Why Your Plan Is Always Wrong And What To Do About It
It’s tempting to treat business or project plans as sacred maps for the future. However, history shows that the most rigid roadmaps rarely survive first contact with feedback, market shifts, or unexpected challenges. Plans provide structure, but what really matters is the foundation—the core beliefs about what matters and why. At Google, initial business plans often omitted revenue projections, organizational charts, or even a detailed product roadmap. Instead, decisions revolved around foundational principles: build for users, bet on technical insight over trends, and iterate with speed. As new data emerged and realities changed, teams re-examined and adjusted their approach, anchored by these core tenets.
This approach isn’t exclusive to Silicon Valley. If you probe the stories behind enduring success in almost any field, you’ll find teams willing to pivot, abandon sunk costs, and shift direction without losing sight of their values. The comfort with uncertainty, and the willingness to embrace rapid learning, separates high-impact groups from ones that cling to outdated plans. Behavioral science points to the danger of “escalation of commitment”—sticking with a failing strategy to save face or avoid loss. Teams that outperform learn to detach ego from initial plans, trusting their core principles as a compass through the fog of change.
It might feel counterintuitive to discard much of what you’ve planned and unnerve your team. But by codifying your principles and regularly interrogating what’s not working, you open the door to smarter adaptation, faster course corrections, and ultimately, bolder success.
To put this into practice, start by clearly writing out the foundational beliefs you want to live or lead by, making sure they reflect what truly matters, not just what sounds good. Then, look at your current plan and honestly mark where reality is not matching your assumptions—be honest, this is about learning, not blame. Finally, schedule a consistent time, maybe each month, to revisit these mismatches, discuss what you’ve learned, and adjust course accordingly. Committing to this cycle will anchor your progress in what matters most, while freeing you from the rigidity that can quietly undermine real achievement. Try starting your own principle list this evening.
What You'll Achieve
Develop a more flexible and resilient approach to planning, cultivating comfort with change and ambiguity, while improving your ability to make quick, grounded pivots that keep progress aligned with your core goals.
Anchor Yourself With Principles, Not Rigid Plans
Write down your core beliefs and guiding principles.
List the main beliefs that drive your work or team's mission. These should be values and foundational concepts (e.g., 'Focus on the user,' 'Value transparency over control'), not tactical goals.
Identify where your current plan departs from reality.
Challenge your assumptions by comparing the current plan to actual results, feedback, or recent data. Highlight mismatches where facts or circumstances have shifted.
Schedule a regular review to adapt and iterate.
Commit to a monthly or quarterly check-in where you, or your team, discuss what the plan got wrong and how to adjust based on what you've learned.
Reflection Questions
- Do I feel a sense of loss or anxiety when a plan needs to change?
- What core beliefs would I be willing to defend even if the plan gets scrapped?
- How often do I set aside time to reflect on what’s no longer working?
Personalization Tips
- For a student launching a club, list out the club's core goals and priorities instead of obsessing over a fixed semester calendar.
- A mid-sized business leader can focus on a central value like 'put users first' to guide rapid product pivots when initial features flop.
- A software engineer working on side projects keeps a set of three non-negotiable principles taped to her monitor as a daily guide.
How Google Works
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