Apr 12, 2022

Write Your Plans with a Pencil

Write Your Plans with a Pencil

Write Your Plans with a Pencil

Nathan King

Your ability to create and execute plans is crucial to your professional growth.

Want leadership to trust you with special projects? Demonstrate consistent delivery on plans. Want a promotion and a raise? Show excellent judgment in following through on plans.  

The problem is that humans are just terrible at planning. 

Planning is so pervasively bad in large part because of the Planning Fallacy. Psychologist Daniel Kahneman coined the term to capture “the tendency to underestimate the time, costs, and risks of future actions.” 

Are you susceptible? Here’s a quick test. On a piece of paper, write at the top of the page, “My Plan for the Next Hour.” Take 5 minutes and write down the tasks that you believe you can complete in the next hour. Now set a timer. At the end of the hour, how many did you get done?

I’ve taken that test, and failed, multiple times. 

The Dark Side of Planning and Why You Should Prioritize Making Plans

Planning forces us to confront a grim reality: we crave certainty and control, but the world is firmly outside of our control.

In carrying out our plans, we don’t control whether someone doesn’t call us back, whether the refrigerator breaks and we spend half a day organizing the repairman to handle it, when a child gets sick and requires postponement of a meeting. 

The absence of perfect information makes it inevitable to underestimate what it will actually take to execute a plan. 

When we can’t complete our plans with sufficient success, we experience significant anxiety. Anxiety erodes confidence and increases the attractiveness of distraction. The next thing you know, you have enough time to work on your plan, but you are binge watching the new Netflix series instead. Anxiety increases the attractiveness of distraction. 

After hours, days, weeks, and months of not succeeding in our plans, we can easily become callused in our approach to plans. We give up on making plans. We become an idea butterfly, fluttering from idea to idea and going nowhere.

Without a plan, we become, as Peter Drucker said, “a prisoner of events.”

The proper place of a plan is to remind us of our intent, and to help us return to a plan when events tug at our attention and take us off course. 

How to Plan without Falling Victim to the Planning Fallacy

Planning is essential to producing results in our careers. Follow these 5 practices to free yourself from the planning fallacy so that you can have greater trust of your planning process and improved outcomes:

1. Visualize outcomes

Every plan should have a clear, measurable outcome, and a specific date on when it will be done. 

Here’s an Example:

You plan to create a dashboard of KPIs in Excel for the executive team. 

Outcome: 60 days from now, begin sending a monthly dashboard with the 5 most important metrics to the entire team. 

With a clear outcome, your mind begins to turn up specific tasks necessary to achieve the outcome:  

  • Get approval from boss on the definitions of these metrics. 

  • Write a database query to pull the raw data from our database

Set meeting with Jill from accounting to get her commitment to provide the financial report no later than the 20th of each month.

2. Break plans into smaller projects

Since our problem with planning is that we are too optimistic, the more challenging it is to achieve it. Tiago Forte has a great post on this, and has named the approach of creating larger outcomes into smaller ones “intermediate packets.

Stay with the example above: if the ultimate outcome is to send a monthly dashboard to the entire team, a smaller project is to get agreement with the CFO, CEO, and Head of Sales on what the 5 most important metrics are and how they would like to see them. That in and of itself could take weeks. It would require multiple meetings, coordinating schedules, mocking up what the dashboard looks like. It could introduce more complexity that would jeopardize the broader outcome of having a team dashboard.

An intermediate packet for the larger plan of “create a dashboard of KPIs in Excel” is to “Get agreement with the leadership team on what the 5 most important metrics are by date ____.”

3. Probabilistic Discounting

An easy way to address our tendency towards optimism when planning is to discount. 

If I think the dashboard project will take me 60 days to deliver, add 25% to the timeline, so that I commit to it being done in 75 days. 

This technique is particularly helpful when forecasting future results. If my plan is to enroll 50 students in the next class, discount that by 30% so that I plan on 35. 

4. Get other people to give you feedback

An important finding of Kahneman is that even though humans are optimistic about their own plans, they are pretty good at spotting problems with other people’s plans

Your plan will benefit from candid feedback. Approach others you trust to explain your desired outcome and your assumptions. Invite them to challenge and make suggestions.

5. Iterate  

Your plan is not the ten commandments, etched in stone. Your plan should be written in pencil, readily revisable. 

As we go along with our plan, achieving or failing at discrete tasks, we will need to make edits. “Every success creates new opportunities. So does every failure,” Drucker wrote. To iterate successfully, we must return to the plan routinely, reflect on what we thought we would accomplish at the outset, and define what we need to change about our actions or even our outcomes.

Your Next Steps with Planning

You are either in the middle of working through an imperfect plan, or you are avoiding making a plan in an important area. Remember that your career depends on the ability to succeed with plans. Set aside 20 minutes today to reflect on the most important initiative on your plate today. Apply these practices and move beyond the planning fallacy. 

The world needs your plans to succeed.




I help leaders and teams achieve clarity and alignment so they can reach their potential


Sign up for my newsletter and I will send you a Life Review and Planning Guide to help you create a better future.

© King Strategic Consulting, LLC 2023