50 powerful men told us their biggest insecurities about being a man

Vulnerability is key to men’s health.
Vulnerability is key to men’s health.
Image: Unsplash/Toa Heftiba
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What does it mean to be a man, and a feminist, in America today?

Baratunde Thurston tells Quartz: “‘Male privilege’ isn’t just privilege. It’s a trap. Patriarchy is a trap. For everyone. We should want everyone to be free.”

Gender equality depends on men and boys questioning that masculinity. We created How We’ll Win: The Other Half, a collection of 50 interviews with industry-leading men, to explore their thoughts on masculinity, feminism, and sexism.

We spoke to Black Lives Matter leader DeRay McKessonQueer Eye‘s Karamo Brown, Hollywood director Paul Feig, Reddit co-founder Alexis Ohanian, AOL co-founder Steve Case, Jane the Virgin actor Justin Baldoni, and dozens more.

One of the most sensitive questions we asked each participant was: What’s your biggest insecurity about being a man?

Below are some of the most striking answers:

Bridesmaids director Paul Feig


“Honestly, from childhood on, it was always about doing something that would be the wrong thing to do in front of a woman, to a woman, in service of a woman. I was an only child. I was very close with my mom, I used to watch a lot of movies and you see so many examples of bad husbands in movies. And I just lived in fear of doing anything that would be considered that way. I mean to this day I am obsessed with always putting the toilet seat down. There were so many jokes of guys who wouldn’t do that, so as a kid I was like, I’m not going to be like that.

Or I would watch movies of a marriage in trouble, and there’d be a husband reading a paper at the dinner table and not listening to his wife. So I said early on, “I’m never going to be the guy who doesn’t pay attention to his wife, or doesn’t treat her as an equal, or doesn’t acknowledge her presence.”

So over my life, I’ve just collected every example of a man doing something that’s not cool, or hurts a woman’s feelings. And I just spent my life just making sure that I don’t do that to the people around me.”

Actor Justin Baldoni


“I think there are anxieties I have as just a human, and some I have specific to my place in the world as a man. Sometimes they intersect and sometimes they don’t. When I strip it way down and allow myself to be the hurt, lonely little boy on the playground, the anxiety would stem from a feeling of not being good enough. Overtime that has morphed into a lot of different fears and challenges: Not being successful enough. Attractive enough. Talented enough. Man enough. You name it. I think in general it just comes down to the way I unconsciously, and sometimes even consciously, compare myself to others and this overwhelming feeling of not being enough for anyone. But then I remind myself that the eight-year-old boy inside me who is still so hurt from being bullied, and teased, and who came home so broken, in reality has so much to offer this world, is loved deeply by many, and is more than enough. And when I can go there, I feel at peace.”

LinkedIn and Greylock founder Reid Hoffman


“I’m always wondering if I’m doing enough. I’m a straight, white man, which means I won the proverbial lottery ticket—the system was created to benefit me. I often ask myself: What more can I do to support women other underrepresented groups and how can I encourage everyone to do their part?”

Penn professor Dagmawi Woubshet


“As a black gay man, I am anxious about how I can become the subject of violence in a world teeming with racism and homophobia. I have tried to draw on my own sense of vulnerability to empathize with women made vulnerable because of their gender difference.”

Collective Health CEO Ali Diab


“As the father of two young girls, my biggest anxiety about being a man is setting a good example of how a man should behave and leaving my daughters a world that is better from a gender-equity standpoint than the one I was born into. As a father, my daughters get to see a side of me that even my closest colleagues don’t, and I am acutely aware of the impact that the smallest interaction with them may have on their impression of how a man should behave.

By extension, as a CEO, I’m very aware of the importance of setting a good example, because a lot of people at Collective Health look to me to model their own behavior at work. As a result, I feel a tremendous responsibility to make sure my actions are consistent with the beliefs I articulate to our people. Otherwise, I’m being hypocritical, and nothing erodes trust in leadership faster than hypocrisy. If I want to ask people—be they my children or our employees—to walk the talk, then I had better be the first one to do that.”

LGBT activist Bisi Alimi


“Being gay. I think this was the biggest anxiety I had as a child and this played out in how I learned to express myself. I was so scared that I would be less of a man, and I remember while I was young and boys calling me their wives. I feel so sad because I had this idea of the second-class nature of women and I never wanted to be like that. I saw how my uncles were treating their wives and the idea of being a girl was just upsetting, and being told that because I act like a girl I would be a wife was just so annoying.

I remember trying so very hard to be a man, though I have no idea what that means. But I tried. And every time some says I am like a girl, I feel really upset and I cry. Growing up, it was very much about, would I be the right man? Would I have a deep voice? How is the best way to walk like a man? It was like a disease eating me up inside and was driving me to the edge.I think aside from struggling with my religion and sexuality, the other thing that makes me who I am today is that I went through exorcism when I was 17, because I just wanted to be a real man.”

Reddit co-founder Alexis Ohanian


“Making it to the gym at least four days a week.”

Queer Eye star Karamo Brown


“I have anxiety that I am not going to be able to check my privilege in the moment and end up adding to the problem. I was born into certain social norms that I fight against daily but by no means am I perfect. I am constantly checking in with myself and the cis/trans women around me to make sure my behavior and language is respectful and supportive. We all must do the work daily.”

Black-ish creator Kenya Barris


“My biggest anxiety about being a man comes from being a father who is raising daughters while at the same time raising sons. In the environment that we’re currently living in, there has been a men vs. women chorus of commentary that I feel has pitted two allies against one another in a unnecessary and unhealthy way. It shouldn’t be men against women or vice versa; it should be everybody against monsters.”

New York Times reporter Walter Thompson-Hernandez


“My biggest anxiety about being a man is reconciling the way society continues to tell me how I should perform “masculinity” and the form of masculinity that I know is more closely related to my essence. I’ve never quite been a hyper-masculine person, I was raised by women and I often feel uncomfortable around hyper-masculine men. It’s taking me some time to realize and I noticed a positive change in my life when I finally accepted it.

But I think it’s especially challenging for men of color because we often internalize so many of the negative stigmas and stereotypes that exist in society about ourselves: that we’re violent, emotionless, and prone to destructive behavior. So many of us raised by men of color who were also products of unhealthy cycles and they—though we love them to death—weren’t always the best teachers when it comes to learning how to practice healthy forms of masculinity. Ultimately, I think so much of who we are as men is centered on fragile conceptions of self-worth and ego, and it often creates a society of repressed men who see violence and aggression as the only answer.”

Bonobos founder Andy Dunn


“While I feel I see things more clearly now, I have a lot of regret for not having begun my career this way. I missed a lot of opportunities, in retrospect, to be an equalizer. And I live with the knowledge that I’m still going to get it wrong.”

Activist Michael Skolnik


“I think of my five-year-old son, Mateo Ali, everyday. I think about how I am raising him to respect girls and women. I think about how others are raising him when I am not around. Not his mother, who is his greatest teacher and a feminist with a capital F. But the other kids at school. The things he sees in the playground. The TV. The toys he wants to buy. The parents of his friends. The stuff he sees when walking through this world. The president. The damn president, who I won’t let him listen to because of the despicable misogyny and sexism that spews from his mouth on a daily basis. Imagine that. We can’t let our boys listen to the president. That is what we are up against.”

Civil rights activist Shaun King


“I don’t know that being a man, in and of itself, is anxiety producing. While I receive death threats almost daily because of the justice work I do, it’s not because I am a man. Nobody is more privileged in this country than a man.”

Freestyle VC Josh Felser


“Where do I start? We are taught at a very young age that the man has to lead, be strong, invulnerable, and dominant. We wear a mask that hides our vulnerability and authenticity. It has taken me years to be okay with crying in private and public. My kids now call me a crybaby, which I guess is a compliment.”

To read the rest of the answers to this question, along with their best advice, and strategies to be better feminists, check out How We’ll Win: The Other Half.