I learned to figure skate in my 20s. The first lesson? How to fall. (Pro tip: land on the meaty part of your butt, not your tailbone.) It wasn’t just about safety—it was about taking the fear out of falling.
As we get older, making changes—even ones we want—can feel riskier. My theory? We have more to lose, and past successes give us more options. The result: hesitation, or worse, paralysis.
If fear is slowing you down, don’t let it lead. Practice falling to take the sting out of it.
Most of us are trained to avoid failure at all costs: Pick the right job. Make the right choice. Choose the right path. It’s exhausting—and worse, it keeps us stuck.
What if, just for a moment, you flipped that mindset?
Instead of trying to be right, what if your goal was to get something wrong—on purpose?
Why failing on purpose works
When we try to be right, we tighten up, overthink, and hesitate. But when we allow ourselves to be wrong, we loosen up, take action, and—ironically—make progress faster.
Decisions are guesses. Experiments give answers. Big decisions seemingly rely on us predicting the future (and we've talked about how that works out...). We stress about making the right choice—so we make none.
Experiments don’t care about being correct. They gather data. And some of the best data comes from getting something completely, spectacularly wrong.
Remember science class? You didn’t have to be right—you just had to test and learn. Imagine if scientists only ran experiments when they already knew the answer… we’d still be waiting on electricity (and I would not be okay!).
Try this: The failure experiment
This week, set up an experiment where your goal is to fail. Pick something light and low-stakes:
✏️ Writing: Write a paragraph (or just a sentence) using only one-syllable words. Awkward? Exactly.
🙋🏼♀️ Conversation: See how long you can talk using only questions.
🎤 Karaoke: Sing your favorite song as terribly as possible—off-key, dramatic, exaggerated.
💃🏼🕺🏻 Fashion: Wear the thing you “save for special occasions” on a random Tuesday.
✍🏽 Drawing: Close your eyes and sketch a self-portrait. No peeking!
Even better, do this with a friend. Yes, that karaoke bar (in your tux?!) is calling your name.
Then, notice what happens:
✅ You survive mistakes. (Wild, I know.)
✅ Your worst-case scenario is never as bad as you imagined.
✅ You learn something—because action, not answers, is what you needed all along.
Now, apply it to what matters.
Where have you been hesitating because you don’t want to get it wrong?
Now ask: How could I fail at this on purpose?
Try it. See what you learn. Hit reply and tell me how it goes.
Need ideas? I’ve compiled fail-safe experiments for jobs, cities, and even relationships.
Next week: What if your problem isn’t indecision—but an invitation to rethink the question?
Don’t let this be your only experiment. Subscribe here and keep testing what’s possible:
To your spectacular, deliberate failure,
Amy
Photo by LOGAN WEAVER | @LGNWVR on Unsplash
