I Asked 11 Men About Their Deepest Insecurities
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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  • Natty

    Thank you for this. I always underestimate/forget about how much pressure society places on men to “perform” (make money) in their careers. Yet another reason we need to break down traditional gender roles…

    • Douglas Pedro

      Chivalry must die!
      Equal rights

    • allen grunden

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  • Daniel Szilagyi

    As a man my fears are making sure that i can have a stable career as i age for one thing, another is trying to stay in shape and be healthy overall ( I don’t really know my full family history so it’s hard to know if i might have issues down the road )
    I used to worry about things like measuring up to friends and other people that i worked with, or trying to be as skilled but i learned over time that it doesn’t really matter and that i’m content with my skills and abilities (which i continue to grow)
    Don’t think i’ll ever really be a shorts guy though, i’m 6’2 and have skinny legs and larger feet (size 11-12 usually) so i think i look silly

  • doublecurl

    man, all I hear when reading these is a reflection upon “status” in a way that doesn’t weigh on women as heavily

    • Chess

      did you read the original piece? When women were asked they also were equally concerned about “status” and career etc.

      • doublecurl

        Yes, I did. to me the vibe in the women’s piece regarding professional insecurities seemed to stem more from a drive for personal accomplishments, not how they outwardly appear to others. the men’s piece reads more as status in the sense of how others perceive them to stack up. just my perception!

    • Ana

      I actually relate much more to the male comments regarding career. As a single woman in her 30s there’s definitely the expectation that I should have this crazy career (and exciting social life).

  • Yep, I find that a LOT of men are insecure about hair loss!
    Career is also a super common one.

    Charmaine Ng
    Architecture & Lifestyle Blog

  • Aleda Johnson

    For the physical insecurities, I now understand how men feel when women complain about insecurities that they either don’t notice or think are perfect. Case in point: a commentor on the “What turns you on?” story who loved bald men, and Will, insecure about his hair loss.

    • Rebecca

      yes! when i read the mentions of baldness i was thinking “man every dude ive dated since i’ve turned 24 ish has been balding, but I don’t care or notice!” a good reminder that a lot of our insecurities are noticed and fostered mostly by ourselves.

    • Kiks

      A man who I was completely head-over-heels in love with a few years before I met my husband (it didn’t work out because of a bunch of situational problems that would’ve never been solved) was a good 4-5 inches shorter than me, and balding. I was obsessed with him because he was brilliant and hilarious and kind, and I also found him very sexy. If you’re a good person, being a “10” in western society’s traditional sense of the word is quite meaningless.

  • Kat

    Hey Jack, 24, worried about success… you’ve got plenty of time! Even if you changed your career in 20 years you could easily become successful then. I’m 29 and I still have no idea what I want to do with my life.

  • Kat

    Also I find it interesting that the comments on the women’s article mostly addressed the individual women whereas these so far are mostly discussing trends etc.

  • elpug

    It is very cathartic to read these. While some a little vague, I think they shine a light on things we all can relate to. It seems everyone worries about finding the right person or the right career and at various ages, too. Thanks for sharing!

  • Paola

    I got really curious thinking about how I would have perceived the answers without knowing the gender of the respondents. When I read the first article (on women’s insecurities), with each answer it felt as if I was having a conversation with a female friend or myself . While on here the empathy didn’t seem to be there, probably because I was thinking about all the aspects in which men have a very different reality to explore in their relationships and careers (as vague and generalised as that might sound).

  • Felix Berger

    I find it uprising that none of them mentioned the size of genitalia. I think is one most of us struggle at some point in our life. Until you go to a locker room and see what others look like it can be good or terrifying to compare yourself with others or have your manhood defined by the size or length. Which is why I believe career and money is a big factor as is one thing women value as a good quality for the man to be able to provide.

  • Such a nice and different post. Career seems to be a huge part of men’s lives. Side note: my husband agrees with Spencer – shorts are not flattering on men. LOL


  • This just makes me even more sure that rigid gender roles are bad for everyone. I am surprised by how common a theme career is, but then I guess I shouldn’t be really.
    La Femme | Unofficially the best lifestyle blog ever

  • Douglas Pedro

    Chivalry must die
    Chivalry is really not compatible with gender equality
    Men owe women nothing

  • Caitlin

    Wondering if the fact that men are largely socialized to not be/appear/admit to being insecure plays a part in how “vague” and fairly standard these responses seem?

  • sassiel

    No! Dennis! Please stop trying to be right all the time! On behalf of all of us—please. It’s ok to be wrong.

  • Abby Colby

    I feel like the insecurities men harbor about their hairlines (or lack thereof) are equivocal to the insecurities many of us harbor about our bodies/weight. If I’m in bed with you, that means I’ve already processed, accepted, and moved on from thinking about what your hair situation is, but I understand how it could serve as a continual hangup. Personally, I’ve dated guys all over the hair loss spectrum, and I care infinitely more about what’s inside your head than what’s on top of it — or not on top of it! That said, it must be really jarring to wake up to less hair, like, every single day…. *Thinks sympathetic thought about men for the first time since October 5th*

  • Inaat

    Loved this. I would love some stories about dating, since I am newly single. Would be interesting getting a guys point of view. Also, would really like to hear about (full time) single dads, seems like everybody has a kid..