To Be Black Is To Be Less Free

Charlie Gilkey
23 min readJul 11, 2016

“Are you black or are you white?”, my teenage black sister asked me. I was somewhere between six and eight — the exact age doesn’t matter nearly as much as the fact that this question was already something I was having to work out and explain.

My mom was white with Native ancestry and my dad was black with Native ancestry. But we lived in Arkansas and this was the eighties — the one-drop rule had created downstream effects such that it was still a basis for determining what category people would put you in. I had enough drops of black in me that I was presumptively black, but I had enough drops of white in me that it called into question my blackness.

That question — “are you black or are you white?” — has been a question that has guided a private odyssey for the last thirty years. Only a sliver of this odyssey has actually escaped my mouth or shown up in my words, but it has very much defined my actions in this world and how I’ve navigated my inner landscape.

It has been a private odyssey for the very simple reason that it has never been safe for me to talk about race. Plenty of other black people do, though, so you may wonder what’s led to three decades of relative silence. It’s probably best to start with why I couldn’t talk about it with my own family.

Not Black Enough

I don’t begrudge my sister for asking me the question. I’ve never been able to tell whether it was coming from a place of love in prepping me to be able to navigate this world or from a darker, more racist place. I experienced her as the most racist of all of my family members and given her age at the time, she was likely trying to sort out how she would treat me and our relationship. It was thus not a theoretical prompt for her, but a very practical one: “how can I love this little person, my own little brother, while still othering him.” ((Before you think “black people can’t be racist,” please read about the four levels of racism and be clear about what you mean.))

Of course, that’s not our conscious script about race and how we relate to others. But in that moment, my sister did separate us: she was black and I was something else. And she was only speaking directly to what it felt like my black neighbors, friends, classmates, family, and elders were trying to figure out, too.

Black people are not born with a blank slate of who they can be in the world. In the context of the time and place I was born, being a black boy meant that:

  1. I would be Baptist or Methodist
  2. I would have some athletic ability
  3. I would be able to dance (and likely sing, too)
  4. I would be heterosexual (and homophobic)
  5. I would be a Democrat
  6. I would likely have a larger-than-average penis (when I developed)
  7. I would be able to fight
  8. I would be funny and smile a lot
  9. I would eat sweet potato pie at Thanksgiving (not pumpkin pie)
  10. I wouldn’t be able to swim
  11. I would be scared of the woods
  12. I wouldn’t be good at school
  13. I would be a thief, lecher, slacker, liar, drug user, alchoholic, or a bully (I could be all, but I was at least one)
  14. I would be wholly incapable of showing up anywhere on time
  15. I would speak a certain way — in my context, a mashup of hood and country
  16. I would be deferential and respectful to white people
  17. I would always be on the edge of criminal behavior if not actively involved in criminal behavior
  18. I would be loud, especially if in the company of another black person
  19. I would be without a father or a strong, respectable black male role model in the home
  20. I would be fearful of the police and go out of my way to avoid any contact with them
  21. I would instinctively give other black people head nods or daps
  22. I would always back and support my people and remember my roots
  23. I would be able to and interested in shooting hoops as a default activity
  24. I would like hip hop, rap, R&B, or gospel music (and conversely, would not listen to rock, country, or classical music)
  25. I would dress sharply (Nike’s, FUBU, Polo, Hilfiger, so on) and have my hair on point

No one made this list for me and many will be outraged that I dare articulate some of the items. Some of these items came from white people, but the majority came from the way black people talked about themselves. And, more importantly, black people preserved and reinforced the norms — even the ones they most despised.

I could keep adding to the list, but my point is to show that these items are what defined me as a black person (in Arkansas, in the eighties). It’s crucial to understand that racial identity, where it has meaning, is highly contextual, so many black people from other parts of the US will see how their experiences and expectations were and are different. Here and throughout this essay, I do not mean for my perspective to be the definitive perspective — it is just my perspective.

You might think the color of my skin should be up there, but skin color is its own complicated discussion point. For instance, you could appear to be white, but if people knew your black family, you were black to white people and “something else” to black people, even if you fully asserted your blackness. High-yellows — black people with light skin tones — often had more clout in the community because they were more attractive to both white and black people, which made their relationship to their blackness troublesome for them, too. The darkest of us were no doubt black, but they were often the butt of many jokes, especially at night or in dark rooms.

My relationship to my blackness become precarious the older I got. By the time my sister was asking me about which category I fell into, I had already violated enough of the norms that it was problematic. Because I spent a lot of time at a pre-school (my mom taught there), I learned how to read and write early, even for white kids. The teachers and elders at that school were white and did their damndest to teach me to speak “proper” English, eliminating words like “dudn’t” and problems like “Me and Ashanti went to the park.” I couldn’t dance, but I loved to swim.

Determining whether someone is black is much like chicken sexing, it seems. The experts at it can’t tell you how they determine it, but their determination is unerring. Until you step out of the line, in which case you can be probationarily black until you do something that’s not black. If your status as probationarily black becomes publicly known, you become a topic of conversation at the barber shop OR you become the thing that can’t be talked about at the barber shop.

As I continued to develop as a child, I did more and more things that “black kids don’t do.” I was a Boy Scout. I won science fairs. I was in the GATE (Gifted and Talented Education) program. I was involved in leadership development programs.

The most distressing thing about my experience as a child was the mixed messages I would get, especially from my black community. The adults and elders would encourage my development as a student at the same time that they’d use that as a litmus test when determining my blackness; black kids would make fun of you, ostracize you, and beat you up (if they could) for being too smart or accomplished. I’d get in trouble for fighting at the same time that they expected me to be able to fight. I’d get approval and encouragement to explore my heterosexuality at the same that I’d get in trouble for doing so.

There was no winning. I later came to understand that that’s one of the fundamental aspects of being black in America: there is no winning. Every victory was measured, tentative, and costly — and could easily be taken away from me.

I also came to understand that I could not be my own person and be black. To be fully black, blackness had to be the foundational element of who I was, and all other dimensions of myself had to be stacked upon that foundation. Much like being a Christian, I had to own and assert that blackness was the rock upon which my life was built.

If you questioned the gospel of blackness, you were no longer black or black enough. In the deeply racist context I lived in, there were no open discussions about this that I knew of, and I learned very early on that a multi-racial kid would not be conversed with about blackness, but rather preached to. White people were ignorant about, hostile to, or uncomfortable with conversations about race and I simply did not have the skillset to ask them to point me to good resources and the black intellectual literature. This was pre-Internet, so even if I’d known to Google something at such an early age, I couldn’t. I didn’t know about the rich intellectual history of black thinkers working through things, so I didn’t know to go to the library and ask about it; I also suspect that the Fort Smith Public Library system would be a bit short on black intellectual literature.

So I didn’t talk about it. I couldn’t win, either. I would never be black enough for black people deliberating my blackness.

I most wanted to be free to be who I wanted to be. I grew up in an Army house and the Army’s main slogan at the time was “be all that you can be.” I did not find much support for this in the black community, including my extended family.

I’m not sure if one can leave the black community while still holding onto their blackness. In any event, rather than trying to fit into the community, I started to not care whether I was in the community or not.

Not White, But (Mostly) Accepted

Fort Smith Public Schools started junior high at the seventh grade. This was a turning point for me, for it was the first time that I spent every day with kids who lived outside of the poor neighborhood I did. My elementary school was predominantly black, which meant that it had a predominantly black culture.

Darby Junior High was something altogether different. New kids from different schools got crammed together, and schoolyard rules kicked off briskly. But there were new rules added to the game — some stifling and others liberating. The stifling part was that the difference between black kids and white kids became very stark. The liberating part (for me) was that I found more teachers and friends who supported my self-actualization.

To be clear, my teachers at Howard Elementary were phenomenal. Mr. Abernathy and Mr. Hendrick were two powerful, smart, driven black men who, along with my father, shaped who I am as a man. The female teachers were strong, smart, driven, and firm teachers who did a wonderful job shaping my views of what women could be. There were only so many of them, though, and they were caught in a system, too.

During our elementary education, teachers and adults guide and shape our development. During adolescence, other teenagers guide and shape our development. The trouble with teenagers is that they resist listening to adults but sometimes don’t know which teenagers are the best ones to be in relationships with.

All of my friends at school were from Howard Elementary, which is to say that all of my friends were black. In the new caste system at Darby Junior High, my friends were fast falling to the bottom with the rest of the black kids. They were (seen as) the troublemakers, the liars, the chasers, the flunkies, and the thugs. To be very clear, I am not saying all black kids or all of my friends ended up at the bottom or acting in these ways, but that there was norming and expectations-setting about it that started to occur.

For the first year there, I was, too. I spent most days in detention after school and was in the principal’s office multiple times a month.

I was different, though. I was also still in the GATE and leadership development programs. I was thus a different kind of problem and irritation to my teachers and principals, for they saw in me someone who could do better, who should do better, but was on the path to becoming another statistic. I remember their faces and their conversations with me about this. I remember Mr. Harris and Dr. Ross — two white teachers who had a stronger-than-they-know impact on my development — struggling to figure out how to tell me about my potential without demeaning where I came from.

At a certain point, I think they figured out that disciplining me was ineffective. They were softies compared to Mr. Hendrick, Mr. Abernathy, and my dad, and given that my mom taught me how to write, I had a near-perfect forgery of her name. Because she was working multiple jobs at the time, she didn’t know how much time I spent in detention, and I was cunning enough to stay just above the level of getting suspended, mostly because I had learned how to intimidate others without fighting and to skirt situations with upperclassmen that may lead to a fight. Much like other people of color, I had to learn how to apply street rules to school rules; I also had to figure out how to not have the street rules negotiated at school to spill out into the streets upon which I walked home. Gang violence wasn’t so bad that it was a constant worry, but it was enough that I realized that some people had crews and I did not. I wasn’t black enough.

Two things flipped the switch for me: 1) the school made it very clear that my behavior would get me expelled from the GATE and leadership programs and 2) I worked at a Boy Scout summer camp for the first time. The fear of being kicked out of GATE and not being able to do my leadership programs ensured compliance but the summer camp changed the game entirely.

At that Boy Scout summer camp, there were new rules about how to be successful, articulated mostly in the Scout Oath and Scout Law. I believed in both then (and do to this day). Also, because I was the only black kid there and the white kids were mostly allies, would-be allies, or byproducts of the “we’re colorblind” way of orienting to race, my race really wasn’t centered in conversations and relationships like they were in Fort Smith. Because race is very much tied to class and they had no idea how poor I really was, they also assumed we were equal-ish on those terms. We were all aware that I was not-white, but it didn’t feel like it mattered much most of the time. It was an all-male camp, too, so we didn’t have to worry about the sticky situations that happen when black and white people want to be romantically involved.

Working at that summer camp was the first taste of real freedom I had ever experienced. It also taught me at an early age that I could get paid to do what I love to do; it took me another ten years to figure out that I could have a career based upon what I loved (and another six years to actually get there). I worked there every summer that followed except for when I went to Boys State (a political education experience) and Governer’s School (a prestigious summer academic program I was selected to attend).

The school year following my work at that summer camp was incredibly challenging for me. I knew where my place in the world was because I saw it in such a stark contrast, but I did not want to return to being the way I was before. I also did not have enough other friends at school and I had already done a fantastic job of branding myself as one of the black kids.

It’s hard to separate yourself from the friends you’ve had for the last eight years. It was if I had moved away, but I was still in the same school. I couldn’t and wouldn’t diss my homies, but I also couldn’t and wouldn’t play the game anymore. I also did not think I was better than them, though I’m quite sure my actions then and to this day seem to come across that way.

At this time in my life, I had developed a deep friendship with Scott, a white kid on the other side of town who went to church and was in Scouts with me. Scott and Becky, his mom, were my lifelines. For reasons I’ll share in another essay, my understanding of family was considerably more fluid and open than others’. I had lots of “moms”; fewer “dads”, but a lot of “uncles.” Scott was a brother and Becky was my second mom. The color of my skin did not matter to either of them. At the time, our families were going through similar-enough challenges and triumphs that what mattered was how we were there for each other, not how we were perceived in the world. Scott would later literally be a lifeline and save me from drowning at the same camp that created a new life for me. Funny how all these things tie together.

Scott and I spent a lot of time together during those next few years. No matter how lonely my experience was at school — how separated I felt — I knew that there’d be a fire to build in my backyard or a roof to jump off of or a camping trip to go on. The Scouts were also another anchor point for me. I started working out in junior high school, so that became another anchor and also a new place to find friends. I took harder classes at school that required enough of my focus that I couldn’t sleep through them and still make A’s. I was in the band, so there were a host of new friends there to make, and we all know how band nerds roll.

I lost my black friends largely because we were involved in different activities and in different classes. I’d see them at football practice, but I didn’t follow them from football practice to detention anymore. My basketball skills were sorely lacking and I’ve never enjoyed doing things I’m terrible at, so the default bonding activity that so many black kids did wasn’t on deck for me. I’d still give them daps, headnods, and bumps, but besides where we’d been together and the color of our skins, there wasn’t much else tying us together anymore.

I gained my white friends in the reverse way. We were in GATE, advanced classes, band, and Scouts together. I was introduced to roleplaying games early on and loved them, so we’d play day- and night-long roleplaying sessions. We quite naturally bonded and became friends through our shared activities; simply put, white kids were interested in stuff I was interested in.

Like all good fairy tales, though, there’s a monster that lurks underground. Everything was good as long as I didn’t talk about race and played by the rules. This was another unspoken rule. Because of the history of our society, white people have the keys to everyone’s career and economic prosperity. GATE could always be taken away from me. My mom had survived cancer, but I took to heart her telling me that I’d have to make it on my own because she may not live through it. Education was my way out of manual labor, working at the chicken plant, or stringing together a string of unrelated jobs to get by.

By this time in my life, I had learned that it was more than GATE that could be taken away from me, though. We saw through Rodney King that there were far worse things that could be taken from us, and the black community knew it all along, too. Their fear and insistence that we stay with our own were rooted in the very reality that the only thing that could not really be taken, beaten, or shot out of us is our very blackness. And that spending too much time with white people made it more likely that we’d end up in trouble or lost.

Rodney King was a turning point in my soul, as well. But it was a conversation that you did not have with white people in the South. There wasn’t room in the black community for a conversation about it; we reacted to it in different ways, we hurt about it in different ways, and we knew it was wrong. The lesson to be learned from Rodney King was that that’s how things really were: we were still getting beat in the street. There was no justice for men with black skin.

We have words like “white privilege” and “police brutality” and “systemic racism” now. We have hashtags and we name names. None of this was a part of my reality in the nineties. What was part of my reality was that talking about race to white people would get you in trouble and breathing-while-black could get you in trouble. It was best for you, all things considered, to be as not-black as possible. That kept you safe and comfortable.

I was not black enough to be black with the black community. I could not talk about race with the black community. I could not be free to self-actualize in the black community.

I dared not be too black in the white community. I could not talk about race with the white community. Because of the onus to be as not-black as possible, I could not be free to self-actualize in the white community.

So, for another two decades, I mostly did not talk about race. Even as I studied ethics and social/political philosophy, I did not make it a primary object of study or discourse. Even as I started added additional studies on human rights and liberation, I did not squarely talk about race. But, at a certain level, it’s hard to examine and discuss the deep structural elements of our society without talking about race.

So why wouldn’t I talk about race, even as a graduate student? Because …

Being A Public Black Intellectual is Career Suicide

Of the many problems our nation has, hostility toward intellectuals is one. It’s a part of our heritage and distrust of elites (it looks like aristocracy) or people who are too European (too much influence). The McCarthy era only made it worse.

Cultural issues aside, our media consumption habits also lead to an under-appreciation of intellectuals. Many people dropped off of this essay after 500 or so words. TL;DR.

So being an intellectual is career suicide on three fronts:

  1. a significant portion of your society will be actively hostile towards you
  2. the portion of readers who aren’t hostile require the condensation of thoughts into accessible, snack-able bits of content that are friendly to them emotionally and cognitively
  3. largely speaking, the only viable career pathway for you is as an academic

The third of those doesn’t seem to be a problem until you experience how insular and stifling the academic community can be. I thought that was the route for me until I felt a very familiar confinement starting to happen. I figured out that, though it’s harder, I have more room to be an intellectual and have impact outside of academia than being trapped within it, and now I’m actively figuring out ways to have my foot in academia enough to have the forum, intellectual stimulation, and access to curious students without having my whole body within it. I have much appreciation for my academic colleagues who make it work for them. (Note that my experience of academia was shaped by my simultaneously being an Army officer and, later, an entrepreneur.)

Add “black” intellectual to the mix and things get much worse. The expectation is that you’re going to be writing about topics people are uncomfortable reading and grappling with, let alone actually buying. It opens you up to an extreme amount of criticism and character attacks from both white and black people. On the one hand, white people really would rather not talk about it or don’t know how to; they’re stifled by their own privilege as much as others are caged by it. On the other hand, black people will dismiss your perspective if you’re not black enough or dare question the rocks upon which they build their identities; years of neo-Malcomite thinking, agitprop, and having their perspective dismissed — as well as their current grief, outrage, and frustration with the status quo — put a charge on the conversation. In either case, you need to be prepared to take a few black eyes and a busted lip before you’re able to have others acknowledge that you have eyes that can see and a mouth that can speak, too. You also need to be prepared to be excommunicated from both communities.

Another way in which adding “black” to “intellectual” is career suicide is that you endanger your autonomy to explore other areas unrelated to race. If you discuss something like climate change or Brexit, it seems random or people wait for some tie-in with your standard topics about racism, incarceration, systemic injustice, the plight of Africans, or police brutality. You become the representation of a perspective and are expected to pursue and advocate issues that singularly champion black causes. But your nature as an intellectual defies the confinement to certain topics, as it’s a way of seeing, examining, and discussing the world more than it is a collection of knowledge domains. Given the rate at which “black” issues show up in the news, you’re always a click away from having to manage your own emotional maelstrom while you figure out what to say about it while it’s still relevant.

The first of those two reasons conjoin with another tension: there’s only so much room for black thinkers, and the more polemical and incendiary ones are going to get the most attention. Shock and awe get attention, no matter how numbing and awful it gets.

A third way in which it’s career suicide is how easy it is to become a “black” brand. For instance, there have been people who have suggested that I own something like “the black David Allen” or the “black Seth Godin.” While I see where that’s coming from — and it might make my marketing life a lot easier — I’d much rather be the Charlie Gilkey. And maybe get to a point in my career where being Charlie Gilkey is a thing that actually means something, not because my name is important, but because my body of work has made an impact and I’ve served my people well.

Clearly, there’s a way in which you can be a black intellectual in a descriptive way. I know quite a few black people who are intellectuals, but they do not call out either their blackness or their intellectualism. Given the above, I know too well why they may make that choice, for I have made the same choice.

It should be clear by now that, by “career suicide”, I do not mean that you no longer have a career. I mean instead that your ability to chart your own career becomes considerably more constrained. For many black people, being able to shape and master our careers is what we strive the most to do — we have overcome discrimination, systemically bad schools, and societal expectations of who we can and can’t be. To lose our ability to go to work and do what we love, on our own terms, is too much.

Silence is not the same thing as inaction, though. For years, I’ve intentionally cultivated diversity without making it a public conversation. I decided to be a mentor to people of color and women throughout my many careers. I would ensure my minority college students were challenged and invited to join the conversation, but not harassed or put in the position where they had to be the voice of a group. I would check in on minority soldiers in my charge so they knew someone cared. I would strategically ensure that women in my units got leadership opportunities without setting myself up to be questioned about whether I was attracted to them. I suggest the names of minorities and women to panels and intentionally seek out and spotlight a diversity of perspectives on my podcast and blog. I haven’t done this in a way that excludes other people or makes it just about getting POC and women in seats; I’ve just spoken up for and championed people who so often don’t get seen.

It’s the “public” piece that I’ve decided to own now, for I’ve been on this odyssey privately for 30 years. Which leads to the question: why now?

Why I’m Going Public Now

I’ve never felt qualified to speak on issues of race at the same time that I’ve been scared into silence. Throughout the years, I know many of my family members have thought that I lost my way or got too far from my roots. The truth is that I’ve spent thirty years finding my way and examining those roots.

But the events of last week converged with a few personal growth threads this last week and shook me to my core.

I was seething at the relative silence of the majority about what’s going on and saw myself in that silent majority. That thread led me to shed some unconscious belief I had picked up from a black conversation leader that white people have a greater onus to fix this shit than I do.

I saw how many black people were jabbing and punching at allies and would-be allies and my heart hurt in a different way. I know they’re jabbing and punching because they’re hurt and they want to jar people into feeling something that might get them to act.

I saw and felt allies and would-be allies stuck in their own silent world of grieving and exasperation, but not knowing what to do about it and not having anything to say about it.

I saw that our words have become so twisted and distorted that they are draughts of poisonous separation rather than the elixir of unity.

I recalled all of the conversations I’ve had with allies, silenced black intellectuals, and unseen peoples of other colors.

I watched two men die. I heard a little girl comforting her mother, unaware of what the death of her father meant for her.

I saw my sister and Becky (my second mom), tethered together in a system of suffering but unable to really see each other.

I looked out at my world and saw that, somewhere along the way, I had become the most accomplished and inspirational black man that many thousands of people personally knew. I talk to them every week, but not about this.

I was reminded that I was still unfree. That not too much separates me from Philando in this system and nation.

It all came crashing down on me. The private part of my odyssey is over.

I have created a career for myself that’s largely independent of the magnanimity of any one person or small group of people. I have no commander selecting me for my next assignment or a dean or board of colleagues that can grant me my next promotion. My GATE program and livelihood cannot be taken away from me by fiat.

And even if it could, I could rebuild it. What got me here cannot be taken away from me because what got me here is who I am and the way I show up in the world.

It is also apparently time for me to figure out where I stand with my own blackness. For too long, I have let others steer my journey, even if they steered by creating a place I wanted to run from. For too long, I have accepted that they are the custodians of blackness and have the power to give and take it from me. They are neither the custodians nor have the power to deny what is within me. They can disagree, but their experience of blackness is no more valid than mine or any other black people.

The context of racism, white privilege, and systemic injustice is different now than it was when I was a kid, just as it is different than it was for my elders. I do not know what racialized kids growing up in the age of the Internet and social media face, but it’s high time that I start asking. It’s high time that I don’t unintentionally force them on their own private odyssey or have my silence teach them how they must be in this world.

Given my experience of the world, I don’t feel that dehumanizing others is a particularly effective or moral strategy at opening up the conversation. Requiring personal emotional reparations from those who are just as trapped as you are and who may not have done anything to you is merely a redirection of the violence, abuse, and mistreatment you have undergone. Making someone drink the poison you’ve drunk does not heal either one of you.

That said, witnessing the poison I’ve drunk may make you ill. That is not my intent, but it may be a byproduct nonetheless. In the end, though, silence makes us more ill.

Much of this essay has had, as its throughline, my quest for unconstrained self-actualization. I recognize that many will find that a very self-centered drive, but my self-actualization is and always has been tied to service to others. I have always grown the most through leadership, service, teaching, and accomplishing tough challenges. In much the same way that I did not want to be deployed for Operation Iraqi Freedom, I am apparently being called to serve in this way.

New Worlds Require New Questions

When my sister would ask me if I was black or white, I would say that I’m neither and both. It seemed right then. It’s such a layered question that, at this point in my life, I’m unsure it’s answerable.

I want to live in a world where we recognize that a question like that is itself a false choice. A world where all kids have a blank slate and some aren’t racialized objects. A world where we don’t need a hashtag to insist that the people of one race be treated as individual persons just as much as others.

We don’t get there via private dreams and odysseys. My freedom is cashed out in the street and, as King rightly said, “our freedom is inextricably bound.” Furthermore, the freedom of the next generation depends on our figuring out how to unite ourselves and prepare them to face the challenges that may very well determine the survival of our species.

I am talking now because I see it’s the only way forward. And I look forward to hearing what you have to share and say, too.



Charlie Gilkey

Author of Team Habits - - and the best-selling Start Finishing. Executive coach, investor, and philospher.