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.