Confessions of a "Soft Man"
I was a master of seduction, but my insecurities made true intimacy impossible
There’s been more than a few enlightening (and uncomfortable) realizations that have come forward in the wake of releasing my last newsletter. Alone, on the open highway, and reflective in the way only the road rushin’ under my wheels can provide, I’ve been busy doing a post mortem on nearly two decades of sex, love, and relationships.
One thing I noticed straight out is that my addictive relationship to sex and dating gave me an inflated sense of power. If I could sleep with any woman I wanted, then I must be a powerful man, right? But take away all the desire and intrigue and emotional dependency coming my way, and I found out very quickly that I did not feel powerful at all. In fact, I felt confused, and super insecure.
Last October, I was pursuing Rachel, a bold, vibrant woman. I fell in love with her writing first — the way she so poignantly painted pictures of love, loss, and transformation through her poetry. Rachel has this outward, tough, and challenging persona. Being more passive myself, I found this to be a huge turn-on initially. But when we started to go deeper in our relationship, I quickly realized how insecure I felt with her. She made more money than me. She’d written more books and essays. She was a (much) better surfer. Our relationship was literally reflecting back to me my own deepest fear: that I was small and insignificant, and unworthy of love. I began to resent her, and when Katherine came along — who was younger, gentler, and seemed to put me, my work, and my life on a pedestal, I quickly jumped in bed with her instead.
I’ve been thinking about Rachel a lot, though, these past couple weeks. I looked her up on IG the other night and nothing’s changed. She’s still loud, still opinionated, still, if I’m being completely honest, a little self absorbed (takes one to know one). I still really respect her writing. And I miss her passion and fire A LOT. Looking at her page, I felt the same pangs of envy that I felt when I first met her. Then it hit me: I didn’t necessarily want to love this person, I wanted to BE this person.
Ah ha! That was the unlock for me. I looked back through my dating history and started to see a thread: Every woman I’d dated long term had something on the surface I wanted myself: My girlfriend in college, Tory, came from massive wealth, Amy was the stylish, Brooklyn cool girl, Stephanie was a restaurant owner and a pillar in her community, Christina was an Olympic athlete, Rachel was badass and outspoken and creative, and Katherine was achingly sexy.
They all had IT. A certain sparkle or shine, something that made them stand out. Something that made my ego burst with pride that they wanted me. But if I really boiled it down to its essence, what they appeared to have was always the same: Power.
I was attracted to powerful women.
I remember a passage in Robert Bly’s men’s work classic Iron John: A Book About Men that always stood out to me. Bly writes that in the wake of feminism and generations of emotionally and physically absent fathers, there was an epidemic in this country of what he called soft men. These men were insecure and uncertain in their masculinity, and therefore, he found, often drawn to vibrant, self-assured, outwardly powerful women who they knew — consciously or unconsciously — could guide them and take charge of their lives.
This glaring mention of a “father/mother wound” (quite literally guidance-starved men seeking a woman to run their lives the same way their mothers had lead their households in their father’s absence) hit me right in the guts. I remember reading the book — given to me by my male therapist — with unease shortly after moving into Stephanie’s bungalow in Silver Lake in 2018. Stephanie was a beautiful badass who owned my favorite restaurant in Echo Park, but my admiration of her take-charge persona began to leak into our relationship. Our roles were a total reversal from the Mad Men era: I’d spend the days emptying litter boxes, doing chores and cooking so the house would be nice when Stephanie returned from a 14 hour day at the restaurant. After dinner, she’d want to fuck, and I’d want to talk. Looking back, it makes me chuckle, but the dynamic was super frustrating at the time. Neither of us had the self mastery at that point to not let it screw up our respect, polarity and chemistry. So, after a few months, I called off the relationship.
It was clear to me on some level after that well-intentioned mess with Stephanie that I was a “soft man,” and that I’d come from a line of soft men (my father had been a soft man who took his own life when the powerful woman who had been funding his life left him). This realization only made my insecurity grow, which in turn, intensified my compulsion to womanize. The unconscious math was easy: I felt powerful every time I scored a “conquest”, but after the early days and weeks of seduction wore off, the same thing happened every time: my true colors would start to show. The closer a woman got to me, the more insecure I felt, and the more afraid I’d get of her seeing through my “I got this” exterior. The truth was, I didn’t have this. Sure, my life looked great on the outside and I had all the trappings of a successful guy, but behind the curtain I was afraid, financially unstable, and generally full of self doubt. So it was only a matter of time until I’d need to leave the relationship to maintain my ego’s smokescreen.
It hurts to see and really own that I’ve never had a chance in hell of staying and building with a quality woman, because of this deep rooted insecurity in my own potency as a man. Sure, I never had any doubts about being able to seduce and charm a woman, to get her to fall in love with me or to give her multiple orgasms, but living with a woman day-to-day made me anxious as hell, just like life as a whole tended to. I can’t tell you how many times I’ve been with a woman who I know now, in my bones, was craving for me to step up and take charge in the relationship, take charge in the bedroom, take charge in my life, or with my finances, but my own deep fears got in the way.
I wrote last time of the affects the “soft man” wound has on guys in this culture. And I see it everywhere. There’s a crisis of confidence in modern men — we’re on the whole anxious, depressed, and scared, lacking guidance or direction — and there’s a huge void of quality information on what to do about it.
Many men have exploited — knowingly or unknowingly — this void. Magnetic, alpha male personalities like Andrew Tate, Jordan Petersen, Donald Trump and Kanye West have become icons touting their versions of maleness, that seem to be valid ways out of the insecurity the average man feels. But these guys are just (innocently?) perpetuating a wounded masculine archetype that is fractured at best when it comes to its effectiveness. Yes, Peterson’s advice to stand up straight with your shoulders back is no doubt helpful at a base level, just like Tate’s encouragement to be your own best advocate (because no one else will be) is helpful. But these guys don’t offer — or embody for that matter — an integrated or healthy approach on how to get there. Peterson is still, at the end of the day, fuming with unresolved rage. And Tate’s hyper rigid approach to living can’t hide his own core insecurity (for evidence, a revealing video psychotherapist David Sutcliffe recorded with Tate a few months ago.)
So what to do if you’re a man who feels insecure, but wants to go about healing that insecurity in an integrated way? Ever since Bly’s heyday in the 80s and 90s, there have been men’s coaches and therapists and facilitators doing beautiful work in this space. And now organizations like EVRYMAN and Sacred Sons are offering in-depth men’s work on a wider scale. These days, you can do everything up and down the scale from work 1:1 with a men’s coach like me, or invest in an online course from Connor Beaton’s great site Man Talks. But whatever you do, create the space in your life to seek out and spend time around quality men. Men who will, as my former coach Bryan Reeves said: witness, support, challenge and celebrate you. This will directly begin to chip away at and rewire the “father wound” that most of us men carry in a big way, and will slowly foster the transition from the sort of adolescent maleness that is the norm in our culture to mature, integrated manhood. Prince to King, if you will.
On my own journey to healing my father wound and identification as a “soft man”, I’ve noticed that when I began to set the intention to be initiated into manhood, the lessons began to appear in less overt, more serendipitous ways, as well:
I remember years ago driving my car out into the vast desert west of Death Valley for a solo camping trip, and on the way, popping a tire. The day was hot — over 100 degrees — and I immediately panicked. For one, I didn’t have any water, and there was no phone signal on the back roads where I was driving. For two, I didn’t know how to change a tire—it wasn’t something my charming, white collar father had taken the time to teach me, along with how to shave or how to throw a punch.
Thankfully, I was able to get the car jacked up on the uneven ground, but I was having trouble getting the final lug off the wheel. (My Volvo station wagon had an anti-theft setup that required a special tool to unlock it fully). I was lying on the hot sand, cursing God and my luck, planning the 15 mile walk back to town that would surely kill me, when I heard a rumble behind me and a lifted Dodge pickup pulled up with three old rednecks in the cab. They jumped out, assessed the situation and me, and the driver gave a little smirk. “Havin’ a little issue with yur Volvo way out here, eh?”
The good ol’ boys couldn’t have been any nicer. They helped me change the tire, get the donut in place, and I cruised back to Los Angeles unscathed. But that episode stuck with me. In the story as I relayed it to friends, I was convinced the Three Wise Men had appeared, Winstons hanging from their mouths, to initiate me deeper into manhood. The first thing I did when I got back to the city was learn how to change a tire.
Other episodes with men have helped initiate me in the previous few years, as well: I’ve worked under men’s therapists and coaches like Reeves, trained 1:1 boxing with an ex-Serbian special forces agent, and learned to hold my own in the lineups at the territorial point breaks up and down the Malibu coast. I’ve cuddled with guys in plant medicine ceremonies and led my own men’s groups, just to name a few of the more impactful experiences, and each test, challenging myself alongside other men, has pushed me further into making “the uncomfortable more comfortable.”
But behind this womanizing pattern, this “mother wound,” lies the deepest insecurity about my own masculinity I’ve uncovered yet. And it hasn’t been “men’s work” that continues to turn the tide. In fact, it’s been the work I’ve done with a female coach, and the circles she runs, that has been the real game changer in letting go of my wounded masculinity, rewiring my “mother wound” and pushing me into this next phase of my life in a powerful way.
I know there’s even more work to do. And the work I’m doing now, the work I was not able to see clearly while blinded by the steady stream of seduction I was engaged in for twenty years, is the most profound work of all. There is a flourishing of my own feminine — the same vibrant, creative, gorgeous feminine I sought out in the women I seduced and left like Rachel — that needs to take place right now, and it needs to take place in alignment with the continued integration of my own healthy masculine. This involves a commitment to being in communion with healthy, integrated versions of both men AND women teachers and peers, who can show me the way forward.
Ultimately, my “soft man” wound was believing — as my father did before me — that I needed a woman to fully experience life. And while a woman, and a family, are no doubt a part of my future plans, there is work to be done to create a rich, vibrant and rewarding life of my own so that I can attract a woman who has also done the difficult-but-rewarding work to step into HER wholeness and experience the full breadth of life that we’ll no doubt co-create together.
Til then, I’m rolling solo.
-Sean