What it Means to be Good Looking

For most of my childhood, the only person who told me I was handsome was my mom. She would tell me that I would be such a heart breaker.  Then I ventured out into the real world and found no such validation.  Occasionally a girl would have a crush on me, but it was never one of the pretty or popular girls.  As far as my friends were concerned, all they knew was that I had a big nose.  I really had no idea of knowing whether I was good looking or not.  I wanted to be… few things were more obvious than the advantages of being good looking.

After high school, I was more focused on building myself up than what I looked like.  I was confident that women were more attracted to character than looks… how else do you explain Jay Z and Beyonce?  So I focused on building character.. integrity.. honesty.. honor.. intelligence.. humor, etc.  I proceeded to date 3 of the most eligible women at my university.  One of them was non-superficial that she could’ve dated a burn victim.  Another thought I was really good looking, but her ex was… rather plain, so not a great measure.  The third was really into the body-builder physique (of which I was not), and that led to some lackluster physical chemistry.  Coming out of university, I knew I had the ability to date beautiful women… but still no clue if I was good looking.

A few years after university, I dated a girl who seemed to be grateful and appreciative of everything in her life.  Even her most significant accomplishments, she would dismiss as good fortune.  It was foreign to me as I’ve always been one to celebrate work ethic.  She was extremely grateful for her looks, and said that I should be too.  I told her that I had given up on trying to understand whether or not I was good looking.  She told me that was ridiculous, and that to deny that I was good looking was to be oblivious of the privilege it afforded to me.  Perhaps she had a point.  Instead of exploring that point, I told her it just wasn’t something I thought about very much and I was pretty happy with the results.  It was the first time someone told me I was basically an asshole if I didn’t think I was good looking.  Well then…

Over the last couple months, I’ve probably been called handsome or good looking more than any other period in my entire life.  As someone who was trying to get back into the dating scene, one would hope those compliments would be coming from interested women.  Wishful thinking.  Almost every one of those comments came from older men in my professional life.  Something to the effect of, “you’re a young, good looking guy, the world is your oyster”.  There was an older Asian guy at my local tech summit who probably told me about 10 times in one conversation that I’m handsome, have a great smile, and should be doing business development for Intel.  He made sure to spell Intel for me.. Pretty sure he was several drinks in.

While it’s easy enough to laugh off, maybe there’s something worth observing here.  Am I good looking?  I’d say that depends on who you ask.  I’ve been told by friends overseas that if you were to drop me in a place like Japan, China or Korea, I’d be like catnip.  Put me in a place like California or New York and probably much less so.  So there are cultural factors at play.  I know facial symmetry makes for bonus points…  A full head of hair…  Good genetics… but  what about personal preferences?  When I was young, I spent a lot of time crushing on girls who just weren’t into me.  There seem to be elements of attraction which are general, while others can be highly individual.

So beauty is in the eye of the beholder, yes?  Seems like an easy out.  But maybe there’s yet another level to this.  Beauty is in the eye of the beholder, but eyes of the beholders tend to follow similar algorithms.  I think it starts with good genetics.  When you mix genetics from diverse gene pools, you end up with great looking kids.  When you let a brother and sister get it on, there’s a 50/50 chance you end up with a cyclops.  We have instincts that pick up on good genetics and we perceive that as physical attraction.  In reality, we’re just instinctively trying to diversify our gene pool.

Good health is perhaps second on that list.  We seem to be in an interesting time where people who are unhealthy and overweight want to be perceived as attractive in the same way that someone healthy is.  In reality, we’re physically attracted to good health and there are different ways we pick up on that.  Are you fit?  Do you have good skin?  Good teeth? Is your hair falling out?  Something I’ve found interesting is that whether it’s a 5’0″ gymnast or a 6’3″ power lifter, I’ve always found a healthy woman to be attractive.

So based on these parameters am I good looking?  Probably.

My genetic background is Scottish, Irish, Jewish, and Austrian.  Not the most diverse gene pool, but certainly not kissing-cousins.    My face is largely symmetrical from what I can see.  I have a full head of hair and mostly straight teeth.  While I take liberties with my health and fitness from time to time, I’ve been a competitive athlete my entire life.  If I had to guess, I would say that I am above average looking.

Great.  Now what?

My concern before was that if I figured out that I was good looking, I’d let it go to my head.  I liked being oblivious to it because it kept my focus on what I thought was more important.  Now that I’m conceding, what changes?  … Nothing…?


I think that at this point, it’s unlikely to go to my head.  I’m appreciative for where it’s helped me, indifferent to where it didn’t, and hope that this baby face ages gracefully.  I’m also understanding and accepting where it may have created unearned advantages for me.  While it may have helped in my dating life, it probably wasn’t as big of a factor as some may believe.  Where I think it’s actually helped me the most is in my professional life.  Just about every person that’s hired me or considered me for a role has referred to me as good looking.  I think that early on, I just saw these compliments as innocuous or inconsequential.  Why does being good looking have anything to do with my performance in the work environment?  I know I look good in a suit.. maybe they were just saying something nice.  But I don’t think it’s that simple.  I think that things like facial symmetry, good skin, good hair, and good teeth make a difference in the willingness of strangers to trust you.  Match that with being presentable and well-spoken, and you’re able to earn trust faster than others.  In the world of business, that’s a very real advantage.

Are there any disadvantages?

I often see a duality around privilege, and good looks seem to follow that pattern.  While I’m grateful for my looks, I’m more grateful for that uncertainty while growing up.  It encouraged me to put my efforts and focus elsewhere, and not everyone is so lucky.  Think about the prettiest girl in your high school.  Was she more likely to be headed to university on a full scholarship or date the captain of the football team?  Was she more likely to get recruited out of school to the field of her choice or more likely to be working as a bartender?  Does she stand a better chance of accomplishing things on her own, or being accessory to someone else’s accomplishments?  From a certain perspective, being good looking provides an easier path than most.  But since when is easy a good thing?

A duality.. and a reality of our world.  At the end of the day, physical attraction has a rather functional purpose: visual markers of good genetic and good health that help you find a mate.  But I can’t help but see the tail wagging the dog a bit.  Rather than understanding how physical attraction plays out among several other factors like personality, resources, intelligence, and group-membership, we talk about it like it’s magic.  We often treat it like something that can’t be explained, and that even if it could, it shouldn’t.  That it would take the romance out of things.  I disagree.  I find the truth to be more romantic than any lie.

I think there’s a fair bit of magic in having an honest understanding of what we’re seeing and why we enjoy it.



My Privilege

This is a topic that I had addressed a couple times in earlier entries.  It came up again the other night between me and someone else.  She wasn’t attacking me or trying to make me feel guilty, but she was trying to communicate a perspective shared by some of her peers.  It got rather frustrating at one point… so I spent some more time thinking about it over the last few days.

I was reading Napoleon Hill’s Outwitting the Devil last night.  For anyone not familiar with the book, it’s an interview between Napoleon Hill and the Devil, in which the Devil must answer all questions honestly.  They explore a great deal, including privilege.  Here’s the passage which inspired me to write this today:

Napoleon: Aren’t people sometimes bound to others by a relationship of duty
which renders it impractical for them to take from life what they want most?

 The Devil: “Duty” is one of the most abused and misunderstood words in
existence. The first duty of every human being is to himself. Every person
owes himself the duty of finding how to live a full and happy life. Beyond
this, if one has time and energy not needed in the fulfillment of his own
desires, one may assume responsibility for helping others.

Napoleon:  Isn’t that a selfish attitude, and isn’t selfishness one of the causes of
failure to find happiness?

The Devil: I stand by my statement that there is no higher duty than that which
one owes himself.

Napoleon: Doesn’t a child owe something in the way of duty to its parents who
gave it life and sustenance during its periods of helplessness?

The Devil: Not at all. It is just the other way around. Parents owe their children
everything they can give them in the way of knowledge. Beyond that, parents
often spoil instead of helping their offspring by a false sense of duty which
prompts them to indulge their children instead of forcing them to seek and
gain knowledge at first hand.

Napoleon: I see what you mean. Your theory is that too much help thrust upon
the youth encourages him to drift and become indefinite in all things. You
believe that necessity is a teacher of great sagacity, that defeat carries with
it an equivalent virtue, that unearned gifts of every nature may become a
curse instead of a blessing. Is that correct?

The Devil: You have stated my philosophy perfectly. My belief is not theory. It is


I’ve found that people have a hard time understanding the nature of privilege or even defining it appropriately.  Most commonly, it seems as though people discuss privilege as a symptom of a grand injustice.  And if you are a recipient of these privileges, you are complicit in the injustice.  And if you are complicit in the injustice, you are now the enemy.

I’ve strained my mind in the pursuit of answers to this topic.  I had to start with a definition of privilege.  My best understanding of privilege is that it represents an unearned advantage.  But I also understood that advantages tend to be circumstantial.  What may be an unearned advantage in one moment may be an unearned disadvantage in the next.  For example, your skin color may earn you a pass in certain neighborhoods while making you a target in others.  More than this though, there is an inherent duality to privilege.

One of my all-time favorite quotes is from Bruce Lee, “Do not pray for an easy life, pray for the strength to endure a difficult one.”  He seemed to have a deep understanding of this duality as well.  An easy life can be filled with unearned advantages while lacking adversity.  A difficult life tends to be filled with adversity which can lead to the greatest of advantages; if you have the strength to overcome.  Consider the simple difference between someone who receives high marks for studying and understanding the content versus someone who receives high marks for having cheated.  One has earned the advantage of high marks while the other hasn’t.  Yet both have high marks.  While many will focus on the marks and say something to the effect of, ‘at the end of the day, it’s what’s on the scoreboard that counts’, they would be wrong.  The scoreboard is superficial and it only matters as much as we choose to prioritize it.  I would argue that what matters more is the knowledge and wisdom gained through the exercise of studying and understanding something; knowledge and wisdom which would be absent from the person who cheated.

In searching the real world for these dynamics, I realized they weren’t hard to find.  It seems as though unearned advantages as especially effective at providing you with opportunities for which you are not prepared.  Perhaps my favorite example is a study showing that people born into wealth tend to make poor leaders.  I don’t think being born into wealth is the issue, but rather, being born into a lack of necessity.  Parents have an instinctual drive to provide their children with everything they need, but lack the foresight to understand that they need adversity more than they need privilege.  And this is when I reflect back on my life… a life which sometimes seems defined by adversity.  It weighs on me at times, but with a clear mind, it leaves me feeling rather fortunate.

When I consider the nature of privilege, and people tell me to acknowledge and be grateful for my privileges, it gets a bit confusing..  So I thought I’d take a second to list some of my privileges here:


  • I am not privileged to have been born in a first world country.  I am privileged to have been born into one of the poorest neighborhoods in a first world country.  I am privileged to have grown up around drugs, prostitution, gangs, and murder.  I am privileged to have learned a more complete perspective of the world at a younger age.


  • I am not privileged to have been born to a family with both parents.  I am privileged to have been born to parents who split when I was a young teenager.  I am privileged to have heard them yell at each other for years while they thought I was sleeping.  I am privileged to understand just how much it takes to exist in a partnership and build a family.


  • I am not privileged to have been born with white skin.  I am privileged to have grown up as a minority and learned what it was like to experience racism at a young age.  More than that, I am privileged to have grown up in a community that helped me understand what racism was and then how to rise above it.


  • I am not privileged to have been born a man.  I am privileged to have been born into a family with a mother and sister who fight fiercely for the empowerment of women, sometimes at the expense of men.  I am privileged to be alive at a time where women are finally stepping into their own, as we all struggle to understand the nature of gender and equality.


  • I am not privileged to be straight or cisgender.  I am privileged to have gone through periods of my life where I questioned my sexuality.  I’m privileged to have learned to keep my mind open to love of all shapes and sizes.


  • I am not privileged to have received a university education.  I am privileged to have had an opportunity to fight hard to earn my entrance to university.  I am privileged that they tried to kick me out after my second year and that I was able to find the strength and focus to return 18 months later.  I am privileged to have gone head to head with a tenured professor who wanted me removed from the school in my final year.  And was most privileged to have pushed myself to my limit in what I could handle personally and academically, and still receive my degree.


  • I was not privileged to have had an opportunity to finish my degree.  I was privileged to have taken a break to get mixed in with the ‘wrong’ crowd.  I was privileged to see the world through a lens I never would’ve have experienced.  I was privileged to have my life threatened at gunpoint.  I was privileged to be asked to choose between my life and the lives of my family.  I was most privileged to have seen and experienced the temptations of that world, with the presence of mind to know that wasn’t my path.


  • I was not privileged to have received top marks from a top university before entering the job force.  I was privileged to graduate into one of the worst job markets since the great depression.  I was privileged to have earned an entry level job, paying $13/hour in one of the world’s most expensive cities.   I was privileged to learn that grades, degrees, and recommendations don’t entitle you to anything.  I was privileged to be reminded that my work ethic will always be my greatest asset.


  • I was not privileged to be someone hired with the expectation of being fast-tracked into management.  I was privileged to butt heads with incompetent management.  I was privileged to learn how to still perform under increased expectations and decreased support.  I was privileged to learn about the nature of corporate politics and to have received the short-end of that stick.  Above all, I am privileged to have had the opportunity to learn so much about the intricacies of big business.


  • I was not privileged to have a dad at home.  I was privileged to have lost him in my mid 20s, before I was ready.  I was privileged to have learned the nature of life and death.  I was privileged to have taken on his responsibilities to the family.  I was privileged to have learned to let his memory inspire my accomplishments.  Perhaps most, I am privileged to understand that of all the shoulders I stand on, his lifted me the highest.


  • I was not privileged to have received an inheritance from my father.  I am privileged that he left that money with me to look after our family and his legacy.  I am privileged to carry such a responsibility that it’s reshaped my approach to life.  I’m privileged to have taken this responsibility so seriously, that I’ve gone to great lengths to understand how it could be handle best.  I’m privileged to have learned that it shouldn’t be spent on making our lives easier.


  • I was not privileged to have turned that responsibility and mindset into an investment advisory role at the most prestigious wealth management firm in the country.  Nor was I privileged to have earned a chance at a top 1% income in my mid-20s.  I was privileged to have repeatedly been put in a position where I had to choose between my integrity and my career.  I’m privileged to have lost my job over maintaining my integrity, and having taken a tremendous financial hit in the process.  I wasn’t privileged to have a tremendous opportunity afforded to me, I was privileged to have invested my life into it and to have it taken away from me in the least enjoyable of ways.  What I learned from that experience is something I would never be willing to give back.


I could go on… but I think the point has been made.  What I’m most grateful for are the strengths I’ve developed through overcoming adversity.  A person who is given a million dollars is a shadow of the person who has earned a million dollars.  I have no interest in an easy life.  I have every interest in becoming the best possible version of myself… and perhaps that’s how I’ve managed to manifest the life that I’ve lived.  Perhaps to be my best self, I must live my most difficult life.  There are times where it feels like the weight of the world is on my shoulders.. and over the years, I’ve felt that weight increase.  Yet it doesn’t feel any heavier.  It’s in those moments, I appreciate how strong I’ve become.

As I continue to move through life, I’ve learned to embrace adversity and appreciate the suffering that comes with it. I’ve also learned to connect that discomfort with an expansion of the mind and personal growth.  And I have a deep understanding of how this leads to me becoming a stronger, wiser, and more capable individual.  If adversity will lead me to my best self while privilege will lead me away from it, why would I ever choose a privileged life?  Why would anyone?  And if I’m right, shouldn’t the presence of privilege promote feelings of compassion rather than a sense of injustice?

Duality of Privilege

When you apply the concept duality to privilege, it creates a rather interesting perspective.  Consider example A:

John is the child of a wealthy family.  His grandfather did very well, and John’s parents never had to work.  John grows up knowing that he won’t have to work either.  John’s parents lead a lavish lifestyle and give John is given everything that he asks for.

As a result of his unique circumstances, John has a unique perspective on life.  In that environment, I could see it being extremely challenging to develop qualities like a strong work ethic, perseverance, or the ability to deal with scarcity.  I could also see it being difficult to develop healthy relationships with others for a variety of reasons.  This doesn’t sound like a life of privilege to me.  Consider example B:

Jane is the daughter of two working class immigrants, and is raised in a rough neighborhood.   Jane grows up admiring the work ethic of her parents, knowing how their sacrifices let her grow up in a better place than where they were from.  Jane doesn’t have much growing up, but she appreciates what she has and learns how to work towards the things she wants.

In that environment, Jane was given several obstacles and challenges which John would be unlikely to face.  I’d like to think there are two ways to look at this.  You could say that John is privileged to not have to work for anything.  Or you could also say that Jane is privileged to have learned a great work ethic when she was young.  Perhaps there’s a key difference between these two though, in that Jane earned her work ethic while John didn’t earn his family’s wealth.  While that may be true, neither Jane nor John earned their circumstances – in this case, their family.  Had Jane been born to John’s family,   would she have turned out any differently?  Had John been born into Jane’s circumstances, would he have developed Jane’s work ethic?  Who’s life would you rather be born into?  If you’re like me and picked Jane’s life because it would probably lead to a more balanced, fulfilling, successful, and healthy life, wouldn’t that be the more privileged life?

When you think about our greats, from Muhammad Ali to Connor McGregor, from J Lo to Jay Z, from Abe Lincoln to Narendra Modi, from Indra Nooyi to Oprah Winfrey, from Ben Franklin to Steve Jobs, and from Charles Dickens to JK Rowling, you start to see a pattern of overcoming a more challenging set of circumstances from a young age.  You know who I don’t see?  I don’t see the children of billionaires.  How often do we see the children of wealthy families behaving as inspiring leaders that move the world forward in a positive direction?

I think that inheritance doesn’t exist in a meritocracy but that aside, I genuinely don’t have any issues with someone inheriting a fortune and then settling down and living a comfortable life with their family.  I just know that’s not the best environment for producing good human-beings.  It looks easy, and nice, and better, but it lacks the struggle, and it’s the struggle which defines us.

The most challenging moments of my life directly preceded my most significant moments of personal growth.  If this pattern stays true for others, is adversity not to be embraced as the fuel of progress?  If so, perhaps privilege represents someone who’s arrived at the destination without having made the journey.  If so, perhaps there’s an argument to be made for an empathetic approach to this whole ‘privilege’ thing.  If we’re lucky, it might be contagious.

My Thoughts on Privilege


A few years ago, a girl I was dating told me to check my privilege.  It was tremendously frustrating for me as I couldn’t understand what she was actually trying to say.  She went on to say that as a good-looking white male, I had all kinds of advantages afforded to me which weren’t available to others.  I reflected on that statement and it still didn’t resonate.  From my perspective, my path had not been easy and both my opportunities and successes were well-earned.  I figured a good place to start would be with a definition we could both agree on.  So we looked it up:


Privilege: A special right, advantage, or immunity granted or available to a particular person or group.


That sounded rather general to me.  By that definition, if white privilege existed, then so did black privilege – and every other kind of privilege for that matter.  Tall people are privileged to reach things off high shelves while short people are privileged to not bump their heads on low ceilings.  If privilege is simply referring to the advantages held by some and not others, aren’t we just talking about people in general?  Maybe.

It would be easy for me to say that white privilege doesn’t exist because privilege doesn’t exist.  I would go on to give an example:  Would you rather be a black man being pulled over by the police in Alabama, or would you rather be a white guy getting pulled over by freedom fighters in West Africa?  Then I’d remind us that while we all share a common blueprint, we all vary in our own ways and those variations provide inherent advantages and disadvantages depending on the circumstance.  If circumstance is the variable that determines if we experience an advantage or disadvantage, then does privilege really exist?  Like I said, it would be easy for me to say that white privilege doesn’t exist because privilege doesn’t exist – but I would be wrong.


Everything that I just said is valid to an extent but I think that there’s another layer to what’s going on here that better represents what we’re looking at.  I think if we explore this a little further, we’ll find some clarity

A granted privilege seems to be simply be an advantage given from one person to another.  What I find curious here is that the word granted offers the possibility of earning your advantage.  Consider a student who has good grades in high school and then is ‘granted’ admittance to a top-tier university – we’ll call her Priya. Now consider someone who had average grades, who also made it into that university after their parents made a significant donation – we’ll call him Bryce.  I think most people would blow the whistle and call a privilege foul here on the latter, but what if the Priya was at a top private school with unlimited tutoring funded by her parents?  What if Bryce’s parents grew up in poverty, worked hard, and were simply making a donation to their alma mater?

This is a rather interesting topic for me because in the context of a social conversation, privilege is what I would consider to be a poorly defined topic.  It’s like we know that there’s something wrong but we’re not exactly sure how to articulate it.  As in many other cases in society, we think we’re dealing in issues of fairness but in reality we’re dealing with issues of efficiency.

Let’s revisit the earlier example in a different context.  Let’s say for the sake of simplicity, Priya is unprivileged and Bryce is very privileged.  Both are admitted to a top-tier university and both approach their degree as an independent effort.  Now they’ve both graduated and while Priya continued to work hard and earned good grades, Bryce worked harder and earned better grades.  Now imagine that in 40 years, we’re reflecting on their life’s work and there’s a clear winner – Bryce.

If this were a real world example, what we commonly define as privilege could’ve led to the discrepancy in university grades and the career but that’s the point.  What if it wasn’t?  It’s certainly possible that Bryce did better because he had more resources at his disposal, but what if his circumstances we’re simply better aligned with his own personal strengths?  What if Bryce simply wasn’t motivated in high-school, but once he had the autonomy and challenge that came with a top-tier university, he was motivated to perform?  And what if his personality and degree were directly in line with his career path?  And what if Priya who worked hard and got good grades her entire life had the genetic blueprint for a world class chef, but became an accountant as a result of her academic focus?

In reality, what we’re really upset at is a series of systems which are inefficient at allocating resources and creating value.  The system we have currently is a ‘fair’ entry system predicated on prior academic performance and extra-curricular activities but it’s also the same system that would see Priya become an accountant and see Bryce not gain admission.  It’s largely a level playing field, but perhaps it’s time to prioitize making sure people are suited up for the right sport and playing to their full potential.

With the progress we’ve made in understanding our genealogy and psychology, along with advances in our ability to collect and analyze data… I smell a revolution in how we determine fit.  Imagine everyone being given the freedom to explore their options, while also being given the information to understand what they’re likely to be best at.  Now imagine everyone having access to the same information and how much more efficient we’d all be… at everything.  The goal isn’t to make privilege against the rules, the goal is to have a system in place that makes the use of privilege seem foolish and counter-productive.

If I were to offer up my best definition of privilege, it would be an applied, circumstantial advantage.  When circumstantial advantages are used to further the collective interests (efficient), people seem not to mind.  When circumstantial advantages are used to further self-interests (inefficient), there’s an issue.  Our issue isn’t with having different strengths and weaknesses from one another.  Our issues aren’t even with those who apply their strengths when competing.  Our issue is those who take the short-sighted approach of putting their own interests ahead of collective progress.  Our issue is with those who use their resources to create inefficiencies in the larger system at play.