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Best Laid Plans: Story and Reflection

by Dr. Tonya Caylor
Jun 11, 2025

I enjoy it when people expand and contrast the meanings of words. It gives me a better grasp of various approaches. I came across a quote from Sahil Bloom that did just that:

"Preparation always beats planning. Planning is based on the expectation of order. Preparation is based on the expectation of chaos. Plan for order, and you'll be destroyed by chaos. Prepare for chaos, and you'll thrive in any condition."

I think I've always developed an "Ideal Plan" for any given presentation, meeting, project, or group/team coaching session. And because I wanted the ideal so badly, it felt like a huge blow when anything sidetracked it. I wasn't able to celebrate the wins. Heck, I couldn't even have told you that anything good happened.

I've evolved in a few areas which have been helpful over the years:

1. I hold loosely to the ideal. (Helpful in most areas of life).

2. I prepare for predictable or common hiccups.

3. I lean into unexpected curve balls, remain flexible, and look for the humor of the situation.

For a recent faculty development session, I implemented all three.

I put in a lot of effort to offer the ideal.

One predictably common issue with any interactive session is running out of time. So, I planned for things I would shorten or skip if our discussion and breakouts went longer than predicted. And I was prepared that a few individuals would not have done the 3-minute prework. Undisclosed to the group, the breakout structure only needed one of three people in each group to have completed it. So, the odds were high that it would work out.

What I didn't prepare for based on the efficiency of communication and the detailed nature of the administrative assistant was for them not to have A. The handout I sent a few days prior. B. A blank notecard for an activity. C. No one to have done the 3-minute prework. D. for them to show up 20 minutes late. (Their lunch was not on campus - which I didn't know)

So, because I was holding loosely to the ideal and was prepared, I cut back on some of the content, shortened a couple of interactive times, and laughed at each step along the way each time one of those unexpected issues was revealed.

Because my amygdala didn't hijack the creative centers in my brain, I was able to pivot quickly, have the group take shots of the slides that would be needed to replace the handout, shift the activity to an easier one not requiring notecards, and laugh with them and realize how perfect the situation was to drive home a key learning point - when your residents come unprepared it can still be a productive meeting. 😂

The official feedback is that it was well-received. 😅

Reflection: What helps you hold loosely to the ideal, prepare a flexible plan, and pivot and laugh when needed? How have they served you? How do you want to expand those skills? What's the first step?

I would love to hear any tips you use.

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