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Ian Winer


Family and Relationships

Ian Winer is an investor, philosopher, humanitarian, writer and public speaker who connects people to the truth of market places and human behavior. Ian is the author of the book, Ubiquitous Relativity: My Truth is Not the Truth. A regular contributor to CNBC, Fox Business, The Wall Street Journal, Bloomberg, and Reuters, to name just a few, he is known for seeking connections through non consensus thinking and making it relatable to everyone.






The other day I was walking into a building in front of a young lady.  I stopped to open the door for her as I have nearly always done my entire life.  After 45 years, this act was habitual; I never gave it a second thought.  But for the first time, something felt different.  I hesitated for a few seconds and wondered whether it was appropriate for me to hold that door.  What if I were somehow offending this young lady, by assuming she would be receptive to my attempt at chivalry?  My pause led to an awkward moment, but I nevertheless performed what I assumed was a small mannerly act.  I have spent some time thinking about that exchange and what it means to be masculine these days.  It has always been confusing for me and seems to become more esoteric each passing day. 

The book I wrote, “Ubiquitous Relativity,” suggests we try to pause on our judgments in order to deepen our connection to others.   Not surprisingly, given its name, I believe the philosophy of Ubiquitous Relativity applies to everything.   Different people who have read the book or its synopsis have wanted to discuss how this ethos applies to different areas of the human existence.  A few individuals in the media have asked me to talk about how this philosophy applies to “toxic masculinity.”  I had never heard that expression up until a month ago, but now it seems that the concept of “toxic masculinity” is permeating the walls of the current zeitgeist. 

I don’t like that term.  I think it does a disservice to men because…who gets to define masculinity and determine when it is or is not “toxic?” I believe each person gets to define words like masculinity for themselves.  I think it is more appropriate to think about how the definition of “what it means to be a man” continues to evolve in the modern world. I thought about my journey in life and how I was a product of multiple environments that reinforced divergent views on masculinity. At forty-five years old, I finally feel like I am ready to admit that I have no idea what it means to be a man in 2019.  Each day I try to do what I think are “right” actions and to ask people how they define terms like masculinity so I can learn more in my quest.  That is my starting point.


The word “masculinity” tends to elicit strong feelings.  I searched for and read the Google definition of the word:



“Masculinity”:  Qualities or attributes regarded as characteristic of men: "handsome, muscled, and driven, he's a prime example of masculinity" Synonyms: Virility, manliness, maleness, vigor, muscularity, ruggedness, toughness, robustness. Antonyms: Femininity.


I want to reiterate that the above definition and synonyms are the search results for the word “masculinity” on May 30th, 2019.  This is not some archaic concept only used to describe cavemen. This is the current way a dictionary describes what it means to “be a man.” 


For most of my life, I was in complete alignment with the definition above. I also was nurtured, and matured, in environments that took this concept of masculinity and then pumped a massive amount of steroids into that idea.  I played ice hockey competitively from the age of four until the end of college. The entire sport is based on mental and physical toughness and dominating your opponent.   I was explicitly told that under no circumstances, no matter how hurt I was, would I ever stay down on the ice.  It was a different time (early 1980s), so the words people used to yell at each other while playing and in the locker room would be considered wildly politically incorrect in today’s world.  Inevitably these slights largely focused on somehow questioning the opponents’ masculinity by calling them a thousand forms of the word “gay” or “woman.”  I spewed this venom as a young child to anyone I wanted to hurt.   I was tough, I was rugged…I was on my way to being a man. 


I continued my ice hockey career while attending the United States Military Academy.  West Point, as it is known, is a difficult place to spend one’s college years.  The plebe (freshman) year is a test of one’s physical and mental toughness.  Everything from pushups to memorizing the front page of TheNew York Timesto uniform inspections was simply part of a “normal” day.  We were literally taught how to eat properly, chivalry, how to write a letter to someone, and other aspects that would be part of the curriculum of any finishing school.  I remember learning what side of the sidewalk (closest to the street) I was to walk on with a woman.  The hard part for me as a man at West Point was the juxtaposition of the emphasis on the lost art of “chivalry” or “polish” against the reality of a testosterone fueled, alpha filled arena which prepared people for combat.  Somewhere between 80-90% of the cadets at West Point were men from 1992-1996, the years I attended the Academy.  We did what I imagine many young men did: We talked about women as objects and numbers, read pornography whenever we had a spare minute and settled arguments with fistfights. This was right at the time “Don’t Ask, Don’t Tell” was being implemented in the military and we were never short on jokes that would question the sexual orientation of another cadet.  The school required boxing, wrestling and close quarters combat classes in order to graduate. One could never be too tough.  As a person just entering manhood in my late teens and early twenties this was all a bit confusing.  I had read about “Renaissance Men” and “Courtiers” who could speak six languages, recite poetry, vanquish all their enemies and then marry the princess.  I wanted badly to be one of those men.  The romanticized notion of a lover and a fighter was something I aspired to, but never became a good example of either.  I walked a delicate tightrope.  On the one hand I wanted to impress all my friends with tales of “hook-ups” and “donnybrooks” and surviving dangerous situations through sheer bravery and honor.  On the other hand, I made sure to call women “Ma’am”, stand up when they walked in the room and hold the door for them.  Thus began an interesting compartmentalization of my manhood. 


The next environment I occupied was the zenith of that Google definition of masculinity: A trading desk on Wall Street in the late 1990s – early 2000s.  That environment was all action, all the time. There was no room for weakness or any emotions outside of rage and excitement.  This was another arena with men occupying well over 80% of the positions. We even used the term “big swinging dick” to describe senior people at the firm (And that was accepted parlance). I advanced my career the old fashioned way: toughness, hunger and a willingness to do almost anything to win.  I gambled, I drank, I partied, I bragged openly about my exploits with women but most of all I actively avoided any real connections to people. I believed every aspect in my life was some kind of competition: Who could drink the most, who could party for the most days in a row, who could make the most money, who could sleep with the most women, and on and on and on.  At the same time, I still fashioned myself chivalrous. I didn’t touch my food on a date until the woman ate first.  I always paid for every meal.  In some bizarre way, the one compartment justified the other.  I believed that if I were really nice to women and modest and classy in some instances, in a twisted way it excused my behavior when I was around other men.


That was my life up until a few years ago when a few chance moments led me to write “Ubiquitous Relativity” and develop the philosophy of the same name. The concept, in its most basic form, is that we each uniquely sense the world and we each have unique emotions attached to those senses.  As a result, we each live in our own universe.  No two universes are the same and we know next to nothing about almost any other universe. Thus, the only way to truly connect with another person is to pause on our judgments of them.  This leads each of us to question our own assumptions and worldviews. 


As I wrote more and began to have my own awakening of sorts, I wondered: What if “being a man” is not at all what I had thought it was for over four decades?  What if this compartmentalization of masculinity was bullshit and a disservice to my own manhood altogether? This was terrifying because I was never one to question my core beliefs.


If my definition of masculinity was the wrong one, was there a right one?  In line with my philosophy, I am not sure there is a universal right definition or a wrong definition of “being a man.” Even if I could define manhood, it would only be a definition applicable to me and not to anyone else.  My definition of masculinity continues to evolve alongside my personal development.  I know now it is ok to be afraid.  It is ok to show that fear.  I don’t need to feel emasculated if my wife is the breadwinner these days (which she is). I can have a real conversation with another man about my feelings that doesn’t involve a bar or a sports game. I can even hug another man without it being considered somehow feminine.


This is why terms like “toxic masculinity” are inappropriate and dangerous. They apply a negative connotation to men and masculinity.  I only know my own experience.  I still feel masculine today, but I do not in any way feel toxic.  I try my best to communicate that to others and to allow myself those moments of vulnerability.  I admit when I don’t know the answers and even try to ask for help every now and then. 


This gets me back to the original moment and the decision on whether to hold a door open for a young lady.  I don’t know the right answer.  I try to have more conversations with women about manhood so I can understand, even if for a few moments, what it means to be masculine in their universes.  It is a process like every other thing in life. I am unwinding over four decades of environmental conditioning and confusion.  I know I won’t get it even close to right in this life.  Each time I pause and think about what I am doing, it affords me an opportunity to consciously examine my long held ideas of the “right” way of living.  I only ask for patience from people when possible.  Navigating this world is not an easy thing, and I will screw up often, but I assure you my intent is good. 




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