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Three questions I ask before making a decision

Posted in the following categories: Decision Making

1. What’s the worst that can happen?

When it comes to creating worst case scenarios, my imagination is particularly vivid. My creativity kicks into high gear as I think about all the awful consequences that can follow from a simple decision gone wrong. I can visualize, in intricate detail, how life as I know it will come to a swift end from a bad blog post, a botched podcast episode, or a dumb question I asked.

But, as the Stoic philosopher Seneca reminds us, “we suffer more in imagination than in reality.” The parade of horribles I dream up never materialize. Yes, bad things do happen from time to time, but they’re never as bad as I imagined.

The cure? Follow the timeless wisdom of Yoda, who said “Named must your fear be before banish it you can.” But Yoda failed to mention one important thing: naming your fears in your head is not enough. Thinking about the worst—letting the amorphous fears of an uncertain future marinate in your head—takes awful consequences and turns up the volume on the drama (all the way to 11).

The naming, I’ve found, must be done in writing—with paper and pencil (or pen, if you’re into technology). Writing your fears down undresses them. Once you lift up the curtain and see “the truth” behind it—a la Wizard of Oz—your fears are no longer the great unknown masses that continue to block you from soaring. Once you see your fears with their masks off, you’ll find that the feeling of fear is often far worse than the thing that you fear. You’ll also realize that, in all likelihood, the things that matter most to you will still be there, no matter what happens.

Finally, don’t let the fears you write down become long-unused archives of memory. I review what I write on a regular basis through a journaling app called DayOne. Every morning, it brings up what you wrote on that very day in previous years. This regularly exposes me to previous fears that I thought were insurmountable but turned out to be speed bumps at worst. Through repeated exposure, I end up inoculating myself and realize that my imagined fears are just that: imaginings.

2. What are my biases and preconceptions?

We tend to undervalue evidence that contradicts our beliefs and overvalue evidence that confirms them. We filter out inconvenient truths and arguments on the opposing side. As a result, our opinions solidify, and it becomes increasingly harder to disrupt established patterns of thinking.

Before making an important decision, ask yourself, What are my biases? What do I know on this topic (or better, What do I think I know?). As Richard Feynman said, “The first principle is that you must not fool yourself and you are the easiest person to fool.”

Also ask, Do I really want this particular belief to be true? If you find yourself skimming through Google results to find that one study that confirms your decision, be careful—be very careful (particularly since you’ll always find that page, especially if you’re willing to click through to Page 10 on the search results).

Another way you can expose your biases is by asking, What fact would change my decision? If the answer is “no fact would change my decision,” you’re in trouble. A person who is unwilling to change his or her mind even with an underlying change in the facts is, by definition, a fundamentalist.

3. Who will disagree with me?

It’s not easy exposing our own preconceptions. It doesn’t help that we live in a bubble and surround ourselves with people that operate on the same frequency. If you’re lucky enough to have people around you who disagree with you, ask them for their opinion.

If you’re not so lucky, then ask people who normally agree with you to disagree with you. I often give trusted advisors early drafts of book chapters and ask them to point out—not what’s right, not what they loved—but what’s wrong, what should be changed, what should be taken out. This approach provides psychological safety to those who might otherwise withhold dissent for fear of offending you.

These three questions often have no easy answers. But they’re well worth asking if you’re in the business of making difficult decisions.

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