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Swimming Down the Sidewalk

Updated: Aug 14, 2020

The Power of Privilege, and the Eye-Opening Effects of Losing it in One Fell Swoop.

Recently I participated in an activity as part of our leadership team at work called Privilege for Sale.* This activity was a part of a larger discussion about race and social justice in the world, as well as within the educational organization where I am the Human Resources Director.

The purpose of this activity was and is to help us understand our privilege, including our blind spots where we may not even realize we have privileges or where we take them for granted.

The way this exercise works is that all participants are given a fictional amount of money ($300, $500, $700, $900 or $1100). They are then given a list of “privileges” that they have to buy with their money. They have to assume that they don’t have any of these privileges on the list in real life, and each one costs $100 to buy. There is a list of 27 privileges that participants have to choose from, and they are supposed to take their “money” and spend it on the things that would matter most, forcing a choice of certain privileges over others.

For a group of mostly white, mostly heteronormative leaders, it was a great exercise to understand not only privilege in the context of the systems that we’ve created, but also to understand intersectionality.

Being made to choose between privileges like “feeling unthreatened and safe in your interactions with authority figures and police officers” and “being accepted by your neighbors, colleagues, and new friends,” is not a fun thought experiment, and for me, it became altogether eye opening when my own privilege was exposed.

I am a white, 37-year-old, upper-middle class, transwoman.

Even before this exercise began, I understood that I hold many privileges that others do not. I understood that even doing this exercise, this thought experiment, is a privilege, while not having these privileges is the reality of hundreds of millions of people living in the US today.

I realized that I hold the privilege, based on my race and income, to not worry about some things that many other trans individuals of color and trans individuals who don’t have stable jobs and a good income have to think about. For instance, the privilege of “being able to receive medical care, including emergency medical care, without worrying that your identities affect the quality of care that you receive,” is something that probably should be on my mind from time to time as a transwoman in Trump’s America; but it’s typically not. I can ignore it because I am white and have money. I can go somewhere else for care. I can pay out of pocket. I can buy good insurance that will help fight for me. I can hire a good attorney to advocate for me. I’ll be taken more seriously because I’m white. The list could go on and on.

But as I started going through the list, my eyes opened to what I really have lost since coming out. As weird as it sounds, this activity broke through my privilege to ignore my losses and my heart began to ache for the things so many have lost or never had, myself included. Those of color, others in the LGBTQIA+ community, and especially those whose identities intersect race, gender, sexual orientation and other underrepresented and marginalized groups, have missed out on the fullness of what this country has to offer simply because of who they are.

In the activity, I ended up with $1100 to spend. The most out of everyone in the group. I could buy 11 out of 27 privileges. We were given a few minutes to decide what privileges we’d want to buy with our money, then were supposed to discuss with the group. As we went around the room to discuss, people said things like “this is an impossible task, how am I supposed to pick between these things?” And, “I started wondering if these applied to my spouse and family when I bought them, then I thought I might need even more money for them to have these privileges too. This is so overwhelming.” When it came to my turn to share what I had chosen and why, I broke down.

I cried as I explained that I didn’t exactly follow directions and pretend that I had none of these privileges. Instead I ended up choosing only privileges that I had lost in the last two years. By simply being who I am and coming out. Going from straight, white, upper-middle class dad, to lesbian, white, upper-middle class trans-mom, I lost a lot. I spent all $1100 fictional dollars on privileges I no longer hold but previously did, and I wasn’t even able to buy up everything I had lost. The list included:

  • The privilege of celebrating your marriage with your family, friends, and coworkers.

  • The privilege of using public restrooms and restrooms at work without fear of verbal abuse, physical intimidation, or arrest.

  • The privilege of using facilities such as gym locker rooms and store changing rooms without stares, fear, or anxiety.

  • The privilege of being able to receive medical care, including emergency medical care, without worrying that your identities affect the quality of care that you receive.

  • The privilege of being accepted by your neighbors, colleagues, and new friends.

  • The privilege of being able to buy clothes without hesitation or fear of being mocked, questions, or made uncomfortable.

  • The privilege of raising children without worrying about family, friends, and your community rejecting your children because of your identity.

  • The privilege of having the health insurance provided through your job cover the necessary medical treatments you need.

  • The privilege of being able to travel without worrying about your safety due to your identities.

  • The privilege of kissing/hugging/being affectionate in public without discomfort, threat, or punishment.

  • The privilege of receiving validation and acceptance from your religious or spiritual community.

The privileges I didn’t have enough money to buy on the list that I’ve also lost in the last two years included:

  • The privilege of being employed as a preschool or elementary school teacher without people assuming you will “corrupt” their children.

  • The privilege of freely being able to discuss your relationship(s) with others.

  • The privilege of having multiple positive TV role models.**

Other privileges on the list that I didn’t lose because my state (Iowa) has state level protections for trans people (although the legislature tried to revoke them last year), but if I lived in another state I may have lost included:

  • The privilege of being able to be a foster parent.

  • The privilege of applying for a job/promotion without worrying your name or identities will hold you back.

  • The privilege of being able to call/access social services without fear of discrimination around your gender and/or sexual orientation.

  • The privilege of living openly with your partner(s).

  • The privilege of being able to share health insurance with your partner(s).

Unfortunately there are a myriad of other privileges I’ve lost by being myself that weren’t even on the list.

Many of them have to do with my entrance into the LGBTQIA community, and many privileges are simply things that most cis-women have never had their entire lives due to sexism and misogyny. Like the privilege of jogging through a public park without getting catcalled. Before I transitioned, I would have never seen that as a privilege. Now I do. I have a much more visceral understanding of the things that my wife has experienced her entire life.

This exercise was so powerful in helping me understand how much privilege I have, and just how much privilege I had as a white, wealthy, man. I know the past few years haven’t felt good for white men, to the point that white men (I’m completely generalizing here) at times have decided to clap back against a society they perceive is telling them they don’t belong. But that’s not what society is saying. The #metoo movement, the #blacklivesmatter movement, and a myriad of other social movements that advocate for people of underrepresented and marginalized identities aren’t saying white men don’t belong. They’re saying this system that was made by white men, for white men, to accommodate white men, has got to change.

It’s not that underrepresented and marginalized people are trying to hurt white men by chipping them off the top of the pyramid, but the calls for change are pointing out that the culture and social systems that make up the United States of America is not what it should be.

The educational system for instance, is not a system built on equity or the ideal that all should be educated. No, the current educational system was built on an idea that only white men should be educated. True we’ve modified it over time to allow others in, but the base of our current system is over 200-years-old and is built on a foundation and assumptions that most of us now understand to be false and downright harmful. For many, this leads to a feeling of being a fish trying to swim down the sidewalk.

There just aren’t the mechanisms built in our societal systems for underrepresented and marginalized people to succeed.

When I came out, I had a choice to make. Keep hiding, and keep all the privilege that came with that, or be myself and lose something. I made the choice which wasn’t a choice at all. I had to be me. I had to be free. I lost a lot in the process. But I did gain the privilege of seeing something from a new perspective and that is this: many have been losing out long before me because of their skin color, their bodily abilities, their religion (if it’s the wrong one), their gender identity, their sexuality, and a myriad of other inherent identities. I now understand this on a much more intimate level. I see this country and these systems that surround us in a new way. Not made for all to succeed, but as sidewalks that some of us are swimming down. I can not only see but can now feel how harmful many of these systems are, and it moves me to change. My privilege is worth giving up if it means freedom for myself and for others. Because as many of the history-altering visionaries who have come before us have pointed out: none of us are free until all of us are free.

*This activity can be found on the Social Justice Toolbox (

**This is changing rapidly for trans people through much more representation on TV and film.


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