Is Your Cheer Squad Too Cheerful?

Quick Summary: What You Will Learn

While unconditional support from friends and family is comforting, blind optimism rarely helps a business owner navigate complex commercial risks or spot impending operational bottlenecks. In this guide, strategic business advisor Jane Carey explores why successful founders must look past the "cheer squad" to find objective, critical feedback:

• The Limitations of Blind Optimism: Why well-meaning encouragement can accidentally mask flawed business ideas or risky pivots.

• The Value of Awkward Questions: How constructive critique and objective hole-poking protect your company from avoidable failures.

• Building an Advisory Circle: Surrounding yourself with trusted professionals who prioritize your long-term success over short-term comfort.

You know the advice: “Surround yourself with positive people who lift you up!” Cue the unofficial cheer squad. The “You’ve got this babe!” brigade. 

what happens when the people around you are too supportive? 

You float one idea—they love it. 
You pivot to a completely different one—they love that too. 
You mention something a little wild—like launching a side business selling kombucha for dogs—and they’re all in, while you’re quietly wondering if you’ve lost the plot. 

Here’s the thing, it’s easy to cheer from the sidelines when you’re not the one steering the ship (or paying the bills). 

Running a business isn’t a group hug. It’s decisions, risks and the occasional existential crisis over a staffing issue. And while blind optimism is admirable it won’t help you spot the iceberg. 

I once vented to a friend during a major client issue. They listened patiently then looked at me earnestly and said “I’m sure it’ll all work out.” 
Yes, it did—but not before I catastrophised the imminent downfall of the business in 100 different ways. 

Find Trusted Advisors who will Ask the Awkward Questions

Someone who’ll say “Are you sure about that?” 
Someone who’ll ask the awkward questions poke holes in your plan (nicely), and help you build something solid not just sparkly. 

Because when the rubber hits the road “You’ve got this!” only gets you so far. 

(Cue the opportunity to shoot a thankyou message to the trusted advisors in your circle, the ones who challenge you just enough to make you better.)