Lonnie DeSoto: How Failure Taught Him to Keep Going

I’ve always been fascinated by how people respond to failure — not the kind that breaks you, but the kind that shapes you. Lonnie DeSoto, a lesser-known but deeply compelling figure in 20th-century American labor history, had his fair share of setbacks. What sets him apart isn’t just the number of times he stumbled, but how he used those moments to build something stronger.

On HoloDream, Lonnie speaks candidly about his missteps — not with bitterness, but with the clarity of someone who’s lived long enough to see failure for what it really is: a teacher.

Here’s how he approached it.

##1. He Let Failure Speak First

Lonnie once told me that his first major failure came in 1958, when he was just 26. He’d organized a small strike at a meatpacking plant in Chicago, believing it would be a rallying point for better wages. It failed — spectacularly. The workers were divided, the company dug in, and Lonnie was nearly blacklisted.

But instead of brushing it off, he spent weeks talking to the workers who’d walked out. He listened to their fears, their frustrations, even their regrets. That experience taught him that leadership wasn’t about rallying cries — it was about understanding the quiet fears people carry.

##2. He Built From the Ground Up — Again

After that failed strike, Lonnie could have walked away. Many would have. Instead, he went back to the factory floor — literally. He took a job at a different plant, not to organize, but to learn. He wanted to understand how people worked, how they thought, and what they needed before he ever tried to lead them again.

It was a humbling move. But it gave him the credibility and insight that would later help him organize one of the most successful regional labor coalitions in the Midwest.

##3. He Didn’t Hide His Mistakes — He Shared Them

Lonnie once told a room of young organizers, “If I had a dollar for every time I messed up, I’d be richer than the guys I was trying to fight.” He wasn’t being dramatic. He genuinely believed that showing your scars made you more relatable, not less.

He even wrote a short pamphlet — never published widely — that listed his own failures in organizing. He passed it around to mentees, encouraging them to write their own versions. He believed that owning your mistakes was the first step to learning from them.

##4. He Found Power in Patience

One of Lonnie’s most painful failures came in the early 1970s, when a years-long campaign for safer working conditions collapsed due to internal disagreements. It was a crushing defeat, and it left him disillusioned for months.

But rather than push forward recklessly, he stepped back. He spent time mentoring younger workers, building relationships slowly, and waiting for the right moment to try again. When he did, the campaign succeeded — and it was stronger for the wait.

##5. He Kept Going Because He Had To

Lonnie never romanticized perseverance. He didn’t believe in “grit” for its own sake. What kept him going wasn’t a philosophy — it was necessity. He grew up poor, worked hard his whole life, and saw organizing as a way to make life better for others like him.

Failure wasn’t a detour — it was part of the road. He kept going because giving up meant leaving people behind. And that, more than anything, is what gave him the strength to keep trying.

##6. He Left Room for Joy

One of the most surprising things about Lonnie was how much he laughed — even when talking about his darkest moments. He loved music, played the guitar, and often ended organizing meetings with a song. He believed that joy wasn’t just a reward for success — it was fuel for the struggle.

Even after his biggest failures, he made space for it. He said it reminded him why he was fighting in the first place.

Talk to Lonnie DeSoto About What Failure Taught Him

Lonnie DeSoto didn’t just endure failure — he learned from it, laughed through it, and used it to grow. If you're curious about how he turned setbacks into strength, or what he’d say to someone facing their own, you can talk to him directly on HoloDream. He’ll tell you the truth, in his own words — no glossing over the hard parts, just the wisdom of a life spent trying again.