What would you do if you knew you would fail?

I just finished Elizabeth Gilbert’s new book on creative living, Big Magic, which was lovely and worth a read. She wrote a good deal about embracing failure. It’s a standard topic for books on creativity and personal growth, but her approach got me thinking about it in a new way.

Often in this work, we’ll ask ourselves, “What would I do if I could not fail?” This question is useful because it helps tease out what parts of our life we may be suppressing or not pursuing due to our fear of failure. Maybe if I knew I would be successful, I would choose a more creative path, like painting or writing or dancing. It’s easy to imagine how good life would be if I was a successful artist! Wonderful!

But that idea of success in a creative endeavor may bring some unexpected consequences — disappointment when that success doesn’t come, or an idea that there is such a thing as “success” to be had.

So let me reframe the question.

What would you do if you knew you would fail? That is, you would fail at it regardless of how mundane or creative the task. That as an Excel-jockey or middle manager, or as a painter or dancer, you might never make it work. You might have a job waiting tables or mowing lawns indefinitely, because you can never quite get that career off the ground.

What would you do then? Would you keep doing Excel, or even graphic design (more “creative,” but still confined)? Would you keep painting, if success wasn’t a thing? If you love those things, they might be worth keeping around even if it means keeping a side-gig to stay solvent.

What do you love enough to do even if it means always being kind of terrible at it, never finding “success” outside of your pure, personal, ego-free enjoyment of doing the thing?

This isn’t groundbreaking, or a complete reversal of how we usually think about these questions. But it helps me think about it in a slightly different way, and maybe it helps you think about it, too.

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