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  • Writer's pictureSaasy Sistah

Interview on the journey to allyship – Ryan Headley (White Male)

Why do you want to tell your story? 

Why did you want to participate in this blog?


Because I believe that even though I am #MMCW, (that my past experiences have led me to a point in life where I feel I went through what I went through so that I can help other #MMCW understand those who are pre-judged due to gender, race, religion, creed, sexual orientation, or other categorical stereotypes.


Thank you, Ryan, your experiences are valid and your input is valuable. (MMCW is Male Middle Class and White.)

What’s your story? 

Tell me about yourself. Who are you, where are you from?


It’s easier to link you here: Ryan’s Story


This is truly beautiful Ryan, thank you for being brave and vulnerable sharing this story with us. I hope that it gives others the courage to do the same.

Your first injustice:

What was the first unjust you witnessed or experienced?


Well, I knew I was being treated “differently” at the end of my sixth grade year when I was “asked out” as a joke. At that age it really means nothing, but I knew I was the target of a joke from a group of people. Other than that, 7th grade when football players were being “selected”. I’m not sure when I experienced my first. It took awhile to find a group of people to wake me up to it. Now it’s everywhere…


Yes, once you wake up it’s hard not to take notice.

Your awakening?

When did you realize that there is a race, class, and gender divided in this country?


I’m still experiencing my awakening. I know it’s there, I hear more and see more all the time. I think Mary Scotton’s keynote at Southeast Dreamin in 2016 really showed it to me. I used to feel like all the WIT groups, and groups that support people of different ethnic backgrounds were simply reverse discrimination and tit-for-tat. Her keynote helped me realize this is not the case. That said, my first few encounters when challenging these types of groups was met with “now you know how it feels” — which isn’t the message that should have been delivered. After explaining why that answer didn’t sit well with me, and the dialog opened more, I began to see and open up to hearing other people’s stories. That “now you know how it feels” answer was also a signal to me that perhaps with more understanding on my part, I can help other #MMCW understand.


Mary is a bridge for many her elegance, grit and grace is to be cultivated. I hate that you received that response when trying to understand. I know that some become jaded and exhausted by the constant explaining, teaching, and learning that this work takes. It’s not an excuse, however, try to be patient with those as we are trying to be patient with #MMCW’s.

What does privilege mean to you?

Describe what privilege means to you personally.


This is a tough question because I do absolutely understand that I have privilege in some areas, but not in all. I don’t necessarily have to worry about walking into a job interview and have my qualifications questions based on my gender or race. That said, I do in all honesty worry more now because companies NEED to diversify that I will be discounted because I’m a white male. If a company is a largely white male already (and I am NOT saying this is right) then my chances are stacked against me. However, this is not my white privilege working against me, it’s now a more level playing field, it’s me not blindly leaning into my privilege, and I’m okay with that. It’s what is right, the right person should get the job based on ability, not anything else… Secondly, I do feel that I do NOT have privilege in other situations. When talking to a member of the opposite sex, especially in the tech industry, I think many men worry that their mere interaction will be viewed as a “come on” or “patronizing.” It’s why I normally wait to be greeted. It also means I’m uneasy with certain references. Example: At Dreamforce 16, I was outside in line with Shonnah, she called me “whitebread” — which I am more than 100% fine with. For me it was fun, but in all honesty and being completely open for the sake of discussion: I had NO CLUE what I could get away with in return. I’m going to ask you here, feel free to do with as you please, but I wanted to use the term “Brown Sugar” in response. It was a playful tone, and I wanted to return said volley, however, I did not. Here’s why: #1 — it could have come across super creepy, as a flirtatious advancement #2 — it could have been very racial, and perhaps there’s some meaning I’m not yet aware of. #3 — it’s part of a Rolling Stones song, that if you listen to the lyrics is very inappropriate in its references to slavery, etc. I opted for restraint. THIS is why I wanna get involved and understand more. THIS is why I started my journey. I simply just don’t understand…


I opted to keep it! LOL. First I would have to say know your audience, If I play with you in this manner I consider you a friend. I would have laughed most likely very loud (I’m smiling right now). Second, it could be a hot button for someone else that doesn’t know you, you can’t just go around calling rando’s brown sugar ;). Know that I will always tell you if what you do or say is offensive in any way. I am not a Rolling Stones fan so I wouldn’t have had a clue. However, there is an R&B song that was popular in the 90’s by D’Angelo (D’Angelo “Brown Sugar”) I would have most likely started singing it. Third, We all make mistakes and fall short; do not let the fear of making a mistake hinder you from learning and growing. Most of us would explain in a mild manner.

How do you think you have benefited from your inherited privilege?

Describe benefits you have received in your life that you think was a direct result of you being part of the majority.


Sadly, I’ve been blind to this — it’s not a question I could probably accurately answer. As I sit in retrospect, it’s hard for me to find a scenario that I could point to definitely and say “for sure, that was my privilege” but isn’t that the blindness at work? It could be? Maybe just about everything I’ve experienced has me here because of my privilege. The school I went to had two African American girls, and one bi-racial boy. So I grew up in small-town middle class America, pretty sheltered from multi-cultural influences. So that answer could easily be “everything I have, I owe to privilege”


I wouldn’t attribute everything that you have to your privilege, you are an extremely smart and talented individual. However, I would say that recognition of that privilege is the first step. That in of itself takes humility recognizing that you have been blind to it is progress.

What do you do to be an ally?

What are some of the things that you have put into practice to be an ally?


I’m always here as a soundboard, to back up, to share opinions and objectivity when I can. I’ve diversified my portfolio, I try to stand up and speak from a place of objectivity when discussions come up with my fellow #MMCW members.


Thank you for extending yourself in this way. Personally; I can say that you have truly made extream efforts on your journey to understanding and allyship. I remember at #DF16 after the Benioff Q&A you came to me and asked my how you could help. I saw the tears and pain in your eyes and the sadness in your voice. That day you helped me fill my reservoir to continue fighting, you showed me the side of humanity that I believe in. You helped refresh my hope because that was real and you helped me remember that people can change.

How could you move from being an ally to an accomplice?

There is a difference between an ally (someone who is a a resource with another for mutual benefit) and Accomplice ( someone who is culpable and has something to lose)


This is really where I need help and yet again why I began my journey. HOW is exactly that question. HOW do I move on to do MORE? Help me help you. A good example: I was telling Shonnah that I created a brief survey, wrote my story (which is linked to above), and shared them with many of the leaders of the WIT movement, etc and asked for feedback, for answers to questions, etc. I shared it with Shonnah, Ashima, Mary, and many others. I got back exactly ONE response. ONE RESPONSE. Here I am, WANTING desperately to become an accomplice, to do more, help more, looking for a good place to start, but nobody stepped up to help me help you. Its why I’m participating today. We are blind to our privilege, and have been blind. When we take off these blinders, this new vision takes some time to adjust focus — we need help in this period, help to figure out HOW we can help. We are taking baby steps…


I hope this post gets you the response that you are looking for. I hate that we are all so busy and we do experience burnout. I will personally do better at my response to requests such as these, one suggestion. I know that it helps me is not to hit me with so much at once try more bite-sized doses they are easier to manage with all of our schedules.

What would you tell other white males about allyship?

If you could encourage other white men to become an ally what advice would you give?


Talk…ask…LISTEN. Understand that feelings are driven from past experiences, don’t discount them because you haven’t had that experience.


I would only change the order, LISTEN (Actively), Ask, Talk. 🙂

Who or what has inspired you?

Is there something or someone that you draw strength from and why?


Ashima…she has helped me see things I wouldn’t normally see. Mary as well…same thing.


I have to say I lean on these two alot as well.

Do you think your efforts have an impact?

Do you think your actions of allyship have an impact? Why or why not?


I think they will start to, right now I think I’ve had very minimal impact.


As I mentioned above you had a major impact on me so don’t sell yourself short.

Thank you again, Ryan, it took so much courage to tell your story and we will all be richer because of it.

You can reach out to Ryan or follow him on Twitter @lifewithryan

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