Watching from the Sidelines

Dear Purple Mailbox,

I'm a 58-year-old white man who has spent nearly four decades in corporate America. I've worked in banking, manufacturing, and healthcare administration. I've sat in conference rooms, attended executive retreats, and spent enough time around boardroom tables to know how people talk when they think certain ears aren't listening.

I've loved Black women my whole life. I know that probably sounds strange coming from an old white man writing to an advice column on the internet, but it's true. I've always admired their resilience, intelligence, humor, and ability to keep moving forward while carrying burdens most people don't even recognize.

I was raised in a small Southern town, and some of my earliest memories are of Black women. My elementary school secretary was a Black woman. The cafeteria manager was a Black woman. The nurse who cared for my mother during her illness was a Black woman. One of my favorite teachers was a Black woman. As I got older and entered the professional world, I kept noticing something. Black women often seemed to be the most prepared person in the room and simultaneously the least protected.

I've watched their ideas get ignored until someone else repeated them. I've seen them be called intimidating for speaking plainly, while white men were called decisive for saying the same thing. I've seen Black women carry entire teams only to be labeled difficult when they finally became tired of carrying everyone else's responsibilities. I've seen people roll their eyes when a Black woman spoke up about unfair treatment. I've heard comments about their hair, their tone, their facial expressions, and whether they smiled enough. I've sat in rooms where people said things they would never say publicly because they assumed everyone present would agree with them.

And here's my confession. I almost never said anything. I wish I could tell you that I always stood up and spoke out, but I didn't. Sometimes I was afraid of becoming unpopular. Sometimes I worried about being excluded professionally. Sometimes I convinced myself it wasn't my place to get involved. The truth is that I was a coward.

I also have another confession. I have never dated a Black woman, despite wanting to many times throughout my life. I've never even approached one romantically. Part of it was fear of rejection. Part of it was worrying that she would think I had ulterior motives. Part of it was fear of how my family would react years ago. And part of it was wondering what kind of man I could possibly be to her if I couldn't even find my voice in rooms where she wasn't present.

I've reached a point in life where I realize fear has been making decisions for me for a very long time. I don't know if I'm writing because I'm seeking forgiveness or because I simply need to admit these things out loud. I just know that I've spent most of my life admiring Black women from a distance while lacking the courage to fully engage with or defend them. What does a man do with that realization when he's almost sixty years old?

Sincerely,

One of the Quiet Ones of Charlotte, NC

💜 Dear One of the Quiet Ones,

First, this letter took courage to write. Most people are willing to confess who they've loved. Far fewer are willing to admit when fear has kept them from fully living in alignment with their values. That level of honesty deserves acknowledgment.

We're living in a time of significant social and racial tension. This isn't really an era for fence-sitting. At some point, all of us have to decide what kind of people we want to be and what principles we're willing to stand behind when it's uncomfortable. I want to challenge you to pick a side. Not a political side, or a racial side. A human side.

You say you've admired Black women your whole life. You respect them. You've noticed the burdens they've carried, the inequities they've endured, and the ways they've often been left unprotected. The question now is simple: What does your admiration require of you? Admiration without action is really just observation. And observation, while comfortable, doesn't change much of anything.

You mentioned fear. Respectfully, I think you may have less to fear than you realize. One of the realities of this country is that white men have historically been afforded an extraordinary amount of freedom to move through society, reinvent themselves, take chances, and recover from mistakes. That's not a condemnation; it's simply an observation about social realities. From where I sit, you have far more room to be courageous than you've given yourself permission to believe.

You also mentioned growing up in a small Southern town. I understand how those environments shape people. We inherit fears, assumptions, and unwritten rules long before we're old enough to question them. But you're not there anymore. You're in Charlotte now, a city filled with Black professionals, entrepreneurs, artists, executives, families, and communities that are thriving in every imaginable way. From everything I've heard and experienced, love and connection are major themes there. I highly doubt you'll be viewed as an outsider simply because you're a white man approaching people with genuine kindness, respect, and authentic intentions. And honestly? I think we've been socially conditioned to remain divided in far more ways than race alone. Politics, religion, class, geography, gender, and generation. We've become experts at drawing lines! I think it's high time for people to start crossing some of them, specifically in love.

As for the workplace, I want you to consider something. You've spent decades watching. Imagine what could happen if you started speaking. You seem to occupy positions where people pay attention to your words and cues. Leadership isn't only about authority. It's also about permission. Sometimes all it takes is one person saying, "That's not appropriate," or "I don't think that's fair," for an entire room to recalibrate. You might be surprised how many people have been waiting for someone else to speak first. Remember: Just because everyone is doing something doesn't make it right. Just because no one is doing something doesn't make it wrong. The version of yourself you're describing in this letter doesn't sound like a hateful man. He sounds like a man who has allowed fear to occupy too much real estate in his life.

The good news? You're almost sixty, not dead. There is still time to date the woman who catches your eye. There is still time to make the comment that changes the atmosphere in a meeting. There is still time to defend someone's dignity. There is still time to become the person you suspect you've always wanted to be. I can assure you that being true to yourself is one of the greatest gifts you can give yourself and the people around you. You don't need permission to be courageous. You don't need permission to love across lines. And you certainly don't need permission to treat people with dignity and speak up when something is wrong.

The sidelines are comfortable. But life has a way of rewarding those who eventually decide to step onto the field. 💜