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The Myth of the Magic Bootstraps

The Myth of the Magic Bootstraps

Last updated on: October 3, 2025 at 10:43 pm by Derrick Day

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The Myth of the Magic Bootstraps 2025-10-03T22:43:34-07:00 Derrick Day

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Systemic racism and Black success in America

Image by DALL-E | Prompted by the author

I Never Had Boots…

America loves a good bootstrap story. The “I came from nothing, worked hard, and now I’ve got everything” tale is practically the country’s bedtime story. The problem? For Black folks like me, raised in “the hood,” the whole bootstrap narrative is bullsh*t from the jump. Why? Because the boots they say we’re supposed to pull ourselves up with were never handed out to us in the first place.

And here’s what makes that myth even more insidious: it ignores the pathology of slavery, Jim Crow, and centuries of economic and social disenfranchisement. These weren’t just “bad times” in history—they were system-wide, state-sponsored campaigns to strip Black people of wealth, dignity, opportunity, and even humanity. The ripple effects of that history didn’t magically evaporate after the Civil Rights Act. They’re alive and well in generational poverty, over-policing, redlined neighborhoods, and yes, in the cultural and social ills like crime and avarice that too many love to point to without context.

I’m not here to give you a syrupy Hallmark version of my life, nor am I here to convince you that I’m some rare “exception to the rule.” I grew up in a neighborhood (Dexter-Fenkell in Detroit) where the only thing abundant was struggle. But thanks to people who loved me enough to invest in me, I built a life that doesn’t fit the stereotypes.

This isn’t just my story, though. It’s also a commentary on why so many other intelligent, hardworking Black folks don’t see the same outcomes, and why systemic racism in America is still the sticky web it’s always been. But I’ll also explain why empathy—not just policy, not just grit, and definitely not empty political promises—is the bridge we all need to walk across.

Growing Up Without Boots

Let’s start where it began: the hood.

When you grow up in a community that’s written off before you even hit puberty, you learn early that the deck is stacked against you. Schools don’t have the resources. Streets don’t have the safety. And opportunities? Forget about it. Opportunity in the hood is like Bigfoot: people swear they’ve seen it, but you’d better bring a camera if you’re going to convince anyone else.

But the hood doesn’t exist in a vacuum. It’s the aftershock of slavery and Jim Crow. Enslavement ripped wealth and stability from Black families before they ever had the chance to build it. Reconstruction was crushed by terror campaigns. Jim Crow locked Black people into segregated, underfunded schools and excluded them from economic opportunity. Housing discrimination, redlining, and predatory lending followed. The pathology is clear: if you want to know why certain neighborhoods struggle, trace the policies that put them in that position.

I didn’t “escape” because I was the smartest or the most disciplined. That’s the part society doesn’t want to admit: there are thousands of kids smarter than me, kids with more hustle, more creativity, and more resilience—but they’ll never get their shot because the system chews them up before they even leave the block.

The Village That Raised Me

If I stand tall today, it’s not because I pulled myself up by the mythical bootstraps. It’s because people around me reached down, grabbed me by the collar, and said, “Come on, dude, we’re not letting you drown.”

My Mother, Shirley

Shirley is the rock of my life. She carried the weight of the world with a fierceness that made you believe the laws of gravity bent around her. She worked two or three jobs at a time and made time to obtain a college education. My Mom raised three children who grew up to be college-educated professionals. She is my sternest coach and, along with my wife, my biggest cheerleader. She didn’t just raise me—she raised my expectations of myself.

My Village Moms

Besides my Mom, I had a whole village of mothers. Gloria, Marilynn, Gertrude, Occula, Mary, Emma Jean, Katherine, and Ethel. I can’t forget my aunts, Yvonne and Ramona, either. All of these ladies influenced, informed, and impacted my life greatly. Each of them was inspirational, and I wear their imprint as a badge of honor. Last but not least, my late grandmothers, Bertha and Martha, who made me believe that my gifts of intellect and persuasive speaking would lead me to do great things in life. All of them reminded me that failure is not an option and, unless it was fatal, it wasn’t final.

Uncle Bob

My mom’s younger brother. A man who was the living, breathing reminder that manhood didn’t have to mean hardheartedness. He showed me discipline, but also compassion. Uncle Bob taught me that you could be tough without being toxic, and that laughter was as necessary as hard work. Most of all, Uncle Bob taught me never to use lack as an excuse for apathy; in other words, always do your best.

My Favorite Teachers

High school English teachers who wouldn’t let me skate by. Ms. Kline, a Black woman, reminded me I had a legacy worth carrying. She taught me that once I realized I stood on the shoulders of giants, I would actually see how far I could really go. Ms. Morency, a white woman, pushed me to expand beyond what I thought I knew. She would always say she hoped to live long enough to see me write the great American novel. Together, they tag-teamed me into believing words mattered—and more importantly, that my words mattered.

My Navy Mentors

When I joined the Navy, I met two men who shifted my trajectory. Ted Albright, my Leading Petty Officer, was a Black man who modeled leadership that didn’t rely on fear. He proved you could command respect without diminishing people. Ted showed me that success was integral with the DNA of my ancestors by teaching me history that wasn’t taught to me in school.

My division officer, Phillip Crowell, was white, and he gave me the kind of mentorship that wasn’t performative—it was real. Mr. Crowell showed me that I was operating beneath my potential and pushed me to think higher and do better. LCDR Crowell told me that if I learned how work with the Navy instead of fighting against it, it would reward me immensely – but, if I didn’t learn how to function the Navy way, it would chew me up and sh*t me out. He didn’t just hand me responsibility; he equipped me for it.

Notice the pattern? My success wasn’t a solo act. It was an ensemble cast production.

The Dangerous “Exception to the Rule” Label

When a Black man “makes it,” society has two lazy narratives locked and loaded.

Exception to the rule.
Translation: “You’re special because you overcame what most of your people can’t.”
Proof the system works.
Translation: “See? Racism isn’t real. If he did it, anyone can.”

Both takes are trash.

Here’s the truth: I’m neither exception nor proof. I’m not the unicorn who slipped through the cracks, and I’m not a poster child for America’s “equal opportunity.” I’m evidence of what happens when community, mentorship, and sheer stubbornness collide in one person’s life.

And I’m also evidence of how rare that cocktail is in a society that has spent centuries manufacturing disadvantages. When you add up slavery’s generational theft of wealth, Jim Crow’s enforced ignorance, and modern systemic barriers, you can’t pretend crime and avarice just “happen” in certain communities. They are symptoms of deliberate disenfranchisement. They’re not excuses—they’re consequences.

Black Excellence Exists Everywhere—but the System Chokes It Out

Let’s kill another myth while we’re here: the one that says Black people don’t succeed because we don’t work hard enough or aren’t smart enough. That’s the racist bedtime story America tells itself to avoid accountability.

The reality? Black folks are grinding twice as hard with half the resources. The work ethic? Unmatched. The brilliance? Overflowing. The problem isn’t capability—it’s opportunity.

You can’t measure success in America without factoring in systemic racism. It’s baked into everything: housing, education, hiring, healthcare, criminal justice. It’s the software running quietly in the background of the “American Dream,” making sure some apps (read: lives) crash more often than others.

And let’s be blunt: when you trap people in underfunded schools, deny them job opportunities, and over-police their neighborhoods, what do you think happens? Desperation breeds crime. Deprivation breeds avarice. That’s not a moral failing—it’s a social equation written centuries ago.

Systemic Racism: The Unseen Gravity

Racism in America isn’t always a white hood and burning cross. Sometimes it’s a banker denying your loan while smiling in your face. Occasionally it’s a teacher who assumes you’re less capable before you open your mouth. It can also manifest itself a job offer that never comes because your name sounds “too Black” on a résumé.

And sometimes it’s the invisible weight of slavery and Jim Crow still pressing down on generations that never had a fair chance to breathe. These aren’t glitches—they’re features of a system designed to privilege some while burdening others. If you’re Black in America, you’re playing the same game on “hard mode” with fewer lives and no cheat codes.

Why Empathy Matters More Than Excuses

Here’s the part where I get real with both my black and white brothers and sisters who’ve found success: it’s not enough to clap for yourself when you make it. Success isn’t a solo trophy—it’s an obligation.

Too many of us, once we reach a certain level, build walls instead of bridges. We forget the ones still grinding under impossible weight. Or worse, we start parroting that bootstrap bullsh*t as if everyone has the same boots we do.

Empathy matters. Not pity. Not performative “I understand.” Real empathy. The kind that recognizes frustration as valid, that doesn’t dismiss anger as “complaining,” and that chooses compassion over condescension. We all need to learn to see things through the eyes of others and realize that “There but for a twist of fate, there go I…”

Hard Work vs. Smart Work: Teaching Both

Yes, we need to teach the next generation to work harder. But that’s not enough. They also need to learn how to work smarter. Hustle without direction just burns people out.

Here’s the twist: working smarter sometimes means knowing when the system is rigged and finding alternative routes. It means mentorship, access, and networks—things historically gatekept from us. And when you’ve got those keys, you don’t hoard them. You hand them out.

Neither the Right nor the Left Has the Answer

Let’s get political for a second. Spoiler alert: neither Republicans nor Democrats are solving this.

The right loves to act like racism is ancient history and if you just “work hard,” you’ll be fine. The left loves to commodify Black pain, making promises they rarely deliver while patting themselves on the back for their “wokeness.”

Both sides profit from the problem while pretending they’re fixing it. The truth? The solution isn’t red or blue—it’s us.

Facing America’s Racist Past (And Present)

Until America stops bullsh*tting itself about its history, nothing changes. This country was built on stolen land with stolen labor. That’s not “controversial”; that’s fact.

Slavery didn’t just end—it metastasized. Jim Crow didn’t just vanish—it mutated. Economic disenfranchisement didn’t just happen in the past—it continues in housing discrimination, predatory lending, mass incarceration, and healthcare inequities.

Pretending racism is over because Obama was president is like pretending your house is clean because you sprayed Febreze on the couch. We have to face the mess—fully, honestly, painfully—before we can clean it up.

Living up to America’s creed that “all men are created equal” isn’t about empty slogans. It’s about restructuring systems so equality isn’t theoretical—it’s tangible.

Success as an Act of Love

Here’s where I land: helping others succeed is the purest act of love. And I don’t mean religious love. I don’t need scripture to tell me empathy and compassion matter. Love, in its rawest form, is seeing another human and saying, “I want for you what I want for me.”

When I mentor someone, when I advocate for them, when I open a door that might otherwise stay shut—that’s love in action. That’s revolution, one person at a time.

Wrap-Up: Boots or No Boots, We Build Anyway

So no, I didn’t pull myself up by my bootstraps. I never had boots. What I had were people—family, teachers, mentors—who refused to let me sink. And what I built from their investment wasn’t just a career, but a responsibility.

Systemic racism is still real. Opportunities are still uneven. Slavery’s legacy, Jim Crow’s cruelty, and economic disenfranchisement still echo in the social ills that plague too many of our neighborhoods. But empathy and action can bridge the gap.

We don’t need to wait on the right or the left. We need to look around, reach out, and lift up.

Because success, at the end of the day, isn’t about proving you’re the exception. It’s about proving love, empathy, and community are the only things that ever really worked.

Are you a black success story? Do you know one? These are my thoughts; your mileage may vary! What are your thoughts? Share them in the comments!

Derrick Day is the author of multiple books and the host of The Forward Podcast.

Follow him on Facebook, Instagram, TikTok, and YouTube

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