Loneliness

I noticed a pattern in my dating behavior recently.  Actually, I think I noticed it a few years ago but suppressed it, afraid it might be indicative of something that I might have to deal with.

I think I’m good at being single.  I keep myself busy with work, friends, and sports.  I enjoy my alone time.  Sex outside a relationship doesn’t do much for me.  And for the most part, I don’t crave to be in a relationship.  Yet every year, I enter the fall a single man, and exit the holidays in some kind of relationship.  Maybe not every year, but close enough for me to see a pattern.

In 2016, I met a Harley Quinn at a Halloween party and we dated until the spring of last year.  Before that was Max, who I met in the fall of 2015.  We dated until the spring of 2016.  It’s been almost a year since I’ve been anywhere near a woman though, and I’m starting to bug out a bit.

As great as my last girlfriend was, I came out of that relationship thinking that I might be asexual.  She was all kinds of awesome, and I was all kinds of uninterested towards the end.  It wasn’t her fault as I had some things I needed to work through.  In that regard, I suppose I’m not very good at multitasking.

Harley and I broke up in the spring.  Women weren’t on my radar at all.  The summer came and went and I still had no interest in women.  I was open minded to the idea that I just wasn’t suitable for a relationship.  I was also open minded to the fact that I might be a touch asexual as I noticed myself getting bored of sex within the first few months in most of my relationships.  I loved exploring, I loved figuring out where her buttons were, and I loved introducing her to new things… but as soon as things became a bit repetitive, I would lose interest.

In the fall, an ex messaged me.  We chatted for a bit and I could see she was angling for something physical so I told her she was probably barking up the wrong tree.  She took it as a challenge and basically took it upon herself to turn me back into a red-blooded male.  I thought it would be an interesting experiment.  We were supposed to meet up one weekend after she wrapped up at some kind of fancy party.  I told her earlier in the day that I just wasn’t into it.  There’s an interesting test that I think most men (and perhaps women?) are aware of: If you still wanna hang out with them after you jerk off, then they’re worth hanging out with.  That was not the case with her, so I eventually told her that it wouldn’t be right to use her to work out my own issues.

On Monday, I downloaded Tinder.  Or perhaps I should say that I re-downloaded Tinder.  I’m probably the minority but I’m a fan of the app and have used it to meet several quality women.  This time around, I’m feeling a bit lost.  My last profile was a head shot of me in a 3 piece suit, talking about working in finance and dabbling in venture capital.  As effective as that profile was, it seemed a bit douchey this time around.  It didn’t reflect who I had become over the last year.  I really didn’t know what kind of girl I was looking to attract, or even what I would even want from them.  I just knew it was different from before.  But Tinder isn’t the place for me to work this out.  I had the app for 2 days before deleting it again.

But I’m playing back into this pattern aren’t I?  Give or take a couple months.  Do I want to be in a relationship?  Probably not.  I wouldn’t even know where to begin.  Am I open to one?  I think so.  Maybe what I’m hoping for is to meet someone new who can teach me a few things about the world and myself.  Or maybe I’m feeling the void of someone who’s already taught me so much.

I probably went through more personal growth in the last 12 months than any other period of my life.  The last time I went through this much growth was when my dad died.  I learned to appreciate the true diversity of humanity.  I learned that embracing what made me different, and being true to myself wasn’t only going to be my greatest comparative advantage, it would also lead to my happiest self.  I learned the importance of not suppressing my emotions and the value of learning how to process and communicate them.  I learned why it was important for me to embrace the parts of who I am which I had neglected, thinking they weren’t necessary in my career.  I learned a greater appreciation for prejudice and the survivorship bias.  I learned to be far more grateful.  And perhaps most importantly, I learned a tremendous importance of keeping an open mind.

Keeping an open mind can be important for a variety of reasons, many of which I learned last year.  Of all those reasons though, one is very important to me.  I had the opportunity to learn all of this when I was dating Max.  She was a few years younger than me, but she had a handle on all of this stuff.  And the things she didn’t know, we should’ve been able to discover together.  Instead of keeping an open mind and seeing her as someone I could learn from, I saw her as a challenge to the path I was already committed to.  Where she embraced her diversity, I was telling her to mind her P’s and Qs.  Where she tried to encourage me to explore, I would tell her that I didn’t have the time.  Where she pushed me to have a better awareness of my emotions, I bought into the myth that I was all robot.  Where she encouraged me to be more grateful, I insisted that I had worked hard for everything that I had.  When she tried to assert herself as an equal who I could learn from, I basically told her that between our age difference and the life that I had lived, there was a good chance that I knew better.  I dismissed the wisdom in what she was trying to help me learn, for the sake of being right and being able to continue along the path I was on.  It’s one of the worst things I’ve ever done to anyone in a relationship and I still feel pretty rotten about it.

In a year where I’ve had more personal growth than at any other point in my life, I couldn’t help but be reminded of Max.  Over.  And over.  And over.  It wasn’t even about wanting to be back in a relationship with her.  It had everything to do with wanting her back in my life. But she wasn’t.

So I found myself thinking about her more and more.  I started playing some of the music she had turned me onto (Phantogram).  I made a half hearted attempt at stalking her social media (largely unsuccessful).  I started to wonder if we would still be compatible (maybe?).  Eventually, I even found myself tossing and turning in bed, wanting her to be within arm’s reach.

When we dated, we fell hard and fast.  Within the first few weeks, we were in love.  Within the first month, we were talking about moving in together.  A month later, we were joking around about having alpha-babies.  Infatuation aside, there was also a deep compatibility that I hadn’t experienced with anyone else.  But she only got half of me.  The other half was career oriented at all costs, and had picked a terrible career to be committed to.  I don’t see an alternate universe in which she could’ve convinced me of that.  I was subscribed to the philosophy that if failure was an option, then you had too many options.  A painful lesson, but perhaps invaluable to my future.

When I think about her now, the word that I can’t get out of my head is ‘equal’.  In the grand scheme of things, I think that we’re all equally valuable to the universe.  But Max was equal to me.  Or maybe I was equal to her.  Or maybe I’m just in awe of the situation and can’t help but hold her in such high regard.  I don’t think it’s that simple though.

I’ve spent most of my adult life hoping to find a partner.  I’ve also spent most of that time not knowing what that person would look like.  I think I have a much better idea now, though it seems incredibly hard to articulate beyond being with someone who’s my equal.  I want to be able to learn from them as often as they learn from me.  I want us to be able to keep an open mind when exploring the unknown together.  I want someone who can hold their own when debating something we disagree on.  I want someone who is valuable to me as I am to them.  And for each of us to be the most valuable person in each other’s lives because we’re committed to bringing out the best in one another.

Maybe that’s what’s going on here.  I have this fixation on becoming the best version of myself.  Seeing the influence Max had on me, I can’t help but think of her as an asset.  The key to my best self.  As romantic as that may sound to some, I don’t think it’s a very functional or realistic way to approach this.

With all the growing up I’ve done, I’m confident that I would make a far better partner for her than I did when we were dating.  Considering the potential we both saw in each other when we did date, I can’t help but be interested in knowing where that would take us today.  Maybe not much further than before.  Maybe much further than before.  I think that would have a lot to do with who she is now.  And therein lies the reality of the matter.

We were in touch over email last week for the first time in about 2 years.  She’s on the other side of the planet working on her MBA.  She’s out there doing her thing, as I always hoped that she would.  Which means I either gotta go get her, hope that she comes to me, or put it out there in the universe and see what happens.  And I’m going with option 3.

I’m sure there’s a romantic, fairy-tale way to approach this… and I wouldn’t put it past me to try something crazy like that.  But I’m still not sure how much of this really involves her.  Had it not been for our most recent communication, she wouldn’t have a clue any of this was going on in my head.  Not to mention there’s always a chance that she’s already dating someone.  Maybe she’s found her soulmate and I’m just being a needy ex.

How much of what I’m feeling relates to the fact that I haven’t been intimate with anyone in almost a year?  How much of this has to do with me usually being in a relationship at this time of year?  How much of this has to do with the loneliness I experience when I don’t have anyone to share my inner-thoughts with?  How much of this is the loneliness that comes from a modern society that’s so connected yet so divided?  How much of this is the loneliness that comes from a world where it costs money to hang out with your friends, but where everyone is struggling financially?  And how much of this stems from the fear that I may have found someone who I could truly build a future with, and may not find another?

The logic in me says that there are a finite amount of people in this world who would make for a suitable partner.  That Max may be one of them, but that she wouldn’t be the only one.  That given where she is, and the phase of life that she’s in, I would probably have better odds looking elsewhere.  Or maybe as the odds play out, I end up with none of them.  The logic in me says appreciate who she is, be grateful for what she’s helped you learn, and focus on the things in your life that are a little more tangible.

But then something else inside me says, what about Max?

I Used to be a Nice Guy.

As a kid, I think I was probably a handful.  But in general, a good kid.  It’s interesting because you might expect that a good kid would grow into a nice guy, and a nice guy would end up with a good girl and everything would work out. Somewhere along the way though, nice guys became not so nice.

I always had a close circle of guy friends, but back in early high school, I started hanging out with the ladies as well.  I genuinely respected and appreciated them as friends, but there would usually be at least one girl in the group I was crushing on.  As a kid, I really wasn’t sure how to approach the situation.  All I really knew is that if I spent time around them, I could probably make some progress.  I’d eat lunch with them.  Talk with them on the phone.   Help them with their homework. Help them with their guy problems…  And I literally got friend-zoned every time.

In grade 11, I met my first girlfriend.  We met at a driving school and I’m pretty sure she had both hands on the steering wheel.  I was lucky because she clearly knew what she was doing and didn’t mind that I was just along for the ride.  It only lasted a few months but at least I figured out how to kiss a girl.  My grade 12 girlfriend was about the same.

I could’ve very easily graduated high school a virgin.  Probably would’ve had I not been easy prey for a pair of girls who weren’t afraid to go after what they wanted.  Instead, I had a couple relationships under my belt and was ready for university.  I remember during orientation week, seeing a girl in my dorm who had the face of an angel, the body of a goddess, and the personality of a cartoon character.  We’ll call her Grace.  She was pretty awesome, and we started hanging out.  Just when I thought I may have been making some progress, she detoured towards an upperclassman.  Not only was the guy a legit womanizer, his personality was mostly cardboard.  It was extremely frustrating for me because I was athletic, I was academic, she and I got along really well, her friends liked me, her family liked me, and I was a nice guy.  Yet she ignored my interest to chase after a guy who literally treated her like an after thought unless he was trying to get laid.

Towards the end of my first year, I started dating our dorm’s resident busty blonde.  There was one point at which she came back to the dorm with another upperclassman, looking a little flustered.  I was a little suspicious.  He was the type to take advantage of a situation like that and she was probably the type to be into it.  We did a little long distance over the summer, where she cheated on me again with her ex back home.  As revenge, I strung her along until she thought things were good, then I broke up with her.  Effective revenge, but a complete dick move on my part.

Ironically, Grace started reaching out to me that summer, telling me about how I was the one she should’ve gone after.  To make matters more confusing, she had just gotten into a relationship with a childhood friend from back home, and the guy was actually treating her well.  She ended up sleeping with him, and then he ended up sleeping with her best friend, who happened to be a gay guy.  As entertaining as that was for me, I felt a little bad for her.

When we got back to school for our second year, everyone was back to being single.  I had been thinking about Grace a fair bit so I told her.  She didn’t have much of a response.  We went out to the big dance in the first week and within the first few dances, she was all up on another guy, so I decided to get all up on another girl.  We were mutually upset at each other’s behavior, and that seemed to undermine any possible momentum we may have had.  From there, she started pursuing a buddy of mine.  This guy was also a dick.  He was easy enough to get along with as a guy, but he also treated her like an after thought.  The more she wanted him, the more he didn’t want her.  I think they slept together a few times, but he had no interest in a relationship.  By the end of the second year, she was dating another buddy of mine who I shared a wall with.  He was much less of a dick, but also the kinda guy who partied way too hard to make it into his second year.

WTF was going on?  What did these guys have that I didn’t? In my head, I would go through the qualities that I had learned women respected:  Physically fit, good hygiene, doing well in school, good circle of friends, social status, respected women, polite, gentlemanly… what else was there?  Leaving university after my second year, I had concluded that women were more attracted and more responsive to men who treated them poorly than men who treated them well.  I knew that I didn’t completely understand the dynamic, but I was fully ready to give up on being the nice guy who was doomed to live out his days in the dreaded friend-zone.

When I got back home from university that summer, I really wasn’t focused on girls.  I was focused on being bad.  Money for school had run out and because of a few other issues between me and the university, they really didn’t want me back.  So I didn’t go.  Instead, I started doing the kinda things that bad boys do.  I spent the next 18 months with ‘the wrong crowd’, doing the kinds of things that people go to jail for.  My inner-circle knew what I was up to but for everyone else, I would just tell them, “don’t worry about it.”  And it worked surprisingly well.

I still wasn’t the type to chase after women, but I started noticing that girls were into me.  Girls who would’ve friend zoned me before were now interested.  My plan was working.

I didn’t even have a clearly defined plan.  All I knew is that when I was a ‘nice guy’, women weren’t interested in me.  When I wasn’t a ‘nice guy’, I was much more attractive.  I gave that a lot of thought.  Maybe the nice guy was too vanilla?  But then it occurred to me that for the most part, nice guys were harmless.  And harmless was unattractive.  There was a lot more to it than that, but maybe I was on to something.

When I got back to university to complete my degree, I proceeded to date 3 of what were probably the most eligible females on campus.  I thought the first was probably a fluke, right place at the right time.  By the third, I knew something was different from my first two years at the school.  I had manifested into the mysterious, hardened, conflicted, complicated guy who still managed to have a bright future, great friends, and a good heart.  Girls were totally into that guy.  I have to admit, it was a lot easier trying to figure things out as that guy than as the guy who could only watch from the sidelines.

When I graduated and came home, I started training in MMA 6 days a week.  I had watched a ton of it on TV and wanted to start competing ASAP.  Within months, I had added a new dimension to my personality.  I now knew that if I ended up in a physical confrontation with another person, there was a very good chance that I would come out on top.  I can’t stress how impactful that state of mind has been on every element of my life.  I spent the first half of my life avoiding violence, fearing that I wouldn’t know how to handle it.  I’ve spent the second half of my life avoiding violence, because I know how to handle it.  The confidence that comes from that state of mind was the final step in building myself into the ‘perfect guy’.

With all the information that I had collected in the first 25 years of my life, I had what I thought was a pretty good idea of what women wanted.  They wanted a guy who’s nice to them, but not to everyone.  They wanted a guy who’s good, but is capable of being bad.  They wanted a guy who can fight, but isn’t violent.  It was like they wanted someone who was a threat, but not a threat to them.  So I literally became the university educated, former bad boy, MMA fighter, investment advisor, who was complicated but with a good heart and a bright future guy.

It would be an exaggeration to say that at this point, I got every girl I pursued, but not by much.  I’ve never been the type for one night stands or picking up girls at a bar so that’s not what I’m talking about.  All I’m saying is that I haven’t been put in the friend zone since.

So how has that worked out for my dating life?  Am I happier?

For a while, it was nice.  Tinder worked like a charm.  Ironically though, the last time I used it was when I landed what many men would think was the holy grail of dating.  I ended up going on a date with a girl who had blonde hair and blue eyes, who looked like a porn-star, worked as a model, and on our second date, tried to bring another girl back to my place.  The second girl she brought back was way too drunk so I took her home, came back, and did the deed.   And felt so gross.  I literally had zero interest in who she was and I’m not the kind of person who looks to date or sleep with someone I’m not interested in.

It was like I had climbed this mountain of self-improvement, so that women would pay more attention to me, only to to realize that the person I had turned myself into was finally capable of landing the kind of woman I had no interest in.  Well then.

That was about 3 years ago.  I’ve had time to reflect.  With the rise of r/niceguys, I’ve thought a fair bit about the path I’ve taken.

The first thing that I had to face was that I spent most of my adolescent and adult life trying to become the kind of guy that girls would be interested in.  When I was young, I modeled so much of my behavior after prince charming.  The good guy, the hero, the gentleman, the nice guy.  That earned me as many female friends as I wanted, but no real relationships.  The girls I did date either got disinterested or cheated on me.  Once I realized being nice didn’t work, I modeled myself after the reformed gangster.  The bad boy, the outlaw, the guy who had seen some shit but didn’t wanna talk about it, and the guy who did bad but now chose to do good.  That earned me as many dates as I wanted, but again, no real relationships.  I was a fixer-upper that women were keen to get to work on, but I had no interest in being fixed.

There’s a dynamic here worth exploring.

There seems to be this cat and mouse game going on between men and women.  But who’s the cat and who’s the mouse?  As much as personal preference came into play, there would always be a few guys that almost all the girls were into.  There were also more than  a few guys who almost all the girls were never into.  To some degree, there was a male hierarchy, that was determined by female preferences in dating.  It was the alpha males and the beta males.

Interesting.

In an age where people are talking about women needing to be more powerful, I can’t help but think this is a dynamic we’ve yet to really appreciate.  Men, in their formative years, model so much of their behavior after what they think will give them the best chance of being with a woman.

As with most major issues in the world, I can’t help but think that this would be easily solved with the use of blatant honesty.  I think a good starting point would be for women to be completely honest about what they find attractive, and communicate how that changes over the course of their lives.  I suspect that most girls grow up thinking that they want a prince charming but as they start to grow into women, they start to realize that life’s a little more complicated than the fairy tales they grew up with.  Turns out that prince charming doesn’t actually exist, and even if he did… meh.  At this point, it becomes an exercise in women exploring what they do want.  It can be tough to be honest about this though.  Especially when you’re trying to maintain an image of innocence, sexual exclusivity, or any other quality that women tend to assume they should be projecting.  It’s not honest though, and it’s confusing the hell out of the guys.

Men aren’t off the hook.  Not even close.  Maybe, in a roundabout way, women facilitated the creation of the ‘nice guy’.  But seriously, how about we don’t play the victim here?  The modern ‘nice guy’ is no longer defined by being a good person.  He’s now defined by the pain and frustration that comes with years of rejection.  And perhaps a mistrust of women, betrayed by the nice guy philosophy which he was convinced would lead to that elusive girlfriend and social acceptance.  I understand where those emotions come from… I’ve experienced that same frustration… but get over it.

If you had focused on you, focused on becoming an interesting and accomplished individual with the patience to wait for the right woman to come along, you probably would’ve been fine.  Instead, you tried to become who you thought women wanted you to be.  You got it wrong.  You thought they just wanted someone who treats them well.  They want more.  A lot more.  They want someone they feel safe around, they want someone who can make them laugh, they want someone who can make them think, someone who can introduce them to new things, someone they can introduce to new things, someone who will truly understand and support who they are.  And etc., and etc.  Not to mention, they want to feel that physical chemistry.  If all you got is nice, it’s not enough.  If all you’ve got is nice, you haven’t earned shit.  Even when a girl says all she wants is a nice guy, they’re still not talking about you.  Until you’ve figured out who you are, found your reason for wanting to be a good human being, and are no longer projecting your issues onto others, you’re not ready for dating.

So what happens when you figure out that women aren’t really looking for just another nice guy?  Well I’m not sure if it’s the default, but a lot of nice guys are becoming assholes, thinking, “shit, well if I’m gonna get rejected, I might as well be an ass about it.”  And maybe there’s this sense of karma where you’re thinking, “You want to date a jerk?  I’ll show you a jerk!”  All that’s really happened though, is you went from the uninteresting nice guy, to the uninteresting asshole.  Or, maybe you were always an ass, but thought that being a nice was going to sweep her off her feet.  Stop it.  It’s not working.  It’s never worked.  It’s unlikely to ever work in your lifetime.  Focus on being a good person, through and through, and move on with your life.  That was my saving grace.  I was always more interested in being a good person than being a boyfriend.  While I was able to play the role of the disinterested bad boy, I think it’s unlikely that the girls I dated would’ve stuck around for as long as they did if there wasn’t more to it.

Thinking back on it all now, had I focused on being the best version of myself, it may have led to fewer relationships, but it probably would’ve led to more meaningful relationships.  Healthier relationships.  The kind of relationships which weren’t, in-part, defined by trying to be what I thought someone else wanted me to be, when in reality, nobody really understood any of  what was going on.

An ENTJ Love Story

I did my first MBTI questionnaire about 12 years ago.  I was in my early 20s and thought personality tests were a bit flaky but humored the 70 question quiz and arrived at the letters: ENTJ.  I started reading the overview and I remember thinking holy shit, this is real.  It told me several things I already knew about myself which seemed to verify its accuracy, but then it told me a bunch of things I didn’t yet understand about myself, which was enlightening.  Then I saw the suggested careers and got a solid ego boost. ‘The Executive’, destined for roles like CEO, Judge, University Professor… clearly I had hit the jackpot.  I became a proud ENTJ, telling everyone about the test and recommending they take it.  Little did I know, ENTJs don’t always experience emotions like others.  I wasn’t  prepared for the world of hurt that I would bring to the girls I dated.

At 28, I tried to lock down one of the greatest women I had ever met, beautiful inside and out.  It made so much sense for so many reasons.  It wasn’t messy.  It was a happy ending waiting to happen.  It was a disaster.  She grew up in a military family that moved around a lot and that meant that family was everything to her.  I grew up in a broken home with a father who worked a lot and a mother who avoided the kids.  My biggest priority was my career, so I could be in a position to give my family a good life, and have the time to spend with them.  I wasn’t willing to compromise on building the foundation I wanted to bring a family into, she wasn’t willing to compromise on waiting that long.  I thought that I was thinking logically while she was thinking emotionally.  I couldn’t understand why she couldn’t understand me, she probably felt the same.  We broke up after a year.  She was engaged 3 months later and was married a few months ago.  I haven’t spoken to her since we broke up but I genuinely wish her the best.

Then came tinder.  I’ll be happy to say that if you are willing to put the effort in, you can find quality people on tinder.  I went on some dates, met some cool people, and even dated one for a few months.

Then I met her.

For today, let’s call her Max.   She was 5’2″, 110lbs, black hair, and had the most amazing eyes I had ever seen.   With all the brain cells I’ve lost over the years (combat sports), I still remember that moment so clearly.  A mutual friend had invited me to a start-up’s open house so I came by for some light networking.  I was on their southwest patio talking to the founders of app that lets you pay for parking at city meters when she was introduced.  I suck at names. I consider them one of the least important pieces of information to observe when meeting someone.  I’ve never once forgot hers.  We stood on the patio chatting for a while and I’m sure I looked ridiculous staring so intently into the eyes of someone I had just met.  Fuck it.

I’m sure one of us was trying to play it cool and broke things off to hang out with other people, but eventually we ended up on one of the couches chatting about finance of all things – turns out she was a CA.  She understands money too? Jackpot.  I got her email, and sent something over soon after.  I’m not very good at hitting on girls, for most of my life I waited for them to hit on me… but Max had me feeling bold.  I don’t remember what I said, but it worked and we had a lunch date.

We grabbed lunch at a spot just around the corner from her work that she had wanted to try.  They had fancy chicken – and it was really good.  We talked about all kinds of things, and of course, the conversation could barely keep up with the things we had in common.  By the end of that first date, I knew something was different… way different.  She was a kind of special I had never known, and I was excited.  I wasn’t alone on this as Max later told me that when she went back to the office, she told her best friend that she just met her future husband.

On the next date, she told me she had just gotten out of a relationship that she still hadn’t entirely gotten out of.  I wasn’t bothered and said I’d give her time and space.  She told me that she had struggled with some addiction issues in that relationship.  I told her about mine.  She told me that she had cheated on almost every boyfriend she had.  I told her that maybe she had yet to find someone worth being loyal to.

It didn’t take her long to move on from her ex (kinda), but she told me that she had a tendency to jump from one relationship to the next and really wanted to see what it was like to be single and date, but she was torn because of what was happening between us.  I wasn’t bothered in the least, I told her to hit up tinder and see where it takes her.  She did, she went on a few dates with a few nice guys, and would then go home, call me, and tell me all about them.  I didn’t mind, because I knew that we had already fallen for each other and that this was just her process of making sure.  We used to joke and say ‘let’s be real… who else but me?’

After a couple weeks of hanging out 24/7, we were walking into a Canadian Tire, and I don’t remember what she did but I just looked at her and said, I….. lesbian you.  I know what I meant, but this soon?  Illogical.  I made a game of it and probably said ‘I lesbian you’ a half dozen times over the next week.  Not long after, we were in bed one night, and she looked at me with those incredible eyes and told me that she loved me.  I was so in love with her – and this time I didn’t try to hide it.

We made attempts at taking it slow, but it wasn’t working.  She was perfect for me in all these ways that I hadn’t even realized were important.  At one point, we looked at MBTI compatibility and even there, we were a prefect match.  We committed to not moving in together before her lease was up which gave us about 9 months.  We didn’t make it.

I was neck deep in a career that was tearing me apart from the inside. I was a rookie Investment Advisor for a top bank, building a book of wealthy clients. .  Part of what she admired about me was that I was able to conduct myself as a professional at the highest levels, but deep down, was still just a kid from the hood.  It wasn’t quite a dual personality, but it was close.  There was the me which tried to abide by banking culture, and the real me.  I had decided that the real me had to step aside and let banker me establish himself in the industry.  Real me always kept one hand on the wheel, but banker me started calling more and more shots for the sake of job security.

The real me understood her, loved her, and appreciated her.  Banker me did too, but banker me also wanted her to be a little more banker-y and a less like herself.  One of her best qualities was her fearless honesty.  But fearless honesty can make for awkward first impressions and awkward first impressions can sour client relationships and spook prospective clients.  I tried to tell her this by asking her to focus on things she had in common with the people she was meeting.  She resisted, saying that when she used to work at a major accounting firm, she was constantly having to behave like someone she wasn’t, and that she had gotten to a place in her life where she finally was able to be herself and felt good about it.  I told her that’s what I wanted for her too, but that I didn’t have that luxury and if I was going to continue along this career path, she either had to find a way to make it work, or I’d have to leave her at home.  Considering that my career forced me to be ‘on’ all the time, in hindsight, that was a ridiculous thing to ask of her.

We never completely resolved that issue, but we compromised to a point where… I’m tempted to say it was good, but it wouldn’t be true.  I imposed my logic, she conceded.  I feel sick to my stomach right now just writing that.  I’m so sorry.  My eyes are literally watering up right now, what kind of ENTJ am I?  She made that concession for me and my career and I will never impose that on anyone ever again.  What makes it worse is that she didn’t concede because I was smart or right, she conceded because she was beyond motivated to make this relationship work.  She would often tell me that this was the first relationship where she wanted to put in work, and do the things we needed to do.  She inspired me.  She was the best.

Then came what actually broke us apart.  She had spent her entire life living in the same city.  It was a world class city, but she was dying to get out.  I couldn’t leave.  My career was tied to my client base which was almost entirely local.  She would say ‘what if it was for the opportunity of a lifetime?’  I would tell her that’s what I already had here.  She would toss out the idea of long distance.  I told her years of long distance after a few months of dating probably wasn’t the recipe for a healthy relationship.  She wanted to go as much as she wanted to bring me with her.  Her company started tossing out the idea of moving her to their SF headquarters.  After talking about it, we decided that we’d delay any moves until we had been together for a year and make the decision then.

It didn’t matter.  She would ask about doing an MBA in Toronto.  Then about a tech job in California.  How cool it would be to live in a place like NY for a couple years.  My response was always the same, if you really want to go, I think you should go, but I can’t come with you, and there won’t be a long distance relationship.  She would persist, but she always decided to stay – until she didn’t.  She brought it up so many times that I didn’t have any other answers to give her – until I told her she should go and that the relationship was over.  She handled herself with class, even when she came back a few days later to get her things.  When she did, she looked at me asking, “is this it?”  The ENTJ was back, I told her it was and went back in the house.

Shortly after an ex started texting me.  We did the deed.  She was the one I had dated just before Max and was still a little hung up on me.  We didn’t use protection.  I should’ve. She told me that I was the last person she slept with, and I trusted her.  Then Max starting texting me We hung out a few times and yes, even some stellar sex for good measure.  We were in a good place.  We knew that we each had things to work on and were eager to work on them so that we could find our way back to each other as better people.  Eventually she told me that it was a bad idea, that breaking up with the goal of getting back together wasn’t really breaking up, and I agreed.  Didn’t change the fact that I was still hoping we’d have another chance down the road.

Then came the dagger.  I was helping my sister move to LA when I got a text from Max.  It read something to the effect of my ex just texted me letting me know that he tested positive for something and I’m really sorry but I needed to let you know.  I said sorry to hear it, but I got tested after we broke up and I’m all good.  That’s not what she meant. What she was trying to tell me is that right after we broke up, she had unprotected sex with her ex, and then unprotected sex with me.  That dagger cut deeper than anything I had experienced and almost every part of me that cared about her shut off almost immediately.  I deleted and blocked her number.  Then she whatsapp’d me so I blocked and deleted her there too.  Then FB messenger – block/delete.  I don’t think it was until she emailed me that I gave her any kind of response.  And I wasn’t looking to talk about it, I was looking to make her face the reality of what she had done, make her feel shitty about it, and then disconnect.

The part of this story that I left out until now is the nature of the relationship she had with her ex.  It was a slow breakup.  She still cared a great deal about him.  He was still in love with her.  They bought a dog together.  I’m not sure if it was familiarity or attachment, but she kept going back.  For the first month or so, she would be over at his place about once a week.  She never hid it from me.  The first time I piped up was when she came to my place from his loaded up on ketamine.  I didn’t need to be jealous to see an unhealthy dynamic.  She responded well.

As the months went on, she would still talk about her ex from time to time, and I really didn’t mind it.  What I did mind was the lingering attachment, paired with drugs and a history of cheating.  Not long before we broke up, he called her while we were driving home and kept her on the phone until about 2am.  Most of that conversation was in my bed.  I could hear him asking her why they weren’t getting back together and the mixed signals she was sending him.  I heard her tell him that she was happy with me, and that she wasn’t trying to send mixed signals.

Years ago, I dated someone who had cheated on all of her exes and waded fearlessly into that as well.  I learned in that relationship that you’ll never know whether or not they’re cheating so trust that they aren’t until you have a real reason to think that they are.  Max was testing my limits of what I considered to be a real reason.  When she told me that she went straight back to him after we had broken up, in my mind, it was like I was the one who had come between her and the person she actually wanted to be with.  Dagger.

After I blocked and deleted her out of my phone, she emailed me pleading to have a conversation.  I told her that having unprotected sex with someone else, and then having unprotected sex with me was a huge issue.  That because of her carelessness, my health is now at risk.  I probably gave her shit for going back to her ex too, but I don’t remember the details.  What I remember most is being hurt, wanting her to feel hurt, and knowing that the best thing I could do was create space between us.

My only communication with with her after that was when I tried to redeem my birthday and Christmas gift cards that she had given me the past December.  It was two tickets to bungee jumping and two for skydiving, something she was excited to do together.  By the time I looked to use them, they had already been used.  Apparently she still had the originals.  Ironically, I had also gotten her a skydiving jump for Christmas, so my revenge was sending her an email letting her know that I wasn’t going to use hers, and I hope she has a chance to enjoy it.  She said she probably wouldn’t as she was moving to San Francisco.  That’s the last I heard from her.  That was about a year and a half ago.

So why blog this?  Why now?  ENTJs don’t deal in heartbreak let alone dwell in it.  Maybe I’m no longer a classic ENTJ.

Remember when I said that my career was tearing me apart inside?  The real me never took his hand off the wheel.  Management kept putting me in situations where I was expected to put the bank’s interests ahead of my clients’ interests. They thought that dangling a 7 figure income in front of me would be enough to compromise my integrity.  It wasn’t.  In those environments, the nail which sticks out is the one that gets hammered.  They started moving me towards the door, so I used my trump card.  I reached out to a senior advisor who spent most of his career in management with the bank I was with.  He had been asking me to join his team for a few years but I kept declining as he was in a small town about 5 hours away and I was invested heavily in the area I was in.  I knew that if I asked for advice, he’d give me the job.  So I did.  And he did.

The move surprised a lot of people.  I think most people would’ve assumed I wouldn’t leave the city that I had such deep roots in.  What they didn’t know is that when my father passed away, he left a few hundred thousand dollars to the kids – in a hold co that I was exclusively in charge of.  Barely enough for a down payment on a house these days, but I knew that I could put that money to work and turn it into a meaningful part of my dad’s legacy.  The only direction he ever gave me with it was that if one of the kids had a business venture worth investing in, this could be for that.

The role that I had at the bank had a base salary in the first year, but then went to pure commission.  The first few years were notoriously lean because the role was mostly wining and dining, and it was all out of pocket.  Being in one of the world’s most expensive cities didn’t help.  Most would fail out of the program for financial reasons and the bank would retain their clients all the same.  In year one, I ran close to a break even.  In year 2, my income was cut in half and I started drawing from the hold co to keep my head above water.  In year 3, I drew less, but still some.  By year 4, I passed break even and was quickly moving towards 6 figures.  The last paycheck before the move cleared my credit card and line of credit.  Replacing the money I had borrowed from the hold co was next.  Protecting my father’s legacy was more important than where I worked, where I lived, and especially more important than any impact this would all have on me.

So I moved to that small town to work under one of the top advisory teams in the whole firm.  Things went sideways quickly.  I got along well with the branch, the team, the clients, and the lead advisor, but again, I didn’t get along well with management.  The branch manager was trying to play politics; I didn’t buy in.  He expected loyalty, but my loyalty was always to my clients and the team.  He figured that out pretty quick.  I was fired 2 months after arriving, against the wishes of the team, and for reasons which would never survive the most basic of HR investigations.

I left the office that day with just as much drive as I came in with.  I am an unstoppable force of nature and this will not compromise my momentum.  It was Monday and I told myself I’d have a new job lined up by Friday.  And then I went straight to the dispensary and bought a pile of weed for the first time since I had got there. Alone, in a small house, in a small town, disconnected from the outside world and no longer being defined by my career, I had an opportunity to figure out what really happened.  Blaming the bank for being shady was a cop out.  I needed to understand what I did, what I could’ve done, and why I didn’t do it.  Success rarely comes easily for me, but this was the first time in my life that I had dedicated myself to something completely, and had failed.

I used to play a lot of texas hold’em.  I think it should be a standard part of any school curriculum because it’s an excellent teacher of probability and the nature of cirmstance.  The best hand you can be dealt can still lose to the worst hand in the deck, if the circumstances aren’t in your favor.  For most people, that’s the nature of luck.  For me, it showed how important it was to create or find the best circumstances for my success.

The bank was a massive bureaucratic entity which marketed themselves to the public as advice, but operated internally like cut throat sales.  Middle management didn’t have the balls to tell upper management that their sales targets were so unrealistic that most people who were achieving them were doing them in a way which was continuing to degrade the trust that the public had in the banks.  I’m a leader and a problem solver that looks to challenge the status quo to make the world a better place for everyone.  They wanted a soldier who would ignore the problems, stay within the lines, and make management look good.  I didn’t realize how much of myself I was giving up to be there.

Shit.  Is this what Max felt when she left her big accounting firm?  She would tell me how much happier she was, how she was finally being herself and how liberating it was.  And I was telling her to go backwards.  Not only that, when I was imposing my logic, I would remind her that I was 3 years older and therefore likely more experienced in these kinds of things.  I grew up fighting for everything that I had.  I learned to convince people that I was right even when I knew I was wrong.  Maybe old habits die hard.  I’m such an ass.

After I got fired, I broke my arm pretty bad.  7mm separation, 6 screws, 2 plates, detached wrist, ligament damaged, and nerve damage.  I refused opiates.  I smoke more weed.  Interesting things happen when a logical mind disconnects from the outside world.  There’s no noise, no distractions, just the universe as it exists.  I learned a lot about myself.  I learned a lot about the world around me.  I learned a lot about my/our place in the universe.

I may not be pocket aces, but I know I’m a hand worth playing.  There are no guarantees in life.  The proverbial bus is always just around the corner, but that doesn’t mean I won’t give it my god damn all put everything I have into this universe and make it a better place for those who are ready to be happy.

There are 3 events in my life that stand out as moments of intense personal growth.  The first was grade 12 when I went from minimal effort and average grades to maximum effort and the grades that I needed to get into top universities.  That’s where I learned the value of work ethic.  The second was when my dad passed away and I learned about mortality and what it means to be responsible for others.  The third was being fired from a career where I gave it my all, and it still wasn’t enough.  That’s where I learned that for me to be successful in that environment, I would’ve had to fundamentally change who I was – or for me to be successful, I had to find an environment that encouraged my best.  To find that environment, I first had to understand who I was and what I had to offer.  During that search, I started to realize that I was weirder than I thought I was.  I spent most of my life trying to fit in, trying to fit the mold the people around me told me I should fit.  I did it well.  It wasn’t me.  I’m so much more.

When I started tapping into my inner weirdness – what made me different – I found genius.  This had nothing to do smarts, but everything to do with finding what made me different from everyone else.  What made me different from everyone else was the source of what I could do better than everyone else.  My niche.  My element.  My gift.  It didn’t apply to just me, it literally applied to everyone.  What would the world look like if we were all given the opportunity to be in our element?  It was an unrealistic concept in the past, but on the verge of mass automation, it’s now a future worth considering.  Then it occurred to me that happiness may be a function of maximum utility.  If you get to spend your time doing what you were built to do, there’s an alignment there which I don’t think can be undervalued.

I went off the deep end didn’t I?  I smoked way too much weed this year.  These concepts are so far detached from mainstream reality that they can’t be real.  So why do I see the universe more clearly than I ever have?  Why does everything make so much sense now? I’ve gone off the deep end…

I’m moving into the unknown, and I have no interest in coming back.  I know how logical my mind is. I know how critical I am of my own thoughts and the information I’m presented.  I know how open minded I am to new information.  I’m tempted to say I’m delusional.  Maybe I am.  But I don’t think I am.  I’m too analytical for that, too pragmatic.   Too honest with myself.

So what do you do when you think you’ve cracked the code to human happiness, and recognize the systems in place across the world that discourage the vast majority of us from coming anywhere near?  What happens when you see the fundamental flaws in these systems and can’t help but can’t help but have an intense motivation to fix them?  What happens when you become fixated on changing the world for the better, but realize how hard the establishment will fight to maintain the status quo.  You solve for x.

But I’m scared.

I’m never scared.  Never.  When I was in my early 20s, I got jumped.  There were a few of them.. they had a knife and someone was getting a gun.  They wanted access to my family to make sure that I wouldn’t go to the police.  They told me if I didn’t give them up, they’d have to kill me.  I respectfully told them that if they’re making me choose between my life and my family’s safety, I choose my family every time.  There isn’t much left to be scared of when you’ve made peace with death.  For the longest time, I thought I would be invincible until I wasn’t.  Nothing could hurt me.  Fear wasn’t unwelcome, it was barely a distant memory.

I’m not scared of pain or loss, I’m scared of being alone.  I’m scared that I’m right about what I see and what I know.  I’m scared that if I follow this path, others won’t be ready to come with.  I’m scared this is a path I’ll have to travel alone and eventually I’ll lose the opportunity to connect – and I’ll be lost and alone.

If what I know is real, it will catch on.  Maybe in my lifetime, maybe not.  But even if it does, I’m not looking for fans.  I’d rather have people appreciate my work than know who I am, but neither would fill this void.  I don’t want to walk this path alone.  I will because I owe it to myself and to the world to give everything that I have, but I don’t want to walk that path alone.

Every person I’ve ever been with, fell for the person I was projecting, not for who I was.  Except Max.  She saw exactly who I was right away, and she fell madly in love with that person.  She used to call me her benevolent robot king.  I was barely the king of my basement suite.  It didn’t matter.  She found me well before I found myself.

When I think about going off the deep end – into the unknown – and talking about things like revolution.. there’s only one person I can see putting up with me.  Only one person who would be brave enough to make that jump.  Only one person who effortlessly understands the depths of who I am.  The only person with whom I’ve ever experienced unconditional love.  It’s Max.

When she and I dated, I was struggling.  I was struggling with my career.  I was struggling with who I was.  I even struggled with my weight after I tore my hamstring.  She got the worst of me… and she loved me anyways.  I refuse to put her though that again.

I started thinking about Max more and more over the last few months.  It was only recently that I realized why.  There’s now this swell of motivation to be better.  I stopped smoking weed.  I cleaned up my diet.  I’m back to training and in best shape I’ve been in a long time.  I’m writing more than I ever have.  I’m getting dialed in.  And none of this is for Max, but I’d be lying to myself if I said it wasn’t partly because of her.

I’m too pragmatic, too logical to hope that she’s sitting around waiting for me to call.  She’s the kinda girl who’s only single if she wants to be.  And even if she was, she lives in SF.  I’m not doing any of this so she’ll take me back, I’m doing all of this because I want to be the caliber of person who’s capable of being with her.

If I’m going to be that person, I need to put in work.  Not just on the physical, but on the emotional too.  I need to be more than an ENTJ.  This story has been an exercise in flushing this all out.  That part about me being scared?  I didn’t know that before writing it here.  There are a lot of things I didn’t know before writing them here.  I did know I needed to write this though.

In a few weeks, when I feel like I have clarity of mind, I’m going to make a YouTube video and send her the link.  It’s going to be an apology.  I want her to know that I’m sorry for trying to change her into someone I knew she wasn’t.  I want her to know that I’m sorry for cutting her out of my life because the truth is I didn’t give a shit about possibly testing positive for an STI.  I was hurt because I had found someone who I knew was so special to me, and I was afraid that I wasn’t nearly as special to her.  I want her to know that I’m sorry I couldn’t give her my best, and that I’ll always appreciate that she found a way to love me so unconditionally when I was at my worst.  I’ll tell her that while I’m not doing this for her, or to get back together, she deserves the satisfaction of knowing that she’s the one who inspired this.

And I guess we’ll see what happens.