Day 4: Why Planning for the Worst Makes You a Better Leader
Turn catastrophizing into contingency planning and free yourself to lead in the present.
Coming Up
Why making a backup plan actually reduces your anxiety (instead of feeding it)
How to map your transferable skills so you know what you’re working with
Three types of contingencies that every leader should map out (to transform “what if?” worry into “here’s what I’ll do”)
Welcome to Day 4 of the Leading Through Uncertainty Challenge!
Yesterday, we talked about focusing on your three-foot world – the immediate zone where you’re in control and where your leadership makes the biggest difference.
But you might have trouble staying in that zone if worst-case scenarios are constantly looping in your mind.
When I asked for questions from readers before I began writing this Leading Through Uncertainty series, some of you brought up specific fears like: “What if AI replaces my job?” or “What if my team gets broken up?” or “What if my position gets eliminated?”
These are very real concerns, and constantly having them playing out in the back of your mind can feel demotivating and paralyzing. They create a constant hum of anxiety that makes it nearly impossible to lead with clarity.
One way to stop these fears from hijacking your focus is to prepare for them. So today, we’re building contingency plans so those fears lose their grip. (Or at least loosen their grip.)
Before we begin, here’s a reminder of where you stand in this challenge:
Day 4: Prepare for the Worst (You Are Here)
Day 5: Understand Your Coping Style
Why Planning for the Worst Calms You Down
Thinking about worst-case scenarios feels scary, but not planning for them creates chronic anxiety.
There’s a massive difference between catastrophizing and contingency planning.
Catastrophizing sounds like: “What if I lose my job and can’t pay my mortgage and lose everything?” It’s a spiral with no action, just mounting terror.
Contingency planning sounds like: “If I lost my job, here’s what I’d do in week one, week two, month one.” It’s specific, actionable, and grounded in reality.
One keeps you stuck. The other gives you agency.
You can’t lead confidently when you’re secretly terrified. When worst-case scenarios feel like existential threats with no plan B, you avoid hard conversations and make decisions based on fear. And your team senses that instability.
But when you know you’ll be okay even if things go wrong, you lead with clarity instead of desperation.
Know What You’re Working With – Map Your Transferable Skills
Let’s imagine for a moment that, like so many people out there, you’re worried that AI might eliminate your role.
This is a heavy feeling that can be very demotivating. I encourage you to challenge it right now by looking beyond your job title and taking an inventory of your actual capabilities.
Here’s how to do it:
