Daring to Fail: Uncovering the Hidden Strengths in Our Struggles

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“Only those who dare to fail greatly can ever achieve greatly.” ~Robert F. Kennedy

How do you define failure?

When something doesn’t go as planned?

When someone tells you they don’t like what you’ve made?

When an outcome doesn’t match your expectations?

I find it increasingly important to define failure. Which seems like a weird thing to do because we’re all trying to avoid it. Even talking about failure feels like it has the power to bring about failure.

No one wants to be labelled a failure. And it’s because of that underlying fear that we end up stuck, miserable, and afraid of the very actions that will release us from that doubt.

Here’s a glimpse into a story I often find myself repeating. I come up with an idea, I get feedback, and I start building. I’m acting from a place of creative excitement where my juices are flowing. I’m swept away by the belief that this idea could change the trajectory of my life.

And then… the outcome doesn’t match my expectations. It doesn’t reach as many people as I thought it would. Or it isn’t as profitable as I thought it might be.

It bloody guts me.

I grasp what I think is the issue. I ruminate on what should have been. I get pissed off because it feels like I’m back at ground zero.

Am I doomed for failure?

That depends on the choice I make next.

Do I give up?

Then you best believe I’m a failure.

Because the life we want reveals itself by taking another step forward.

As Winston Churchill said, “Success is not final, failure is not fatal: it is the courage to continue that counts.”

You’ve heard of the Fortune 500, right? It’s a term that gets thrown around a lot, especially in business circles.

The Fortune 500, an annual leaderboard published by Fortune magazine, ranks the 500 most revenue-generating companies in the United States. It’s a snapshot of business success. Yet, a glance from 1955 to 2019 reveals only 10.4% of companies remained on the list.

This stark turnover underscores a crucial lesson: Success is fleeting without continual adaptation.

And therein lies peace of mind.

The point isn’t to climb the peak and stay there. These places that feel like destinations are nothing more than sandcastles, eventually washing away with the tide.

The point is to use what you’ve learned and apply it to your next adventure.

So how do we decide which direction to take after a “failure”?

How can we know which choice will lead us to the best possible version of our lives?

Failure = feedback.

We can only tell where something is in relation to something else.

Putting in the effort means we have something to compare and contrast it to.

There’s a tendency to focus on what the tiny sliver of companies did to succeed, but far more can be gleaned from what the majority didn’t do and why they disappeared.

What did they stop doing?

What did they foolishly ignore because they wanted to be right?

Why did they stop asking questions?

Why couldn’t they see their blind spots?

Whether it’s a failing business, someone who has plateaued with their health goals, or a parent who can’t connect with their teenager, they all share one commonality that led to their failure: They stopped seeking feedback.

Meaning they no longer put in effort. The one and only action that gives us clarity.

I remind myself of this when I’m hyper-focused on the outcome. I feel like a helpless failure because I’m ignoring the actions that will change the outcome: the inputs.

Thomas J. Watson, a former chairman and CEO of IBM, identified fear of failure as the reason we don’t experience momentum in our lives: “Would you like me to give you a formula for success? It’s quite simple, really. Double your rate of failure. You are thinking of failure as the enemy of success. But it isn’t at all. You can be discouraged by failure, or you can learn from it, so go ahead and make mistakes. Make all you can. Because remember that’s where you will find success.”

Don’t like the taste of your spaghetti bolognese sauce (the outcome)? Change the ingredients (the inputs).

Here’s the lesson I’m still learning: This takes time. The most effective way to change the outcome is by changing one input at a time. If I switch out all the ingredients at once, I’m back to playing a guessing game.

But if I try San Marzano tomatoes instead of diced tomatoes? Oh, hot damn. We’re cooking up something delicious, and now I understand what brings me one step closer to the outcome I want.

In the context of my creative pursuits, instead of discarding a project, I engage in more discussions to understand what isn’t working. I ask: Have I offered a valuable solution to a widespread problem? Have I demonstrated how my solution works? Then, did I adjust the project and clearly convey the changes to those who provided feedback? This keeps me on track without guesswork, acknowledging that the first iteration, untested, often fails.

It feels a hell of a lot less daunting to approach failure like an experiment.

Transform failure into a laboratory. Each misstep is an experiment, a finding. Adjust one input at a time, observe the change, and inch closer to your desired outcome. This week, change one ingredient in your strategy, whether at work, in relationships, or in personal goals. Observe, learn, iterate.

Life is a constant iteration, a series of experiments where failure morphs into feedback, driving us closer to the life we envision. Remember that every step forward, no matter how small, is a step boldly taken toward your dreams.

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