Willing to Fail Unlocks Success for High Achievers

I asked my clients this past week: How do you want to FAIL in 2025?

I watch their eyes widen as they instinctively respond:

"I don't fail." 🤬

"I don't want to think about failing." 🤬

"I'm not interested in failing - I've worked too hard to get where I am." 🤬

Failure is the ultimate taboo, especially for high achievers.

But here's what I want you to consider: Where could you deliberately stretch yourself to the point of possible failure in 2025?

A friend of mine harbored a deep passion for real estate...for years. She accompanied me on every house-hunting journey for my last two house purchases. As her passion grew, so did her dream of becoming a realtor. But the questioning voices persisted: How would she manage the kids? What would people think of her career pivot?

Staying stuck in those questions would have been the real failure. Not taking the real estate exam would have been failing ahead of time.

We fail each time we say no to something we deeply want.

Instead, she chose to risk failure. She passed the exam and, with lightning speed, had record sales that unlocked possibilities for a new career and life she hadn't even imagined.

Here's the lesson: The risk wasn't that she might fail the exam; the risk was failing on herself.

I intimately understand this journey. This past year, I launched a program and got crickets. One registrant felt like a grand fail. BUT launching the program created enormous credibility for my brand, along with visibility and exposure.

Another example: When I decided to transition from a corporate CRO to coaching, the questions haunted me: Am I better than coaching 😁😩😲? Would I be good enough? What if I wasn't successful? What would my peers think?

If I had remained paralyzed by these questions, mostly fueled by my and others' judgments, I would not be writing to you today.

Being willing to fail has taught me that the strategic by-products of intentional failure are invaluable.

Think of a marathon runner who gets injured at mile 18. Are they a failure for not crossing the finish line? No – they're a marathon runner who logged countless training miles and, most importantly, saw themselves as a marathon runner long before race day.

On my path to becoming a coach, every "failure" built my foundation. There were many! Risking failure actually helped me build an unshakeable belief in myself.

A CEO of a successful agency initially balked at my intentional failure question this week. Everything shifted when he reframed it as reaching beyond his comfort zone to create the next level of business.

He later wrote me: "I loved your question today: 'How am I going to fail next year?' At first, I had no idea what you meant, but welcoming the risk and being okay with learning from it even if I don't succeed is so powerful."

Too many of us don't go for No: Unwilling to embrace the fears and the demons in our heads that say it's too risky.

This Week's Practice: Ask yourself...

-Where are you failing by not even trying?

-What if your next level of success is built on your willingness to fail?

Then ask:

-What would 𝘺𝘰𝘶 do differently if you knew you couldn't fail?

Erin Halper, Founder & CEO of The Upside, wrote about that question HERE.

Remember: Your next failure might just be the key to your greatest success.

But if you don't try and risk failure, you've already failed.

As Wayne Gretzky famously said, you miss 100% of the shots you don't take.

Here's to your intentional failures in 2025.

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Me Considering My 2025 Failure Last Week in Guatemala