Room to Fail Forward: What My Friends Taught Me About Access, Privilege, and the Weight of Perfection

Most of my best friends growing up were Black. Not because I was trying to prove anything, but because they were real with me in a way I didn’t often find elsewhere. No masks. No manipulation. Just truth—raw, direct, and unfiltered. They told it like it was, and in that raw authenticity, they showed me things I wouldn't have seen otherwise.

I had friends from both worlds—white and Black, privileged and underserved. That gave me a unique vantage point. I could see, with increasing clarity, the stark differences in how the world treated white kids versus Black kids. White men versus Black men. White women versus Black women. The contrast wasn’t subtle—it was everywhere. And once I saw it, I couldn’t unsee it.

One of the first moments that really opened my eyes to what it meant to move through the world as Black happened when we were just teenagers, wandering through the mall in downtown Portland. We were doing what teens do—browsing clothes, shoes and other items we couldn’t afford, laughing about what we’d buy if we had money, imagining futures that felt far away but still within reach. And then the security guard started following us.

At first, I didn’t fully register it. But as we moved from store to store, and he kept trailing behind, never quite hiding it, it hit me like a brick: he wasn't following us. He was following them. My friends. And the only reason? They were Black.

I knew these guys. They were getting As and Bs at a private, college prep high school. They were respectful, kind, intellectually curious, and driven as hell. At the time, I admired their drive without fully understanding it. Later, I realized it wasn’t just ambition—it was survival. The world demanded perfection from them just to give a fraction of what I received by default.

That night, one of them was worried about his older brother. He had joined a gang, and things were getting dicey. I didn't press; I just listened. He'd joined, not because he wanted to, but because it was the only option that gave him access to money—the same money we were all joking about needing for those overpriced items at the mall. It wasn’t a fantasy for him. It was survival.

In that moment, though it really didn't solidify until later, after I'd had some time to process it all, I felt it...I knew it: "I don't know what it's like to never be allowed to fail."

I had the kind of access that gave me choice, and with that choice came the privilege of failure. I could mess up, regroup, and try again. I had room to stumble, space to misstep, and still keep going. They didn’t have that luxury. They had to be nearly perfect, even as kids—still learning how to think clearly, regulate emotion, and simply exist in a world already stacked against them. Because one wrong move could be the end. The first fail could be the last. How is that fair or equitable?

That’s what access really is. It’s not just about opportunity. It’s about margin. Room to stumble without being destroyed by it. Room to figure it out. Room to be a teenager.

We can’t build a just world if we refuse to see how uneven the starting lines are. If we don’t acknowledge that some of us are running on paved tracks while others are dodging potholes and broken glass barefoot. Yet still running.

This isn’t about shame. It’s about witnessing. It’s about love, empathy and compassion. It’s about doing better because now we know better.

If we want justice, if we want peace, if we want a world where love is more than a word we say when it’s easy—then we have to start here:

With eyes open. With hearts open. And with the courage to ask: how can we make more room to fail forward—for everyone?

Start here:

• What access have I been granted that I rarely question?

• Who around me might be carrying the pressure of perfection just to survive?

• How can I expand the margin—for myself, for others, for the world?

“Not everything that is faced can be changed. But nothing can be changed until it is faced.”—James Baldwin

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