Why Playing It Safe Is The Riskiest Move: Embracing Failure to Drive Innovation

Failure. The word alone makes leaders squirm. We’re wired to avoid it, outrun it, or disguise it with buzzwords like “fail forward.” But let’s be real—most organizations would rather not fail at all. And that’s exactly why they struggle to innovate.

The truth? Failure isn’t the opposite of success; it fuels it. Every flop and “well, that didn’t go as planned” moment is a chance to refine and reimagine. In The Art of Membership, I explore why leaders must create environments where risk-taking isn’t just encouraged—it’s expected.

Yet, many organizations get stuck chasing the perfect idea while smothering creativity in approval processes. An Avenue M poll found that while 85% of association executives say they handle new ideas well, there’s still major room for growth.

The problem isn’t a lack of ideas—it’s fear. But not taking risks is actually the biggest risk. In today’s rapidly changing world, playing it safe means falling behind.

That’s why I emphasize an entrepreneurial mindset—testing, learning, and pivoting based on real feedback. In my keynote, Take More Shots, I share strategies for overcoming barriers to innovation. The organizations that thrive aren’t the ones that avoid failure—they’re the ones that embrace it, learn from it, and use it as a launchpad for something better.

So, what’s your next shot?