The following is a summary of the first 33 years of my life. Kind of like a thus-far-autobiography.
It should be noted that I am an unreliable narrator… as all narrators are. Because my perspectives are only my own. I’m sure some facts are muddied by my highly fallible human memory, especially in my childhood years. I’m sure people close to me would tell parts of this story vastly differently than I would. But this is my life, as I experienced it.
I was born on April 21st, 1987. I was over ten pounds (4.67 kg) at birth. In other words, I was a big baby.
I was also a very speedy delivery. I came out in under two hours. Between lunch and dinner, so my mom didn’t have to miss a meal to deliver me.
Because of the speed of my delivery (apparently it’s good for the baby to spend some time in the birth canal because a bunch of stuff gets squeezed out of your lungs), they had to put me in an incubator to monitor me for my first few days.
My dad likes to tell the story that when he went up to the glass window of the viewing area, with me in an incubator in a sea of babies who were almost all exclusively premature, it was immediately obvious to him which one was his kid. He says that I came out and said, “Hi dad!”
I was the youngest of three children. And my two parents were together when I was born (and are still together to this day).
I was a baby for a while, until I wasn’t.
When I was a toddler, my sister was like a second mom to me. Very sweet. Very nurturing. She would even tie my shoes when I was capable of doing it.
Sometime around me being five years old, my brother (the oldest sibling) decided that he didn’t like me anymore and started to be mean to me. Not wanting to be on the losing side of the battle, my sister naturally joined his side and followed along.
They were awful to me for many years. I regularly cried myself to sleep. I felt excluded, unwanted, and alone.
The best way I can put it is that it felt like psychological warfare. They took every opportunity they had to put me down, exclude me, or remind me that I was annoying. They used everything they could against me. If I was too excited, it was made fun of. If I cried, they made fun of that. If I made it known that I liked something, then they knew to keep it from me. It felt like my emotions… my joy, my sadness, my excitement, my hurt… were all weaponized against me. It felt like their words and actions kept me stuck in a cage, like there was no room for me to exist.
I still remember the feeling of burning with hurt and rage while I was trying to fall asleep.
Because of the constant bullying, I even tried cutting myself when I was eight years old (I still have the scars). Cutting myself was the first and, for many years, the only time I got close to sending out a visible call for help. I figured if there were scars on my wrist, then maybe my parents would notice that I was hurting.
I wanted to be loved by my siblings so badly. I wanted nothing more than for them to simply include and accept me. I was a sweet, sensitive, caring, loving kid, and I felt like how much I loved and how sensitive I was were liabilities. They felt like deficiencies that were being used against me.
One way that I tried to gain my siblings’ approval (and, in my mind, increase the likelihood that they would eventually be nice to me) is that I never told my parents that they were mean to me. Not once. Because I just wanted them to love me and I didn’t want to do anything that could even remotely threaten that. And so the many years of bullying that went on was completely hidden from my parents.
There was a rule in our household that we weren’t allowed to hit each other. And so my siblings never hit me. But they used everything else at their disposal to make me feel awful.
(I was 27 when suppressed memories of my childhood came flooding back, and I desperately wished that they had hit me in ways that left marks, in order to give me physical proof that yes, it happened, and yes, it was awful. I resented that it was only emotional abuse and felt like if it had left physical marks then it wouldn’t have been suppressed/buried for so many years.)
One warped belief that was borne of this time in my child-mind is that I believed that everyone in my immediate family hated me, that they didn’t want me, and that I was a mistake. And I believed that my siblings were the only ones brave enough to say it to my face. Even though, in reality, my parents were always SO kind and loving towards me… even if they couldn’t see through my mask to the pain that I was hiding from them.
Because of this, I progressively tried to make myself as needless as possible. I tried to ask for less and less. My fear was that if I had too many needs, then there would be some (unknowable, unpredictable) moment when the other shoe would drop, and my parents would say, “Alright, that’s it. Get out. Your siblings were telling you the truth all along. You were a mistake and you aren’t wanted here.”
I remember thinking (between 7-10 years old) things like, “I don’t get to have a family”, “My pain doesn’t matter”, and, “I have to be a millionaire by 30 or I’ll kill myself.” I was absolutely drowning in shame. I felt guilty for being alive. I felt a deep sense of wrongness because, as my inner dialogue went, “If my own family can’t figure out how to love me then how will anyone else in the world love me?”
The childhood themes I’m touching on here will all manifest in later parts of my story.
So to recap, I was born, my sister was very kind to me for the first few years of my life, then my siblings turned on me, bullied me for years, and I thought that my family hated me.
In my pre-teen years, I was super into WWF wrestling, Pokemon, making short comedy sketches, Gameboy, and girls.
I remember spending the majority of my waking hours thinking about girls (a trend that would dominate the next 15 or so years of my life).
Does this girl like me? When I am going to have my first kiss? If I say yes to dating this girl then does that mean that I’ll be closing off the opportunity to date that other girl who I actually like more?
I mean, that’s really it. Aside from filming funny videos, watching wrestling with my guy friends, and playing Gameboy, I pretty much just thought about and talked to girls as much as I could.
Here’s a photo of me talking to my then-girlfriend on a cordless house phone (which was a big deal and felt super high-tech back in 1999) on my family’s backyard trampoline. My mom thought it was so funny that I was having hours-long conversations with my girlfriend while practicing my front flips on the trampoline.
In some ways, high school was great for me. In other ways, it was super painful.
When I first went to high school, I remember feeling an overwhelming sense of relief. I felt like this was a step in moving away from my family and into something closer to my own adult life.
I made a close group of friends fairly quickly. For years, we would all spend the majority of our evenings, weekends, and summers skateboarding and filming skate videos (my friends were way better at doing tricks than me, so I ended up filming and editing all of our skate videos). And I also hung out with the theatre kids a lot. Basically, whatever forms of theatre/art/performance there were to engage in, I loved doing them all. I acted in plays and musicals. I was in a punk band with my two best guy friends. I would regularly play shows (with my band and also solo, acoustic shows) in neighbouring suburbs. And I was super into photography, film making, and video editing.
Have you ever seen the movie The Royal Tenenbaums? I used to joke that me and my siblings were like the three siblings in that movie. Each one had their own unique zone of genius. My brother was the book smart genius… my sister was talented in everything athletic… and I was talented in everything artistic.
Another thing that happened during high school is that my obsession with women and dating intensified.
Because the pace of learning in high school was painfully slow for me, I remember thinking, “This is not the game that I want to win. The traditional education path will not be for me… I’m going to win in some other way. So I might as well just soak up the people skills that comes from dating a lot.” And so I made dating my focus.
I consistently put in as little effort as possible into my school work to get by with decent grades, and then put all of my mental and emotional bandwidth into dating. I basically had girlfriends constantly from 13-21, with a one year reprieve in the 11th grade when I wanted to see what happened when I took a year off from dating anyone (I got on the ‘honour roll’ for good grades for every semester of the year, and found it all profoundly boring). For whatever reason, I just knew that I would learn more from dating and socializing a lot than I would from memorizing a bunch of useless facts.
Now, despite having a superficially positive experience in high school, I still had a deeply permeating sense of wrongness and shame in my bones. I felt guilty for existing. I felt like I didn’t deserve to be happy. I felt like life was a farce and I was only trying it out for a time.
“Sure, I’m smart enough to get by, and charming enough to date a few girls, but sooner or later everyone will figure out how fundamentally unlovable I am, and this will all end.”
Because of that, another thing that happened during high school was something you would have already heard about if you’ve been closely reading my work for the last few years.
When I was 15 years old I tried to kill myself.
I had been carrying around a large bottle of painkillers for over a week before the day that I decided to swallow some unknown, high number of them.
I did it because I just didn’t want to exist anymore.
I felt like I had been playing make believe. Like, no matter how many people treated me like they liked me and cared about me, it would eventually come to light that everyone hated me, and they would turn on me just like my siblings did.
After a decade of feeling like I was an annoying, unwanted, unlovable person, I felt like I would be doing my family, and the world, a favour.
I remember swallowing the pills, a handful at a time along with a can of orange soda, on a wooden bench a block away from high school, and thinking to myself, “Sure, my parents might shed a tear or two”, but I believed that the dominant emotion that they would be feeling is relief. Relief that their unwanted, unintelligent burden of a shitty kid would be gone.
After my suicide attempt, I stayed in a children’s hospital suicide watch overnight ward for three nights. I wasn’t allowed to have a belt, shoelaces, or metal cutlery.
When my parents came to visit me in the hospital and I could tell that they had been crying, it truly fucking baffled me. It fried circuits in my mind to see them hurting over my suicide attempt. “You’ve been crying over this? I thought I was doing you a favour…”
After being released from the children’s hospital suicide ward, I was put on anti-depressants, and over the coming year I met with various therapists who I found to be abysmally incompetent and unwilling to connect with me like a person.
“Oh yes, please Mr. 65 year old psychiatrist hiding behind a clip board… let’s attempt to have an intimate conversation about my pain while I sit here and feel like a fucking lab rat.”
After a few months of trying anti-depressants (and feeling worse) and trying out multiple therapists (and feeling even more disconnected from people), I simply got better at pretending that I was fine. I didn’t feel like there was room for my pain in my family, so I just buried it and got on with my life.
Needless to say, this is why I have written so many pieces about mental health, depression, suicide, and suicide rates among men over the last decade. It is a topic near and dear to my heart. I know intimately what the inner dialogue of a suicidal person sounds like. I have cumulatively had many months when the thought of killing myself felt very compelling.
I can now (at the time of writing this) safely say that those thoughts are well behind me, and the idea of playing god and removing myself from the planet feels ridiculous.
I have seen so many people whose lives have been irreparably impacted by the suicide of people closest to them. Even though it isn’t en vogue to say so, I have come to believe that taking my own life would be a painfully selfish act to engage in. Depression itself is a highly self-obsessed place to be. It is a perpetual prison of ruminative ego thoughts. Which is why volunteering, or doing things for others, is one of the best things that depressed people can do to get re-engaged in their lives once more.
But I digress.
So yes. High school. I dated a lot. I tried to kill myself when I was 15. And I engaged in a lot of creative pursuits, and relished the opportunity to do so.
At the end of high school I thought that I should try to make something of myself. And, having progressively fallen in love with filming and editing short films from the ages of 12-17, I decided to apply to film school right away, as taking a year off post-high school didn’t appeal to me in the slightest, and I got in.
I went to film school (or, the motion picture production program) at Capilano University for three years (since that’s how long the full program was back then) from 2005-2008.
During this time, I also started my first business (doing wedding photography), worked in a restaurant as a server part time for three years (liked the people, didn’t like the mile-a-minute multi-tasking), and realized that I liked making creative works myself, but didn’t like working in film production (the hours were terrible and the majority of the people in the industry over the age of 35 were miserable).
During university, I also started dating someone who I had had romantic energy for during high school, but thought that she had been way out of my league.
Well, turns out, I was wrong, and apparently she had also liked me, and sent me some very explicit signals, but they went over my head because I wasn’t in a place to believe that she liked me when I was 14 years old.
So, we dated for a year. At that point in my life, it was the most open hearted and loving I had ever been to any girlfriend. I would bring her flowers for no reason. We would spend hours just lying in bed and staring into each other’s eyes. At one point, I even recorded a four-song CD of music that I had written and performed for her. Yeah, I was that smitten.
I pictured our lives together. I absolutely adored her. And I could feel that she felt the same way about me.
Then, one day, shortly after our one year anniversary, she blindsided me with a particularly vicious breakup.
The breakup that changed my life
She told me that she wasn’t attracted to me anymore. That she felt smothered. That she thought that my sensitivity and emotionality were repulsive. She even told me she wondered if I was gay.
We sat in the front seats of my parents car as she lay into me for over half an hour, and I just sat there, completely silent and awestruck… too surprised by the breakup that I didn’t even feel like I had any bandwidth to be upset with.
After around forty minutes of sitting there and receiving the verbal abuse, the pain started to set in, and I inwardly made a promise to myself that I wouldn’t let anyone else ever have that level of power over me ever again. That no one should ever again be able to get access to my heart that deeply.
“Women will ask for your vulnerability and then use it against you. My emotions are wrong and disgusting. If I show my emotions to women, I will ruin the relationship and it will be my fault.”
And so began a several year stretch of my heart shutting off to women completely, and deeming them unsafe to be vulnerable to.
The breakup also served as a catalyst for me launching into my new career path.
Spending my summers photographing weddings had lost its lustre, and waiting tables left me with a few handfuls of cash but emotionally depleted.
One faithful evening, I was sitting in my bedroom and I Google’d something along the lines of “How to figure out what you want to do with your life.” And one of the listicles that I found on the second page of the search results prompted me with the question of, ‘What types of books do you tend to read for fun?’
Looking around my room, I quickly realized that I had exactly ONE book about film making, and over 200 books on dating, relationships, sexuality, family systems, and marriage.
Relationships! Psychology! Of course! This is where my passion had been guiding me all along.
Knowing that I didn’t want be a general therapist (too general) or a divorce counsellor (too late-stage in the game for my tastes), I decided that I would do the next best thing. I decided to research to see if there were any dating/relationship focused businesses in Vancouver that I could get a job at, and make myself useful.
I found one (called Social Fluency) and decided to email them with a message to the effect of “Hey, I want to take your six week program, and potentially work for you guys. Also, your staff headshots on your website are terrible. How about a work trade? I’m a professional photographer and I’ll shoot new headshots for every one of your staff in exchange to take your $2,500 course for free, knowing full well that I want to be an instructor for your company in the next three months.”
Within six hours, I received a reply, which basically said, “Hey, interested in a work trade. Let’s talk more. Meet me at Kits beach tomorrow at 2pm.”
We met up, hit it off, and we agreed that I would take the photos for their staff, and that I would pay half price for the six week program.
They also made it clear that they didn’t have enough money to pay me to work for them. Utilizing my youthful confidence I told them that within a couple of months I would help them generate more revenue, and they could pay me from that.
I started right away. After my third week of taking the class, I was already shadowing other teachers and teaching my own new classes. Within three months (of fully unpaid work) I had become the head instructor and the other instructors all stopped teaching. A couple of months after that the company had gone from 1 or 2 classes a week to 4 or 5, and they were paying me a monthly salary for the value that I was bringing.
Within the first year, we became the market leader in Vancouver and our two other competitors both folded. I felt like I had won. At this point, I was 22 or 23 years old and I had tasted my first hint of success. I was hooked.
Working hard felt great. Helping people (we had classes of men and women) transform their lives for the better was an addictive high. And I got to be creative, reworking the core program curriculum and creating new programs and offerings.
I had finally found a way to utilize my core gifts and see people’s lives expand, grow, and thrive in real time.
I had found my calling.
While the core curriculum was fairly generalized (we primarily taught conversation skills, body language, assertiveness, eye contact, etc.), I found that it was a good foundation for me to tap into my love for being a teacher, while also keeping me accountable to something greater than myself. In other words, even though I was in my early/mid-twenties, it was very easy to not go out partying every weekend when I had this passion project that I could sink my teeth into. I didn’t want to show up hung over to work when I had 8-12 people every night that I wanted to do my best to support in their journey.
While I have a fairly strong hermit/isolator aspect to my nature, feeling ‘tied’ to this business, and to supporting people, really helped me balance myself overall.
Another, I guess you could say, ‘benefit’ to teaching at that company was that I went on a multi-year dating tear and learned even more about myself.
I learned that although I could turn on charm and confidence at the drop of a hat, there were some shadow aspects to my psyche that I had yet to integrate.
One of the most significant things that I learned, through this phase, that I had yet to integrate was my anger. And this showed in how a decent percentage of women responded to me. It wasn’t uncommon for me to be sexually or romantically interested in a woman, only to have her tell me that she didn’t see me that way. Now, to be clear, only a minority of women who I had interest in responded to me this way, but it still showed me that there was enough of a pattern that I could tell that there was something there for me to learn.
A major turning point in my process came when my first sex coach reflected back to me that the primary reason some women weren’t seeing me as a sexual option was because I didn’t have any edge. In other words, my anger had yet to be integrated, and certain women could feel my internal lack of power, potency, and ability to set consistent boundaries (what’s often referred to as being a ‘nice guy‘).
With this newfound insight under my belt, I decided that I had to take matters into my own hands and find appropriate, embodied mentors in the area of sexuality.
Integrating my shadow through BDSM
There’s something very unique about the energy in a sex party.
Everyone is either having sex or about to have sex, but everyone is doing their best to not look at the sex, talk about the sex, or get too physically close to the sex. Now, going by public rules of engagement, I understand why that’s so… but there’s a low level of cognitive dissonance going on in the room. You can start a conversation with someone knowing that you could be inside of them (or have them inside of you) in the next five minutes, but you still have to start off with the perfunctory small talk about how your day’s going, what you like about each other’s outfits, and whether or not you’ve been to one of these before.
Anyways, back to me.
I learned so much about myself through spending time in BDSM dungeons and sex parties. Just like I think that everyone would benefit from talk therapy and travelling to countries other than the one they were born in, I also think that the vast majority of people would benefit from going to a sex party. Even if they don’t participate, that’s fine. Simply being in the room while many people are having sex around you is a multi-layered lesson in increased self-awareness in itself.
I realized that I really enjoyed being sexually dominant, I didn’t like being sexually voyeuristic, and I also didn’t like being polyamorous (even though I frequently engaged in poly relationships, for reasons I will get into in the next section).
While I certainly hadn’t been a sexual shut-in before my years of dark sexual energy integration, I learned so much about myself (and about sex, and about people) in those years. And I’m so grateful that they happened.
After a few years of galavanting through sex clubs in Vancouver, Montreal, and San Fransisco, I eventually began to feel like the mask of identifying with my dark sexual energy began to feel heavy and ill-fitting. So I set it aside for a few years.
I’ve come to believe that every phase of our learning and self-discovery should feel like that. Try it on, and utilize it for a while as you glean the gifts from it. Then, once it feels like you’ve gotten what you wanted, let it go, transcend that level, and keep whatever fragments of it you still want to use moving forward.
Something else that emerged through my years of being a dating coach and frequenter of BDSM dungeons is what I would refer to as a…
Or, at the very least, an over-reliance on sexual compulsivity as a coping mechanism.
After being a dating coach for a number of years and spending a good part of my free time in sex clubs, I came to a point where I felt like finding new sex partners had become too easy. I know, cry me a river. But the challenge didn’t seem to be there in the way that it once was, and I felt disheartened by it. Like an addict chasing a bigger and better high, I wanted something more.
While I certainly didn’t have an awareness of my sexual compulsivity at the time (at least not in the earliest years of it), I did feel a gnawing sense of wanting to have as many sexual partners as possible.
There were a couple of years where I would be seeing three to four women simultaneously (who all knew about each other by the way – just because I was caught in the throws of addiction didn’t mean I ever felt comfortable lying to people) while also going to licensed massage parlours and sex workers. It wasn’t uncommon for me to be sexual with different women four or five days a week. Which, given what my baseline sex drive is, is far beyond what would have been considered normal or healthy for me.
There’s an often quoted line in Alcoholics Anonymous that goes, “First it was fun, then it was fun with problems, and then it was just problems.” And this saying completely lined up with my experience of my years of sexual compulsivity.
First it was fun and novel and exciting. Then it started to wear down my soul and I felt at least intermittently exhausted by it. And in the final stages I was avoiding anyone who knew me intimately at all, sleeping with five people per week, and spending thousands of dollars on sex workers even when my conscious brain knew that it wasn’t bringing me anything of value.
It wasn’t a case of “Oh I could really go for some exciting sex right now”, as much as it was a case of “I’m in so much fucking pain right now that I either need to get drunk by myself, or see a sex worker.” In the final months of my sex addiction, I was engaging in increasingly risky sexual behaviours that were taking me to a darker and darker place. And eventually I had just had enough.
It doesn’t take a Jungian psychotherapist to connect the dots and figure out that my compulsive desire for sex was driven by my underlying shame and childhood wounding with women.
What better way could I feel accepted and loved by women than to have them allow me to be momentarily inside of their bodies?
But the high never lasted. As time went on, the need grew bigger and bigger. Until it got so loud that I couldn’t ignore it anymore.
I started attending S.A.A. (sex addicts anonymous) several times a week.
And while I would love to tell you that I was super committed and just launched myself into it immediately… the truth is it took me somewhere between 6-12 months before I really let myself go to meetings consistently.
There were even a few months, near the beginning of my recovery process, when I had a spreadsheet of where all of meetings were, and I would make sure that I went to different meetings in a rotating fashion so that people would never see me at the same meeting more than once every two months. That’s how ashamed I was! I was intentionally making myself scarce at various twelve step meetings so the other addicts couldn’t get to know me, or try to get close to me.
This even translated into the type of sex that I allowed myself to have with my partners. I would have more polarized, dom/sub sex because there was less tenderness in it. And if a woman I was seeing attempted to introduce more loving tenderness or heart connection into our relationship, I would quickly pull away and find a way to end the relationship.
There were years where I wouldn’t allow myself to lay my head on the chest of my partner. It was too intimate. Too vulnerable. And, remember, I had to keep my heart from women because I just knew that all they would do was walk all over it and stab me in the back. So yes. Emotional distancing it was. At this time in my life, I was 24 years old.
Blowing up my life in 48 hours
After a few years of leading nightly group sessions for men and women, the dating coaching business started to veer into an increasingly dry, neutered, corporate territory (with a focus on teaching social skills to business people) and I was trending in an increasingly sex and taboo focused direction. After three or four years with the company, I decided to part ways with being a dating coach.
But that’s not all!
On the same day that I quit that job, I also ended a year long monogamous relationship, and started to throw away/donate/get rid of over 95% of my physical possessions. I wanted a fresh start. I had had my life’s first panic attack weeks prior and I knew that something needed to fundamentally shift in my life. Turns out, almost everything needed to shift.
Goodbye job. Goodbye misaligned romantic partner. Bye things, income, and clients.
After 48 hours of blowing everything up… I had a nearly empty bedroom, and a phone that now had zero incoming communication (seeing as my girlfriend and my clients made up 100% of my phone’s notifications back then).
Having created some spaciousness in my life, I then had some energy to look at everything with clearer eyes.
I knew I wanted to create things. I knew that I wanted to help people in some way, likely with their interpersonal skills. But the idea of being a dating coach felt superficial and less important that it had once felt.
On day five of self-reflection (veering into unproductive rumination), one of my favourite clients that I had been working with reached out and asked if I would work with him 1-on-1, in order to do some deeper work together. The idea excited me, so I said yes.
Within two weeks, I was working with him on a weekly basis, and two other clients who had reached out to work with me in a 1-on-1 basis. I had a full client roster and hadn’t even tried to market myself. I saw an opportunity.
I was already enjoying working with these people 1-on-1, as it allowed me to go deeper with them than I had been when it was a 1-to-10 ratio of people. But I wanted to make sure that I wasn’t just falling back into a familiar groove. I wanted to get out of my usual context and make sure that I was making these decisions from the deepest part of my heart.
So I booked a one-way ticket to southeast Asia, decided to start an online business, and I told my friends and family that I wouldn’t be returning to Canada until I was making a self-supporting income from my brand new online venture.
Leaving the nest for long-term travel
I packed up the biggest backpack I’d ever seen and I flew to Thailand. I ended up living there for two months, and during my visit, I wrote, published, and marketed three short e-books.
I knew that in order to give myself an early shot of confidence, I’d want to see some online sales sooner than later. Just to prove to myself that, yes, this was possible.
I still remember my first ever book sale. I had published my first book… and was sitting on the edge of my bed in a $10 a night hotel in Bangkok… and the sales counter (after refreshing the page for hours) eventually went from a 0 to a 1. I immediately started crying tears of joy. I just knew that if I could sell one thing on the internet (and make $0.35 of profit) that I could sell a million things online with patience and persistence.
Within 60 days of landing, I was making over $2,000 per month in recurring book revenue (all from self-publishing!) and I signed my first new coaching client. I was off to the races.
When my two month visa ran out, I went to Bali for six weeks. And when that trip came to an end, I went and lived in Paris for a month.
It was in Paris that I met and dated a beautiful hearted woman named Linnea.
Now, remember, at this point in my life, I had never been more emotionally shut off to women. I was a madman workaholic, just cranking out article after article for my newborn baby site.
And there was one particular moment when Linnea and I were out for a walk (on our first date) and it just started pouring rain.
We ended up walking in the downpour for over three hours.
After the first hour of getting drenched, I started to get quite cold. Noticing this, Linnea took one of my hands and enveloped it in her miraculously warm hands.
This simple, loving act from a relative stranger shifted something in me. I felt my heart begin to thaw for the first time in years.
The warmth of her hands, and the intimacy of the gesture, immediately seeped into my bones. I had spent so many years running away from the warmth, touch, and affection of women that this gesture got me at my core.
I stayed in Paris for nearly a month, and I ended up seeing her at least every other day that I was there.
After just over four months of being away from my hometown, I flew back… having successfully gotten my new venture off the ground, and started to settle in – prodigal son style.
Having launched my new business (the website that you’re on right now), I experienced a newfound sense of freedom.
I got to wake up every day and create whatever I wanted. I was able to write articles that reached millions of people across the world. And I got to coach clients whose hearts I cherished.
The only thing that felt misaligned is that the idea of calling myself a dating coach started to wear on me. It didn’t feel right. It felt superficial and unimportant.
After months of stewing in my thoughts about it, I ended up enlisting the help of a professional acting coach who specialized in helping actors pick out their unique gifts. Within minutes of meeting me she told me two things that shifted my perception of myself forever.
First, I had always held the story that I was highly feminine. And she corrected this by saying, “You aren’t feminine. You’re just sensitive. Sensitivity isn’t inherently feminine.” This might sound simple, but it was profound for me at this point in my life. Yes, I WAS highly sensitive. And yes, I did still have a masculine leading energy.
Second, she told me that she wasn’t surprised that I felt disillusioned with the title of dating coach, because she saw me as someone whose process was about continual deepening and evolution. She said, “You’ve moved beyond helping people get into relationships. So what’s the next layer of it for you? Maybe you’ll be a relationship coach, or an intimacy coach.”
Upon hearing this, I immediately teared up. It felt true in my bones. I did want to go deeper. I wanted to help people maintain deeply nourishing intimate relationships (because that’s where I wanted to go in my own process next, and we all know that teachers teach what they most need to learn).
So, dating coach was out, relationship coach was in.
Within two years of starting my business, I had reached millions of readers, sold tens of thousands of copies of my books, and was making a six figure income. I felt profoundly proud of myself, and was excited for what was to come.
Soul mate relationship
In the summer of 2015, while living and working in Montreal, Canada with one of my best friends, Facebook showed me a “People you may know” in my browsers sidebar.
Her name was Amy and she was stunning. Not only that, there was a softness in her eyes that compelled me to click on her profile.
I spent the next couple of hours diving into her profile, blog, and readily available offshoot links.
From what I gathered, she seemed to be strong-willed, confident, artistically inclined, and extremely caring and kind hearted. All traits that I admired in myself.
So I decided to message her from across the country.
Here’s something random…
I don’t know you, nor do you know me.
I saw you pop up in my “People you may know” sidebar a few weeks back and I was absolutely stunned. To be honest, I thought yours was a fake profile because you were so gorgeous. I lost about ten minutes of work time because my brain had to reboot after seeing your profile picture.
But that’s besides the point of this message…
I’ve since stalked you (in a readily-available Facebook kind of way… not a telescope kind of way) and found out that you’re super driven, hard working, and passionate about many things. Congrats on the graduation and top honours.
The real reason I wanted to send this is that you, in a roundabout way, have given me faith that there are quality women who are beautiful, driven, and humble… all at the same time.
I don’t expect anything in return from you from this message. I just wanted you to know that I see what you’re putting out into the world, and I applaud it. I’m very impressed by you.
Have a great weekend.
Three weeks later, she messaged me back, we ended up hopping on a phone call and hitting it off, and we agreed to meet up in person when I was back in Vancouver.
What followed was 18 months of what I would call a ‘soul mate relationship.’
Now, to clarify, many people consider the phrase soul mate to mean that you’re destined to be together. But the more I looked into the true meaning of the soul mate relationship, it is more about how you’re destined to cross paths in order to have a relational head on collision that wakes both of you up more fully. In other words, it’s less about a durable love and more about shaking off egoic cobwebs and revealing your deepest truths.
Amy and I were both people that were very known in the community. In other words, people knew of us, but no one really knew us intimately. We were both in ivory towers of isolation of our own creation. And the greatest gift that this relationship gave both of us is that it forced us to both to move toward community like we never had before.
It was a painful, challenging, dramatic year and a half that really rocked both of us.
I am eternally grateful for all of the lessons that I gleaned from the relationship, and Amy will forever be in my heart (and apparently, also in my neighbourhood! As we currently live two blocks away from each other).
One of the biggest gifts that revealed itself through this relationship was really gaining clarity on how much I had isolated myself in my life.
After years of pouring myself into the creation of my business, something started to dawn on me. I had sacrificed my friendships, and social connections to a very high degree. In essence, I had turned my back on almost everything that wasn’t about cranking out work and creating value for others. I had barely been exercising. I barely saw my friends anymore. And I barely made time for anything that could be classified as fun, leisure, or pleasure. My only fun was hitting the ‘Publish’ button on new articles. My only joy was making progress in building up the size of my audience.
But the work that I was doing wasn’t coming from a clean place of simply wanting to help people, it was coming from a wounded place of wanting to be constantly providing value so that I could disprove my worthlessness.
After a particular psychedelic journey that absolutely handed my ass to me, I realized how profoundly lonely I had become.
At some unconscious point in my journey I had turned my back on anything that could nourish me, and I was in a never ending sprint to feel valuable via my work. Once I had realized this, I knew that something had to change.
A few weeks later, I found out that a local men’s group community was having an open house, that I thought I should check out.
Coming into community
A random May evening in 2016, I sat in a circle of about 50 men, and proceeded to silently judge all but two of them.
‘Look at these fucking losers. These unsuccessful, unmotivated, ineffective west coast wimps. I bet I make more than everyone in this room. What am I even doing here? What a waste of time.’
At the end of the two hour meeting, it turned out that the two men who I had not judged (because they were successful and I saw them as more similar to me) were both going to join the weekly men’s group on a trial basis. Each man only had to commit to the first four weeks. And I shook hands with one of the men that I liked and we agreed that if the group sucked, we would splinter off and start our own men’s group.
Well, I continued to judge the men in my weekly men’s group for the first two months of being a member. Obviously, all of this judgment and withholding were simply me protecting my own pain, and projecting my fears and insecurities on to them (which everyone tends to do in any form of group work).
Somewhere between the 2-3 month mark (in retrospect, it truly is a feat that my ego lasted that long with where my mind was at) I finally came clean.
I told my group that I had been silently judging them. That I had been holding back. That I felt like I was better and smarter and more accurately attuned than all of them.
And then I got even more honest.
I told them that I had been struggling with my on again off again relationship for the last year and I was emotionally exhausted from it. I told them that one of my best friends had been killed in a car crash a few months prior and I didn’t know how to process it. I told them that I had been feeling extremely burnt out from working so hard for so many years, and I was struggling to get by with how little available energy I had. And I told them that I felt lonely, suicidal, and in a completely isolated world of my own making.
In other words, I simply let them see my pain.
In group work, it is common that we interact with the circle like we used to interact with our family system. And, true to form, my M.O. with my group had been to provide as much help as possible while being needless and happy the rest of the time. So when my mask cracked, it cracked hard.
Admitting to my group that, yes, I was human, and yes, I had problems was revelatory for me.
It was through this simple act that I began to let people’s support into my life. I started to lay down my protective shield of specialness and separateness, and allowed myself to be seen as a flawed, struggling human.
Over the coming years, I continued to go deeper in my process with my men’s group, and I concurrently started to lean into the healthiest friendships of my life (most of whom I met through this therapeutic growth community).
I also engaged in four years of intensive group shadow work, which was an absolute fucking doozie of a time from which my stories could fill their own book. Suffice it to say, these years of group work gave me a handle over my mind more than anything else had up until this point. I processed my anger towards women, I owned my shadow self’s judgmental and self-destructive nature, and many more challenging things were confronted, accepted, and moved through.
All of this steeping myself in group work, community, and close, intimate friendships began resulting in me…
Softening and trusting
My 30th birthday was one of the most beautiful, nourishing days of my entire life, and also a total shit-show for my ego (that wanted to run and hide).
Because I’d long held the belief that I would have succeeded in killing myself by the time I had turned 30, this birthday was highly significant for me.
It was also the first time I had allowed myself to have a proper birthday in my adult years, where I allowed my friends to witness and celebrate me.
So I thought, hey, if my ego is struggling this much to just have people be there to love and support me, I might as well throw gasoline on the fire.
My ten closest friends, who had come to know me intimately through our previous three years of weekly group therapy, all gathered around and drowning me in love via what we affectionately refer to as an appreciation circle.
I sat in a comfortable position on a pillow on the floor, and then my friends, one by one, sat opposite me and spent several minutes each telling me what they most love about me.
Now, right off the bat, for some of you reading this, this might sound really nice. And for others, it might sound utterly terrifying. I was in the latter camp.
I cried so much in the day leading up to my birthday party. The idea that people who actually knew me were going to sit opposite me and publicly acknowledge me and tell me nice things about myself was so scary. My bullied, heart-bruised inner child was afraid that some, if not all, of the people present were going to reveal that it was all a ruse. That they’d just been fucking with me all along. And that they secretly hated me and just wanted to have the whole thing be an extended joke.
Yes, that’s how self-absorbed our egos are. A part of me honestly thought that sane, reasonable people would cumulatively waste years of their lives colluding in an extended practical joke just to gather around and reveal that they hated me and the whole relationship was a farce. What a sneaky little fuck our egos are! Making everything about us.
Anyways, they loved me up real good. I bawled my eyes out. It was healing. And I really, really started to allow in the truth that people loved me and cared about me. That the world wasn’t out to get me. And that I was safe to receive the kindness and love of others.
I was 30. I hadn’t killed myself. And I was letting people love me. What a joy!
30-32 were relatively uneventful. A few months before turning 30 I switched from being in a men’s group to running a men’s group (in the same affiliated community). I kept writing, releasing new programs, and coaching clients. For the first time in my life, I felt deeply content in being single. I wasn’t craving a relationship, nor was I being run by an aversion to it. I just genuinely loved where my life was at.
And I eventually decided that, you know what, maybe I could be in a real, committed, nourishing long-term relationship with someone who loved me fully. Because I was sure getting a lot better at loving myself, so it stood to reason that someone else could do the same in close proximity.
Meeting Demetra and moving in together
Months after I made this decision, someone unexpected and pretty spectacular floated into my life.
Well, technically, she floated into my life years prior.
Demetra had hired me for a coaching session at the end of 2017. It was a one-time call. I gave her some helpful feedback, and we were on our merry little ways.
When we first met (online, in 2017) we were both in relationships, and so didn’t think much of each other in a romantic context. But because we were both aware of each other’s work, we loosely followed each other and were long-distance admirers of each other’s writing/work/art.
Fast forward two years, and through a series of serendipitous events, we reconnected, and it was revealed that we both had crushes on each other. Dozens of multi-hour phone calls later, Demetra decided to come and meet me in person (in the summer of 2019).
We hit it off right away.
The energy was electric. Our overlap was obvious. Our complementary strengths were laughably aligned. Even the emotional work that we each had to do (because everyone’s got their stuff to work on) were themes that the other was well equipped to be with.
Our first ‘date’ was a month long, and at the end of that month Demetra decided that she was going to sell all of her things (that were back in L.A.) and move in with me.
Without a doubt, the most significant aspect to this relationship (for both of us) is just how fully we are able to meet each other. We both have had experiences where we always felt like we were settling with aspects of our past partners… whereas this relationship is the first time I’ve ever been able to say that I feel completely met on all levels. We’re compatible physically, emotionally, intellectually, and spiritually, and we both have aligned visions for our lives and the impact we seek to have on the world.
Now, here we are a year later, and this has undoubtedly been the most healing, loving, grounded, nourishing relationship of both of our lives. We’re currently spending our days largely being indoors and avoiding the majority of people (because, you know, world wide pandemic and stuff).
Reprioritizing my values
Over the last year, it has been a wild ride for my ego to really soften its grip over my life. The goal is no longer to squeeze 12 hours a day of work out of myself. I don’t obsessively write and build my audience using all of my waking hours. There was a conscious decision that I had to make a year ago when I really had to feel into the reality that my needs were going to be more diversified. For the majority of my 20’s, my sole focus was building my business. And build it I did! But often at the expense of my social life, my body, and my sense of balance and joy.
Now, my work is still a very significant part of my life. But I also make time for Demetra, for my family, and for my friends.
I even learned how to start having naps within the last year (nap credit: Demetra)! So I am living proof. Someone can go from a compulsive, shame-fuelled workaholic, to a soft, receptive, easy(er)-going person.
Discovering my identity-level attachment to not receiving
Something else that was revealed to me over the last year (in therapy – holla!) was that I had been operating with an identity level attachment to not receiving from others. And this dynamic was showing up in both my business and in my relationships.
In my business, I realized that I had written well over 600 free articles, and only ever released ONE product. In other words, there were 600+ ways to receive free value from me, and only one way to reciprocate any energy back to me (and even then only for the male half of my audience).
In my relationships, I was a great giver, but a terrible receiver. I wouldn’t ask friends for support. I still sometimes felt nervous about receiving tenderness from my partner. And just, all across the board, my identity was that I was someone who was here to give, but I was not all that interested in receiving.
Unsurprisingly, this was a vestigial factor tied to my childhood. The safest survival mechanism I thought I could deploy as a young child was to be as needless as possible, and so of course I found myself playing out that same dynamic in my modern life.
The breaking point where this piece really dawned on me was when one of my female readers (who I knew had been following me for years) messaged me something to the effect of, “I just love your writing and I can’t thank you enough for consistently putting out such valuable information. But, if I’m being honest, a part of me feels guilty! I wish there was some way I could give back to you after all these years. When are you going to create a course for women?”
The reason that this message really landed for me was that this woman sent it to me on a week when one of my closest friends had essentially said the exact same thing to me. That she wished she knew how to support me better, and that she felt like I just didn’t have needs.
That week, I really saw, with the most clarity in my life to date, how I had constructed walls around myself so I could throw slabs of value over the walls, but I wasn’t all that accepting of allowing myself to receive anything back in return.
So, I made a decision that I was going to start creating more products for my audience.
This past month, I put out my first ever video course for women (which you can check out here), and I have plans to put out a few more products (both for men and women) over the coming year.
When it comes to receiving, it’s almost as if there’s been this firehose of love being sprayed at me for years, and I’ve just been sitting there, stubbornly gripping a rain coat that covered all of me. Now, to give myself credit, these themes started to soften 3 or 4 years ago, but I see how they’re crumbling even faster and more thoroughly over the past year.
Stepping into my mission more fully than ever before
Along with the newfound commitment to allowing myself to both give and receive, I feel like there’s a corollary willingness to step into my life’s work more fully than ever before.
It may sound strange to hear from someone who already has a perceived level of success (80 million readers, featured in a bunch of fancy places, etc.), but I feel like I’ve been manufacturing my smallness in a way over the last ten years. Or, as David Deida would put it, I haven’t been playing to my “edge”.
This next year, I feel more ready than I’ve ever been to really step up.
I’ll be writing more. Loving more fully. Receiving more fully. And creating more products than I’ve ever made, and really pouring myself into them, like I never have before. I’m going to start leaving it all on the playing field, and not just playing to a low, safe ceiling that I know I can hit.
So, if you’ve ever wanted to see more Jordan Gray in the world, you’re going to like what I have coming up.
What I hope the next decade has in store for me
I can’t predict the future. But there are some things that I hope will happen over the next ten years.
I hope that my readership consistently ends up being over 3 million readers per month on my personal site.
I hope that I start consistently generating over $10 million per year from my business.
I hope that my work gets to be featured in GQ, Maxim, Men’s Health, Time, Playboy, and a slew of other high level publications that I have yet to be featured in.
I hope that I get married to Demetra.
I hope that I will continue to have the deepest sense of community with my closest friends.
I hope that I will get into the best shape of my life, and my body will be strong, capable, and completely tension free.
I hope that the best sex of my life has yet to come.
I hope that I get to a place where receiving (praise, tenderness, affection, etc.) is effortless and easy for me.
I hope that I will eventually reach over 500,000,000 (half a billion) people with my writing, with over 250,000 people going through one of my online programs.
And I hope that the world will be better.
That people will be even happier, and kinder, and more fully emotionally expressed. And the outdated notions that women can’t be public about their love of sex or that men aren’t allowed to cry will be cultural narratives of the past.
This is the world I envision. And, in the work that I do and the people I talk to every day, I see this as an absolute inevitability. And I’m excited to see that version of the world come to fruition, day by day.
So yeah, that’s been my life so far.
I felt riddled with shame for many years and decided to over-compensate by proving my worth by being a hyper-productive success robot. When that proved to be exhausting and misguided and isolating I came into community and re-integrated with the people around me. Now, I am allowing myself to receive the love and support and kindness of others like never before, while also stepping up into my full, heart-driven potential in the world. And, in case you were wondering, my present-day relationship with my siblings has never been better.
I hope that this was fun/moving/impactful for you to read.
Thank you for reading this far, and for coming along on this journey with me. I very much appreciate it. Writing this piece was quite challenging for me at times, but knowing that you were going to read it is what kept me going. So thank you. Yes, you.
Ps. If you enjoyed this article, consider sharing it with a friend who you think would benefit from it and/or your social media following. If you want to go deeper into my work, you can find over 500 articles on this page, you can work with me directly by clicking here, or go through one of my ridiculously stacked, value-dense programs over here.