Dare to fail or dare not to fail


Hey Reader,

Most high performers aren’t afraid of failure.

They’re afraid of what failure would say about them.

This newsletter will explore the thin line between daring to fail and daring not to fail, and how that difference decides how much of your potential you ever get to maximize.

Let’s dive in.

💭 “She kept failing… and kept going anyway.”

Before Spanx became a billion-dollar brand, Sara Blakely was selling fax machines door-to-door.

She hated it.

But every day, her dad asked her one question at dinner: “What did you fail at today?”

If she had nothing to say, he’d be disappointed.

Not because he wanted her to fail. But because failure meant she tried something new.

Years later, when she had the idea for Spanx, she had no fashion background, no business training, and no connections.

Manufacturers and investors weren’t really taking her seriously.

But she kept showing up anyway.

Then one manufacturer finally agreed to help her because his daughters believed in the product.

That was the first crack.

The real turning point came when she walked into a Neiman Marcus meeting.

She didn’t really have a polished pitch.

She took the buyer into the bathroom, put the product on, and showed what it actually did.

And the buyer placed the first major order on the spot.

The rest is history.

The guts to keep going, even though she’d fail, became the reason she won.

🧠 Dare not to fail

You’ve gotten very good at winning.

You know what you’re great at.

You know the shots you can make with your eyes closed, and you won’t fail.

So you take those over and over again.

Avoiding things that may threaten that sense of competence.

It’s not entirely that you’re avoiding failure.

You’ve built a reputation for winning.

I mean, who would want to ruin that?

You’re avoiding situations where your identity might take a hit, or your confidence might feel fragile.

So you choose paths where your competence is guaranteed.

And without realizing it, your reputation starts making decisions for you.

I bet you, it’s not entirely worth it.

That’s the fastest way to cap your potential.

❤️ Trust your guts; dare to fail

Daring to fail starts when you stop needing to be always certain.

When you trust your guts deeply, even in the face of uncertainty, you stop waiting to feel ready.

You stop needing everything to make sense before you begin.

You stop overthinking timing.

That alone creates relief.

You feel challenged again.

You start trusting yourself more.

You become curious about what lies ahead instead of being afraid.

You’ll still feel the fear of failure, but it’s no longer threatening.

You realize it shows you where you’re growing, not really where you’re lacking.

You’re no longer carrying the pressure to always be right.

And because of that, you start engaging your work differently.

You experiment more. You’re open to taking risks, and you adapt faster.

You’re open-minded when things don’t go as planned.

You’re growing, soaring… and of course, thriving.

You'll never have to feel that perceived cycle of underperformance.

🤲 Bet on yourself

I get it.

It feels good to hold onto something that feels so great.

But it pays more to dare yourself to explore your higher self.

Start by practicing any of these 5 steps to bet on yourself:

  1. Confront your comfort with being the best. Ask yourself: Am I choosing this because it’s right for me… or because I know I’ll look good doing it? If I wasn’t guaranteed to win, would I still take this shot? These questions pull you away from reputation and toward the real truth. That’s where courage starts.
  2. You have to care deeply. You’re not going to be the best at anything, not even the best version of yourself, if you approach uncertainty with nonchalance so you don’t feel hurt. You have to trust that the love of the pursuit will be big enough to hold the hurt of failure.
  3. Pursue goals bigger than your need to get it right. Ask yourself: Does this goal challenge who I am, or showcase who I already know how to be? What part of me is scared here? Ego or my actual ability? That’s how you separate fear of readiness from fear of a bruised ego or image. You’re building momentum.
  4. Be in rooms that make you uncomfortable in a good way. Ask yourself: What part of me comes alive in groups where I feel slightly outmatched: fear or hunger? This will reveal your emotions when you’re not in control. So before you walk into the room, ask yourself: “What skill, insight, or perspective am I here to absorb?” Not “How do I make sure I look impressive?” That’s how you let go of pressure and keep yourself present.

🎯 Failure isn’t the enemy

Where in your life are you still choosing safety over discovery?

What part of you is waiting to be met on the other side of trying something that doesn’t guarantee a win?

Failure sucks.

But it’s also inevitable and necessary.

In the words of Ralph Waldo Emerson, “Do not go where the path may lead, go instead where there is no path and leave a trail.”

Dare to fail.

Make a masterpiece.

That’s how you leave a trail.

With appreciation,

Huw

Huw Edwards

Founder & CEO, h3.xyz

Whenever you're ready, here are 2 ways I can help you:

  1. Join my free #75Hard Community: for those inspired to undertake the transformative #75hard program to build mental toughness for greater achievements. You also get to be surrounded by other overachievers at different levels of the program.
  2. Later next year, I will be launching an exclusive new mastermind for founders and CEOs on how to become unstoppable, unfuckwithable, and unapologetically live up to your potential. I share 10 years of experience leading organizations, buying businesses, starting companies, and doing crazy endurance feats. This program sets the stage for a new era of empowered elite CEOs & entrepreneurs.


Book a free Clarity Call to see if you are fit for the program.

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The H3 Connection

A weekly newsletter for ambitious achievers on how to align your Head, Heart and Hands to find more fulfillment in your career and life.

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