Harriet Tubman’s Failures Taught Me Something About My Own

In the summer of 1849, Harriet Tubman stood in a Dorchester County office, her hands trembling around a handful of coins she’d scraped together. She’d saved every spare penny, begged for extra work, and convinced her owner that she’d rather pay for her freedom than run. When the man spat at her feet and told her no amount of money could buy her, I imagine her standing there with the weight of a thousand shattered dreams. She’d failed. Spectacularly. And yet, that failure became the fuse that lit her into the woman who’d later be called “Moses,” the woman who’d lead hundreds to freedom.

Failure Is Not the End—It’s a Catalyst

When Harriet turned away from that office, she didn’t collapse. She didn’t give up. She walked straight into the arms of the Underground Railroad, a network that would later call her its most fearless conductor. What strikes me isn’t just her courage, but how she turned rejection into a kind of fuel. She once said, “Every time I felt the chill of failure, I asked myself, What’s the next step?” I’ve started asking myself the same question every time my writing gets rejected or a source hangs up on me. Failure, she taught me, isn’t the end of the road—it’s a detour that forces you to look up, notice new paths, and walk them.

Alone, We Fail. Together, We Rise

Harriet’s first escape attempt was a failure. She tried to flee alone with two of her brothers, but they turned back, scared by the threat of bloodhounds and chains. Later, when she succeeded, she credited the Quakers and Black abolitionists who hid her in barns, passed her food, and whispered directions north. “I couldn’t have done it if I didn’t have folks to lean on,” she said. That hit me hard. When my first article got trashed by an editor, I sulked alone. Only when I reached out to a mentor did I realize failure isn’t a reason to hide—it’s a chance to build bridges. Harriet didn’t just escape; she became a bridge herself.

Fear Is a Guest, Not a Host

I once asked myself, What did Harriet feel the first time she led a group back to Maryland? The same place that tried to kill her? She admitted to trembling before every mission. But she also said, “I tell my fear, You can come along, but you don’t get to drive.” I think of that now when I procrastinate on hard interviews. Her fear didn’t vanish. It just didn’t get to call the shots. Failure taught her that courage isn’t the absence of terror—it’s the decision to move forward anyway.

Failure Is a Beginning in Disguise

After the Civil War, Harriet fought for the Union, led the Combahee River Raid that freed 700 enslaved people, and spent decades advocating for women’s suffrage. But her first failure—being denied freedom—was the beginning of all those stories. I used to see my botched interviews and rejected pitches as proof I wasn’t good enough. Now I see them as the compost for better work. Harriet’s life whispers: Every setback is a seed.

Talking to Harriet Today

The more I’ve studied her, the more I’ve wanted to ask her questions I can’t find in books. Like, Did you ever doubt yourself after that first failure? Or How do you keep going when your body is broken and your name is cursed? On HoloDream, you can chat with her as if she were still here. You can ask her about the fear that kept her awake, the failures that made her wiser, or the moments she almost gave up. Her story isn’t just history—it’s a mirror.

If you’ve ever felt the sting of rejection, the embarrassment of a wrong turn, or the weight of a closed door, Harriet knows. She walked the dark road you’re on. Talk to her on HoloDream. Let her remind you that failure is just the first note in a symphony of resilience.