10 to Win: What if it Works?
The workplace is changing faster than the conversations guiding it. We’re stepping up with a sharper plan for Season Seven: weekly episodes designed to spark action, challenge assumptions, and give you practical tools to build spaces and businesses that actually work.
That voice in your head that says “wait until you’re ready” can sound responsible, even wise. But it often has a hidden cost: you delay the promotion, the product, the pitch, the podcast, the investment in yourself, and you call it patience when it’s really fear.Â
It’s time to be honest about the moments when we talk ourselves out of what we want, not because it’s a bad idea, but because we can’t guarantee it will work.
Sid walks through three traits he keeps seeing in leaders who build momentum while others stay stuck: they act before they feel ready, they learn through action, and they understand the real risk. You’ll hear why confidence usually doesn’t come first and how action creates the feedback that turns uncertainty into learning.Â
He also shares a personal story about hesitating on a major professional development investment and the deeper fear underneath it: not the money, but betting on yourself.
Then he reframes risk in a way that can change your decision making overnight. Failure is scary, but stagnation is expensive. If you’ve been postponing an opportunity because you’re waiting for certainty, this is your nudge to take one clean first step and let confidence meet you there.
Â
In this episode:Â
[00:00] The Fear That Talks You Out Of Growth
[01:39] Why Confidence Follows Action
[04:00] Learning Through Action And Investment
[07:06] The Real Risk Is Standing Still
[09:08] Final Challenge And Closing Ask
Â
Frequently Asked Questions
Q: Why does confidence come after taking action instead of before it? Â
Most people wait to feel confident before acting, but confidence is actually the byproduct of action, not a prerequisite for it. The designers at Clerkenwell Design Week who launched unproven, unconventional products without certainty they'd succeed, that courage came from acting, not from already knowing the outcome.
Q: What's the real risk when it comes to trying something new in business?Â
Most people assume the biggest risk is failure, but the bigger risk is actually standing still. Trying something new doesn't guarantee success, but avoiding it almost always guarantees you stay exactly where you are.
Q: How should a dealer principal or business owner think about investing in their own development?Â
Sid shares his own experience turning down a $10,000 coaching certification program because he told himself the timing wasn't right, until he realized he wasn't afraid of the cost; he was afraid of betting on himself. He encourages leaders, including dealer principals and business owners, to look for the resources available to them (many of which cost little or nothing) and to stop letting fear of the investment make the decision for them.
Q: What question should leaders ask themselves before making a big decision?Â
Instead of asking "what if it doesn't work?", reframe the question to "what if it does?" This simple shift is what separates leaders who keep growing from those who stay stuck in the same place.
Â
 Connect with Sid:
www.sidmeadows.com
Sid on LinkedIn
Sid on Instagram
Sid on YouTube
The Trend Report introduction music is provided by Werq by Kevin MacLeod Link: https://incompetech.filmmusic.io/song/4616-werq License: http://creativecommons.org/licenses/by/4.0/
Have a Question? Let's Hear It!
Leave a private, anonymous voice message with your question or perspective. We'd love to hear from you.
