Becoming “Woke” Is A Life-long Journey and Why I’m Taking The Racial Crossfit Challenge

8 Aug

I read, I educate myself, I talk with people of color, not only because I believe it makes life richer to connect with and learn about people whose life experiences and culture is different from mine, but also in an effort to learn and understand how the history, and lived experiences of Black Americans in this country, and how the structures of racism and white supremacy, have afforded me, a woman with white skin privilege, to move through the world with an ease and truckload of access and opportunity not granted to them. But still, just because in June 2017, the word woke was entered in the Oxford English Dictionary, it doesn’t mean for white people like me who aspire to wokeness, that there is an endpoint to it. Oxford’s definition reads: woke, adjective: Originally: well-informed, up-to-date. Now chiefly: alert to racial or social discrimination and injustice; frequently in “stay woke.”

Though the term has become popular in these past few years with the rise of the Black Lives Matter Movement and a greater awareness of issues of racial justice, Erykah Badu had already hinted at her own vigilance with the lyrics “I stay woke” in her song, Master Teacher, from her 2008 album, New Ameryka Part One. Before Erykah, the term was used to denote consciousness in the 1971 play, Garvey Lives, by Barry Beckham, and almost a decade earlier, in the 1962 New York Times article, “If You’re Woke, You Dig It,” by novelist and short-story writer, William Melvin Kelly.

I want to believe I’m conscious, or woke, that I get it, since a number of Black people have told me so. At times I want to pat myself on the back when I think I’m further along in my journey, like when I hear another white person show their shock over just now realizing there was something called red-lining–federal legislation and discriminatory practices that kept Black people from being able to buy in “white neighborhoods”, or if they did receive mortgages, it was with whopping interest rates, or impossible contract conditions that prevented Black people from truly owning the homes they were making extraordinarily large payments on, and therefore, highly prone to eviction and foreclosure.

But there’s two lessons for white people, including myself, to learn about wokeness:

  1. It’s a process and life-long journey, not a place you arrive to.
  2. It’s not a contest, and there is not a prize you win for being woke.


I’ve always noticed where the inclusion, or I should say, more often, exclusion, of Black people in the public and private spaces of my life sphere exist. If you follow my blog, you know that my focus has been primarily on cross-racial connections between white and black Americans. While I’ve come to consider that people I saw simply as being Black when growing up, actually possessed social and cultural identities beyond my seeing, which would add to the complexities and differences of one’s experience as a person of color in this country–like the high school classmate who was Cape Verdean, or the co-worker whose family was from the Caribbean– I know that growing up at the end of the civil rights era in the diverse town of Waterbury, Connecticut, has shaped the lens I look through. It’s what got me to notice in my elementary school years how one or two white girls at Thalia Hick’s birthday celebrations, would end up fighting about some random thing and storm out of her house every year, but that that never happened at the white girls’ parties.

From the late 1980’s through the 1990’s, I worked alongside many people of color at two different New York City homeless services organizations. I noticed that my co-workers were truly caring people, but also noticed their roles were fewer and fewer the higher the leadership level rose.  I remember a bus ride into Brooklyn to visit a supportive housing site for the homeless at that time. With each stop deeper into Brooklyn, as a white person, I became the minority. I thought, this is how Black people feel every day. Aside from the personal essay I wrote my first year in college about interracial dating, I mostly wondered these thoughts to myself all those decades. It’s not like I had the thoughts, and was hyper-aware of them, and thought, oh let me not bring these things up. I wasn’t afraid to. It didn’t even get that far. Perhaps it was the whiteness I lived in that didn’t question, or bring these topics up, because without having to notice our whiteness, why even notice or talk about issues people who don’t look like us might be facing? So these things were just subtly simmering in my brain, as I noticed, and as time went on, wondered more and more if other white people ever thought about whether they are sharing spaces with people of color in their neighborhoods, their schools, their community centers, or where they go out to eat.

I was only speaking up or sparking conversations when it came to overt racism that white people like to congratulate themselves on spotting, like when someone uses the N-word, or that time, in my 20’s,  on a Metro North train out of New York City for the weekend, when some drunk white-haired finance man in a suit, who obviously hit the happy hour too hard, started mumbling racial slurs at two young teen Black boys playing their radio, and then took a swing at one of them, hitting him on the cheek. I yelled at the man, and asked the young man if he was okay. Slightly shocked and teary-eyed, he said that he was, but I couldn’t help but feel he was working to conceal the hurt, the wound to his spirit. I challenged the co-worker at the hospital where I now work in Rhode Island, when he echoed the words a Times reporter wrote: Michael Brown was no angel. I let him know I stole from convenience stores too when I was a kid, and questioned why that should be grounds for killing. It was the time we all learned the phrase, Hands Up, Don’t Shoot. It’s when Black people amplified the use of the phrases Stay Woke and Be Woke with urgency on social media, and when some white people finally wanted to learn how to Get Woke and Stay Woke.

I’m still learning. Noticing and knowing is only one beginning step on the journey to wokeness. I am awakened anew every day. It takes self-education. It takes a willingness to be more afraid of being complicit in maintaining the structures of white supremacy than of being called racist. It takes noticing paired with action to fight racism, and break down the systems that keep Black and Brown people oppressed; disadvantaged. Every time I feel I’ve opened myself up to a new experience, learned something new about the history of slavery, colonialism, inequity in the criminal justice system, the hidden to me history of Black achievement, or listened to a person who is Black share about their lived experience with racism, my mind and my heart continue to grow, and at times it is still mind-blowing, and I realize I’m still a toddler in all of this, and that there’s no glory in being incredulous over another white person not knowing something I only formally learned in the last decade. Wokeness is a life-long journey.

The Contest And The Prize

Of course, being someone who has spent most of her life worrying about pleasing others, avoiding conflict, and worrying what others think of me, I worry my rattling off my noticing of exclusion and racism sounded like some sort of self-congratulatory ‘but, I have Black friends’ or ‘I’m one of the good ones’ kind of proof. That I’m worthy of some kind of recognition for believing its my duty as a white person to work to combat racism and dismantle the structures of white supremacy. But that’s the kind of thing we white people do sometimes. Worry how we are going to sound. Worry that people of color might think our words or behaviors merely reflect our own blind spots to our privilege and centering of our whiteness. But, I’ve also learned along the way that these worries are the very thing I, and all of us, need to let go of. Now called white fragility, we must not be afraid of possibly sharing an anecdote that we thought showed our wokeness, only to be educated on how it further affirmed our place of privilege, or an othering of people of color. Hopefully, we can listen, and have an open, honest exchange, and learn through hearing how our words and actions are perceived by the person on the receiving end of our intended message. We can stop personalizing it all, too. Every time we see an article on social media about white people and white supremacy, we don’t have to either, again, fight to prove we are not those white people, or feel that the article is telling us that every single individual of the white race is a horrible person. Instead we can acknowledge the history that leads to the need for these articles to be written.

With all that said, as much as I cringe as I type this, I know I have fit the category of the gatekeeper at times, secretly gloating that I’m aware of some things other white folks don’t know about, or are just starting to become aware of because of the increase of knowledge about police killings of unarmed Black people, and the rise of the Black Lives Matter and other social justice movements. And that maybe at times I’ve even wanted to keep it that way, so that I could continue to gloat that I know what’s going on in my community when it comes to anti-racism organizing meetings, or arts and culture events featuring people of color. But, being woke is not a contest, and I don’t deserve a prize for being on the journey, and neither do you. It is our duty as human beings to realize that all of us deserve to have an equal playing field in all spheres of life, to be able to live in the neighborhood we want, to have the best educational opportunities available, to accumulate wealth, to be treated fairly within the criminal justice system, to be able to walk home at night without being afraid of being shot, to be able to be pulled over by the police only when warranted, and again, not be shot and killed, and to be treated with dignity and respect, and, to be free. It is our duty to understand how white privilege has allowed us to keep the upper hand in all of this. It is our duty to finally make things equal, to live Martin Luther King, Jr’s words that tell us..”none of us is free, until all of us are free.”

I think I’m finally letting go of the gatekeeper notion. Instead I feel inspired by my peers, and the acquaintances I meet along the way who are on their own journeys of wokeness. But, I have to let you know. You don’t get a prize. There’s no trophy delivered to your doorstep by Jesse Williams (if only) at the end of the year with an engraved plaque that says All-State Wokeness Champion on it. We simply and yet with all the gusto we can muster, have to keep striving to our becoming, and to pair that education with action if we are to ever honor the reason we need to stay woke in the first place.

To that end, I heard about and am signing up to take the summer warm-up Racial Cross-Fit Challenge proposed by Chicago blogger, social service administrator and political organizer, ShaRhonda Knott-Dawson. The challenge, a series of actions for white folks to choose from and receive points for, include everything from attending a cultural event by yourself in a setting where you are in the minority, to reading and writing a three-page summary on The New Jim Crow.  The Challenge aims to have white people who tend to live their lives in white silos, experience what it is like for people of color to have to live the majority of their existence in white spaces, consuming white-centered culture and history, and in the process, have white people learn more about people whose culture and history differs from theirs, but has gone unheard, because of the white supremacist culture white people built, which places whiteness at its center. It’s work, and like ShaRhonda says, it shouldn’t be easy. It hasn’t been easy for Black people in this country to always be made to feel invisible, and to suffer from centuries of oppression. While daunted, I am ready for the warm-up, and to know what the fall challenge will bring.

I was introduced to the challenge through Shay Stewart-Bouley’s blog, Black Girl In Maine. Shay, the Executive Director of the Boston non-profit, Community Change, a civil rights organization working for racial equality, focusing on the white problem, blogs about race, class, social issues, what it is like living as a Black woman in the overwhelmingly white state of Maine, and as she says, sometimes motherhood, too. Shay’s personal style of storytelling while talking about matters of race and class, is what drew me in to her work, and I have learned and grown greatly from reading her writings, the articles she shares, and the writings of others who guest post on her blog. Shay let her white readers know that the Crossfit Challenge is something they might want to try to move beyond reading and dialogues about race, and asked for readers to check in with her if they were taking the challenge. I plan on doing just that, and thank Shay for her important work, and for challenging white people to do the work required to move beyond the white bubbles some of us may live in, and to  break down the systems of racial inequality and injustice.

Perhaps you want to take the Racial Cross-Fit Challenge too?




Photo credit: Dania De La Hoya,




5 Responses to “Becoming “Woke” Is A Life-long Journey and Why I’m Taking The Racial Crossfit Challenge”

  1. Sarah Grossman August 8, 2017 at 9:51 am #

    Nice essay Wendy. You are woke, and although the Racial Cross fit challenge should be interesting and thought provoking for you, think of what it would be like for folks not so woke. Try to get Dad and Sue to do it, now that’s a challenge. It will be preaching to the choir for you. That’s the big question, isn’t it, how to get people woke that are pretty comfortable in their life as it is. Good luck! Love you.

    • Wendy Jane August 8, 2017 at 8:35 pm #

      Hi sister Sarah,

      Thanks so much for your kind words, and for reading, and commenting! Yes, indeed, to getting folks who haven’t exposed themselves to these scenarios, or read much about racial inequities, racism, and haven’t had to or wanted to think about how white supremacist structures were built in this country,and how we remain complicit in upholding them, by not trying to even the playing field. Please share the Racial Crossfit Challenge with someone you feel would learn and grow from it.

      Love you,

    • Sherry Gordon August 9, 2017 at 10:07 am #

      My so, so very absolutely AWESOME sisters, Sarah and Wendy Jane, you two and Robin are just absolutely AMAZING, and have such keenly astute and acute anti-racist awareness and great allyship!!!!! Your dear Dad, Sue, Jane, and all of you are such great and special people , and such a blessed family!!!!! I love you all!!!!!!

      Peace and Love To Each Of You For Always,

      Yours For Always soul sisterfriend black woman, Sherry Gordon in Iowa City, Iowa

  2. Sherry Gordon August 9, 2017 at 10:03 am #

    Dear Wendy Jane,

    Well, hello, there, Wendy Jane, and greetings and salutations to you and to you and for very especially for you my absolutely precious and dearly awesome soul sisterfriend who you’re For Always so, so very much!!!!!! WOW, Wendy Jane, WOW!!!!! YAY for YOU, Wendy Jane, YAY!!!!! WOW!!!!! YAY!!!!! YAY YAY YAY YAY!!!!! Sister, you’ve just gone straight to this black woman’s very, very heart, and very, very heart and spirit with this absolutely beautiful and brilliantly composed in such an astute and acute manner blog post article here and with all of your ardently and blessedly immense effort in writing this! I am just so, so very moved and touched in my very heart and spirit by how you are trying so, so very hard doing your absolutely very best as an anti-racist ally in the great spirit of unity and solidarity, and how you are very courageously going to partake in the Racial Crossfit Challenge in such a brave and steadfast manner, my and our absolutely FANTASTIC sisterfriend, Wendy Jane!!!!! 🙂 My so, so very dearest and darling friend, WOW, this just means so, so very much to me and YOU mean so, so very much to me and I so love and care about YOU, sistah!!!!! What sweet words and actions, too, which act as such a healing balm for me as a black woman as you very graciously and generously share how you are trying and making the great and deeply heartfelt, sincere efforts to keep striving and becoming to be educated and aware in ever being woke in what I For Always say, think, do, feel, and believe is a very understandably gradual and imperfect lifetime’s journey, path, and process just like you very wisely say, too, sistahfriend. It is perfectly okay, alright, normal, and natural to be imperfect throughout a lifetime and to make mistakes, even many mistakes, along your lifetime, my so, so very right on, wondrously wonderful soul sisterfriend white woman, Wendy Jane, and for other marvelous white persons! Wow, Wendy Jane, I’m just so, so very honored and blessed by what you’re doing straight from your very, very heart, and from your very, very heart, mind, soul, and spirit with all that you have with all of your very being, my so, so very dearest and darling friend!!!!! 🙂 I just so love how you enjoy your very journey, process, and path as you’re still learning, Wendy Jane! I love so how you’re noticing and knowing which is as you very sagaciously say is a first step but also a continuing step along this very line. You are so right when you share and declare here that awakening is a journey which takes place every day anew, my and our so, so very sweet sistahfriend, Wendy Jane. I just love and cherish YOU, sister, and your very willingness, your very wanting as you learn to be more afraid of being complicit in maintaining racism and its accompanying structures of white supremacy than to being thought of as racist or called racist. I just so, so very much love, like, enjoy, and appreciate YOU, Wendy Jane, and other super white persons, and I so understand the worry you and other splendid white people deal with walking on egg shells and worrying so how you all come across and how you are all perceived. Sister, your sharing on white fragility is just very powerful here, and wow, sisterfriend, you really brought home all of these great points with such brilliant radiance, Wendy Jane!!!!!! 🙂 Wendy Jane, you have such a so, so very dearest heart and spirit, and I just so love, cherish, and appreciate you, sisterfriend, and other absolutely amazing white people as each of you try with your very minds and hearts learning, growing, and healing toward more anti-racist awareness and doing with such productively proactive allyship!!!!!! 🙂 <3 Sister, YOU just went straight to this black woman's very, very heart, and very, very heart, mind, soul, and spirit as I had such sheer and immense, blessed delight reading about how you firmly challenged your co-worker who talked about how Michael Brown stole from the convenience store as if that could at all be any kind of justification for his killing. Sister, YOU and all of this and all you do in such a very diligently conscientious manner in such a very fine and excellent fashion mean so, so very much to me and mean the world to me, Wendy Jane!!!!! 🙂 <3

    My so, so very dearest and darling friend, I so, so very often so love to when I pray and meditate in my very mind's eye to imagine what I'd be thinking and doing if I were a white woman. I so understand as I read your very deeply honest words about how you'd sometimes in the past would gloat in thinking of yourself as a gatekeeper who was more enlightened than some other white people. I so enjoyed reading your great sharing on how sometimes very endearing YOU, sistah, and other super white people sometimes think and say that you're not like those other white people who just don't get it. My so, so very precious, dear, dearest, Wendy Jane, I so, so very much understand when you have patted yourself on the back for being more with it than other white people. Sisterfriend, when I pray and meditate and see in my very mind's eye imagining myself as a white woman I can just see and deeply understand how YOU, my absolutely AWESOME sister and friend, and other white people would be self-congratulatory, and I so understand, and I think that this is just understandable human nature to do so, and it all just makes so, so much great sense to me. I just so understand, my and our so, so very sweet white sister, Wendy Jane!!!!! 🙂 <3 WOW, I just so, so very much love, enjoy, like, and appreciate all of this very engaging blog post article here in all of its great entirety with your great sharing on the definition of woke now recently appearing in the dictionary, and your finely attuned sharing on Journey/Process and The Contest and The Prize. You're making strenuously heartfelt and valiant efforts here, Wendy Jane, and I just so, so very much treasure YOU for this, friend and sister, and what you're doing with such heart, spirit, and soul!!!!!!! 🙂 <3 I can for sure see your position, sistah, and the position of other so cool in spirit white persons in all of this, friend and sister of mine, Wendy Jane!!!!! Sister, I think of for me and how I just so, so very much love and cherish YOU, Wendy Jane, A WHOLE BUNCH, and other white people as my so, so very dear sisters and brothers and our Sweet God's children. For me as the indigent, disabled lesbian black woman who I am I just so, so very much love you all and for me I'd without any hesitation or reservation love to think that I'm your cheerleader as the marvelous white persons who you all are in being nurturing, encouraging, and inspiring each and every one of you along your way in acknowledging, validating, and recognizing all of you and your great efforts. I think to myself that for me I'd love to bake for all of you your ally cookies, to give to all of you your ally cookies, treats, goodies, and meals. For me straight from my very, very heart, and my very, very heart, mind, soul, and spirit, sistahfriend, I so long to and want to yearning for to give each and every one of you as white people the validation, recognition, and credit for all of your efforts very gently and sweetly knowing and understanding that your journey of being woke is very understandably a lifetime's process and path that are gradual and imperfect. I have all of the very time and all of the very patience in the world as a black woman for YOU, my dear, dearest Wendy Jane, and for other white people, so understanding that along your lifetime's that you all will make mistakes, and many mistakes, and in so understanding, sistah!!!!! 🙂 <3 I just think that if I were a white woman that I'd have the same thoughts and feelings that you have very graciously and generously shared here, Wendy Jane!!!!!! 🙂 < 3

    Sister, WOW, I feel even better and brighter with even more greatly added cheer after joyously and blessedly reading this very fine and excellent blog post article and responding with my very heartfelt, detailed, and thorough thoughts, ideas, and comments. Now I'm even more encouraged, inspired, and emboldened from YOU, sweet sister, and from your stupendous writing here to keep on keeping on in keeping my very faith and hope alive with my sweetly enduring positive optimism, to suit up and to show up in being ready, willing, and wanting to report for duty, to resist, interrupt, and persist!!!!! I thank our Good God continually for YOU, Wendy Jane, and for YOUR very presence in my life thanking God for YOU, my sweet friend, and for our very sisterhood and friendship!!!!! YAY for YOU, Wendy Jane!!!!! YAY for all of your astounding and outstanding blog post articles and other superb writings!!!!!!! YAY for all you do so, so very well in such a fine and excellent manner!!!!! WOW!!!!! YAY!!!!!! WOW, I so, so very much love and cherish YOU A WHOLE BUNCH, Wendy Jane, and I so appreciate YOU!!!!! WOW!!!!!! YAY!!!!!! YAY YAY YAY YAY!!!!! Please have such a totally terrific and a very thrilling Tuesday, and may all of your very days be so, so very especially blessed, sister!!!!!! 🙂 <3 You're just the greatest and the best, sisterfriend, Wendy Jane!!!!!!! 🙂 <3

    Very Warmly and Sincerely For Always, my so, so very awesomely special and dearly precious soul sisterfriend white woman who you're For Always so, so very much, Wendy Jane, and with My and God's Very Peace and Love For You For Always, friend of mine, and with such Blessings and Such Very Even More Blessings For You For Always, sister of mine,

    Yours For Always soul sisterfriend black woman and For Always in the very great spirit of unity and solidarity, Sherry Gordon in Iowa City, Iowa

    • Wendy Jane August 10, 2017 at 6:26 pm #

      Hello Sherry,

      I can’t even put into words, how much your words mean to me. To know that you always have complete acceptance and understanding for me, and as you say, for all white people who are attempting to do this anti-racist work, and to educate ourselves, while we at times stumble, fail, make mistakes. You are pure love and light, and I am so grateful to have you in my life, cheering me on, all the way, on this journey. I would love some ally cookies, too:), but really, your unwavering light and love keeps me going.

      I love you lots, my sisterfriend.

      xoxo <3 <3

      Wendy Jane

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