Ship It Scared

Standing on the beach in Punta Cana, I watched my daughter grab a surfboard for the first time. No lessons, no perfect conditions, just pure determination. Within minutes, she was up, wobbling but moving forward. Shortly after, I hesitated at a boat’s edge, overthinking the jump into the crystal-clear water for snorkeling. The irony wasn’t lost on me: here I was, writing about decision velocity and bold action, paralyzed by a simple jump into paradise.

That moment crystallized what I’ve been observing across enterprise software all year. We’re halfway through 2025, and the uncomfortable truth is clear: The best moment to launch your critical initiative was January. The second-best moment is right now.

January Was Perfect, Today Is Crucial

Too many teams started the year waiting for more data, clearer market signals, or reduced risk. While these cautious strategies felt prudent, they’ve proven costly. Colleagues and competitors who embraced uncertainty by launching AI initiatives, restructuring teams, or pivoting their strategic direction are now miles ahead. Their early actions, imperfect as they were, have generated valuable insights, rapid learning, and tangible market advantages.

Why “Shipping Scared” Beats “Waiting Confidently”

There’s never complete clarity or perfect certainty, especially in rapidly evolving spaces like enterprise AI. But leaders who ship even when they’re scared gain an invaluable advantage: real-world feedback. Every iteration provides clarity, reduces ambiguity, and accelerates decision velocity. The alternative of waiting until confidence replaces fear only magnifies uncertainty and amplifies risk.

As I’ve explored in my decision velocity framework, the ability to make quality decisions quickly has become the defining competitive advantage. When you’re standing at the edge of the boat, more analysis won’t make the water warmer. But jumping in immediately gives you the data you need to navigate.

The Trust Dimension: How Action Builds Confidence

Just as jumping into the water was the only way to see the incredible marine life below, taking action, even imperfect action, is often the only way to gather the data that builds real confidence. When teams see leaders willing to “ship scared,” it creates a powerful trust dynamic:

• Vulnerability becomes strength: Teams trust leaders who acknowledge uncertainty while still moving forward.
• Learning accelerates: Real-world feedback builds competence faster than any amount of planning.
• Psychological safety increases: When imperfect action is normalized, innovation flourishes.

The organizations building trust fastest aren’t those with perfect plans. They’re those willing to iterate publicly, learn openly, and improve continuously.

AI’s Acceleration Effect: The Compound Cost of Waiting

As I discussed in The AI Adoption Cost Paradox, the true cost of delayed AI implementation compounds exponentially. What seems like prudent waiting in H1 becomes crippling disadvantage by H2:

• Technical debt accumulates: The gap between current state and required state widens daily.
• Change resistance calcifies: Each month of delay makes eventual adoption harder.
• Competitive gaps become chasms: Early movers gain compounding advantages in data, insights, and capabilities.
• Implementation costs multiply: What would have cost $1M in January might cost $3M by December.

Organizations that decisively integrated AI capabilities into their workflows now have a pronounced lead. They’re continuously optimizing based on live feedback and rapid insights. Conversely, those still evaluating or cautiously planning risk falling irrecoverably behind.

Your 6-Month Action Plan

Here’s how to ensure you’re not looking back in December wishing you’d acted sooner:

1. Clarify and Commit: Clearly define what success looks like and commit publicly and internally to immediate action.
2. Ship Small, Ship Fast: Launch a pilot project within the next two weeks—whether an AI integration, customer experiment, or team restructuring—to gather real-time insights and build momentum.
3. Optimize Through Feedback: Rapidly integrate user and market feedback into iterative improvements. Each step forward reduces ambiguity.
4. Double Down on Decision Velocity: Eliminate unnecessary layers of approval and empower your team to move swiftly and decisively.

Act Now or Pay Later

The message is straightforward: Action now, even if imperfect, outweighs flawless execution later. Don’t wait for the anxiety to fade; embrace it as confirmation that you’re pushing meaningful boundaries.

Just as my daughter’s fearless approach to surfing reminded me that progress requires action, not perfection, this mid-year mark is your wake-up call. The cost of “waiting confidently” far exceeds the discomfort of “shipping scared.”

Take the leap into your strategic initiatives now, just as I finally jumped into the water. Your future self will thank you.

The Challenge Question: What initiative have you been perfecting in PowerPoint that could be generating real-world feedback by Monday? And more importantly, what’s the real cost of waiting another month to find out if it works?