The Bravery Behind the Breakthroughs: What If You Dared to Fail?
For much of my life, I equated success with getting things right.
Top grades, prestigious scholarships, and landing a role in an industry so competitive it felt like winning the lottery — these were the markers I chased. And for a while, that definition of success worked. It gave me direction, confidence, and opportunities I’m deeply grateful for.
But here’s what it didn’t prepare me for: the emotional risk that comes when you step off the well-trodden path.
When I transitioned from being an investor to becoming a coach, the rules of the game shifted. Suddenly, I wasn’t just pitching investment ideas — I was pitching myself. And that brought an entirely different kind of vulnerability.
Would people take me seriously?
Would anyone even return my calls?
Would I be able to find clients — and create something meaningful?
It turns out, the biggest hurdle wasn’t rejection. It was the fear of rejection. And the only way through was to rewire how I thought about failure.
Because failure wasn’t the problem. Avoiding it was.
Here’s what helped me keep moving forward, even when the outcome felt uncertain:
🌀 I started asking myself three simple, grounding questions:
1️⃣ What if I don’t try?
Inaction has its own cost. Sometimes, the regret of not trying can linger longer than the sting of failure.
2️⃣ What if it works?
What if the thing I’m afraid of is actually the thing that leads to my next breakthrough? A little optimism can open big doors.
3️⃣ So what if I fail?
When I actually named my worst-case scenarios, they rarely felt as catastrophic as my inner critic made them out to be. Most “failures” are recoverable — and every one brings insight.
These reframes have helped me take more risks — not recklessly, but with more heart. They’ve guided me in launching new projects, initiating courageous conversations, and choosing growth over comfort.
So if you’re hovering at the edge of a decision, wondering if you should leap, I invite you to sit with these three questions.
Because sometimes, the real success lies not in avoiding failure — but in daring to face it head-on.
And the boldest moves we make? They often start with a quiet, brave what if.
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