When your options are too similar
Better Question: What’s the worst that could happen?
“Damn.”
I took shelter when the sky opened up. I was in Epcot as part of a multiday trip to Disney World, where afternoon rain exists as a persistent possibility.
The squad (my family) was currently on a mission to secure nourishment. I had rejoined them after a side quest to upgrade my coveted Jedi badge. (The person guarding the area where you could make your own lightsaber was less than helpful, but I digress…)
Huddled under three feet of a roof overhang, my family debated what to do. Should we wait and hope the rain stops so we can continue on to the Food & Wine Festival? Or should we call it quits and head back to the resort so we can dry off and eat lunch?
Some consulted their weather apps, noting conflicting predictions. Others tried to find something, anything, to support their case, including pointing to the food cart a few feet from us and saying, “There’s a food stand right across from us — it must be a sign.”
We could have easily waffled until we were thoroughly soggy.
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What’s the worst that could happen?
Meet Fredkin’s Paradox: the more similar two choices are, the harder it is to decide, even though the difference in outcome is negligible. We get stuck searching for a distinction that doesn’t exist so we can make a decision.
Stuck can look like going down a rabbit hole trying to gather more information. Or going round and round grasping for certainty that we are making the “right” choice. Or inventing justifications that we say until we believe them. Or even making up patterns and signs to increase the level of comfort we feel in our decision.
What my family needed (aside from more umbrellas) was contrast, something that made one option sufficiently different from the other so that we could then compare them.
To create contrast, ask “What’s the worst that could happen?” Now you’re considering and stress testing the downsides instead of trying to pick between equally good upsides or options so similar they cannot be distinguished.
That question can also free you from having to be right and empower you to take action. Not moving generally means no new information.
Here’s how to put it into practice →
As an individual, when you face equally attractive options or cannot commit to a path, ask yourself, “What’s the worst that could happen?”
In business, the question is the same, but the stakes are higher because there are more people and moving parts involved.
In both cases, you can adjust based on what you learn once you move.
Back under the overhang, both options would achieve the mission objective: food.
If we continued on to the Food & Wine Festival, the worst that could happen was that we’d be wrong about the rain letting up and thus soaking wet while trying to eat. If we went back to the resort, the worst that could happen was that it would stop raining. In that case, we’d eat outside at the hotel and visit the Food & Wine Festival another day.
We went with option #2.
And as it turned out, it rained most of the night.
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Hi! I’m Katie
I run The Better Questions Project. In addition to writing this newsletter, I speak, cultivate a community, and work directly with teams. Here’s how you can work with me: