Ever feel like you’re caught in a cycle of endless planning, constantly tweaking strategies while your team waits for something to happen? I’ve been there. Stuck in the strategy trap, where the comforting illusion of productivity keeps you from actually leading. Spoiler alert: it’s not as productive as it feels.

In my experience, strategy can easily turn into an excuse for inaction. The real culprit? Fear—of making mistakes, of failing, or of not having all the answers. We get so bogged down in trying to create the perfect plan that we end up doing nothing at all. The worst part? While you’re busy refining that plan, your team is losing trust, momentum is fading, and opportunities are passing by.

Why Leaders Get Stuck

It’s easy to see why so many leaders fall into the strategy trap. Planning feels like you’re moving forward, but in reality, it’s just a way to delay action. I used to think, “If I plan everything out perfectly, success will follow.” But here’s the truth—no plan survives first contact with reality. Over-planning is just a fancy way to avoid risk.

When we endlessly tweak and revise, it’s not because we’re being strategic—it’s because we’re afraid of stepping into the unknown. But the real world doesn’t reward planning. It rewards action. That’s a lesson I had to learn the hard way.

The Real Cost of Over-Planning

Over-planning is sneaky. It feels like progress, but it’s actually costing you more than you realize. For one, it kills your momentum. You spend so much time “perfecting” your strategy that you never actually get to the execution part. And without execution, there’s no real progress.

Worse yet, it poisons your team’s culture. Your people are waiting for you to make a move, but instead, they see endless planning sessions, revised timelines, and shifting priorities. They start thinking, “Is anything ever going to happen?” And when your team loses faith in your ability to lead, that’s a tough hole to dig yourself out of.

How I Broke Free from the Strategy Trap

So, how did I escape? It wasn’t easy, but I had to make a conscious shift from perfection to action. Here’s what worked for me:

1. Progress Over Perfection

I had to accept that perfection was an illusion. Instead of aiming for the perfect plan, I focused on making progress. I started taking action, even if it wasn’t 100% perfect. And you know what? Action breeds clarity. Once I got the ball rolling, I could adapt and adjust on the fly.

2. Small Leadership Experiments

To break the habit of overthinking, I started treating leadership like a series of experiments. I’d try something small, see what worked, and make adjustments. These mini-experiments allowed me to gather data, make informed decisions, and most importantly, keep moving forward. The more I experimented, the more I learned—and the more confident I became in taking bigger actions.

3. Getting Comfortable with Risk

Taking action means embracing risk, and that’s something we, as leaders, tend to shy away from. But here’s the thing: staying stuck in planning mode has risks too—like losing your team’s trust or missing out on opportunities. I had to get comfortable with risk by starting small and gradually building my tolerance. I realized that most decisions aren’t irreversible, and that gave me the confidence to act.

4. Building an Action-Driven Culture

Leadership is contagious. Once I started taking action, my team followed suit. We shifted from endless meetings and planning sessions to a culture that valued doing. I rewarded initiative and experimentation. Suddenly, we were all moving forward instead of just talking about moving forward.

The Bottom Line

Strategy is important, but don’t let it become a security blanket that keeps you from leading. The real magic happens in the doing. If you’re stuck in the strategy trap, it’s time to break free. Focus on progress, not perfection. Run small experiments. Get comfortable with taking risks. And most importantly, start leading with action.

If you’re ready to stop planning and start making things happen, join me for my upcoming LinkedIn Live session, where we’ll dive deeper into how leaders like you can break free from strategy paralysis and drive real results.