10 surefire ways we fail as men (Part 1)

Do you ever feel like you're coasting or stuck on a perpetual rollercoaster of life, with a fast pass to the front of every ride? Or maybe you feel stuck and aren’t sure what the next step is to take you to the next level? I’ve been there too. After sending out a form to fellow men and reflecting on my own challenges, I realized, "Let me lay out the 10 ways we might be shooting ourselves in the foot." This blog isn’t here to give you all the answers, but it’s meant to highlight areas and approaches that might need a fresh look. While we often hear about what we need to do to succeed, I want to focus on the 10 ways we inadvertently set ourselves up for failure.

In this first part, we'll dive into the first five points, setting the stage for the second part where we'll uncover the remaining five ways we might be undermining our own progress. Without further ado, let’s get started.

1. Avoiding Difficult Conversations:

I don't know about you, but difficult discussions are, well... difficult. One area where men often struggle is having difficult conversations—whether with themselves, their boss, significant other, or friends. It's been a work in progress for me, even as a social worker, where I am honored and privy to help others enter this arena. Yet for me, especially with my personality of not wanting to rock the boat in relationships, I've had to learn through trial and error how to properly undertake these conversations and go from being a coach to becoming a player, so to speak. However, the growth, depth of connections, and energy and freedom I've experienced are things I couldn't have imagined. And trust me, there are still difficult discussions that need to be had and ones I'm still learning to navigate.

So many men struggle with these conversations, whether it's with family, friends, spouses, dates, or most importantly, themselves. Growing up, I didn't really witness how to have tough conversations. I didn't know how to be vulnerable, or that by actually committing to these conversations, I would come out the other side stronger. But this isn’t unique to me; many men I’ve spoken with have faced similar challenges.". How many of us carry this weight on our chest, or a lump in our throat, or maybe it's this little voice within that doesn't stop telling us we're hiding our true selves from those around us? How many of us wish [fill in the blank] just knew [fill in the blank] about us?

Do you feel like your life is lacking intimacy, respect, connection, joy, the feeling of being alive? Well, have you had those tough conversations with your spouse, your boss, your coworker, your friend, or most importantly, yourself? Now, I'm not advocating airing it all out every time about anything. What I am saying is that we need to get comfortable being uncomfortable, especially when it comes to bursting the fantasy we may be living versus reality. I read somewhere that when we say we don't want to make waves, what we're really doing is trying to protect ourselves from stating our needs. Yes, there is a time and a place for everything, and yes, there is a way to have these conversations, as I would come to learn (when setting up the table for dinner or running errands isn't the time, you know, to discuss how you're struggling with mental health challenges or that you want to quit drinking, etc.). But these conversations must happen.

There's no safety like the one that comes from having tough conversations. It will be painful at times, but the alternative is never really tapping into the depth, beauty, and success one can experience. Shame will definitely rear its ugly head and make it feel unbelievably hard to follow through, to open up, to start these talks. Yet having tough conversations is something we need to zero in on if we want to avoid failure.

2. Neglecting Physical Health:

I remember sitting around the Shabbos table one week with my family and my uncle, who had recently moved to Los Angeles from New York. I must have been in my late teens, like 18 or 19, and we were discussing something about the Kinus Hashluchim (the gathering of all the Chabad emissaries in New York). I don't recall exactly how it came up, but I remember mentioning that they should really implement classes or sessions about nutrition and mental health. Long story short, it became a very heated discussion to the point where my brother ended up apologizing to me the next day.

If I asked you to conjure up an image of peak physical and emotional health, I highly doubt you'd picture a Jewish man. Growing up religious, especially within a community that emphasizes being spiritual and living a good and Gdly life, can make discussions about physical and mental health feel threatening. I get it, I really do, and I'm not even going into the practical ways we set ourselves up for failure (the foods we eat, the kiddush clubs and kiddushes, the lack of healthy restaurants, the void and lack of push for opening avenues for working out, discussions about physical activity and nutrition, etc.). I'm talking about the foundation, the core, and I believe it's not so much a lack of care as it is misinformation. I believe it stems from fear and total confusion regarding what the Torah says about health.

We mistakenly thought that if we teach about the body, we might come to the conclusion that "I am my body," and thus truly worship the physical, losing sight of the reason we're down here. Due to this fear and confusion, neglecting our physical health sets off a domino effect of challenges and struggles throughout life, ironically impacting our spiritual pursuits as well. This mistake of not teaching our kids and community about the body and living healthily isn't shielding them; it isn't teaching them how to live a meaningful life beyond just material pursuits. The days when we thought we could avoid these conversations or "not bring it into the house" are long gone. And let's not think that neglecting our physical health stays with us physical health affects your children, your spouse, your job, etc.

There's a famous line: "A small hole in the body is a big hole in the soul." From the perspective of the body being a vessel for the soul, let's take that and apply it to the following example I heard. If you have a diamond, a beautiful precious stone, would you leave it in a tarnished and broken setting or a beat-up box? I bet not so how much more so with one's soul. Look, we need to make the shift from "If we talk about the body, we might end up saying 'I am my body,'" to "I have a body." Let me repeat: from "I am my body" to "I have a body." Physical health isn't diet culture they're separate. Taking one's health seriously is an approach to life; it's an identity. It's not "I don't eat processed foods or sugars, etc.," it's "I live healthily, so automatically the choices I make are those that bring about health." When we eat right, when we move our bodies and work out, or find a hobby that demands physical exercise, this all directly affects how we approach our relationships, our work and career, and ourselves. For the sake of this blog, I won't go deeper, but physical health is wealth it's truly the bedrock for almost everything else in our lives.

3. Financial Mismanagement:

The number of men I've come across who either fall on one extreme or another regarding finance is astounding. They're either maxed out on credit cards or they'll do anything to not spend money, even to the detriment of the bigger picture of life. For me, I didn't grow up with money and wasn't taught anything about it, but one thing I knew was that I never wanted to go into debt, and I would definitely play it safe. Yet, I also never learned about investing beyond a savings account, so I basically lived in the extreme of not wanting to spend money. And it's in these two extremes that, as men, we really set ourselves up for failure. (And I want to emphasize, that I ain't blaming anyone for anything, as so many of us were brought up with zero or near-zero guidance or discussions around these topics, but it sure is our responsibility to change it around.)

As a community where having money and discussions around real estate, cash advances, and sales are prominent, it can feel pretty crappy to be the guy who doesn't own a house or have a nice car or any of these physical possessions. This can lead some to overspend on credit cards, thinking they’ll resolve it later. I'm not advocating for those who say, "Don't get credit cards and just always play it safe." What I am saying is that in many ways, we need to return to the basics of finance. What I'm advocating for is realizing that understanding where your money is going and what's coming in will bring about some real concrete truths and direction. We need to leave the notion of "my net worth equals my self-worth" but also not live in a space where money directs all our decisions.

I've seen men whose every decision is filtered through the lens of dollar signs, yet they fail to look at the bigger picture: "I'm living at home, not pursuing my hobbies, not creating memories, won't fly out to date, etc." I hold space for this I'm not in any way, shape, or form hating on it as much as really trying to bring awareness to this concept. Life is meant to be lived, and yes, money is integral to one's existence, but as my mother used to say, "You can always borrow money if needed, but you can never buy or borrow time and health."

If you're wondering why you feel sad, aren’t tapping into your full potential, or are struggling to find your soulmate, I challenge you to look within and ask yourself if your focus on money might be contributing to it. Or perhaps it’s the opposite maybe you’ve never really set a goal or direction for your finances. I'm writing this from a place of financial challenge, just like so many others. So, I’m not coming to you as if I have all the answers, but I can definitely say from my own experiences and from those who have shared their stories with me (and those whose journeys I’ve witnessed) that we need to grow and mature in the financial world. And remember, it’s not just about how much money you’re bringing in but also your relationship with it your spending habits, etc. We can’t let it rule us, nor should our focus be solely on money. What we can and must do is ensure that we aren’t setting ourselves up for failure. Or said another way, money itself isn't a bad thing (obviously), but an obsession with it can lead us down paths we wouldn't want to take. If our relationship with money needs some work, that's perfectly okay. But let's be proactive about it and not let it steer us toward failure.

4. Emotional Immaturity:

"Between stimulus and response, there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom." - Viktor E. Frankl.

Some of you may be hearing this quote for the first time, while others may have encountered it many times before. But within these few words lies profound truth and a guiding light it’s truly remarkable. You see, many men were never taught about emotions, not even on a basic level. My career literally demands that I invest in and immerse myself in the world of emotions, and I’ve come to see that, as men, we often experience emotions differently whether it's anger, love, worry, fear, shame, etc. For so many of us, we've subtly (and not so subtly) learned to "stuff it up and man up." We’ve either had our emotions repressed by others, or we’ve suppressed them ourselves.

How many of us truly know what we’re feeling at any given moment? How many of us are aware of the pain we carry? How many of us know how to handle anger, sadness, or loneliness? How many of us recognize that it’s okay to grieve the changes and chaos that life throws our way, rather than breaking down inside, shutting off, or distracting ourselves? How many of us live by the slogan “What doesn’t kill you makes you stronger,” using it as an excuse to ignore our pain and hurt rather than facing and processing it? And perhaps most importantly, how many of us are willing to admit these aspects to ourselves? As men, we need to get in touch with our pain, as that will literally set us free. It’s often easier to pretend we’re unaffected than to admit we’re hurting or scared. But pain has a deep wisdom one that, if numbed, suppressed, or distracted from, can wreak havoc internally and externally. Pain can guide us toward where we need to grow or develop. It might be telling us that something from our past still haunts us and needs attention, or that there’s a part of us that needs to be recognized if we’re going to be truly authentic and strong men.

It’s by admitting our weaknesses that we gain our strength. The more we accept our emotions and pain, the more we can respond to life. And the more we can respond, the more we can create the life we want, rather than feeling like life is happening to us. Emotional maturity isn’t about not feeling so-called negative emotions or being able to take anything that comes our way. It’s about developing a rich emotional language for your experiences, feeling them, and processing them. It’s about taking responsibility instead of placing blame. It’s about recognizing where you might be making others bear the brunt of what you’re feeling, thinking they need to change, and unconsciously holding them responsible for your experiences.

Emotional maturity is moving from "I don’t know why I feel this way, I don’t like it, so let me tap out," to "I know what I’m feeling, it’s uncomfortable, but I know how to work with this and who to reach out to if necessary." It’s not about vulnerability for vulnerability’s sake, but so that you can be a man who, as Viktor Frankl said, can see a situation, experience a feeling, and still respond as a mature, responsible man. To become a man of emotional sovereignty as Connor Beaton would say. So lean into your pain, learn about yourself, and understand what it’s guiding you towards or what you’ve been hiding from. To become your best self, you need to embrace your emotions and respond accordingly with compassion, love, understanding, and positivity.

In a way, this is what this whole space is about. We aren’t just going to sit down and share feelings in a big kumbaya, but we will be honest about our experiences, hold each other accountable, stop shame from dictating our lives, and call each other out when we aren’t keeping to our commitments. And we’ll do this not out of competition, but out of honor and respect for our own journeys and for those around us. So let’s go from numbing to knowing, from distraction to discovery, and from setting ourselves up for failure to forging a path to success.

5. Rigid Mindsets:

When I met my wife, let me tell you, there were quite a few things I thought were a bit too far out, to say the least energy healing, zodiac signs, deep intuition, etc. (and yes, I will not get into it here, haha). I also remember conversations with friends about health and spirituality where I literally thought we might be living on two different planets. Yet, as I’ve gotten older, I’ve come to realize that I truly don’t know that much. As the saying goes, “If you think you know everything, you know nothing. If you think you know nothing, you know something.” - Jayce O'Neal. Or "The more you know, the more you don't know." And lastly, "A fence to wisdom is silence" - Mishnah 1:17.

As men, especially those who grew up and live a religious lifestyle, so much of the way we acquire knowledge is through debates and arguments. But when we enter our inner world the space where we try to make sense of life, ourselves, ideas, and people we can’t approach it through arguments and debates. We need to approach it with curiosity and openness. This doesn’t mean you don’t have a blueprint or map for how you approach life, but it does mean you’re open to updating it.

Many of us set ourselves up for failure by failing to update our life maps.. Trust me, I get it. It’s hard as men not to go straight into that competitive mode, that killer instinct (we are programmed and built to be task-oriented and solution-focused), but there’s a time and a place for that approach. The real power lies in having a strong foundation while maintaining an approach of curiosity. There’s immense power in realizing you don’t know much. It’s another one of those counterintuitive spaces where to really gain something, you have to realize how little you actually know.

I’m not talking about your morals and values; I’m talking about how we approach our map of life. Many of us, sadly, stop updating our maps in our 20s and 30s, even though there’s so much change that continues to happen. How many of us hold onto outdated beliefs whether about parenting, education, or other topics without realizing that this information is from when we were 15? Or perhaps our upbringing has led us to view certain areas of life rigidly. One huge indicator that you’re stuck in rigid thinking is all-or-nothing thinking, personal attacks, or feeling overly heated about something. This doesn’t just apply to our interactions with others (spouse, friends, coworkers, etc.), but it starts at home, within ourselves. How rigid have you been with yourself? When was the last time you gave yourself the benefit of the doubt? When was the last time you laughed at yourself not in a negative way, but because of how little we actually control in life and how big our egos can get?

We often see the older generation as rigid and dogmatic about education, therapy, or exploration, but how rigid are we about our own beliefs? How curious are we about gaining new information, both internally and externally? Adopting this approach not only helps us gain true knowledge and wisdom but also leads to smoother relationships, better outcomes, and a healthier mind, body, and soul.

And remember, having a strong foundation doesn’t mean you can’t be curious or open to new ideas. In fact, it’s the stability of our core beliefs and values that allows us to explore with confidence and without fear. Research on child development, such as the Circle of Security, shows that for children to explore effectively, they need to feel secure in their foundational relationships. Similarly, as adults, having a solid base of principles supports our curiosity and growth. However, it’s also crucial to periodically reassess and refine our foundations. True curiosity thrives not from a lack of structure but from a well-established base that we continually examine and adjust, allowing us the freedom to explore and evolve.

Conclusion:

In Part 1, we tackled five key areas where many of us stumble from avoiding tough conversations to dealing with financial missteps. These aren’t just setbacks; they’re chances to transform and grow. By facing them, we’ve made the crucial first move toward turning these obstacles into stepping stones.

But we’re far from finished. In Part 2, we’ll dive into the next five areas that could be affecting our success areas we might not always be fully aware of. These are the hidden challenges that can quietly undermine our potential.

This journey isn’t just about identifying obstacles; it’s about stepping up and becoming the strongest versions of ourselves. By confronting these hidden challenges, we’re not just overcoming barriers we’re unlocking our full potential and setting the stage for true success and fulfillment. Hope to see you in Part 2 as we continue to uncover and tackle what’s been holding us back, empowering ourselves to rise to new heights.

#KeepBecoming