The 'Bad Boy' Dilemma

I don't know if it's fair to say that nice guys "always finish last," but I definitely think there's evidence to support that being too nice as a man is not conducive to being seen as a leader or the prime candidate to head a government, a company, or even a household. Think about your favorite movie or TV show: how is the male lead presented in that production? I'm willing to bet that he is ruggedly handsome, strong, assertive, and at least a little dangerous. He probably has two or more women vying for his attention at any given time. He probably exhibits two or more of what are known as the "dark triad" of personality traits: narcissism, Machiavellianism, and psychopathy. And he's probably portrayed as generally being a "badass" or a "bad boy" who has the capacity for showing kindness and compassion in rare moments when the situation is appropriate but is generally unemotional, unattached, and uninterested in anyone's concerns except his own.

Masculinity is viewed differently across cultures, but what most cultures share regarding what defines masculinity is a focus on one's ability to compete and dominate others. I'm sure this is, at least in part, rooted in the man's historical role of needing to be a warrior to defend his home and country. The men who were most successful, not just in defending their homes and countries, but also in expanding their homes by conquering the homes of others, are the men who are most memorialized in history. Even men who were known for being kind, loving, and mostly concerned with serving others, like Jesus or Martin Luther King Jr., are remembered the way they are because they defied the rules and social norms of their time, which was dangerous. Both of these men were ultimately murdered, and their willingness to sacrifice their lives undoubtedly and substantially influenced how they are remembered and celebrated as men whom other men should model themselves after.

The men in the environments I was raised in all had "bad boy" qualities as well. There was something about being a risk-taker, a rule-breaker, and having a willingness to be violent, coupled with being emotionally aloof, that was not only celebrated but expected by the men around me. I didn’t just observe this at home but also on TV. Much of the persona I crafted for myself came from the TV shows I watched growing up, which means the masculinity I aspired to mimic was often based on what I imagined fictional characters would do in a given situation. I wanted to be like Will from The Fresh Prince of Bel-Air, like Zack & Slater from Saved by the Bell, like Shawn from Boy Meets World, and like Eddie from Family Matters.

Though these characters grew up in different environments, what they had in common was that they were all rebellious heartthrobs, desired by women and admired by men. Since I wanted to be seen in the same way, much of my personality was formed through observing these characters and trying to be like them. This eventually led to a self-image of myself as a "bad boy" like them, whether or not I was truly deserving of that title. However, the biggest "bad boy" I admired and most wanted to be like was someone even more inaccessible to me than fictional TV characters: my father, a man who did what he wanted, got what he wanted, and didn’t care who got hurt in the process.

'Little Leroy' and 'The Dog Man'

I think my mom had a thing for bad boys. From what I've been told, she wasn't always an angel herself. I've heard stories about how much of a 'thug' she was in her youth—never afraid to speak her mind or even put her hands on people. My father recently recounted a story to me where she chased him out of her house at knifepoint after she'd found and flushed some drugs of his that he'd stashed there. And though she may have been looking in all the wrong places, what I know for sure is that my mom was always looking for love. A real love. A consistent, stable, secure love. I don’t think it’d be fair to call her a hopeless romantic, but deep in her heart, I believe what my mother desired more than anything was to deeply love and to be deeply loved in return. And perhaps she would have been able to realize this desire if she wasn’t so attracted to emotionally unavailable men.

From what I've been told, my older brother's father was a big-time drug dealer in Brooklyn, NY, which played a large part in my mother's decision to move back to South Carolina while she was pregnant with my older brother—so he wouldn’t be tempted to follow in his father’s footsteps. My father was a dope boy as well, though to a much lesser degree. I mean, he certainly ran the streets as much, if not more, than the biggest drug dealers of that time, except he wasn’t chasing money so much as he was chasing ass.

Consciously or unconsciously, my mother was attracted to men with a bit of darkness to them, and I wholeheartedly feel like it's because it resonated with the darkness within herself. Though she might have had more 'success' pursuing men who were more 'straight and narrow,' the heart wants what it wants. Instead of settling for a 'good guy,' my mother’s strategy—and what I think is the strategy of many women in similar positions—was to get the 'bad boy' she actually wanted and then turn him good. Of course, this way of thinking was a recipe for disaster, because while people can absolutely change, and while they can be inspired to change by those around them, what ultimately determines whether someone will change is whether they want to change themselves. And my father didn’t want to change. So, though my mother brought him into her house, prayed with him, fed him, and loved him to the best of her ability, she could never turn him 'good' because he didn’t want to be 'good'—he wanted to be bad. And I wanted to be like my dad.

When I visited my pops as a kid, he would often bring me around his friends, and one of the nicknames they endearingly called him was "The Dog Man." He was awarded this title not because he loved animals, but because he had a reputation for doggin’ women, or rather, being a womanizer. My parents had split for good by the time I was three, so I don’t remember much about their dynamic together, but what I do remember very well is that my father always had a woman in his life. I was constantly being introduced to some new lady, going over to her house and sitting awkwardly while they hung out or attempting to make friends with her or whoever’s kids were there at the time.

I remember often being called "Little Leroy," being told how handsome I was and how I was going to be "just like my daddy" when I grew up—that is, someone who uses his looks and charm to attract a collection of women that he has no intention of committing to. And though I absolutely hated being called "Little Leroy," seeing how my father was admired by his male friends and desired by the women in his life deeply impacted me. Even though I despised my father by the time I became "active" in the streets, there was always a part of me, deep down, that wanted to be a dog like my Pa—and when the opportunity presented itself, a dog is what I became.

I've read that what womanizers crave is not sex, but power, and in my experience, this is true. Some psychologists believe that womanizers are often the sons of fathers who "escaped" their mothers, either by never fully committing to them, being workaholics, alcoholics, or using some other means of avoiding real commitment. Womanizers grow up believing that manhood equates to always being outside of a woman's control. This obviously means commitment is never a real possibility for a womanizer, because committing would mean he's not a "real man." Since womanizers don’t grow up with a healthy example of masculinity, they are instead served a version of manhood that is deeply rooted in the aforementioned "dark triad" of personality traits. They lean into their "bad boy" persona, which certainly attracts plenty of opportunities for connection but simultaneously makes real intimacy impossible, because a large part of the "bad boy" image is rooted in being a rebel, not being conquerable, and committing to no other will than your own.

And I guess that’s fine, as long as you’re satisfied with shallow, meaningless connections. I suppose it’ll work for you as long as you’re young, handsome, and surrounded by women who are so naive that what they desire most in a partner is that he looks good and is desired by other women. But when you start wanting something deeper, and when both your looks and the looks of those you typically pursue begin to fade, you might find yourself in a situation similar to the one my father is currently in—a situation I’m determined not to find myself in—where you’re almost 60 years old and have never deeply connected with another person, simply because you don’t know how to. Therein lies the crux of the "bad boy" dilemma, the greatest issue with seeing oneself in this way: it forces you into not just physical but also emotional isolation. Sure, you have the freedom to do whatever you want, but you lack the connection that makes doing whatever you want meaningful. And all you’ll have to show for your years of "bad-boyism" is a trail of broken hearts, wasted potential, and stories that would only impress immature men who have lived lives as empty as your own.

Can't Stop, Won't Stop... until you get caught

I definitely don't see myself as a 'dog' anymore and quite frankly don't have enough women interested in me at the present to even begin to be qualified as a 'womanizer' but there's a part of me that still does feel like a 'bad boy' in how I like a little danger, I hate conformity, I despise dumb-ass rules, and I really, really struggle with the concept of authority. Luckily for me, this hasn't gotten me into any sort of permanent trouble—yet, but recently, we've all witnessed how the 'bad boy' lifestyle eventually catches up to us all, regardless of how rich or powerful we might be, and regardless of how many years being 'bad' made our lives feel and look 'good'.

The downfall of self-proclaimed "bad boy" Sean "P. Diddy," "Puffy," "Brother Love" Combs has been poetic in a way because it illustrates and exposes just how toxic hip-hop culture can be, especially regarding how women are perceived and treated. I love hip-hop. It's such an integral part of who I am. As much as I studied and modeled myself after the characters of the '90s sitcoms I highlighted earlier, I studied and modeled myself after rappers even more. So even though my father wasn’t a constant presence in my life to indoctrinate me with his own form of toxic masculinity, I received it in other forms, and one of the most prominent forms was through the music I listened to—music whose version of masculinity centered around men being aggressive, violent, emotionally unintelligent, and motivated solely by greed, pleasure, and the desire to conquer other men. Music that often portrayed women as nothing more than disposable objects to be used and discarded when their usefulness was exhausted or when something better came along.

What has recently come out about Sean Combs and his abusive behavior toward the women he was in relationships with is proof of how damaging the attitudes of this culture can be and how dangerous the "bad boy" self-image can become if we don't grow out of it. The fact that there has been essentially radio silence from his peers in hip-hop is proof that many of them have engaged in similar, if not worse, behavior. When you're a "bad boy," other people are just means to an end—that end always being pleasing yourself. And when others refuse to continue being an object of your pleasure, "bad boys" show just how bad they can be by being physically, mentally, and/or emotionally abusive. Perhaps the biggest issue with seeing oneself as a "bad boy" is that remaining a boy means remaining immature. The fact that Sean Combs is nearly 55 and was still behaving this way is proof that an attachment to the "bad boy" image thwarts growth and keeps us locked into a time and mindset that is childish, regardless of how big our age is.

I don’t know if I’ll ever have kids, but if I do, and if I have a boy, I’d likely, consciously or unconsciously, pass on some of my own "bad boy" personality traits to him. If I had a girl, I’d consciously or unconsciously try to guide her away from boys who exhibit "bad boy" traits—and therein lies the biggest dilemma I’ve faced with seeing myself as a "bad boy" all these years: living with the hypocrisy of knowing that I wouldn’t want my mother, my sister, or my daughter to be associated with someone who behaves like I've behaved in my past.

There’s a subtle but critical difference between something feeling good and something being good, and while I’ll be the first to admit that sometimes it feels extremely good to be bad, being bad often leads to outcomes that are harmful for all parties involved. What I’d want for my daughter or my sister to have, and for myself to be, is not a "bad boy," but a "good man"—a man with an edge, for sure, but also a man who does not encourage or celebrate violence, yet is not afraid of it. A man who is confident and charming but uses his confidence and charm to inspire others, not to manipulate them. A man who is assertive but rarely unkind. A man who doesn't resist being "conquered" by a woman because he’s already conquered himself. And because he has already defeated the enemy within, he feels no need to make an enemy out of his partner.

There’s a real possibility that Sean Combs will never be able to go home again, and I’m sure during the time he’s going to spend in prison reflecting on the actions that got him where he is, he will often ask himself if being a "bad boy" was worth it. I’d be really surprised if the answer is anything other than "no." I really hope that he serves as an example, as I hope that I have, that being a "bad boy" isn’t all it’s cracked up to be and that what’s infinitely more important is being a good human.

What's Going On With Me?

Is it just me or has time been even more slippery than usual lately? It's hard to believe that it's already Fall. I had a nightmare the other night that the temperature was already in the 30s ☹️🥶 and though I was glad to wake up and find that we're not quite there yet, the reality is that winter is quickly approaching which for me means, not just an outer but an inner darkness. I'm a bit of a homebody through every season but that definitely is intensified when it gets super cold outside and I try avoid leaving the house unless absolutely necessary. And though that might be comfortable for my body, it's dangerous for my mental health so this year I'm going to make a conscious effort to not be so isolated through the winter months and still try to get out and connect with others.

I'm a bit concerned about the upcoming election. Though I hope that we collectively choose the lesser of the two evils, I don't think either choice is going to automatically or necessarily improve our situation as a country. Don't get me wrong, I certainly feel like one choice is much better than the other but despite who is chosen it's going to leave another half of the country angry and in despair which will have consequences regardless. I think both here in the U.S. and abroad, populations of people are more divided than ever and that is in large part due to social media, how easily accessible misinformation is, and our natural inclination towards tribalism—something the current media landscape exacerbates by tuning algorithms to serve us views that are already aligned with what we believe to be the truth which leaves very little room for nuance and very little possibility for diverse connection or community. That being said, I kinda feel like all this is necessary as a sort of reset that will ultimately bring things to a more balanced state—or, at least, that's what I'm hoping for.

I'm feeling the need to do another community check in so if you hopped on a call with me earlier this year, be expecting a message to set up a time sometime in the near future where we can hop on a call and catch up on what's transpired this year. And if we didn't hop on a call earlier this year, I'm still always willing to chat so don't be afraid to reach out if you feel called to. Since this year blessed us with five Sundays in September, I'm going to take next Sunday off from publishing a themed, full length newsletter but will still send out something to the subscribers with some thoughts and/or other interesting things I've stumbled upon on the internet during the week. Talk to you then.

With love,

Micheal Sinclair 💜