
We’ve already covered the strategic value of predicting how you could fail when you’re trying to establish a new habit or quit an old one: Imagining the situations that could lead you to slip up gives you a chance to mitigate them in advance.
One thing we haven’t discussed that I’ve come to see as equally important is the emotional value of imagining failure.
Here’s what that looks like:
- Think about what it would be like to fail.
- Picture it in vivid detail.
- Imagine what you would tell people.
- Try to really feel what you would feel in the aftermath of slipping up.
You should do this because the shame of an imagined failure is a powerful motivation to avoid an actual failure.
When I first got sober, this practice helped keep me from relapsing.
Before Macklemore got famous, he often wrote about his struggles with drug addiction: songs like “Inhale Deep” and “Otherside.” One song in particular, “Starting Over,” is about a relapse. The song puts you in his shoes, giving you a taste of the shame he felt about his failure. I listened to this song a lot when I first got sober. I only just realized, over a decade later, how much it helped.
I also frequently had dreams where I relapsed. Each one gave me a chance to experience how I would feel if I slipped. I would wake up feeling hot and ashamed; it could take several minutes before I realized it was just a dream. These “practice failures” made it crystal clear that I really didn’t want to relapse.

Sometimes you learn the hard way, as I did when I took a bad fall skiing. It’s far better to learn from other people’s mistakes, as I did with Macklemore’s relapse. But you can also learn from your own imagined mistakes.
So if you’re at risk of failing at something really important, take a few moments now to imagine what failure would look and feel like in detail.
It won’t be comfortable, but that’s the point.
