I Asked 11 Men About Their Deepest Insecurities

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Photo by Leonard Nones/Conde Nast via Getty Images.

When I asked adult women to tell me their deepest persistent insecurities, their answers spanned a diverse spectrum of topics, from the physical to the emotional: acne, cellulite, weight, intellect, career, relationships, etc.

I asked a (slightly smaller) group of adult men the same question and (couldn’t help but) compare their answers to those of the women who submitted. Though they touched on many of the same topics, I detected two differences worth mulling over.

For one, a number of men were quite vague — almost amusingly so. I had to suppress the impulse to send follow-up questions: What expectations? What about your career? What does “success” mean to you?

Separately, although both men and women were open about their physical hang-ups, the actual hang-ups specified were quite different (to the extent that if I were to draw a Venn diagram showcasing the body-related insecurities mentioned by each gender, there would be hardly any overlap.)

It goes without saying that these are simply my personal observations as the self-appointed compiler and thoroughly unofficial anthropologist. Read the responses from men I polled below, and if you’re inclined, go back and compare them with how women responded to the same query. I’m curious to hear what you think — thoroughly unofficially.


“I’m insecure about my career. Feels as though a path does not exist for me and that I’ll never earn enough.”

Jon, 32


“I’m a little insecure about many aspects of my life including love, career, family relationships and my intelligence. I’m most insecure about my career right now because that’s where most of my energy is geared toward. Paradoxically, it’s also probably where I have seen the most improvement in that time period. Positive self belief, optimistic action, reading and working all help fight insecurities. I like to dive into subjects like philosophy or cosmology when I’m anxious; they help bring an expansive perspective.”

Henry, 24


I am insecure about whether I measure up to my expectations.

James, 64


“I am insecure about my dating life, or rather, the lack thereof. As I enter my thirties it feels increasingly isolating to be single and not actively dating. When friends ask me if I’ve ‘been dating,’ I almost always lie and tell them I’ve been going out with women frequently. I have become a perpetual third wheel and it feels humiliating.”

Jack, 30


I hate wearing shorts sometimes…My skinny legs don’t always look good in chinos.

Spencer, 27


“I’m insecure about…comparing notes on ‘success’ with old friends or new people I’m introduced to. Am I far enough along professionally? Am I doing enough ‘exciting’ things in my personal life? It sometimes feels like weirdly keeping score. Oh, also, my height. Still waiting on that growth spurt.”

Ryan, 29


Hands down what I’m most insecure about is my success and career path.

Jack, 24


“I’m not alone at all here, but physically, I’m incredibly insecure about the hair loss that has recently befallen me.  I didn’t think it was going to strike until it did.  And even then, I didn’t really think it was happening.  I now look at other dudes with man buns, slicked back luscious locks, or a sweet haircut that I could never pull off.  My thoughts vacillate somewhere between ‘you don’t know how good you have it’ to ‘I just wish I had done that while I could’ to ‘Do I look like my grandfather at 29?’ to ‘Is my head too big to pull off the bald look?’  I feel so superficial complaining about it, but when I look in the mirror, it’s sometimes all I can see.”

Will, 29


I’m most insecure about being wrong or not knowing the answer to a question. Even as I grow older I feel that I have to be right, fully prepared and all-knowing.

Dennis, 58


 “I’m still insecure about my parenting abilities — or perhaps lack thereof.  I have two daughters and four step kids, and trying to navigate the ‘being a good dad’ thing is a source of constant internal intrigue. Am I firm enough when necessary?  Am I too soft, and why?  What are my blind spots?  Am I taking every opportunity to model a life in service to others, to each other, and one that matters. What am I missing?  What more should I do? Are they okay? Really okay?  There is no playbook for this fatherhood thing; at 52, I am still trying to sort it out.”

Scott, 52


I was much, much heavier in my youth. While I lost the weight, the resulting stretch marks and loss of elasticity in certain areas of my skin still make me super timid about taking off my shirt. Also, my hairline.

Matt, 29

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