How a Plan Turns Into a Trap
Making an effective plan means knowing when to let reality override it.
One of my clients recently spent his Sunday making a new, detailed financial model. He wanted to create something to support his decision making as the company entered a new phase of growth.
Initially, the exercise worked. Creating the model helped him slow down, organize his thoughts, and work through the company’s data. He felt responsible and confident.
But as time passed, the model ran into the reality of the business—which is always unexpected and often unpredictable, especially in early stages.
That’s when his model became his trap.
Instead of letting reality reshape the plan, he tried to force the business to comply with the model. Each new piece of data felt threatening and every decision felt like a test.
A plan should give you support, but it will never give you total security.
When we ask our plans to provide certainty instead of clarity, our leadership suffers.
It creates:
Fear. Reality becomes the enemy and in-depth reflection feels dangerous.
Rigidity. Decisions feel like tests, making your options limited and narrow.
Poor decision making. You’re led by projections, hopes, and fears instead of reality.
A plan is an essential guide, but reality has to remain the authority.
The best plans hold your anxiety while keeping you in touch and responsive to the company’s current moment.
What a Plan Should Do
A good plan has three essential roles.
1. Get you in contact with reality
We think of a plan as future-focused. It’s how to get “there” or how to get “that.”
But good planning begins in the past and present.
The most important part of a financial model, for example, isn’t projecting forward—it’s gathering data on the current state of revenue, customers, costs, timing, etc. Only from that grounded understanding does forward movement make sense.
A plan is doing its job when it forces you to look clearly at what is. Only then can it help you imagine what could be.
2. Provide the safety to think
It’s hard to think creatively or make decisions without guardrails.
Paradoxically, limits often give us freedom. Too much space can make us freeze.
Plans can serve as those guardrails. They give you something concrete to follow, push against, revise, or even walk away from.
A good plan isn’t a prediction. It’s a tool to help you hold uncertainty without shutting down.
3. Tell you when it’s time to change course
As you grow, plans should function as scaffolding, temporary structures that support movement.
Using them means deciding when to revise them.
Making the comparison between what you planned and what you see makes it easier to see and evaluate your assumptions and strategies.
Getting Attached to Plans
When we’re too attached to our plans, they don’t serve any of their roles.
They do the opposite: they distance you from reality, increase fear, and make it harder to change course.
Sitting with uncertainty is incredibly uncomfortable.
Plans and models support us in these moments. Making them gives you a real way to engage with your uncertainty, and having them gives you something to lean on as you grow.
But we often lean too hard or without enough awareness.
We hand authority over to our “plan” to relieve the pressure, and then forget we made the plan. The plan becomes the ultimate authority, and every decision has to be measured against it.
Instead of feeling relieved, the pressure is renewed.
This attachment leaves us stuck in internal conflict—charging ahead with what you decided was “best” while knowing in your gut something isn’t right.
Making a Supportive Plan
Making a supportive plan means getting to know your own fear.
This won’t eliminate it. But when you know you want certainty, you create a little space between the wanting and acting. That space is what lets you stay in contact with your company’s reality.
But, even when you can recognize your own anxiety, you’ll still want certainty. So, the best plans have checks built in.
They define what you’re aiming for and when it’s time to reassess or change your approach: what outcome would tell me this isn’t working?
Try this out with a small assumption from a current plan. Ask yourself:
What would I expect to see if this assumption is correct?
What specific outcome would tell me it’s not working?
What would I do next if that signal showed up?
The contradictions that show up between your plan and your reality aren’t problems. They can act as signals that put your feet back on the ground.
Instead of asking, How do I make the plan work? You can focus on what those signals are teaching you.
A useful plan asks you to take it seriously without treating it as truth. Your job is to hold the tension between clarity and uncertainty.
This work keeps your attention split in the right way, with one eye on where you are and the other on where you’re going.
See you next week! 👑
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