial and leadership skill sets, that kind of lots of people were telling me or in demand everywhere, really important everywhere, but also weren't necessarily being cultivated in the nonprofit sector, either as intentionally or with the level of kind of resource that places like an MBA program would bring to it. So did that. But a couple years after that in for profit consulting, the firm called the Boston Consulting Group, trying to deepen those skills, exploring if there was a different kind of lever for impact from the private sector, before ultimately coming back to education but through those roles at TNTP. And then ultimately, education.

Analiza: Thank you, Melissa. And I want to bring us back because your explanation of growing up as a Taiwanese American in a predominantly white neighborhood, and seeing the discrepancies within your own family have the opportunity gap. And I'm curious, thinking back about this because we were told things about what it would take to succeed and what it would take to rise in your career. And if you'd plan to do nonprofit, I'm curious if you can remember a few of these myths that you were told by family or teachers. And what you found was actually true. And what you found were actually not?

Melissa: My experience was more just not actually knowing what else was out there. Sort of actually an only understanding and knowing about the career path that I had literally seen in my family and that my family had access to so my father was an electrical engineer, but he just gave them the engineering track. My mom had been a teacher at some point, she started a small company with my dad doing, you know, kind of like small scale entrepreneurship, but she worked part time growing up so I didn't have a lot of broad exposure to bears through my parents. And even if I think about my extended family, you know, folks were a lot of engineers, some doctors Like, you know, my uncle from my mom's side worked in more sort of like retail settings, service settings. I didn't know about this whole class of careers in the nonprofit sector in general management either.

The myth that I think that I probably internalized was one of meritocracy. And just being really achievement oriented is kind of like the path to success if you just keep working really hard if you keep really grinding. And if you work hard enough, like you'll get to that next thing, the myth of meritocracy, like doesn't take into account, what's your context? And where do you start in the race, you know, for the finish line? And what kind of opportunities do you have to develop, we have to like, unpack, you know, what privilege and what isn't, you know, in our own lives, and in the systems that we're operating. But there's also I think that like a fulfillment that's implied in striving and being the best that is like fully possible, and not always, like the SIR being the best is like, often not possible. And being the best or achieving continuous achievement may or may not be fulfilling, right? I think that that's one of the things that I have grappled with our lesson learned over time, particularly around, like how valuable it is to learn through failure, how important it is to fail, and also how valuable it is to take risks that allow you to learn, and that's I think that achievement orientation kind of builds a risk aversion, you know, I mean, Put differently, like, a fixed mindset orientation growing up, as opposed to a growth mindset orientation growing up, and having some of that can play out over years and making some lessons harder over time.

Analiza: There's so much there. I'm thinking to myself, this idea that there are specific careers, and the careers are the ones we know of, and actually, there are so many more outside of what is in front of us. The second is that if you work hard, you'll achieve. It's all about working hard, doing your best. The third is that achievement is fulfillment. And maybe not always, that's true. The fourth is, don't risk, don't fail, do the very best you can but really don't take a ton of risks. So entrepreneurship and things like that just are less interesting, and harder to choose because you're just trying to go on this meritocracy achievement path. And so these are really great, because I learned these two as a kid growing up and trying to be the best kid I could be. And I'm curious for you, Melissa, through the different paths you've taken. Is there a particular example that comes to mind for you, where you learned one of these lessons and are a couple of them?

Melissa: Yeah, I think the failure lesson is the one that I've liked, worked on the most over time and feel those maybe where there's like, feels like the one to start with. I had an awareness that there were, or even in college, that I felt myself holding back on efforts in places that were hard, and actually capping my own learning and exploration and opportunities, because I was afraid of failing. And I could recognize that happening while it was happening. But I wasn't yet able to disrupt the behavior. So I was actually like, you know, Princeton is the kind of place where there's a lot of social pressure to conform. And there's a lot of people going in paths that were completely unknown to people going into investment banking, people going into consulting, people going into these like business fields, I didn't know anything about them. And there was a bit of pressure to be like, gosh, to all these people who majored in econ, and engineering and are going into these fields, they know something that I don't know, should I be trying for this. And so there was as much as I was drawn to the social sector for like, very genuine like this, were my heart. And it's where I spent my career. And it's like, I wouldn't trade it for the world. But there was also a sense of like, I think I can get a job here. I think I can, I think I can find a place to contribute. And it felt a bit like state planning in some ways. And so I wasn't able to kind of recognize this in myself, but not as able to confront it. And then, you know, I had some failures early on in my first job. I had a lot of qualifications as a newly minted, you know, college student, but I also had no experience like really working in the real world, right.

I had a couple of internships I had, you know, had responsibility, but it's very different than having kind of a like a nine to five job and I was responsible for editing our newsletter and at one point, you know, I like sent to print a newsletter that had typos in it and my boss was so she's wonderful. I worked with her for a long time. She was so disappointed and she was so angry at me because it was a really expensive startup organization. It was not like this was a mistake with consequences and she also was really betrayed and damaged with trust. And I think it was one of those that was one of the first times I had made like, a real mistake with real consequences and the consequences getting paid for like not that huge, right? It was money, it was time, but I really damaged her trust and faith in me. And that was hard.

But I had to; there was the two of us at that point, it was me and this founder, sitting in the basement of school, trying to start this organization. And our primary means of generating income was sending this newsletter to people who might support our work, and they could send donations back, right. So this was an important thing to us was also how we were spreading the word about the organization. So there was no choice but to kind of pick up the next day and go back and do that editing, like read the article, read all of our articles, really carefully fix all those mistakes and get it back out to the printer. So I think that was like an important experience of like, that felt awful. And I got through it. And I recognized that I was going to have to work twice as hard to kind of like, you know, to do that work well, later. I think that experiences like that gave me more confidence and being around young people and watching kind of the importance of their own learning experiences and seeing their bravery. Like the tick fellows. They were pushing them to try new things to try new experiences. We were pushing them to be on their outer limits. And I recognized, like, Am I really doing this right, myself. And that's part of what pushed me to, you know, to leave teak to kind of expand my boundaries and go do something like go to business school, right? That was a little bit of a leap of faith and giving, trying something that I didn't know that I would be good at trying to feel more competitive. I ran for Section president as even like, that was me putting myself out there. And I did not win. And I was not surprised that I didn't win. But it was the thing that I was like, I should try this. I've never liked running for office, even though I sort of feel like I have something to contribute. And I can be good at this job. Right? So there were a bunch of experiences like those even going to consulting was a, you know, the career counselors who are saying, this is like, this is a hard path, it's super competitive, like, you don't really have a background, that's going to make sense. So you're gonna have to work twice as hard.

I think I had to prove to myself that I could put in the work on something that I wasn't expected to be successful at. And that if I did that, like, you know, I was successful in that endeavor, right? So there were this set of experiences, you know, most of which aren't clear, some of which are clear, mistakes or failures, but many of which are like much more of a muddle, right. Like, was I successful in business school, I mean, I graduated, I learned a bunch of non people, I have friends, like, Yes, I was successful. But that experience was also very difficult on a bunch of personal levels while I was there. And I think that that whole stretch of time was a series of me pushing myself out on the ledge and forcing myself to take a leap. And, you know, some like whether it was a clear success or a clear failure or something in the middle, kind of realizing that like, I could handle that, or I could survive it, I could learn from it. And I would like, get better for the next time.

Analiza: It makes sense that there are these paths in the road and to make turns when you don't know where the road is headed. Those are risky. And yet, there's, as I listen to your story, there's a piece of, I want to try to do it and see if I can do it. And wow, I can do it. And then what's the next thing where it's going to be hard as well, I might risk and fail, I will risk and I might fail, but I'm going to try to do it anyway. And I want to tie that idea to this concept of striving. You'd mentioned before that when you strive to achieve that we expect fulfillment. So I'm curious if that theme applies here in your hard, hard work, whether it was HBS, or onto consulting, and working there for multiple years. I'm curious, did you feel fulfilled?

Melissa: Yeah, I don't know that I felt fulfilled in those years. I mean, then that's because there's so much more to life than just I think I felt a lot of fulfillment, my first kind of six or seven years at it, I was doing work I really cared about I had community that I felt really connected to I lived in New York City for that whole time. And, you know, six, seven years in New York City as somebody who wasn't from there, like I stayed long enough to like, make it my own. And I spent most of that time in Alphabet City in a very particular neighborhood and had friends from lots of different parts of life. So I felt really, do you think I felt fulfilled in that period of time, and I didn't, I didn't have a family yet. But it was like I was in my 20s. And I didn't feel like I needed that. But I had community and I felt grounded. I think that as I was going through this next phase, which was necessary to kind of realize the ambitions I had for myself professionally, I think I sort of started to like, hit a ceiling and work wasn't as challenging. I was offered a path to stay at the tech fellowship and take the leaders. You know, our founder was getting married and living in California. So there was an opportunity For me to stay on and leave the organization, but ultimately I kind of recognized Gosh, I'm a big fish in a small pond here, this is the only job I've ever had, I want to expand my horizons for me to feel fulfilled, I will need to kind of, you know, test myself a little bit and try something different to myself a bit more. So I do think that the whole pursuit was important to feel satisfied and fulfilled. But I certainly don't think it was enough. And that kind of phase of the journey that I was talking about where I was testing myself a lot, I don't think wasn't feeling particularly fulfilled. And that was, I think a combination of it was a hard period, I didn't feel as grounded.

I mean, as a graduate student, you're moving between you're changing communities, you're building new communities, you're moving between communities, HBS was, I did not have a great experience at HBS. On a personal level, it was, you know, I described it as being a highly conformist, risk averse and sexist place, which was a really hard place to be as a older student, I was super old, but I was seven years at a college and kind of like the older quartile, probably in my class, as a woman, as a person from a non traditional background, as somebody who saw the world pretty differently from many of my peers, it was a difficult place to be, you know, speaking out a different truth than other people kind of, you know, expected. And so that was like a part experience.

And my time in consulting was like, interesting, and pushed me to grow, but wasn't like I didn't have at that point, I was like, wanting to find a partner. And I like thinking about other parts of my life. And it was, in some ways work was actually planning a lot of that out that period of like, really testing myself and pushing myself to take risks was less about trying to seek fulfillment, I think and seek achievement, as much as it was almost exposure therapy to not achieving, and recognizing that's not the end of the world. And that is not necessarily an indictment on me as a person. And that was like, I think that was really the work was the flip side, the negative side of that, which is like, it's okay to not be successful. And that doesn't actually like, that doesn't define, right, like it was more about, I think, times that it didn't work out as anything else.

Analiza: I really appreciate the idea that we can try things that we might not be great at. And that might not lead to anything in terms of the next step, wanting to, for example, be a full on partner, as a consultant. And it's okay, we can try things. And that's the point. We tried it. And actually, now we're clear, we don't want to do that. And so, in the course of my career, I was reminded of this book that I just heard about, called the Second mountain. And as we look at these careers, and think about next steps, and pivot points, where can we contribute? Where can we learn? Where can we grow? And then also, where can we build a community, because that's something I've heard in your story, especially those first years at a college, when you felt like you were contributing to something bigger, you're part of a team, and also part of a neighborhood of people that you felt close to, and you're learning and growing. And it felt so in sync until six years later, you're like, I want to continue to grow in a different spot. So there's change. And so it brings me to this question of becoming CEO. And I'm curious, did you have in your sights, I'm going to be CEO of an edge, perform organization one day, as you plan this career? I'm curious if that was something that you had always wanted?

Melissa: No. One word answer is no. Part of why I left TNTP, which was like really how I got to this seat was I was at this really tend to be at the time was like three or 400 people. It was becoming a professional services organization.My heart is not that was one of the things I learned at BCG, I was not cut for, like professional service organization like it was I'm more of an operator than a consultant. And I had had these roles at TCP that were where I got to be like a little GM, like a little mini, you know, like general manager or leader of a specific line of business. And I loved that. But Scott Morgan came and talked to me and I was like, wow, this is kind of my dream job. There's like a bunch of thorny problems here that don't have clear solutions. I like that kind of thing. It's an executive level role. I'm interested in trying that out. But I actually saw myself often. I often saw myself as being better suited to playing the number two role, but 10 months into my tenure at education pioneers. You know, I think Scott, like to recognize that he wasn't the right leader for the right phase, decided to step away. And then pioneers were actually headed towards a financial crisis that was partially but not fully diagnosed. I got pulled into this CEO and enterprise leadership position, and we didn't really have the time to do a national search, it was clear that we needed to make some changes, and we all kind of like we looked around and it sort of became clear that I was probably the right person to kind of step into spots into Scott's seat. So I would say that it was definitely not my plan. If I hadn't ruled it out, but it was definitely not in my near term plan, there's a great quote, which I am not going to be able to identify who said it at this moment. But I heard it in the Dr. Kay conference. And it really stuck with me, which is 50% of the crisis. Leadership is the decision to like, take a step forward, I had a moment I had a choice. And I think that I didn't necessarily feel like I had a choice, I felt like I had a lot of obligation to the team and the people in the organization and the work, I really believed in the mission and the work. And so I think I felt, you know, duty to step into the role as well, like, there was a need for something and I could contribute, I don't know, you know, if I will seek out other enterprise leadership roles, because they're hard, they're, they're lonely, they're hard. And I think you've got to really, you know, be up for it and have the energy and commitment for it. And so I could find myself in a very different kind of role after this one.

Analiza: There is an interesting point about what you had mentioned, about not necessarily wanting the role, and even after this role, not necessarily pursuing the top role again, and it's a theme that we hear in research, and other women, like yourself, are really amazing at their careers, they don't tend to want the top seat, it's all about the work, let's do the best we can really mission driven. And while we have our male counterparts, who are like, Yep, I want the top seat, I can have the most impact there. It is about some power. So it's interesting to see the contrast and that there is some, you know, gender bias in play. And so I'm curious, because you just mentioned, the top role is incredibly difficult. So could you share a time when you learned what it would really take to be successful in your role, and also being a mom also tried to have a personal life?

Melissa: I'm still learning, even with all of that context training perspective. And I had read I, you know, through again, HBS news networks, like you read things in HBr, and whatever about the jump, right, and how lonely it is at the top. And I was still kind of unprepared for how far the distance was between being the chief program officer on an executive team, to being the CEO, and suddenly not having any peers. And suddenly, not having a boss, only having a board, I think that like leading in a crisis forced me to figure out how to compartmentalize for my own sanity. And I had really tiny kids, they were, you know, probably roughly two and four when I became CEO, I think that through that my ability to compartmentalize and recognize that I can't be both a CEO and a mom, at the same time, I need to be focused on being a CEO and the moments that I'm doing that. And then for my own sanity, I need to be focused on being a mom when I'm doing that.

And so I think I drew boundaries around certain times, and then but also just my own kind of mental energy and space. I think I also just had to get comfortable with being good enough. And that was really hard because I had gotten to the positions I've been in by being excellent, you know, and that that was the bar and I was striving for excellence. And now it's a question of like, not can I do things excellently? But can I do all the things or enough of the things or the like, really, it's about can I do enough of the most important things well enough that we live to fight another day as an organization that my kids can continue to grow and make progress, right. And it's I think, consistently making those calls but that involves being comfortable not doing everything and data is hard and continues to be hard.

Analiza: Thanks, Melissa. Such a thorough answer. Alright, we're gonna move to our last questions. Lightning round. Are you ready?

Melissa: Yes.

Analiza: Okay, chocolate or vanilla?

Melissa: Chocolate.

Analiza: Cooking or takeout?

Melissa: It depends. Cooking.

Analiza: Climb a mountain or jump from a plane?

Melissa: Climb a mountain for sure.

Analiza: Have you ever worn socks with sandals?

Melissa: I don't think so.

Analiza: How would you rate your karaoke skills on a scale of 1 to 10 and 10 Bring Mariah Carey ?

Melissa: 7

Analiza: Recent book you read?

Melissa: I just finished Harry Potter. Number six, my daughter.

Analiza: What's your favorite way to practice self care?

Melissa: I like spending time with friends, especially in beautiful places.

Analiza: What's a good professional development you've done?

Melissa: I am currently in a heart cohort 39 which has been amazing so far, and I'm still in the process, but it feels super profound and important. To her. It's amazing.

Analiza: What's your definition of a Boss Mama?

Melissa: Oh, man. I think that's the wonderful thing about that phrase is it can mean so many different things. But I think that moms boss right, right moms who are leaders in their organizations, I think that's really incredibly important community and corporate people. So that means that to me, but it could also just be a mom. I'm just tossing in anything, right? Because I think that term can play as well. What advice would you give your younger self? I push myself to take those risks earlier to start experimenting and leaning into like being as focused on like not taking learning for granted being as focused as learn on learning as achieving.

Analiza: Where can we find you like LinkedIn or any other social media?

Melissa: LinkedIn was good, I'm working on my social media. Let's put it that way. So there, I do have a Twitter handle, it might become more active sometime soon. But does have LinkedIn and Twitter probably.

Analiza: And last question, do you have a final ask recommendation or any parting thoughts for the audience?

Melissa: I think we just we, the last few years have been an exercise in like finding the space where we can be both gentle with ourselves and each other and give each other ourselves and each other Grace without compromising. Like what it is we're trying to do. I think finding that boundary is so hard and so important, so that we can continue to do all this really important work, but in ways that aren't in ways that are truly sustainable, truly sustainable in that like, we actually have, you know, the people and energy and the capacity to keep at it because the road is long.

Analiza: Melissa, thank you so much for your time and sharing your story. I really appreciate it.

Melissa: Thank you. It's good to talk to you.

Analiza: Thank you so much for carving out time today to hear today's podcast. Three things before you go. First, if you found it helpful, please leave a five star review. Second, please share with someone else you can share the link and posts on Facebook and say check it out. Lastly, I want to thank you for being a listener and you can go to get a free self care bonus called Juice your joy at Analizawolf.com/freebonus. Thank you so much