Last week, my husband Marcelo and I watched the first episode of HBO’s Insecure, which IMDB describes as “follow[ing] the awkward experiences and racy tribulations of a modern-day African-American woman,” Issa Dee. About five minutes in, Marcelo paused the show and said, “I like this, but the title doesn’t make sense. Issa’s so beautiful, how could she be insecure?” Marcelo and I talk about gender inequality on a daily basis, so I knew the question was really a comment meant to start a conversation — one that has continued internally for me all week long.

So, let me tell you about my battle.

I was lucky enough to MC a recent summit for young women on resilience hosted by Running Start. Our original working title for the event was FAILURE because women are too socialized to fear failure (which can hold them back from taking risks like running for office). The Resilience Summit (its final name) was a positive day filled with strong women talking authentically and publicly about bouncing back. I was completely in my women’s empowerment element when a man approached me during the coffee/cookie break to ask why I had chosen my outfit for the day. I told him truthfully that it was first clean thing I saw that I knew fit on a morning when I was rushing to get to work. What I didn’t mention was that a couple weeks earlier I ripped three different pairs of pants in a single week at work. Perhaps they were old, but I had probably also gained weight, so I was trying to avoid wearing pants at public events.

Like many women, I’m accustomed to men making comments (negative or seemingly positive) about my appearance. Whether it’s the cashier at a local 7–11 telling me how much he liked my body (I stopped going to that one) or a man I sometimes ride the elevator with at work who’s said he doesn’t like my outfits or that he thinks my shoes are inappropriate. I’ve learned to insincerely laugh, awkwardly smile, turn away or redirect these types of inquiries or suggestions.

Tweet from Christina Ayiotis, with photo of Melissa Richmond starting the event.

But during that particular snack break, my usual defenses didn’t work. The man kept pressing. Did I choose the dress because it was pink? Did I think it made me look hot? Did I think I was better than the other females in the room? Wasn’t it inappropriate? The dress was pink because I got it for my sister’s wedding reception and it matched what my mother was wearing. I didn’t think it made me look hot. In fact, moments before this encounter, I had been hesitant to retweet a quote because it included a photo that I thought made me look fat (an unforgivable taboo for women appearing in public.) And, the other women in the room (who he referred to as “females”) were my colleagues and friends — my professional network and support system. So, no, I didn’t think I was better than them. But, after all of that questioning, I started thinking that maybe the dress was actually inappropriate.

I finally stopped his questions by saying, “I’m the MC. It’s my event. I can wear whatever I want.” And even though I consider myself a confident woman, I walked back to the stage feeling insecure. It was harder to stand up and introduce speakers when I knew for certain that the negative internal dialogue I was already having about the dress was being reinforced by a man in the back of the room. A man who had paradoxically also just accused me of choosing it because I thought it made me look hot and therefore better than other women, which made it inappropriate.

Although I was distracted by this conversation and by my increasing concern about my appearance, I was also pleased with the day because the Resilience Summit was a tremendous success! The people who spoke (Congresswomen and a Congressman, a Canadian MP, plus business leaders and celebrities) were vulnerable and inspiring in talking about their failures. It was hard not to get wrapped up in their amazing energy. But as we debriefed at the end of the day I had a sinking feeling and even felt compelled to apologize to my team for dressing “inappropriately.” I was worried that I had failed and embarrassed them.

The response of my Running Start colleagues was unanimously supportive and loving. They didn’t think my dress was inappropriate and were anxious to see if we could figure out who the man was. Interestingly, as far as we could tell, he didn’t RSVP or check in. He just showed up. And not only did he attack my dress and professionalism, he had also taken the time to make a strange criticism of the event. He thought businesswomen on a panel who were asked about #MeToo should have been compelled to disclose a specific personal experience because he was so sure they had one, rather than offering their thoughts on the movement. And with me, he won the battle. In that moment, he made me feel insecure about my body and my choice of what to wear.

But I won the war. Because I was the MC. Because the Resilience Summit was a home run. Because I have the platform to write about the experience for POLITICO’s #WomenRule. And because I am going to tweet this article out as a comment on the photo in which I thought I looked fat and then email it to every attendee of the Resilience Summit with pride, hoping he somehow made it onto our email list.

P.S. To Issa Rae (the creator and star of Insecure) and Marcelo, it took me a week to crystallize my thoughts: I hope the show is called Insecure because Issa is fighting feelings of insecurity thrust on her by the world, not because she is insecure. And I hope I can say the same about myself.

Melissa Richmond is the Vice President of Running Start, a nonprofit, nonpartisan organization that trains young women to run for political office. Melissa worked for Gov. Mitt Romney for 10 years and is a graduate of Brigham Young University, George Washington University Law School, and the Women’s Campaign School at Yale.

Candid About Confidence

“What would you do if you knew you couldn’t fail?”

I bet you’ve been asked that before. Would you ever try to get your writing published? Tell your crush how you feel? Run for office?

Too many people, especially young girls, are taught that things are only worth trying if there is some guarantee of success. Failure can seem like a miserable dead end instead of what it actually is — the only path to learning, growth, and confidence.

Girls’ leadership researcher Rachel Simmons flips that question on its head: “What would you do even if you knew you would fail?” Translation: what experiences are worth it, even if the end result isn’t a success?

At Running Start, we train young women to run for office, and our message is that the mere act of running is worth it in and of itself. Regardless of whether you win an election, by running, you are building new skills, expanding your network, and setting yourself up to do better on the next try.

The key to all of this is CONFIDENCE. Lately, lots of people have been talking about it. Earlier this year, Rachel Simmons released Enough As She Is: How to Help Girls Move Beyond Impossible Standards of Success to Live Happy, Healthy and Fulfilling Lives. Katty Kay and Claire Shipman just translated their groundbreaking research for a new audience with The Confidence Code for Girls. Pop stars are even singing about it. This July, Running Start is holding a summit on how to build political confidence by learning from failure.

But what does confidence and failure mean to actual young women? We sat down with four of Running Start’s high school summer interns to see how they see confidence affecting their everyday lives.

What does being confident look like to you?

Caroline: To be confident is to be self-assured and to believe in yourself. Confidence manifests itself in a number of ways, from being outspoken, to not being afraid to present your ideas, to being a leader. To have confidence is to know and to accept who you are.

Sidney: I relate confidence to passion. I’ve found that those who are passionate about something are more confident than those who aren’t. For some people, confidence is a terrifying concept, but if you are truly passionate about something, whether it be derivatives or Charles Dickens, the passion is able to override the fear, and will make you confident.

Mallory: To me, being confident means being able to trust in myself and my abilities. Confidence means presenting my ideas without disclaimers that undermine their credibility. Growing up, I often thought I had to know all the answers or speak the loudest to be confident. However, I now see confidence as being able to take ownership of my strengths while also being comfortable enough to ask questions, learn, and take risks.

Maia: I guess confidence to me is more about unapologetically being myself, and less about not caring what people think about me. I think that this distinction is key because it makes the idea of confidence much more accessible to everyone.

How would you rate your current overall confidence level?

Caroline: Overall I am a fairly confident person. I am generally outgoing, and I feel comfortable in large crowds. I have never felt afraid to speak up in either social or academic situations. I am a take-charge person, and often will be the first to step into a leadership position if given the chance.

Sidney: It depends on the situation. Outside of social situations, I would say that I am extremely confident. It takes a lot of self-confidence in order to attend college abroad, and I’m not scared to speak up for myself in a professional setting. When it comes to social situations, I’m timid, but I’m working on it.

Mallory: I would say that my self-confidence is a work in progress. I often catch myself second-guessing my decisions or doubting my argument if someone in class disagrees with me. However, throughout high school, I’ve gained a greater awareness of these habits and have consciously pushed myself outside of my comfort zone by doing things like running for student government. Today, I’m confident in my academic skills and enjoy embracing new experiences.

Maia: I honestly don’t think I would rate it pretty high. I’m a pretty nervous person and having any sort of attention makes me uncomfortable. However, I do think that since the beginning of high school my confidence has grown tremendously. I have many people to thank for that and I am now someone who is even comfortable bragging about myself.

Do you see a difference between the boys’ and girls’ confidence in high school?

Caroline: In my experience, boys and girls my age have very different levels of confidence. This is especially obvious in an academic setting. Girls tend not to answer questions in class unless they are 100% sure they are correct, whereas boys will just throw out an answer. Girls are afraid to be incorrect in front of a group of people; boys aren’t. In social settings, I feel that young men and women are equally likely to speak with confidence.

Sidney: I would say that there definitely is a difference between boys’ and girls’ confidence in high school. Confidence levels depend on the individual, but generally speaking, the boys are more confident socially while the girls are more confident academically. I think this divide has more to do with perfectionism than anything else; the boys aren’t afraid to make mistakes, leading them to take more risks, while the girls spend a tremendous amount of time perfecting their work.

Mallory: Though I attend an all-girls high school, I participate in weekly Government Club meetings with my brother school. At these meetings, I’ve noticed that the boys give speeches more frequently, and they also frequently do so with little to no notes. In contrast, some of the girls, including myself, feel reluctant to talk unless they have done prior research or have a fully written and edited speech. I think this difference reflects how women often internalize the pressure to be perfect and, as a result, don’t feel confident enough to just stand up and speak their minds.

Maia: I don’t think that there is a difference in the level of confidence between to two, but I think that the boys, that I know at least, all seem to show their confidence a lot more. Meanwhile, the women I know have this wonderful secret confidence that I think they don’t exude as much in everyday life.

How does failure affect your confidence? How do you rebuild your confidence after failing?

Caroline: In school and in sports, we are taught to avoid failure at all costs. There is an incredible pressure to never fail at anything. This means that when people do fail, it is often a huge blow to their confidence. However, failure can in fact be helpful. Succeeding after having failed over and over again can increase your confidence immensely.

Sidney: I find that failure often helps me gain the confidence necessary to not fail in the same capacity again. Oprah once said that, “failure is a great teacher, and if you are open to it, every mistake has a lesson to offer.” I’m a life-long learner, it’s in my DNA. My great-aunt was Superintendent of two counties and her life philosophy taught me to develop a deep appreciation of learning. I don’t think anyone is eager to fail, but I’m definitely eager to learn, and that love of learning helps me to rebound from failure without diminishing my confidence.

Mallory: Simply put, failure never feels good. In the moments and even days after the experience, failure has, for sure, negatively altered my confidence. I distinctly remember one interview that didn’t go as well as I had hoped. When asked about what I could contribute to the program, I found that I could not talk about my own skills. At first, I felt defeated and embarrassed. However, it’s crucial to me to view failures as opportunities to learn. I sat down with one of my mentors, and we discussed what went well and what didn’t during the interview. Her support helped rebuild my confidence. She also told me not to let one experience discourage me. Sometimes the only way to build confidence and comfort is through experience.

Maia: I think when dealing with failure there are short term effects and long-term effects. In the short-term yes, it might bruise your ego and hurt your confidence. However, I also think that the great thing about confidence is that it grows, so the failure will help you learn and in the end make you a much more confident person.


Caroline, Sidney, Mallory, and Maia are high school seniors gaining professional experience at Running Start as part of special senior year projects.

Caroline Tornquist will attend Dartmouth College in the fall. The most recent thing to boost her confidence was having her prom photos featured on her friend’s body positivity Instagram account.

Sidney Hobbs will attend the University of St Andrews in the fall. The most recent thing to boost her confidence was her Cum Laude induction in April.

Mallory Moore will attend the University of Chicago in the fall. The most recent thing to boost her confidence was a hug from her sister.

Maia Paz will attend Georgetown University in 2019. The most recent thing to boost her confidence was giving an award acceptance speech.


With Jessica Kelly, Leadership & Programs Director at Running Start.

Building Confident Women, Starting with Myself

It was supposed to be a relaxing weekend, no big plans. But that totally changed when my boss asked me to speak at an event she could no longer attend. I had less than 24 hours to prepare for a panel about taking political action. My co-panelists included a candidate for governor and a candidate for lieutenant governor. I spent the entire day before the panel at the office questioning myself: “Can I do this? Am I capable enough to represent my organization?” I even asked my colleagues several times, “Are you sure I can do this?” “Absolutely!” was always their reaction.

It certainly felt like a contradiction that I was representing an organization that works so hard to fight the confidence gap that makes women believe that they lack the skills to lead in politics, yet I found myself doubting my own skills. I was unsure of my ability to speak about the importance of overcoming insecurities, taking political action, and ultimately running for office. It wasn’t until the very last minute before I sat down at the panel that I said to myself what I told the audience seconds later as an opening line: “You are capable.”

I wish more young women could hear those exact same words while growing up and as teenagers, as their confidence starts to decline: “You are capable.” I hope women will look at the mirror and say, “I look like a politician,” at the same rate as men. I’m fighting for a future where women don’t have to be told seven times that they should run for office before they even consider it as a possibility.

But until that happens, we must remind women that if we don’t fight to attain powerful positions ourselves, other people will. We need to reassure women that they are qualified, in order to stop the unfairness of women having to work twice as hard to get half as far. Because we know that when women run they win at the same rates as men. We know that better decisions are made when women have the space they deserve at the table. We know that more young women will make great leaders when they see more female role models to follow.

And I will not stop fighting until I see that happening.

As I sat on the panel beside three successful women, I reminded myself that I am also a successful woman. The speaking engagement went so well! I could certainly tell from the audience members that hearing from confident and empowered women, empowered many more women to own their confidence.

That’s why I’m so excited for Running Start’s upcoming Resilience Summit on July 12th. The Summit will focus on overcoming impostor syndrome and bouncing back from failure. Seeing and hearing successful women admit to struggling to feel qualified and think of themselves as capable after setbacks is powerful. Fear of failure shouldn’t stop women from exciting opportunities — just like I didn’t let it when I rose to the challenge and took the stage.

Born and raised in Puerto Rico, Natalie Caraballo earned a double major in Public Relations and Political Science at the University of Puerto Rico. In 2016 she moved to DC to intern for Senator Harry Reid. She then joined the Hillary Clinton presidential campaign, serving as an organizer in Alexandria, Virginia. Natalie strongly believes that women need and deserve stronger political empowerment at earlier stages in their lives, which is why she joined the Running Start team as the Operations Assistant.

Currently, Natalie volunteers for two Puerto Rican diaspora organizations, aiming to empower civil society in Puerto Rico. In her free time, she likes to learn German and discover new cities around the United States and the world.