The emotional imprisonment of the modern male

Nov 2013, Washington, DC: I fell in love with R* way too quickly. I was on the heels of a serious breakup and trying to convince myself I was ok. She was getting over the pain of a failed engagement. It seemed like we fit together perfectly (if also, toxically) and dated for a few weeks. It felt big and real and exciting.

Then, without warning, she vanished.

I was wrecked.

I was depending on this relationship to make me complete. Without it I could feel my already fickle happiness and confidence slipping through my fingers.

When I realized R* was gone, I went on a seemingly endless walk along the National Mall.

I thought to myself, “That’s how life is. People will make you happy for a little while, but then they’ll hurt you mercilessly. You’ll have to pull yourself up, find another person to make you happy for a bit, and try to delay the inevitable pain. Enjoy the next 60 years asshole…”

I don’t remember the exact moment or what triggered it, but being abandoned by R* made me realize something important: I am directly responsible for my life experience.

My happiness, health, emotional well-being, success, and everything else that I care about? They’re my responsibility. I can’t outsource them to anyone else, not even a girlfriend. Somehow, I had missed that for the first 27 years of my life.

The subtle crisis of masculinity

When I look at the boys and men of my generation, I notice that we seem to be experiencing a crisis of masculinity.

Many of the men I meet struggle to understand their emotions, fail to form deep connections with the people around them, lack a sense of vision, and fail to source drive and validation from within. This leaves them feeling isolated and alone and deprives the world of their potential contributions.


What follows are the six biggest problems I notice men dealing with today. In each section, you’ll find an explanation of the problem, as well as practices, ideas, and guidelines on how to solve it.

Along the way, we’re going to cover everything from erectile dysfunction and the fear of being unlovable to flawed masculine archetypes. I’ll conclude with a call for men to embrace their raw masculinity.

This article clocks in at nearly 4,000 words. If you’d like to jump around, you can find an overview of the article below. Clicking the link will bring you straight to that section.

Problem 1: A lack of deep purpose

Problem 2: An unexpressed fear of being unlovable

Problem 3: Sexual shame, confusion, and posturing

Problem 4: Difficulty embracing, expressing, and processing complex emotions

Problem 5: Flawed male archetypes

Problem 6: The delusional desire to be self-sufficient

Practices for the modern man

A return to raw masculinity 

1: A lack of deep purpose

Many of the men I meet drift through life. They find a job that pays the bills, marry someone they almost love, have 2.4 children, and then fill the remaining space with beer, TV, video games, and other sources of white noise. This isn’t a terrible existence, but it lacks a deep sense of purpose.

I’ve noticed that many men -myself included- live more vibrantly and powerfully when they are rooted in a sense of personal purpose.

One man may find purpose in striving to become the best athlete at his gym. Another may feel driven to write poetry. A third may want to end poverty. The specific purpose varies from man to man and is likely to evolve over time. What matters is that a man pursues his purpose purely for himself.

The best way to find purpose is to spend time alone. Create silence within your life. Do not distract yourself with books, friends, or TV. Go for long, undistracted walks. Meditate. Journal. Remain open to the thoughts, ideas, feelings, and realizations that come to you. It’s difficult to predict when clarity will come. Don’t be surprised if it comes quickly. Don’t worry if it takes time.

If spending significant time alone and in reflection doesn’t feel right to you, consider discussing your search for purpose with a few people you trust. Listen carefully to their feedback, but don’t feel bound to it. Trust yourself.

When you feel a sense of purpose starting to animate you, ask yourself, “Does this feel like the best way for me to engage with the world?” If the answer floods you with energy and excitement, you’ve found the seeds of your purpose. Now begin living that purpose. Your purpose may change, expand, contract, or morph over time so be sure to periodically check in with yourself.

2: An unexpressed fear of being unlovable

When men fail to process and express complicated emotions, they build walls around their hearts. These walls make receiving love very difficult. Many of the men I know readily give love and compassion to other people, while being exceptionally hard and cruel to themselves.

If you have never learned to love yourself, consider approaching the problem from two angles. First, ask yourself the question, “If I deeply loved myself, what would I do differently?” Chances are you’d prioritize your health, fill your day with treats for yourself, and set stronger boundaries in your personal and professional life. When you start doing these things, you’ll begin to chip away at the walls guarding your heart. Start now.

Secondly, you should work to heal old wounds. This includes digging into your life story, feeling the pain and sadness that you’ve been avoiding, and accepting yourself as you are, warts and all.

This work is best done with a coach or psychologist who specializes in this style of heart opening work. However, if you’re going to attempt it on your own, here is what I suggest: write out your entire life story in a stream of consciousness narrative. Do not judge anything that comes up. Instead, pay attention to the times when you were being cruel to yourself and the times when others were cruel to you. When you notice these instances, connect to the emotion and sit with it.

3: Sexual shame, confusion, and posturing

The messaging men get about sex is as straightforward as it is destructive: the more women you sleep with, the more of a man you are.1 If you choose not to have many partners – or if people don’t find you sexually desirable – you’re not much of a man. Men are also told that sex is primarily a physical (as opposed to emotional) experience.

Obviously, this is bullshit, but it’s bullshit that runs deep in men’s psyches.

On one end of the spectrum is the man who becomes consumed by sex. He studies pick up artists, builds his social life around trying to meet women, and measures his worth by the number of partners he’s had. Without necessarily meaning to, he ends up thinking of women as objects and failing to understand them as humans. Many of these men end up feeling as though women are adversaries and that love and sex is a power struggle.

The other extreme is the man who feels shame around his sexual identity and attempts to suppress it. Instead of pursuing love and sex, he quietly resolves to stay in and masturbate. When he does have sex, he feels guilty, as though his partner is doing so at her own expense. When these men fall in love, they find themselves perpetually being friend-zoned. This becomes discouraging, and they end up feeling plagued by fears of being unlovable or undesirable. They feel tragically flawed.

What men need to do is develop a healthy attitude towards love and sex. They need embrace their sexual identity, without becoming defined or consumed by it.

Doing so starts understanding a few simple truths that most men fail to realize about sex:

  • Sex is one of the most vulnerable, intimate things that two people can do together.
  • It’s normal to be uncomfortable about sex. Unfortunately, the discomfort leads to men avoiding real conversations about it.
  • Though many men deny this, sex – even casual sex – is a highly emotional experience. If it weren’t, men would stop pursuing women and just stay at home masturbating. Obviously, that’s not what happens; the physical presence of another human matters. A lot. If you can connect with the other person emotionally, the experience is better.
  • Sex with strangers tends to be isolating.
  • Erectile dysfunction is deceptively common. To put it bluntly, about half of my guy friends have called me at one point because they were experiencing erectile dysfunction.
  • Premature ejaculation is also deceptively common.
  • If you suffer from either erectile dysfunction or premature ejaculation, the first step is to talk to your partner about what you’re going through. Yes, doing so is hard. However, virtually all men are delighted to discover that their partners are accepting and nurturing. In many cases, honest conversation helps solve the problem. If it doesn’t, consider talking to your doctor.

Overcoming sexual shame requires being honest with yourself about your experience with sex and love. From there, the approach to getting what you want from your love life varies from man to man. Here are my best suggestions if you’re struggling:

If you are afraid to make a move, or if you are plagued by isolation, stop watching pornography and spend less time masturbating. Try to eliminate pornography entirely and only masturbate once or twice a week. This will build up the sexual energy in your body and force you to dwell in reality. Many men find this extremely difficult so if you slip up be sure to be easy on yourself.

If you’ve been putting a lot of pressure on yourself to date, get laid, get married, or if your life is dominated by the search for love or sex, remove the pressure. Intentionally take a month or two off from dating. Doing so will force you to find happiness and validation from other sources. Earlier this year I took four months off of dating to focus on myself. My goal was to build a life I loved on my own, and then find a partner. When I decided to start dating again, it took almost no time at all to find a great partner.

If you’ve been going on dates from time to time, but struggling to connect, change your goal.  Your goal should be getting to know the person you’re dating, nothing more. Ask questions. Listen. Instead of being quick to judge, seek to understand. If they ask questions about you, be as honest and vulnerable with your answers as you can.

If you’re ashamed of sex, dig into your past. What did your caretakers, religion, or culture tell you about sex that made you ashamed? Did you have a traumatic experience like rape, molestation, or sexual embarrassment that you’ve been avoiding? The more you understand the root of your problem, the easier it will be for you to unravel it.

4: Difficulty embracing, expressing, and processing complex emotions

B* is a close friend of mine. When his wife was in her second trimester, they had a miscarriage. B* didn’t tell anyone. In fact, the only reason I know they miscarried is because his wife told me.

Of all the problems I see facing modern men, the most significant is the inability to connect to and process their emotions.

Boys learn not to express vulnerability. As children we are told that, “Real men don’t cry.” If we do cry, we’re likely to be mocked. Boys who express fear or sensitivity are called, “Pussies.” Through years of social conditioning, emotional suppression becomes habit for most guys.

If a man never works to rewire his relationship to his feelings, all of his negative emotions remain unexpressed and pent up. This blunts the positive emotions and leads to a deep, penetrating sense of isolation. It also results in temper problems and unpredictable flashes of anger.

Fortunately, all people can learn to connect to their emotions. Here’s how:

First, get clear about how you feel. The easiest way to do this is through honest reflection. For connecting to simple emotions, going on a walk or journaling works well. For untangling more complicated emotions, you’ll likely need a few days of reflection. Personally, I like to go into the mountains or to the sea. If you are not the type to spend several days on your own, another approach is to talk through the issue(s) with people you trust. It’s important that you feel comfortable being honest and vulnerable around them and that they won’t shame you for your vulnerability

By holding space for reflection, you’ll be able to connect to yourself. You may be surprised by what you discover. Do not judge what comes up – that will only create further closure. Instead, stay open. If you cry, you cry. If you laugh, you laugh.

Second, use curiosity to get to the root of your emotions. Upon reflection, you may notice, for example, that you’re frustrated because your girlfriend lectures you about appropriate social interaction. When you notice a feeling that you find difficult, ask yourself why you feel that way.

Perhaps you’ll discover, “I get frustrated because I don’t think I need any help with social interaction.” So you ask, “Why does it bother you when people think you need help with social interaction?” And so on and so forth until you get to the root of the feeling.

Third, once you’ve uncovered a difficult emotion and gotten as close to its root as you can, express it. Expressing your emotions can happen through a wide variety of methods, including, but not limited to:

  • Artistic creation (music, painting, wood work, etc.)
  • Controlled rage (like smashing plates, pounding pillows, hitting a punching bag, etc.)
  • Conversation
  • Sports
  • Writing

Finally, if you’ve noticed that you need something, give it to yourself. Perhaps you need time away from your spouse, you need to rest more, or you need your kids to respect your boundaries. Start giving yourself the things you need. By prioritizing yourself, you’ll be better equipped to take care of the people you love and influence the world around you.

The end goal is to be able to understand what you’re experiencing in any given moment. Many men will discover that the more adept they become at expressing and understanding their emotions, the more smoothly their entire lives go.

5: Flawed male archetypes

One of the biggest problems facing modern men is a lack of healthy male archetypes. The three most common have tragic flaws:

The 1950s man. These are the guys who get caught up in gender roles and feel the need to be the provider. They get insecure if their partner makes more than them. They deny the value – and at times, the existence – of their emotions. When they are struggling with something, they remain closed off to the world and the people around them. They’d rather suffer in silence than risk being vulnerable and asking for help.

The millennial man-child, more commonly known as the nice guy. These are the guys who lack a strong sense of self and are afraid to be assertive. They can’t handle emotional friction and avoid confrontation. They have a quiet sense of entitlement that prevents them from taking responsibility for their lives. When I was dating R*, I was one of those guys.

The third, and perhaps most common, is the reformed frat boy. He can hold down a job, but lacks genuine ambition. He makes an ok boyfriend, husband, and father, but fails to form deep connections with himself and the people he loves. He’s learned to use humor to disarm uncomfortable situations, instead of doing the hard work of leaning into them.

Missing from all of these archetypes is what I believe to be essential for the modern male: a drive to shape the world, emotional fluency, and a reverence for calculated risks. More on that later.

6: The delusional desire to be self-sufficient

Men seem to suffer from the delusion that in order for their success to be valid, they have to achieve it entirely on their own.

In reality, there is no such thing as a “Self made man.” There are only those who ask for help when they need it and those who fail.

Personally, I’ve relied heavily on help from friends, family, and professionals. They’ve helped me financially, emotionally, mentally, materially, and physically. Assistance from other people has grown my business, led me to happiness and purpose, healed me after breakups, and delivered Gatorade when I was hung over.

But asking for help doesn’t come naturally to me. It’s a skill I had to learn. It felt like swallowing my pride. If you’re a man that needs to learn to ask for help, I’d encourage you to go through the same process I went through:

First, reflect on the times when you’ve been asked to help other people. There’s a good chance that you felt happy someone asked for your assistance. It probably made you feel needed and important. Realize that other people will be happy to help you. You’ll contribute to their inner desire to be needed.

Second, start by asking for something small. Ask to borrow a few bucks from a buddy at work. Once that becomes more comfortable, ask for advice on a project. Keep moving the line until you’re able to ask for all the help that you need. You’ll notice that in doing so, everything you care about comes more easily to you.

Finally, when other people ask you for help, provide assistance with as much grace and humility as you can.

Additional practices for the modern man

Though I’ve included suggestions on how men can embrace their masculinity throughout the article, I’d like to make a few additional recommendations. As always, pay attention to the ideas that excite you and make you nervous.

Stop pretending to be strong and allow yourself to break already. Virtually all men pretend to be stronger than they are. This is a form of emotional immaturity, and it leads to self-loathing. Allowing yourself to break from time to time will improve your life by clearing negative emotion and offering perspective. Additionally, when you finally allow yourself to break and feel the pain you’ve been denying, it will burn off. In its place you’ll find a stable base of resilience and true strength.

Spend time in solitude. This can be a road trip, a camping trip, a silent retreat, whatever. The point is to spend time alone, focused exclusively on yourself. For a few days each year, minimize your engagement with the outside world. It’s easiest if you keep your phone and computer off.

Learn to master your vices. For most people, this is as easy as intentionally taking a month off from them. This allows you to regain control over yourself. If you smoke cigarettes and drink coffee every day, stop smoking and drinking coffee for a few weeks. If you go to the horse races after work, take time off. If you’ve been playing video games daily since college, take a month off. If you always watch porn when you masturbate, eliminate pornography for a while. You may return to your vices if you choose, but make sure that you’ve mastered them first. The goal is to be in possession of yourself.

Periodically host or attend a guy’s night. Personally I like poker nights, but going to a baseball game, hitting a cigar bar, or doing a whiskey tasting all have a near universal appeal.

Reach out to your guy friends more often. Call to say hi. Invite them to a game. Tell them a funny story. Whatever. I promise they are just as lonely as you are, and they will be delighted to hear from you. In fact, if they’re being honest, it will likely be the highlight of their day.

Learn to deepen your presence in this world. One of the greatest masculine gifts is presence. The more you deepen yours, the more powerful you will become. You can do this through meditating, reflecting, journaling, focusing on one task at a time, and spending time in solitude.

A return to raw masculinity…

I’ll leave you with a sketch of a man who has embraced his masculinity. This is the man I strive to be, and it’s the man that I so often see lacking in modernity.

He has the courage to face – and shape – his internal and external reality. He is engaged by building a life that is an authentic representation of his truth. He knows that there is a time to lead and a time to follow, and can distinguish between the two. He accepts that he is – and always will be – a work in progress.

He keeps his body and mind sharp. When he enters a room you can feel his presence. He approaches his shame, fear, anxiety, tension, and truth with openness and vulnerability. He embraces his sexual identity without letting it define him. He knows that he must periodically enter solitude to connect to himself. Doing so allows him to share his deep gifts with the world.

He periodically approaches the precipice of his comfort zone, and then peers over the edge. He invests in himself and the people around him. He understands the importance of making himself vulnerable, even when it’s scary. Especially when it’s scary.  

He measures his success in life based on two simple questions: is my life an authentic expression of my truth? Are the people and communities that I care about better because of my involvement? He trusts that if he can answer, “Yes” to these questions, money, sex, love, connection, happiness, meaning, and eventually contentment will follow.


  1. This section is written from a heterosexual perspective. I’ve chosen to do this because I can only write about what I know. To pretend like I understand the reality of a homosexual, bisexual, pansexual, transexual, or queer man wouldn’t only be ignorant, it would be offensive.

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6 thoughts on “The emotional imprisonment of the modern male

  1. Brilliant! Reading this has helped me have a deeper and more compassionate perspective on the men in my life – both past and present. There is much to learn from this expression of your honest and heart-felt advice. Your vulnerability and transparency is honourable! Thank you!

    1. Georgina – I can’t tell you how much this means to me. Thank you. That you’re even investing energy into understanding the men in your life is such a gift to those guys. 🙂

  2. Great article, I just read David Deida’s book and your summary reminds me of his book. All men (and women) should read this.

    1. Whoa. Thanks Eva. Your comment delighted me so much I just read it out loud to the people in the room with me. So glad it resonated with you. 🙂

  3. I’m in my early 50s and have only just accepted that my reason for being doesn’t have to be something that will profoundly change the world. While I would love to positively influence the people I come into contact with, I am content in the knowledge that I actively strive not to negatively affect others.

    Your insights into the male psyche have resonated with me and given me the opportunity to look at myself in more compassionate way. As a Gen X male, I certainly carry my share of baggage and am guilty of being overly harsh and critical my perceived failings. I realise that I am a flawed individual, as most people are, but it does not make me a bad person. I can live with that.

    I’ve gotta say though that it has taken a lot of soul searching and introspection to overcome some of the issues associated with my upbringing and am glad that I have a very supportive partner of 25 years. She has put up with a shitload of my “stuff” over the years. I’m also glad that we don’t have any offspring as I know how self destructive I have been.

    Your writing has been cathartic to me and is inspiring me to try to find my own voice. I would love to be able to articulate my thoughts and feelings as well as you do. Keep on giving.

    1. Wow. John. First of all, thank you. Your note really makes me smile. And honestly, if you simply strive to avoid negatively affecting others… that’s pretty damn good and ultimately will leave the world better off. The good thing too is that being in your early 50’s means you still have a lot of life left.

      And you’re 100% correct: being flawed doesn’t make you a bad person. It makes you normal. Being about to confront your “flaws” makes you brave and courageous. And keep doing that soul searching and keep working to overcome the stuff associated with your upbringing. That’s beautiful (and insanely difficult) work. And definitely keep being gentle with yourself. I get the sense that you’re a way better guy than you give yourself credit for.

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