Fail, Learn, Repeat. The Heartbreak and Hope of Trying Again

Failing Forward: The Messy, Beautiful Path to Success

Failure. It’s a word most of us dread. It feels heavy, messy, and sometimes downright painful.

Yet, if you ask any successful leader, entrepreneur, or even that friend you admire for their resilience, they’ll tell you that failure wasn’t their end—it was their beginning.

In this week’s episode, I shared a raw and honest look at what it feels like to fail forward and the lessons I’ve learned through perseverance, quitting, and ultimately finding my way to alignment. But here, I want to go a bit deeper.

Let’s talk about how to navigate failure when it feels like it’s crushing your spirit and why it’s a necessary part of growth.

Why Failing Forward Feels So Hard

Failing doesn’t just bruise our egos; it challenges our identity. We wonder: Am I good enough? Did I make the wrong choice? Why isn’t this working?

Those questions are normal, but they don’t define your worth. What matters is what you choose to do next.

But let’s be honest—acknowledging that doesn’t make it feel any easier in the moment.

The Difference Between Giving Up and Letting Go

One of the most challenging lessons I’ve learned is discerning when to persevere and when to let go. This is not the same as “giving up.”

• Letting go is an act of courage. It’s recognizing when something no longer aligns with your values or goals. (The purest form of Letting go is "Obedient Surrender”, but we’ll get into that another time)

• Giving up is abandoning something because it feels hard, without truly asking yourself if it’s still worth the effort and reward.

Think about your current struggles. Are they asking you to persevere or let go? Answering that question with honesty and self-compassion can be transformative.

How to Fail Forward with Grace and Grit

Here are three strategies to navigate failure without losing your momentum or your spirit:

1. Reframe Failure as Feedback:

   Instead of asking, Why did this happen to me? ask, What is this teaching me? This simple shift can turn feelings of defeat into opportunities for growth.

2. Celebrate the Courage to Try:

   It’s easy to measure success by outcomes, but don’t discount the bravery it takes to show up in the first place. Whether you succeeded or failed, the act of trying is worth celebrating.

3. Focus on Progress Over Perfection:

   Every step forward, no matter how small, brings you closer to your goals. Perfection is a myth, but progress is proof that you’re moving in the direction of growth.

Remember This…

The fear, frustration, and exhaustion of trying again are all part of the process—but so are the breakthroughs, the wins, and the deep sense of fulfillment when you finally see it all come together.

So, the next time failure knocks you down, let it teach you, not define you. Dust yourself off, adjust your strategy, and throw it again—because the life you’re working toward is worth every scraped knee and dirt-covered moment.

Ready to Persevere with Purpose?

If you’re feeling stuck or overwhelmed by the challenges in front of you… I’ve got a framework to help! Together, we’ll unpack what’s holding you back, reconnect with your deeper purpose, and craft a plan that leads you to freedom, joy, and fulfillment.

Let’s talk. Click here to schedule your free discovery call.

Here’s to failing forward with faith, grit, and grace.

We got this!

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