There’s something irritating about the phrase “don’t overthink it.” It’s not just the dismissiveness, though that’s part of it. It’s the presumption. The person saying it assumes they have clarity you lack, that their view of “enough thinking” is the gold standard. For people who make their living solving problems or creating new ideas, this phrase cuts deeper than it should. It feels like a slap at the very thing you’re good at—your ability to think deeply and carefully.

But here’s the uncomfortable truth I’ve wrestled with over the years: sometimes they’re right. Not in the way they say it or the tone they use, but in the principle hiding beneath their words. Deep thinking is critical, but it’s incomplete. Overthinking isn’t just about thinking too much—it’s about failing to shift gears when the situation calls for it.

Thought is the foundation, not the structure

In the work we do—whether it’s designing a product, writing a piece of code, or solving a customer’s problem—thinking is where everything starts. It’s the foundation. If you don’t take the time to think, you end up with shallow solutions, bandaids instead of cures.

But the mistake we often make is treating thinking as the whole structure. We overdesign the blueprint, trying to predict every possible scenario before laying a single brick. The longer we stay in that mode, the harder it becomes to transition to building. Why? Because building introduces chaos. Reality doesn’t care about your perfect plan. Once you start, you’re going to find cracks in your thinking, things you couldn’t have anticipated no matter how much time you spent on it.

That’s not a failure of your thinking. It’s just the nature of reality.

Movement makes it possible

I’ve learned this lesson the hard way in my own work. When we’re building a new feature or tackling a tricky problem, there’s always a temptation to think our way to perfection. But what we’ve found over and over is that momentum beats mastery.

If we just get started—build something small, ship it, see how people react—it almost always leads to better results than the “perfect” solution we could have dreamed up in isolation. That’s not because we didn’t think carefully; it’s because thinking alone isn’t enough. Execution fills in the gaps.

In fact, the best thinking often happens after you’ve started. Action forces clarity in a way that planning never can. It exposes what matters and what doesn’t, what works and what needs to change.

A better way to say it

Here’s the problem with “don’t overthink it”: it frames thinking and action as opposites. They’re not. They’re partners, each improving the other. Deep thinking is essential, but it has to feed into action. And action isn’t the enemy of thought—it’s what refines it.

So instead of saying, “don’t overthink it,” maybe we should say:

• “Let’s move forward and see what happens.”

• “We’ve thought this through—now let’s let the real world teach us.”

• “What’s the smallest step we can take to start learning?”

These phrases don’t diminish thinking; they honor it while encouraging forward motion.

The work of showing up

This principle doesn’t just apply to work. I see it in my personal life, too. Take exercise. I’ve wasted so much time trying to perfect the plan—choosing the “right” program, optimizing every detail. But at the end of the day, the best workout is the one you do. The most important step is showing up.

The same is true for almost everything. Whether you’re trying to start a business, write a book, or learn a new skill, overthinking can become an excuse not to begin. The fear of imperfection keeps us stuck in planning mode. But the truth is, you don’t need a perfect start—you just need a start.

Thinking and doing: the real dynamic duo

“Don’t overthink it” frustrates me because it oversimplifies the issue. The problem isn’t overthinking; it’s the failure to balance thinking with doing. The real magic happens when the two work together. Thinking sets the direction, and doing helps you navigate.

So the next time you feel stuck in your head, don’t stop thinking—just let your thinking evolve through action. Because the work isn’t just about coming up with great ideas. It’s about testing them, refining them, and learning along the way.