10 surefire ways we fail as men (Part 2)

Welcome to Part 2, where we continue our exploration of the factors that can impact our success as men. In Part 1, we identified five key areas that can hinder our progress. Now, we’re diving into the next five critical points additional aspects that play a significant role in our journey to success.

These next five areas are crucial to understand as they contribute to the broader picture of what shapes our ability to thrive. By addressing these factors, we gain deeper insight into our path forward and how to overcome potential barriers.

Let’s dive into these next five points, discovering how they impact your personal journey and help you become the unique, best version of yourself as a man.

6. Fear of Failure:

As men, we deeply value competence and skill, often tying our self-worth to our achievements. Growing up, the icons the stars, the legends, those who seemed to have it all were the ones who excelled in sports, music, academics, and beyond. Their skills and achievements set them apart, and there’s nothing wrong with striving for greatness. In fact, much of this space is dedicated to empowering men with the tools, skills, and confidence to become their best selves.

Yet, many men grapple with the fear of failure, which is essentially a fear of fear itself. We wrestle with thoughts like, “What if I’m not good enough?” or “There are so many people better than me; maybe I’m just not worth it.” These thoughts can paralyze us, making us hesitant to take risks or embrace new opportunities. Ironically, allowing fear to dictate our actions often leads us to failure by default. Fear isn’t something to banish; it's a fundamental part of being human. But what defines true masculinity is not letting fear halt our progress.

So, how do we tackle this? The approach is twofold:

1. Connect with Role Models and Learn from Their Failures: Engage with people you admire and listen to their stories of setbacks. This can shatter the myth that successful individuals were fearless. For example, Georges St-Pierre, a legendary mixed martial artist, openly admitted to experiencing intense anxiety and fear before his fights. Despite being a paragon of masculinity, he acknowledged his vulnerabilities. Knowing that even the most accomplished figures battle fear can be incredibly freeing.

2. Reframe Failure as a Stepping Stone to Success: Embrace failure as an integral part of your journey. As Thomas Edison famously said, “I have not failed. I've just found 10,000 ways that won’t work.” Winston Churchill echoed this sentiment with, “Success is stumbling from failure to failure with no loss of enthusiasm.” These perspectives remind us that failure is not the end, but rather a crucial component of the road to success. Embracing this mindset allows us to unlock our true potential.

Personally, my father-in-law exemplified this approach. I’m profoundly grateful for his lessons in resilience. He built a successful company from the ground up, navigating countless highs and lows. As Susan Jeffers aptly puts it, “Feel the fear and do it anyway.” Experiencing fear isn’t a weakness; it’s often a sign that you’re pushing boundaries and moving towards your greatest potential. Embrace it, and let it propel you forward.

7. Lone Wolf Mentality:

If I asked you to picture the most masculine guy or list 10 characteristics of what it means to be a “real man” (and yeah, I’m putting “real” in quotes), chances are asking for help or leaning on someone else wouldn’t make the cut. But here's the thing: this is exactly where so many of us trip ourselves up. I'll be straight with you I’ve been on both sides of this. I’ve had moments where I just powered through things on my own (warrioring on, even if that’s not a real word), and times where I asked for help before even thinking things through on my own. The truth is, we’ve been programmed to believe that figuring it out alone is the only way to prove our worth. That if we don’t, we’re somehow less than less of a man, less of an alpha, less capable.

As Dr. Fredric Rabinowitz, a psychologist at the University of Redlands, puts it:

“Because of the way many men have been brought up—to be self-sufficient and able to take care of themselves—any sense that things aren't OK needs to be kept secret. Part of what happens is that men who keep things to themselves look outward and see that no one else is sharing any of the conflicts they feel inside. That makes them feel isolated. They think they're alone. They think they're weak. They think they're not OK. They don't realize that other men also harbor private thoughts, emotions, and conflicts.”

This whole lone wolf idea we cling to? It’s based on a false pretense, often driven by shame or simply not knowing how to build meaningful connections with other men. We’ve been led to believe that to be a “real man,” we have to bottle up our pain, avoid vulnerability, and just handle it all ourselves. But right there is where we’re getting it wrong. The power of opening up is that it frees you you quickly realize you're not alone. The truth really does set you free, and once you see that, you feel a greater drive to step up, take responsibility, and go after greatness.

There’s a saying: “Strength in numbers.” And for us men, finding a group of like-minded people who we can genuinely open up to is crucial, whether it’s in work, relationships, or life in general. It's about letting go of the idea that we have to be superstars all on our own and embracing the concept of building a team. Just like in sports, chemistry matters more than any one player’s individual talent. This isn’t just about emotional maturity this is about moving from independence being the holy grail to recognizing that interdependence is where real magic happens. It's about finding other men who are on the same journey. It's about quality over quantity when it comes to your connections.

We have this natural drive to push forward, to take on the world alone and yeah, that can set us up for failure if we’re not careful. So, take that energy, but use it in the right way. Go out there and find your pack.

8. The Missing Piece: Role Models in Daily Life:

When you’re going through a crisis, it’s almost second nature to reach out to someone. Maybe you’re facing a major life decision like a career move, deciding where to live, or thinking about marrying someone so you turn to an older brother, a rabbi, or a therapist. In these moments, seeking guidance feels natural. But here’s something I’ve noticed: there’s a common thread among men, and it’s the lack of role models for everyday life.

Let me explain. The other night, I was learning with a friend, and we found ourselves discussing how to view our past and what kind of space it should occupy in our lives. The conclusion we came to? The past is secondary when you have a direction, an aim, a future you're striving toward. When you're working on yourself, being self-aware, and focused on where you're headed, the past naturally comes up, but it shouldn’t weigh you down. It’s the future that defines you, not your past.

As a social worker, I spend time unpacking the past with people, helping them make sense of their experiences. But where the real magic happens is in the blend where the past informs but doesn't dictate the future. That’s where I see so many men struggle.

There’s this drive, this potential simmering under the surface for so many men. They know they’re meant to contribute something real, something meaningful to the world, but they can’t quite figure out how to get started or even what their target is.

And that’s where role models come in. Who do you look up to? Is there someone whose way of navigating relationships, crushing their work goals, unlocking creativity, or embodying spiritual and physical balance makes you pause and say, “I want that”? And if there is have you ever actually reached out to them? Asked if they’d mentor you or even just hear you out?

For some, that role model might be their father. If that’s your reality, I hope you’ve deepened that connection and found guidance in key areas of life. But a lot of men didn’t have that kind of father figure. For many of us, figuring out what it means to be a man and how to embody that across different areas of life is tough.

So where do you turn? How do you unlock your full potential? This is where the power of role models steps in not just for the big, life-altering moments, but for the everyday grind.

In Chabad, there’s a concept called a mashpia, a spiritual mentor, and when done right, it’s a game-changer. But I think there’s something to be said for having multiple role models for different aspects of life. You might have one person who crushes it in their career, another who sets the standard for family values, someone who’s a fountain of creativity, and yet another who has unmatched spiritual depth.

Here’s the thing: it’s not about becoming them. You’ve got your own unique gifts, your own life circumstances, your own contributions to make. For some, having multiple role models across different areas gives a wide range of inspiration. For others, it might be one or two key figures that really make the difference. The point is, find what works for you. Whether you draw from a variety of influences or stick with a few, remember, it’s not about copying them. It’s about using their inspiration to become the best version of you.

9. Neglecting Spiritual Growth:

I’ve struggled with my Judaism, just like many of us have. I had my frustrations with rabbis, the education, the judgment, the lack of empathy for real human experience, and so many other areas. But fast forward a good amount of years, and I’ve reached a place of deep, authentic connection in my spiritual journey. How I got here? That’s a story for another time. And it’s still a daily effort constant work, awareness, and more. But today, I want to focus on something I see time and again where men set themselves up for failure: the neglect of spiritual growth.

We can’t separate our spiritual life from our everyday actions and decisions. They are interconnected, deeply influencing each other. And the failure I’m talking about? It doesn’t just stay in the spiritual realm it affects every aspect of our lives because our spiritual core is at the center of who we are. This isn’t about becoming more religious it’s about becoming wholey. It’s about embracing a holistic way of living, where all parts of who we are our spiritual, emotional, and everyday selves are in alignment. (Yes, I mean wholey vs. holy).

Let me share a personal story. I grew up Chabad, and I still very much consider myself Chabad with a love and deep connection to Rabbi Nachman (and others). My life has been shaped by the Chabad community my parents are Shluchim, I went to Chabad schools, and most of my friends are part of this world. Then, after I got married, I was introduced to a man named Gedale Fenster, a teacher from the Breslov tradition. His teachings profoundly changed my life. I remember how hard it was to even consider his classes. For those who don’t know, Chabad is very focused on its own teachings, which are incredibly deep. It’s not that we’re discouraged from learning other approaches, it’s just that Chabad Chassidus offers so much depth in its own right.

But at that moment in my life, I needed something different. And it wasn’t by chance that I came across Gedale’s teachings.

Long story short, it was almost as hard for me to open up to his wisdom as it was when I was struggling with my own religiosity. But something inside me knew I needed this. Now, three years later, I listen to Gedale’s teachings daily. I don’t hide it, and I don’t question whether it’s ‘right’ for me as a Chabadnik. My soul is fed by it. I gain clarity, a sense of wholeness, and my relationship with G-d with Hashemhas never felt more real or fulfilling.

But here’s the thing: this isn’t about becoming more religious. It’s about growing spiritually in a way that resonates with your soul. It’s about finding what you weren’t taught or didn’t realize you needed. It’s about returning with a new perspective, a healed heart, and a holistic approach to life that touches every part of who you are. This isn’t about being religious; it’s about being wholly embracing a faith that integrates every part of our being and celebrates our unique journey.

This is where I see many of us fall short. We stop growing spiritually, but we think we’re evolving because we’re moving. In truth, we’re just running away from the deeper work. So many of us were raised in a Judaism where we weren’t seen as individuals with our own needs. We were thrown into the same system Welcome to 7th grade, welcome to Shiur Bais, welcome to Beis Medrash without a personalized connection. Maybe your experience was painful within your family or in the community or maybe you didn’t have any major traumas but were never taught anything that spoke to your soul. You didn’t fit the mold and no one adjusted the system for you.

Perhaps you saw families or leaders put Judaism above health, safety, and empathy. Or you were made to feel guilty for your natural desires and struggles. I’m not here to harp on the past, but the truth is, for many of us, Judaism became entangled with pain, restriction, or even trauma. Leaving seemed like the only way out if you wanted to live a life of joy, health, and peace.

But here’s the catch: we fail ourselves when we don’t come back to examine our spirituality. We don’t stop to ask ourselves what it means to be Jewish, why we feel so intensely about anything Jewish or Orthodox. I think many of our communities are waking up to the truth that Judaism, at its core, is about connection a relationship with G-d, with Hashem.

Many of the men I talk to feel like it’s too late they’re just on a different path. Or they say, “I’m good where I am, I’ve found my space.” But when we dig deeper, when we make room for the pain or confusion, it’s clear they’re still hurting. They want to feel alive, to feel loved, and their souls are still burning inside, waiting to be seen and spoken to.

And here’s another thing: it’s not about leaving everything behind. Walking away might quiet the pain, but it doesn’t satisfy the soul’s deep need for connection, for meaning, for wholeness.

A lot of us turn to experiences that seem to tap into that deeper space but they don’t quite hit the mark. Whether it’s traveling, psychedelics, music festivals, or even chasing connections with women, sure, some of these things can offer healing . But none of it will fill the deeper void we’re trying to address.

As Rabbi Ahron Moss says:

“One's Jewishness is not a belief, a feeling, a conviction, or a lifestyle. It is a state of being. We can either celebrate it or fight against it. But it will always be there. So why not celebrate it?"

This is for all of us. We need to return to our spirituality with new eyes, a healed heart, and a holistic perspective. And again, this isn’t about becoming religious it’s about becoming whole. It’s about embracing a faith that integrates every part of our being, that allows us to grow spiritually, emotionally, and as complete human beings. We all need that growth, that deeper connection, no matter where we are on our journey.

10. Striving for Work-Life Balance Without Redefining Success

As an Orthodox Jewish man navigating the pressures of business and entrepreneurship, I’ve often found myself caught up in the relentless pursuit of success. The messages we receive as men are often about sacrifice and suffering being the guy who’s in the office until 9 PM, missing birthdays and celebrations because we’re told that’s what it takes to “kill it.” But maybe it’s time we rethink what success really means.

We’re conditioned to chase financial success, to hustle hard, and to push ourselves to the limit. But what if true wealth isn’t just about the numbers in our bank account? What if it’s about being rich in relationships, health, and spiritual life? And what if we’re setting ourselves up for failure by not applying the same determination to finding balance in our lives?

I remember talking to someone recently who was grinding away to build his business, but he admitted that it was taking a toll on his family. Sure, he was in a beautiful office, hustling and making moves, but his kids were at home without their father, and his wife was at her wits’ end just trying to keep it all together. Or maybe it’s not always that extreme but how many of us are living on autopilot, not truly present in the moments that matter, because work has consumed our entire existence?

Look, if you want to be successful, you will definitely need to make sacrifices and peel back some layers to become your best self. Building a business or reaching the top isn’t something you can just check in and out of from 9 to 5. But we set ourselves up for failure when we don’t approach balance with the same seriousness. If you and your spouse are on the same page about sacrificing for work, that’s awesome. Until then, it’s crucial to differentiate between being rich (financially) and being truly wealthy = having a complete picture of life.

Being present, finding balance, and redefining success to include all areas of our lives are not just optional they’re essential. We can’t afford to sacrifice everything else in pursuit of one-dimensional success. True wealth comes when we learn to invest in our relationships, health, and spiritual life with the same intensity we bring to our work.

Conclusion:

There’s a lot to digest in these ten steps, and remember, this is a lifelong journey hence the “Keep Becoming” mantra. Focus on one area where you can start making changes and consider reaching out to other men for support (our men's groups are a great place to start). These are challenges many are facing, so you’re definitely not alone.

These blogs aren’t just about pinpointing obstacles; they’re about using these insights to elevate yourself and your surroundings. Each point is a chance to refine, grow, and move forward on your path to success and self-actualization.

#KeepBecoming