Chitra Ragavan

Erin Walczewski

Ep. 11 — A reluctant beauty pageant winner finds a unique path to a Harvard education and develops a passion for public service / Erin Walczewski, Attorney, Cooley, LLP.

When Erin Walczewski first entered the Miss Iowa beauty pageant, she never expected to win. Her goal was simply to win some scholarship money for college. To her surprise, the skeptical contestant won the Miss Iowa crown.

Walczewski wouldn’t realize for a long time what the true prize was from that competition.

Still a reluctant participant, Walczewski went on to the Miss America contest, which she lost. But it would prove to be the best loss of her life, giving her the opportunity to do a year of public service in her home state and develop confidence, poise, and invaluable public speaking skills plus enough scholarship funds to get her into college.

Competing in those early beauty pageants continued to have a profound effect on Walczewski’s life and career. She won a prestigious scholarship with powerful mentoring, which eventually got her into Harvard Law School; later, a job on the 9/11 Commission’s Public Discourse Project (PDP) where her public speaking skills from her beauty contest days helped her play a key role in educating the American public about the terrorist attacks; and the opportunity to teach law at Georgetown University and later at Harvard.

As a pro bono counsel at Cooley law firm, Walczewski recently had the chance to go to the U.S. Mexico border to provide legal advice to women seeking asylum.

There, in the process of counseling these emotionally, physically, and psychologically traumatized women, Walczewski truly understood how the Miss Iowa and Miss America contests, in teaching her to communicate with and help those less fortunate than herself, had become gifts that keep on giving.


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Chitra:   Hello and welcome to When it Mattered, a podcast on how leaders are forged in critical moments and how they deal with and learn from adversity. This episode is brought to you by Goodstory, an advisory firm helping technology start-ups find their narrative.

Chitra:  My guest today is Erin Walczewski. She’s a former Miss Iowa who competed for Miss America and went on to earn a law degree from Harvard Law School. She works as an attorney and a lecturer on law at Harvard. Before law school, Walczewski worked in national security notably on the 9/11 Public Discourse Project and she also taught high school English in Japan.

Chitra:   Walczewski currently serves as pro bono counsel at Cooley where she counsels non-profits and earlier this year traveled to the US/Mexico border to provide legal counsel to women seeking asylum. She also is a frequent public speaker and presenter. Erin, welcome to the podcast.

Erin Walczewski:   Hi Chitra, thanks so much for having me.

Chitra:   It’s great having you. What led you to compete for Miss Iowa?

Erin Walczewski:   It’s a funny question. I was just thinking about that in preparation to do this interview with you. And it almost, the fastest way to explain it is that I accidentally won a beauty pageant. We don’t actually call them that. The Miss America organization is very clear that it’s not a beauty pageant, it’s a scholarship competition. That’s actually a joke in the movie, Miss Congeniality, if you ever saw that, which I found hilarious.

Erin Walczewski:   But really I was looking for scholarship money. And at the time I was looking for ways that I could help finance my own college education and found out, found out through a recruiter about the, a local competition for Miss Iowa. And in a nutshell, I said, “No, no, no. I don’t do pageant things.” And they said, “Well, if you compete all five phases of competition, you win a minimum scholarship of $50.”

Erin Walczewski:   And I thought, “Well, I could complete five phases of competition.” And I did. And very surprisingly to me, I ended up winning the local competition. And they said, “So now you have qualified and you’ll go on to Miss Iowa.” And I said, “No, no, no, no, no. That’s a real thing. I’ve heard of Miss Iowa before. I can’t compete there.” And they said, “Well, if you compete all five phases of competition at Miss Iowa, you win a minimum scholarship of $500.

Erin Walczewski:   So I went to Miss Iowa and I competed. And again, very much to my surprise, because I was a novice at this, I won Miss Iowa. So I won closer to $10,000. And then they said, “Now you have won the right to compete at Miss America.” And there I really dug in my heels. And I said, “No, that’s an actual thing. You know, that’s on TV. I don’t think I can do that.”

Erin Walczewski:   And they said, “Well, just for completing all five phases of the Miss America competition, you’ll get $5,000.” So I went to Miss America. I did not win. That’s where the pattern ends. But I got $5,000 for being a non-finalist and another 5,000 for winning what they call the Miss America Scholar, which is an academic award there. So, altogether I got about $20,000 for college.

Erin Walczewski:   But more importantly, be that everyone who loses Miss America goes back to their home state and serves their state for a year of public service promoting a social impact topic that they really care about. So at the young age of 19 and 20 that gave me the opportunity to run a Children’s Literacy Program in Iowa and raise money for that. Which was the entree to so many things now that I can see in my career in terms of public speaking and teaching and a lot of those things.

Chitra:   It’s not often that you hear someone say that they accidentally won a beauty pageant.

Erin Walczewski:   Well, it’s funny because my current job now involves a lot of business analysis. And when I was kind of in the midst of things, I had decided a profit maximizing way to do pageants, which was, I called it a win, lose, win, lose, win, win, win. Which was essentially you can only win a state competition once. Once you go to Miss America, that’s it.

Erin Walczewski:   So you can’t compete again in future years. But it’s not just the winner of the state competition who gets money, the runners up get money as well. And so, I laugh now looking back at my 19 and 20 year old brain thinking about this, but my view toward the profit maximizing way and the most scholarship money possible was to win a local and then lose Miss Iowa. Win another local the next year, lose Miss Iowa again. Win another local, win Miss Iowa, win Miss America. That was the profit maximizing way to go about things because you’d be earning money the whole time.

Erin Walczewski:   But I was, I guess very fortunate in that I won the first time. So it didn’t maximize my scholarship, but it really did maximize the benefit to me in terms of all those opportunities that I just mentioned.

Chitra:   So what did you do next? I guess you went onto college and then after that you did some interesting things.

Erin Walczewski:   That’s right. So I finished college. I went to Truman state university in Kirksville, Missouri. And then in my junior year, mostly because of the public service work that I had done through the children’s Literacy Program, won what’s called the Truman Scholarship. That’s a national scholarship, very similar to the Rhodes or Marshall or Gates that’s for juniors in college who intend a career in public service.

Erin Walczewski:   And because I had an entire year of public service and could show that I had raised $99,000 in support of children’s literacy and had done all this programming that led me to the Truman Scholarship and through the Truman Mentoring Program, they had a very robust system of mentoring where they encouraged people to work between college and law school.

Erin Walczewski:   So, I worked for a while for the federal government, I worked in public relations, I taught for a year in Japan on a teaching fellowship there, and then used all of those experiences to apply to law school, got into Harvard Law School mostly because of the Truman Scholarship. So you can see how from my perspective, at least, all of these things have kind of snowballed off each other.

Erin Walczewski:   So I went to Harvard Law School, graduated from there, became a lawyer, and almost immediately started teaching first at Georgetown actually, and then at Harvard.

Chitra:   And you also had a stint serving on the 9/11 Public Discourse Project. Tell us a little bit about the project and the work you did there and what it taught you.

Erin Walczewski:   Sure. So the 9/11 Public Discourse Project, was a non-profit follow on to the 9/11 Commission. So, as people might remember, the 9/11 Commission investigated the events surrounding the attacks of September 11th and then created a report that had 41 recommendations to increase the security of America.

Erin Walczewski:   They put these out in a report that was unique among government reports. It’s one of the only reports ever that’s become a national bestseller. But part of that was because it was so eminently readable and was written with a narrative in mind. And it started with a chapter that talked about September 11th, 2001 was a cloudy Tuesday, which really made it accessible to the American people.

Erin Walczewski:   But after the 9/11 commission’s investigation work was done, the commissioners themselves and the people on the staff really felt like there was more work to be done to educate the American public about what those recommendations were. So, they created a follow on non-profit called the 9/11 Public Discourse Project. There were just six of us who worked on that, but we worked for two years in Washington, D.C going around the country, talking about the recommendations of the report, answering people’s questions about both the report findings and the recommendations.

Erin Walczewski:   And there again, I was, I think 23 at the time. We had more requests coming into the 9/11 PDP, which is what we call the Public Discourse Project than the commissioners could handle themselves. There were 10 commissioners, five Democrats, five Republicans. All of them had gone back at that point to their regular jobs. And we had more requests for public speaking and for Q and A’s with audiences than we could accommodate.

Erin Walczewski:    So at the time, I had a lot of public speaking experience even as a very young person. And so, the staff of the 9/11 PDP thought it would be a good idea for me to start fielding some of the requests that were coming in for colleges and universities. So, I did that for two years. I traveled around the country and I gave speeches and answered questions about the 9/11 report and the national security recommendations that came from there. And I really do think it was a good connection for college students to see a young 23 year old woman who was explaining these things and talking to them and addressing their concerns about these things at a time when those things were really top of mind for a lot of Americans.

Chitra:   Now, did all of that confidence and poise that you got competing in these beauty pageants and then subsequently all of the work you did in public service, did that help you? Because you were very young going around talking about the 9/11 attacks and it’s a very, very important project that you were working on. Was that helpful to you?

Erin Walczewski:   Oh, absolutely. I don’t think I would have done it had it not been for the year that I spent doing public speaking as Miss Iowa. So, it’s so funny now because I think people tend to think of pageants as frivolous or superficial and I think people can have different experiences. There are lots of different pageant systems and there are big differences among those systems.

Erin Walczewski:   My personal experience was that the experience that I got, particularly from the public speaking and the public events, doing that for a year when I was just 20 years old and doing that on a near daily basis and sometimes multiple times a day is probably the only reason why that’s a significant portion of my career now and was when I was working for the 9/11 Public Discourse Project.

Erin Walczewski:   Because it’s the at-bats and that building of the confidence that you just mentioned that gives you the confidence to be able to say, “You know, I’m happy to field questions from an audience.”

Erin Walczewski:   When I first started, I was really nervous because a lot of times in the pageant context you’re answering questions about either yourself or your social impact platform. So for me that was children’s literacy, that was something I had studied as an undergrad. My mom is a professor of early childhood education. My sister has a master’s degree. This was a very frequent topic of conversation around the dinner table. So I felt very comfortable with that subject matter area.

Erin Walczewski:   When I went to the 9/11 Commission, to their non-profit, I was very new to national security. So when I first started those public speaking engagements there, I was nervous that I would be caught out as not knowing something or that I’d go to a university and some professor would put me in my place by answering, asking some question that I had no idea, you know, given complex context in a region or the area where I wasn’t familiar with the history there. But that’s just not what I found to be the case.

Erin Walczewski:   I found that people were genuinely interested to know what had happened and really interested to know how the commission worked and what the recommendations were. And that I knew backward and forward. So I had a really positive experience and I like to think that those events helped people understand things better too.

Chitra:   A lot of women, as you know of, we all struggle with kind of the impostor syndrome. And it sounds like that’s something you were able to overcome. Because here was a subject, you were steeped in, you had the confidence, you had the knowledge, and you’re able to get out there and share what you knew with other people.

Erin Walczewski:   The imposter syndrome is real and I have spent 11 going on 12 years now at Harvard and I think people assume that everyone who makes it to a very prestigious university feels great about themselves and knows that they’re on the top of the world. But I have worked with literally hundreds, possibly thousands at this point of students and I can tell you the imposter syndrome is alive and well.

Erin Walczewski:   And I think that one of the best things to help people get over it is to really think about your connection with the audience. I actually feel really comfortable in front of large groups of people. And that’s one of the things that has been such an advantage to me in the types of work that I’ve chosen to do.

Erin Walczewski:   I love thinking about what is it that I really want to talk to an audience about? What is that connection? How can I stand in front of a relevant audience and give them something of value? And I think that focusing on those points, focusing on the message, the story that you want to tell and what you want to leave them with and how, what they get out of it is probably the best way to get over the imposter syndrome.

Chitra:   There are many women’s groups, many feminists who are critical of beauty pageants because of how it represents women. It’s just, it represents, they believe, you know, an aspect of women. But it’s so interesting to hear the tremendous value that you got just from competing in these pageants.

Erin Walczewski:   Yeah, that’s something I have thought about a lot. So, like I said, I chose to do this when I was 19 years old and I don’t… and even as a thoughtful 19 year old, I didn’t have nearly the context for what pageants have been historically, what they’ve represented, their connections and disconnects with feminism in America and around the world. But I’ve thought about it and even studied it a lot since then.

Erin Walczewski:   And with the unusual vantage point of having done them. And I will say, I may have mentioned this already, not all systems are the same. So I cannot speak with so broad a brush to say that everyone would get a benefit from doing any pageant system because I do not believe that that’s the truth. I do think that for me personally it was an incredibly positive experience.

Erin Walczewski:   I do because of both the scholarship money it gave me, the opportunity it gave me to be essentially a non-profit entrepreneur while I was in college, taking a year off between my sophomore and junior year to run a children’s literacy program, to do that fundraising, to do those public speaking engagements, and then how I was able to leverage that forward with the 9/11 Commission’s Public Discourse Project work, with my work as an attorney now, as a public speaker, as a teacher, as a lecturer on law school, all of those different things.

Erin Walczewski:   But I can’t pretend like everything about a pageant is positive. You know, people take things different ways and what’s empowering for somebody may feel belittling to somebody else. So, I think that for everybody, it has to be a very personal decision about whether you want to do it, whether you even support it.

Erin Walczewski:   For me, the Miss America organization, which is a non-profit organization focused on things that I really cared about. They score the interview very highly, they have a talent portion, and I was classically trained as a piano player. They emphasize the same kinds of things, including community service and scholarship and academics that I wanted to do.

Erin Walczewski:    So the other things like evening gown and swimsuit, which are actually being reduced right now in the 2019 climate for the Miss America Organization, those were extra things for me. Those were not at all my focus.

Chitra:   You currently serve as pro bono counsel at Cooley. And your focus is women seeking asylum at the US border among other things. Tell us about the work you’re doing. How involved are you with this issue? Where do you go and who are the types of clients you’re dealing with?

Erin Walczewski:   Sure. So, I work for a private law firm, but a private law firm that has a robust pro bono program. So these are lawyers who donate their time for free to people who meet our eligibility requirements for free legal services. So, a lot of what I do is counseling non-profits. And again, I see ties there back to the literacy program that I was running when I was 20 years old.

Erin Walczewski:    I of course, like everything in life, I wish I knew then what I know now because sometimes when I’m gaining new areas of expertise in non-profit law and non-profit management, I think, “Oh, I should have done that 20 years ago.” But the other component to it is, is what you just mentioned, which is individual representation. So for example, earlier this year I traveled down to the US/Mexico border to a very small town in Texas called Dilley.

Erin Walczewski:   They have one of the largest detention facilities there for people who come across the border seeking asylum. This particular facility where I volunteered is through a program called the Dilley Pro Bono Project. It brings lawyers from around the country down for a week at a time to spend, sometimes 12 or 13 hours a day in a detention facility, giving very short legal counseling sessions to women with children. And that’s specific to the facility that I was working in. It’s only women with children who have come across the border and are seeking asylum.

Erin Walczewski:   I’ve read a lot in the news about people worrying that the lawyers are coaching them on what to say. And it always kind of makes me do a little bit of a double-take because a lawyer’s job is to counsel their clients. But I think the implication is that lawyers tell the people what to say or give them false information so that they will qualify for asylum, which of course it would get you disbarred.

Erin Walczewski:   It’s not how things work at all. There’s no need to do that. The women that I talked to… So I talked to a lot of women over the course of the time that I was there. There’s an enormous room full of people and you take one, you counsel her in a small room off to the side. And you ask her why she came to the United States and their stories, Chitra, are terrible. I can’t even get into the details, but it’s… These days they’re mostly coming from the Northern Triangle countries. So that’s El Salvador, Honduras, Guatemala.

Erin Walczewski:   And these are places that, where the police and law enforcement either cannot or will not protect them from daily violence, extortion, threats to themselves, threats to their children, things that you and I have probably never had to deal with. So we help them understand how their story connects to American law, which is the same thing that lawyers do for all of their clients.

Erin Walczewski:   Because the way I explain it to people is a woman tells me about her parade of horribles and the 10 most terrible reasons that she has come to the United States seeking safety. And I’m able to tell her focus on numbers two, six and seven because those are the ones that have a connection to American asylum law.

Erin Walczewski:   Essentially under asylum law, you’re trying, you’re showing that you have a well-founded fear of persecution based on one of five grounds. And those grounds are race, religion, national origin, political opinion, or particular social group. So, there’s no reason why somebody from El Salvador would happen to know these details of American law. So you have essentially 30 minutes with a woman to establish a relationship, establish rapport, hear her story, and then explain to her the grounds for asylum in a way that she can then tell her story to an asylum officer in something called a CFI, a credible fear interview, which is the first stage to being allowed to stay in the United States long enough to apply for asylum.

Erin Walczewski:   If she passes that credible fear interview, she’s allowed to stay for at least the amount of time it takes to apply for asylum. And if she doesn’t, then she’s deported back to her country of origin. And I don’t have the exact statistics here, but the difference between being able to speak with a lawyer even for a short amount of time is staggering.

Erin Walczewski:    I’ll ballpark it to say that I, one of the things I read said without a lawyer, something like a third of the people pass their credible fear interview and with a lawyer it’s closer to 98 or 99%. But it’s because a lawyer can help tell you, you know, you may have had this incredibly terrible thing happen to you, that’s one of the reasons you came. But if that doesn’t have a connection to American law, you’d be wasting your time to focus on that when you’re interviewing with the asylum officer. The second reason is really the one that has a basis in American law.

Chitra:   And what you’re doing is helping them focus their narrative because likely these women are probably in extreme emotional and physical distress. They’ve come across the border and now their fate depends on answering the questions in the right way.

Erin Walczewski:   That’s absolutely right. And it’s really up to them to be able to convey that well-founded fear of persecution to the asylum officer. But as you said, these are not ideal conditions for anybody. You know, we were seeing people within a day or two after they crossed the border, they are first in essentially a ICE detention facility or some other similar facility. And then they come to the family detention facility where we were helping them. But usually the terrible things have been happening to them for a while.

Erin Walczewski:   And then there’s a straw that broke the camel’s back. You know, some of them literally being chased out of their homes by gangs or other people who are threatening them or people who are persecuting them because of their religion, because of their political opinions, because of other things. And so, they have this harrowing journey. Many of them it’s sometimes difficult for me to talk about because all of the women there have children.

Erin Walczewski:   Sometimes you would start with what you thought, what I thought. Or sometimes I would start with what I thought was a basic opening question, like how many children do you have? And that question in itself would cause some women to burst into tears because they had two children and they could only bring one of them with them because they only had enough money to pay for the passage for one.

Erin Walczewski:   And so, they’re in a real life Sophie’s choice situation. And then trying to explain to me how they made that choice and what the factors were that they were considering when they were deciding which of their children to essentially save and which one they were leaving behind.

Erin Walczewski:   So as a mother myself, I have a five year old and a seven year old, that was really hard for me to listen to. But the thing that got me through it was knowing that, our short conversation was better helping prepare them. The last woman that I met with when my week was over had a seven year old boy and a five year old girl. And I have a seven year old boy and a five year old girl. And at the beginning of the conversation we were, you know, bonding over some shared experiences with sibling rivalry and with brothers and sisters taking each other’s toys and that sort of thing. And I thought, “Wow, we have a lot in common.”

Erin Walczewski:   And then very quickly the conversation turned to how she handles that when she has to move her children in the middle of the night because of violence in her neighborhood or against her family. And that’s was just such a stark reality check for me to realize I’ve never had to move my children in the middle of the night because somebody was trying to attack us.

Erin Walczewski:   So, it was a really important and meaningful experience for me as an attorney to know that I could be some small help with these people in this part of their journey.

Chitra:   How do you deal with sort of your own emotional health when you are listening to all of these stories and having to help them in a very stressful moment?

Erin Walczewski:   The biggest part of it for me, I had a background when I was, for 10 years at Harvard, I had done some sexual assault response counseling. And I had to go through extensive training to be able to do that. That was a skill set that I really had to draw upon when I was counseling the women for asylum because of helping people who had been through traumatic experiences and that sort of thing.

Erin Walczewski:   But the biggest factor that really helped me was acknowledging it. If somebody is sobbing and can’t go… continue with a story, or if something that she says is bringing tears to my eyes, it doesn’t do me any good personally to pretend like that’s not happening. So you know, pausing or taking a breath or even pausing to say, “I think your daughter is lucky to have you as a mom,” is the kind of thing that I think is a true human emotion and is something that helped me get through that.

Chitra:    So looking back, you’ve had this amazing career trajectory and one that’s fairly unconventional. You know, you’ve participated in beauty pageants, you went to Harvard, and now you’re helping women seeking asylum on the border. Looking back, does your journey seems to make sense to you? There are these common threads. So, what advice would you give to other women, to others who are forging ahead with their careers in terms of, because there are so many cookie cutter rules and you, and to some extent I’ve had a very unconventional career too. We’ve sort of not really taken account of these rules. What lesson would you impart to people based on your own experience?

Erin Walczewski:   I think it’s important to be self-reflective at every stage of your life and to really take stock of what you enjoy doing and what you’re good at doing and then figure out how to make that a meaningful part of your life and your career. You know, you said, everything makes sense now. Everything makes sense in retrospect because in hindsight you can see those patterns and you can see how those connections lead from one to the other.

Erin Walczewski:   But that it doesn’t always feel like that when you’re in the moment. So, if I think back about what I imagined my life would be when I was younger, I always thought that I would be a lawyer and that my type of lawyering would be helping people. I always wanted to have kids. I never could have predicted though what a large role teaching and public speaking would play in my life and I never could have imagined the details. I never could have predicted the nuances of the work that I do now or the personalities of my kids.

Erin Walczewski:   And those details are really the beauty of life, I think. So, being open to those things I think is the best advice for going forward.

Chitra:   Looking back on your career and on your early days competing for Miss Iowa and for Miss America, is there one moment, a story, an experience that helped you the most to deal with adversity and to deal with the course of your life?

Erin Walczewski:   As Miss Iowa, the most surprising moment I can think of was when they actually announced my name as the winner. I was truly in shock and I have unflattering photos in the newspaper that show me in this state of shock. And then you know right away the sponsors come out and they handed me keys to my new car and the car says Miss Iowa across the front.

Erin Walczewski:   And that all felt so surreal that that was kind of the threshold. That was the watermark point of now you’re doing this thing, now you’re, you know, you have committed if you won. I thought this commitment meant nothing because I had thought I had no chance of winning, to taking a year off of college, to doing this community service work.

Erin Walczewski:   But if there was one moment, I think that really helped me in the kinds of things that you were just asking about, it was actually in my work with the 9/11 Public Discourse Project. I had traveled to in the West and was doing a public forum there with questions and had a very hostile audience member who was a 9/11 conspiracy theorists and thought that I was there to spread lies from the government and ended up having to be removed by the security of the building that I was in because he became so hostile and aggressive and threatening to me.

Erin Walczewski:   So that was a little bit of a scary experience because I had never gone through anything like that before with an audience member who was openly threatening me in front of a group of people before. But when I got through it, the rest of the audience was so on my side and was so rooting for the kinds of ideas that I was talking about that it showed me how getting through a small piece of adversity can really strengthen your resolve and can really actually end up being a positive experience.

Chitra:   Erin, this has been a great conversation. Where can people learn more about you?

Erin Walczewski:   I’m on the on the web, on Harvard’s website, on Cooley’s website. I teach classes outside of Harvard, standalone classes on everything from negotiation, to design thinking, to small talk and I travel around the East Coast a lot.

Chitra:   Fantastic. Do you have any closing thoughts?

Erin Walczewski:   Thank you so much for including me. I think what you’re doing here in highlighting people in their narratives is a wonderful way to help people connect with your audiences and I just want to thank you for inviting me.

Chitra:    Thanks so much.

Erin Walczewski:   Thank you.

Chitra:   Erin Walczewski is pro bono counsel at Cooley Law Firm and an attorney and lecturer at Harvard Law School.

Chitra:   Thank you for listening to When it Mattered. Don’t forget to subscribe on Apple podcasts or your preferred podcast platform. And if you liked the show, please rate it five stars, leave a review and do recommend it to your friends, family, and colleagues. When it Mattered is a weekly leadership podcast produced by Goodstory, an advisory firm helping technology start-ups find their narrative.

Chitra:   For questions, comments, and transcripts, please visit our website at, or send us an email at Our producer is Jeremy Corr, founder and CEO of executive podcasting solutions. Our theme song is composed by Jack Yagerline. Join us next week for another edition of When it Mattered. I’ll see you then.