Failure – Grandpa Bob Encouraging Leadership

Fear Only Needs One Example

Some of the fears running things in our lives were never ours to begin with. We watched someone lose and decided losing was the lesson. We watched someone speak up and get burned, so we got quiet. We watched someone try and then called their failure a warning. We told ourselves we were being realistic when we were just hiding safely behind their wreckage.

We rarely see the whole picture of someone else’s failure. We don’t see the blind spots, the ignored warnings, the weak foundation, the compromises nobody talked about, or the timing that was just off. We only see the ending, and then we build ourselves a new law out of it.

Something inside us says, See? That’s what happens.

No. That’s what happened.

One word. One syllable. The difference between a lesson and a life sentence.

Fear is a fast learner. It sees one example and it moves. It doesn’t wait for data. It doesn’t wait for context. It doesn’t wait for us to think.

Sometimes that’s exactly right. Some roads do end in ruin. Some boundaries are wisdom. There are dangers in life that should be taken seriously the first time, not the fifth.

But fear can collapse categories too quickly. It can treat a predator and a conversation as though they deserve the same response.

One difficult conversation becomes I’ll never bring that up again. One rejection becomes I’m done. One betrayal becomes Trust no one.

Fear stops being a warning. It becomes a tyrant. And tyrants imprison more than they protect.

Sometimes it isn’t safety we’re protecting. It’s our pride. Our delicate image. The deep terror of being seen trying and coming up short. That type of fear can sound like logic. It can sound like experience. And it can rob us quietly for years.

I’ve seen people let one example define them. One disappointment. One humiliation. One loss. One story, often somebody else’s story, lodged deep in their imagination.

But one example is a terrible god. It asks for too much. It explains too little. And it leaves too many good things untried.

Fear only needs one example.

Our wisdom must decide how much authority we give it.

Photo by Silas Baisch on Unsplash

Lessons in Failure – the Mark of a True Leader

There’s a saying that often floats around in entrepreneurial circles: “Fail fast, fail often.” While the origins of this phrase are up for debate, its lesson is clear. Failure isn’t just an inevitable part of leadership. It’s one of the most defining. How a leader reacts to failure (their own or their team’s) can reveal their true character and shape the trajectory of their future success.

But here’s the thing: writing about failure and leadership can quickly sound like a series of cliches. We’ve all heard the platitudes about “learning from mistakes” and “rising stronger.” But there’s a deeper message about what truly separates those who lead with integrity and vision from those who crumble when things go wrong.

When failure strikes, leaders face a choice. They can own it, adapt, and come back stronger. Or they can point fingers, wallow in resentment, and stall out. The decision often happens in an instant, but its impact can last a lifetime.

Great leaders take ownership of failure, even when it’s not entirely their fault. Why? Because owning failure builds trust. When a leader says, “This didn’t go as planned, let’s discuss what we’ll do to fix it,” they inspire confidence. They create a culture where the team feels safe to take risks, knowing that mistakes are part of growth, not reasons for punishment.

When leaders blame others, they erode trust. Pointing fingers, whether at the team, external circumstances, or bad luck, signals an unwillingness to reflect and adapt. Over time, this creates a toxic environment where innovation dies and progress stalls.

“Fail fast, fail often” isn’t about being reckless. It’s about embracing experimentation and accepting that not every idea will succeed. Failing quickly means you can pivot sooner, learn faster, and ultimately get to a better solution.

This idea requires two things:

Humility: The willingness to admit when something isn’t working.

Agility: The ability to adapt and try again without becoming paralyzed by setbacks.

Elon Musk is a great example. From continual iterations of experimentation and failure at SpaceX—including multiple RUDs (rapid unscheduled disassembly in rocket speak)—to the challenges Tesla faced in scaling production and support, he’s built companies on the idea of learning through failure. Musk doesn’t see failure as an end point. He sees it as feedback. A necessary step on the path to success.

To handle failure effectively, leaders need more than optimism. They need a process. Here’s a simple approach that works (notice I didn’t say it’s an easy approach):

-Recognize the failure and what it means. Be transparent with your team.

-Reflect on what went wrong without assigning blame. Focus on systems and strategies, not personal shortcomings.

-Identify key takeaways. What worked? What didn’t? What’s worth trying again?

-Adjust your approach based on lessons learned.

-Recommit to the goal with a renewed focus and determination.

Failure doesn’t only teach leaders how to solve problems. It shapes their emotional intelligence (if they allow it). Leaders who’ve faced setbacks tend to have more empathy and patience. They’ve had to overcome multiple failures themselves, so they know how challenging failures can be for their teams.

When leaders normalize failure, they create cultures where people aren’t afraid to take risks or push boundaries. That’s where breakthroughs happen.

The mark of a true leader isn’t perfection. It’s how they handle failure. Whether they embrace it as a teacher or fear it as an enemy. The choice of owning mistakes, adapting, and persevering defines not just their success, but the success of everyone they lead.

The next time failure arises, ask yourself: Will I let this moment shape me for the better? Will I lead my team through it with grace and determination? Will we learn from this failure?

The answers will set the course for everything that follows.

Photo by David Trinks on Unsplash

Some Things I Know to Be True

Airplanes generally don’t crash due to one failure, or unexpected event. They rarely crash when a second failure happens. It’s usually the third unexpected event that brings it down. This tragic truism in real-life plane travel can be applied to life. Consider your own “plane crashes.” Were they preceded by just one failure, or unexpected event? It was probably the second and third failure that actually brought things down. We learn more from failures than successes. Even better are the lessons that come when we honestly and thoroughly investigate our own plane crashes, and the series of failures that caused them.

Speaking of success. Success is all about definition. The only definition that matters is the one you create for yourself. Success, by any definition, won’t bring truly transcendent happiness.

Transcendent happiness comes from within. Its foundation is a belief in something greater than yourself. Something that you can’t touch, taste, see, smell, or hear.

Speaking of something greater than yourself. Love is the most powerful force in the universe. It transcends all time and space. Love can’t be stopped by death. Being loved, and loving others, fills your soul. Love is free, and yet it has infinite value.

Teaching your son to cook blueberry muffins for his dad is one of the best gifts a mom can give to her son (and husband). Texting a photo of that cooking lesson to his grandpa is a great way to demonstrate truth number four.