The Strategy That has Expired: Hidden Costs of Ignoring What No Longer Works

A Moment of Reckoning

There’s a moment in every leader’s journey— when something you built, trusted, or believed in… starts to no longer work.

It doesn’t break overnight. It just… stops working.

The system, the strategy, the business model. What once made you successful no longer works. 

But instead of naming it, we try to manage it. We tweak it. Ignore it. Push through it. Because letting go feels risky. And holding on feels responsible.

But here’s the truth we often forget:

✨ The longer you hold on to what’s no longer working, the more it costs you.

Not just time or efficiency. But clarity, creativity, trust. And eventually… buy-in.

Because your team can feel it. They sense when you’re forcing what’s expired. They mirror the resistance you’re suppressing.

And suddenly, it’s not just a broken process. It’s a quiet disconnection. A ripple of disengagement. A culture of compliance, not commitment.

But it doesn’t have to stay that way.

The Work of a Courageous & Adaptive Leader

When you have the courage to name what’s not working, you create space for something better.

When you invite your team into the conversation— not just to solve it, but to shape it— you turn resistance into resilience.

We don’t resist change because we’re stubborn. We resist because we don’t feel safe leaving it behind and stepping in to the unknown.

Our biggest fear is not failure, it’s losing success and letting that thing go can feel like losing success. 

Your job isn’t to have all the answers. It’s to create a culture where honesty is welcome, and evolution is normalized.

Because the strongest teams aren’t built on perfection. They’re built on shared ownership of what comes next.

So this week, ask yourself:

🌱 What am I still holding onto… that no longer holds me? 🤝 What conversations am I avoiding… that could actually build more trust? 💡 What truth needs to be spoken… so we can move forward together?

You don’t have to fix it all today. But you do have permission to stop pretending it’s fine.

Call it out. Lean in. Lead forward.

With love, ✨ Sky + the Transcend Team

Reflective Prompt What’s one thing in your leadership or team culture that’s no longer working—and what first step could you take to name it with honesty and care?