The Peril of Overthinking: Cicely Simpson on Moving from Decision Paralysis to Action

In a recent LinkedIn post, Cicely Simpson explores the common leadership pitfall of excessive deliberation, arguing that true progress often comes not from prolonged thinking, but from decisive action. Simpson highlights how the desire to plan and analyze can become a form of procrastination, creating an illusion of productivity while actual movement stalls.

Simpson shares a personal anecdote to illustrate this point, recounting a situation where she spent three weeks agonizing over a team restructuring decision. “I built the case for it. Then the case against it. Then rebuilt the first case again,” she writes. “Nothing about the decision changed in those 3 weeks.” This period of intense thought, she explains, left her exhausted but no closer to a resolution. It was only after making the decision that tangible learning and progress occurred.

The Illusion of Progress in Planning

The core of Simpson’s argument centers on the idea that “planning feels like progress.” This is a subtle trap, she suggests, because it mimics the sensation of accomplishment without requiring actual risk or movement. “You can spend an entire day turning a decision over, arrive at 5pm with nothing moved, and still feel like you worked hard,” Simpson observes. This feeling of having worked hard, despite a lack of tangible outcomes, can reinforce the behavior of overthinking.

According to Simpson, this tendency is deeply rooted in our brain’s natural inclination to weigh risk against safety. “Endless deliberation is structural, built into how your brain weighs risk against safety,” she states. “Given the choice, your brain will pick the safer one every time, then call it being thorough.” For leaders, especially founders or those expected to have all the answers, this internal pressure can exacerbate the problem, leading to a perpetual state of refinement rather than execution.

Building Trust Through Action and Course Correction

Simpson posits that effective leadership involves embracing action and learning to correct course openly. She criticizes the notion that a plan must be perfect before implementation. “The plan is never quite finished. There is always one more version worth working through first,” she notes. Instead, she advocates for a more dynamic approach.

The leaders who build trust, in Simpson’s view, are those who “make a decision, then correct their course out loud, in front of everyone, without pretending they got it right the first time.” This transparency and willingness to adjust post-decision fosters credibility and demonstrates a commitment to progress over perfection. Her advice is direct: “Decide. Move. Then let what happens next show you where to adjust.”

Simpson concludes by emphasizing that clarity is not always a byproduct of more thinking. Sometimes, “clarity doesn’t always come from more thinking. Sometimes it only shows up once you’re already in motion.” She challenges leaders to identify areas where they might be “still thinking instead of deciding,” suggesting that developing the ability to decide faster, without sacrificing judgment, is a critical leadership skill that can be cultivated.