I started reading Liz Plank's For the Love of Men: A New Vision for Mindful Masculinity, and it opens with the author's experiences asking men this question (emphasis mine):
The more I read about men’s relationship to directions and maps, the more it explained the absence of a substantive and open conversation about masculinity. While women are encouraged to ask questions, men are expected to pretend like they know everything even when they don’t, even when it comes to large and existential questions about their gender and their lives. As I traveled across the world, from Iceland to Zambia, I asked men the same question over and over again: What’s hard about being a man? Every single time I asked that question it was like I had just asked them if unicorns can swim.
It was met with a pause, a smile, and then followed by another long pause followed by the words: “I’ve never actually thought of that.” When I asked women that same question about their gender—in other words, when I asked women what was hard about being a woman—it was like I had asked them to name every single thing they loved about puppies. I got nearly the same response from every woman I spoke to: “How much time do you have?” Judging from the conversations I would strike up with (half-)willing strangers, women had spent a lot of time thinking about how their gender impacts their lives, but men visibly hadn’t. While that conversation had been blossoming with women for decades, for men, accepting directions was proof that the system was broken, which goes against the natural impulses of what being a man means: not to admit confusion or ask questions.
I thought it was a worthwhile question to consider, and I'm interested to hear how people here on Tildes would answer it.
Also, while I'm confident in our community's ability to apply the principle of charity, I do know that discussions about gender online can often become contentious. I would very much like this to be a place for people to be able to share open and honest truths about themselves, even if those are difficult or revealing. If you are replying to someone, especially someone who has just opened up about their own personal experiences or beliefs, please make sure you are being thoughtful and considerate when doing so.
Finally, while the question is specifically about men, I don't want to limit responses to men only. I think women and non-binary people definitely have valuable insights into masculinity as well and I welcome your voices should you choose to answer.