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12/18/2025

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But, What If It Works?

Sara Blakely had every reason to listen to the ‘what ifs’. In 1998, she was 27 years old and selling fax machines door to door. But, she had a big idea that consumed her - footless pantyhose … yea, I would’ve never thought of that either. Problem was, she had no business experience, no connections, and no money beyond the $5,000 she'd scraped together from selling fax machines. That didn’t deter her though, she started calling hosiery mills where she received a consistent response - no. 
Every voice around her would have compiled an impressive list of ‘what if’ doomsday messages. What if you waste your money? What if people laugh at you? What if you fail again? She went for it anyway. When she was rejected on the phone she still chose to drive to North Carolina to pitch her idea to manufacturers in person. She got the same response from every person she talked to though - a smug chuckle or an even more painful explanation of just how dumb her idea was. 
But Sara never waivered. She remained married to the question on the other side of the coin - what if it works? Rather than ignore the obstacles, Blakely acknowledged them and ran directly towards them. About three weeks after her trip to North Carolina, one of those mill owners in Charlotte decided to give her crazy idea a shot. 
As it turns out, the owner had run the idea by his three daughters who had each loved the idea. And, with that, Spanx was born and is now a household name. Blakely became the youngest self-made female billionaire in history … all because she chose the ‘what ifs’ of possibility over the ‘what ifs’ of failure.

Why Should We Care?
Without question, the most impactful leaders choose the ‘what ifs’ of possibility. Most people default to catastrophic "what ifs" with all the reasons something won't work, all the ways they might fail, and all the judgment they might face. These aren't irrational thoughts, they're a result of our brain trying to keep us safe. But, safety and excellence don’t always go together.
I'm not suggesting we act like everything is sunshine and rainbows or that we ignore reality. Sara Blakely didn't pretend the manufacturers weren't laughing at her. She didn't minimize the fact that she had no business experience or industry connections. She acknowledged all of it while never straying from her insatiable curiosity that it just might work. 
When you focus on all the reasons something might fail, you're paralyzed. When you acknowledge those reasons but then focus on the possibility of success, you're energized. Same circumstances, different question, completely different outcome.
The questions you ask yourself determine the actions you take, or don't take. Leaders consumed with ‘what if it fails’ thinking make conservative, fear-based decisions designed to minimize downside. They optimize for not looking bad rather than for creating something meaningful. But leaders who learn to ask ‘what if it works’ make bold, possibility-focused decisions designed to maximize impact. They're willing to look foolish in pursuit of something that matters. 
The people who change the world aren't necessarily smarter or more talented, but they're just willing to live in a different ‘what if.’ What if this crazy idea actually changes everything? 

REAL TALK - Action Steps
Shifting from ‘what if it fails’ to ‘what if it works’ thinking requires intentional practices that retrain your brain to focus on possibility rather than catastrophe. Here are a few ideas to get you heading in that direction:

  • ‘What If’ Comparisons 
    • Take the idea or challenge you're currently facing and create two columns. In the left column, write out all your specific fears around your ‘what if it fails’. Then, in the right column, write an equal number of ‘what if it works’ possibilities. For every doomsday scenario, force yourself to imagine a corresponding positive outcome. Both sets of ‘what ifs’ are equally possible. This practice redistributes that attention more accurately. 

  • Possibility Anchoring
    • Ask yourself: If this works exactly as I hope, what does that look like? What becomes possible? Who benefits? How does this change things? Allow the ‘what if it works’ scenario to take hold. Before your ego gets involved, spend time pursuing the idea rather than defending it or explaining it. Anchor in possibility before reality.

  • Create Evidence
    • Create a running document of times when you or others pursued something despite the odds and it worked. Add times when you took a risk and it paid off. Celebrate attempts rather than outcomes. The goal is to build evidence that your fear-based ‘what ifs’ aren't any more valid than your possibility-based ones. Both are speculation. You get to choose which speculation to build your life around.

Every significant opportunity you'll ever face will come with a list of reasons why it won't work. Those reasons will be logical and sometimes accurate. The question isn't whether those fears are valid, it's whether you're going to let them be the only voice in the room. 

Checkout Surrender the Outcome on Amazon and order The Score That Matters with Ryan Hawk & Brook Cupps. The latest blog from Blue Collar Grit can be found here!
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    I'm a teacher, coach, and parent seeking excellence while defining success on my own terms.

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